0117 – Choosing The Right Freelancing Niche w/Connie Holen


Connie and Chris discuss choosing the right freelancing niche for your interests, how to avoid burdening your clients with project management, and ways to look at the client discovery process.

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There are 5 client situations stopping you from earning $100K, right now. Do you know what they are?

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You can find Connie on Twitter and Instagram, or visit her consultancy, Pixality Design.



Started out generalist
Struggled with marketing (time and strategy)
2 years ago, committed to positioning
Started making connections
Prospects started coming to me

Been at it 5 years

Treated choosing the right freelancing niche as a full-time job

Had an interest in fitness & the niche generally

Used a very calculated process to find the niche

* Worked with Philip Morgan in a mentorship
* Tried a couple of other niches before choosing the right freelancing niche
* Eliminated a few industries
* Took 5 months to get fully-positioned

Yoga/fitness needed to offer online scheduling
Industry leader was hard to use
Helping new students have a smooth, clear process

Clients are sold when they call already
Don’t have to close sales
Don’t have to convince
Not talking about process
Comparable proof in the portfolio

Still a struggle to audience-build outside of referrals
80% referrals (due to positioning)
Listed on industry-appropriate directory sites
SEO yields some traffic

* Easier to target SEO after choosing the right freelancing niche

Guest posts
Massage/Day spas/Yoga journals, etc
Outreach to software vendors for referrals
Booker.com* guest post

How to do outreach

* Primary & secondary industry media outlets
* Do some research, check their archives, see if they do guest posts
* Start making a list
* Use submission forms or email contacts

Workflow originally was Basecamp w/standardized messages:

* Changed w the new positioning
* Traditional biz owners
* Don’t want to spend time at the computer
* Got easily overwhelmed
* Now, it’s all email
* I hide the PM software from the client
* I cut & paste the client emails into the system
* Cut & paste standardized messages back
* Project start is a month out from closing & down payment* time for discovery


* It always works out better when you don’t start building right away
* Many business owners don’t have answers for those intake questions
* Clients don’t know they need to know these things until they’re asked
* Checklist of things to do (gathering logins, inspiration image, get a photo shoot scheduled, gather content)
* Give a site map early in the process to help them know what content they need

Full Transcript:


0116 – Code When The Baby Sleeps w/Ryan Battles

Freelancing with kids profile photo Ryan Battles

Ryan and Chris discuss freelancing with kids, specialty positioning, and how to cultivate the habit of writing to market yourself.

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There are 5 client situations stopping you from earning $100K, right now. Do you know what they are?

Find out who they are and what to do about them with this free 5-part email course.

You can find Ryan on Twitter, or online as the founder of Harpoon, financial planning, time-tracking, billing, and budgeting platform for creative studios.


On freelancing with kids – Code when the baby sleeps

Get frequent referrals from peers

Moved from “small business” positioning to Expression Engine specialist

Ran some Google AdWords

Got great results – booked 3 months out

Benefitted from lack of competition

DirectorEE of EE developers

Began to have to evaluate job offer vs freelance issues; always decided to stay freelance

2 years in, became more proactive about goal-setting

Built Harpoon as a planning tool for freelancers

Had to learn how to market articles better to amplify the reach of these posts

Focus on the habit, not the result – write consistently

Don’t focus too hard on one article for marketing yourself

From freelancing with kids to a “scratch your own itch” product to full-time product

Full Transcript:


7 Freelancing Trends For 2017

7 freelancing trends for 2017 cover photo of a peacock

The business of freelancing is changing rapidly; anyone active in the industry can see it. My own experience leads me to see certain trends that are already in effect, and are poised to really take off in 2017. Some of the freelancing trends of 2017 will help us, and some can hurt us. Here are the most important 7 trends, and what they mean for all of us.

1) Massive numbers of millennials will start freelancing.

It’s been reported that millennials tend to want to switch jobs frequently – about every 2 years – and avoid the boredom of doing the same job in the same place the same way, in the same place, day after day. And who could blame them? Although the gig economy has been a thing for the past few years, a couple of factors are going to accelerate this trend in 2017:

  • Culturally, the stigma surrounding remote work is virtually (no pun intended) gone.
  • More companies than ever before are more open to using freelancers than ever before.

In other words, freelancing is becoming increasingly normalized. This adds up to tons of opportunity for a workforce that is increasingly choosing to eschew full-time work and instead make the leap into full-time freelancing.

Although the freelancing trends for 2017 means that the influx will be comprised of mostly millennials, it’s not 100%. While most of the more mature and established members of the workforce will stick to the “sure thing” and remain in the traditional employment they’ve become accustomed to, we’re likely to see an uptick in the number of “graybeards” deciding to test the freelancing market.

With a massive influx of fresh talent and an accompanying – if smaller – increase in experienced workers in the freelancing marketplace, the overall market is due to become very competitive before 2017 is over.

Hint: to overcome objections of youth & inexperience, have a case study or two that allows you to demonstrate results to prospective clients.

2) Niche – and even micro-niche – positioning will become increasingly important.

freelancing niche
Have you found your freelancing niche yet?

It seems like you can’t throw a rock in freelancing circles without someone talking about positioning. Again, this is an existing trend that we’ll see accelerating in 2017 thanks to a confluence of cultural and educational factors.

Although larger firms and small, established generalist firms (like mine!) will likely continue on just fine, the increasing number of new freelancers will make for a more competitive market. This increase in competition will force solo operators and small agencies alike to stratify into increasingly specific niches and micro-niches.

Those who don’t specialize or hyper-specialize will likely be pushed toward bottom-of-the-market work. Look for marketplaces like Upwork to be more competitive at the end of 2017 than they were at the start (this is both good AND bad for those making use of these marketplaces).

Specialist positioning is undoubtedly helpful in a number of ways, but the question that remains to be answered is, how niche is TOO niche? 2017 may be the year that freelancers find themselves pushed to find an answer to that question, as they narrow their specialties further and further, hoping to position their offerings favorably against increased competition.

Hint: if you’re not already positioned with a specialty, look at your existing body of work and reverse-engineer the problems and verticals you’ve already solved problems in, then market to that vertical, for that problem.

3) Informal partnerships of otherwise independent freelancers will become more common.

For years, my own firm has been what I refer to as a “merry band of mercenaries” – a gelled team that works together on a regular, ongoing basis, while remaining 1099 workers and maintaining all the appropriate boundaries required by the IRS (the guidelines are clear and strict).

Additionally, my firm has formed alliances with other small firms, with each of us providing labor related to our specialty in order to complete a project owned by one firm. These alliances will prove to be increasingly important in 2017 as freelancers take on sophisticated but finitely-scoped projects that require specialty labor, but that do not allow for the hiring of a regular employee to provide that labor.

It sounds like a fragile arrangement, but “specialists collaborating with specialists” is one of the very oldest ways of working, and it’s not only one of the more interesting freelancing trends for 2017, but more critical than ever.

Hint: making use of some decent project management software – Basecamp or Asana, for example – will make these arrangements much more manageable.

4) It will become increasingly more difficult to stand out online…

It’s not always this easy to stand out.

To say that it’s very difficult to rise above the noise online is an understatement. At one point, merely having a blog or podcast ensured some degree of traffic and notoriety. Now, these things are considered bare minimum signs of life for your freelancing practice online.

In 2017, most online marketing efforts will languish, with a small layer of “super-winners” at the top claiming the majority of the traffic, clicks, leads and sales. Smart freelancers will have to learn how to capture sub-segments of sub-segments of this traffic that would ordinarily go to the “super-winners”, and claim these leads as their own.

Hint: stick to marketing channels that allow you to best communicate what makes you valuable. Invest in effective marketing-education tools and training, like Tiny Marketing Wins, to help you.

5) …which is why personal networking & referrals will remain king.

We live in what is supposed to be the golden age of online lead-gen and marketing automation, yet the great majority of freelancers find that their online marketing efforts yield zero return – or worse, a net-negative return. By far, the #1 way that freelancers  get new client work is via their network, not via stranger-leads that come in due to any kind of automated marketing.

The fact that it’s harder and harder to stand out online will make personal network marketing and referral work more of a source of leads, not less, and many freelancers will give up on trying to attract “stranger leads” online and instead use those automation tools to go deep on personal network marketing.

To be successful amidst these freelancing trends for 2017, it’s important to learn to create more “referrable moments”, meet more valuable contacts, and do a better job of turning one-off projects into long-term relationships with recurring work. Outside of the super-winners, freelancers that don’t go deep into relationship marketing will find that their blog posts, podcast episodes, and social media updates will continue to go unread, unheard, and unseen by prospective clients.

Hint: for going deep on email marketing to your network, I recommend Drip; it’s got everything you need to do either outward-facing lead-gen campaigns or inward-facing nurturing and referral-soliciting campaigns.

6) Lifestyle will become more important than earnings…

house with white picket fence
What’s YOUR dream?

The Golden-Era American Dream – that anyone can get a stable job that pays enough to own a home and raise a family on one income – is dead and buried. The 21st-Century American Dream can be summed up in one word: flexibility. Sure, we want to support our families, but we also know we’re not going to be able to do it in partnership with one long-term, predictable-schedule, single-location employer.

Well, if we can’t do that, what can we do? We can work flexible hours. We can work remotely. We can work while traveling. We can work with a variety of clients, on a variety of projects. We’ll still earn a great living, but that will be less the focus than it used to be; the focus will increasingly be on having flexibility – being less dictated to, having less conformity demanded of us, and having more say-so in our overall careers than traditional employment ever offered those to whom it also offered long-term stability.

Hint: look for like-minded clients who respect work-life balance themselves, and don’t expect you to run headlong into death-march projects.

7) …even though earning potential will continue to rise.

Make no mistake, whatever the American Dream may be, it still takes money to attain it, and the freelancing market will continue to offer ample money. Rates will likely fluctuate a bit as newer, less-sophisticated operators flood the market and depress rates (at least for low-end work) but the market for established operators who can offer clients clear value propositions and proven track records will remain healthy.

One of the most encouraging freelancing trends for 2017 is that in certain niches and sub-specialties, effective rates are expected to increase by the end of the year, putting many freelancers in a strong position at the start of 2018.

Hint: figure out where your offerings exist on the value continuum and try to shift them close to where money is generated.

0115 – Creating a Repeatable Consulting Process w/Kelsey Kreiling

repeatable consulting processes on the $100K Freelancing show

Kelsey Kreiling is the co-founder of Presence Agency, where she and her business partner Mallory Ulaszek have created Week of the Website – a weeklong website design process, helping non-profits, early stage businesses and hospitality groups launch their websites on Squarespace in just five days.

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There are 5 client situations stopping you from earning $100K, right now. Do you know what they are?

Find out who they are and what to do about them with this free 5-part email course.

You can find Kelsey on Twitter, or online as Presence Agency on the web, Facebook and Instagram.


Matching budget to functionality

Clients go in thinking Squarespace is DIY
– They can’t build what they envisioned
– They can’t even do that

More of a CMS choice than a diy tool
– Templates are good but limiting

70 websites in 1.5 years
– Speed is the sale

Acuity scheduling integrates w Squarespace

Working in hospitality
– Bars & restaurants
– Running a digital publication
– Opening new concepts; asked for help w web
– Knew what they were investing on websites ($2500 – $3500)
– Thought maybe Squarespace would satisfy this need at this budget

Mallory pitched Kelsey on redoing *her* hospitality groups websites
– Did a proposal
– First few sites were traditional agency-style; too process-heavy
* This was not working
* Almost walked away
– Visited Squarespace offices
* Cold e-mailed & asked to come talk

Changed to a repeatable consulting process to emphasize collaboration
– Proactive communication
– No sense of ownership; it’s not my site
– Client gets to watch & participate in the process

Clients come in with various levels of technical ability
– Everything done on google drive
– Daily emails
– Uberconference
– Calendly

This repeatable consulting process isn’t for everyone
– we need a certain kind of client

How to get client for this repeatable consulting process?

Person-to-person marketing
Almost all referrals
– Via someone we already know
Teaching workshops
– Week Of The Website lite for existing sites
– Catch “Done With you” “Done With You” “Done For You” continuum

Squarespace specialist page listings
– Networked with other firms to handle overflow

Have to be careful about how much to grow and how much to take on
Framing cost vs investment
Helping the client understand their business
Scheduling & balance is important for building the right business for our lives

Full Transcript:

Chris:                    Welcome back to another episode of the $100K Freelancing Podcast. I’m your host, Christopher Hawkins, and today my cohost is Kelsey Kreiling of weekofthewebsite.com and presenceagency.com. Kelsey is the co-founder of Presence Agency, where she and her business partner, Mallory Ulaszek, have created Week of the Website, a week-long website design process, helping nonprofits, early stage business, and hospitality groups launch their websites on Squarespace in just five days. Kelsey, that sounds amazing. Welcome to the show.

Kelsey:                 Thanks, Chris. I am super excited to be here.

Chris:                    Okay, now, everybody listening, raise your hand if you didn’t know that a Squarespace consultant was a thing. I had no idea. That sounds really interesting.

Kelsey:                 I would not say that that is a super common thing yet, but it is a really fun thing to be. It’s fun to be on kind of the cutting edge of a way that a product is being used kind of differently in the industry. Our clients love it. We love using it. We love the Squarespace team. It’s really been a fun ride to get to use the product so much.

Chris:                    I may be a bit of a WordPress bigot, but I’m willing to say that if I asked most people, they would say, “Wait. Squarespace, that’s like for end-user mom and pop, DIY, don’t know what you’re doing and don’t want to spend any money customers.” How do they have money for a consultant if they’re using Squarespace? How does that whole thing work?

Kelsey:                 What we found is that our clients fall into a couple of different buckets. First, there’s people who have started using Squarespace, realized that they like it, but want something that looks better than what they can throw together on their own. The other bucket is people who have no idea what they want or need and just want us to build them the website, where, at that point, we talk to them about Squarespace. We talk to them about the reasons why we love it and really share with them the reasons why we think it’s good for clients like them.

When it came out, it was definitely more of that DIY, kind of like portfolio site, but over the last few years, they have worked so hard to build it into such a robust CMS: things like Acuity scheduling being able to be dropped into a page, like a scheduling widget, in three seconds. OpenTable can be fully integrated with the site. They have a pretty robust eCommerce section, where you can build a store with hundreds of products and multiple product types and variations.

We once built a website for a custom jewelry designer, where her products would have four different chain lengths and three different metals and four different sizes for the medallion, and then you would customize what it could say on it. It’s really remarkable how much they have grown and changed over the last two years, but mostly it’s super easy to use, right? It’s built for people to be able to create their own websites, which means for us, it’s built so that we can build a gorgeous website for a client who has a smaller budget than they would normally be able to spend on a designer and a developer.

Then we get to leave them with really great training and a ton of tools that are already built into the Squarespace product, so they can actually use and maintain that website on their own, which, for small businesses, who, as you mentioned, don’t have a huge budget; for nonprofits, who definitely can’t allocate a salary toward someone to just maintain their web presence or have a designer on retainer, we’re able to take them through a training of how to use their website, and then connect them with the Help Team at Squarespace, who really are on demand for most things, at least 12 hours a day, to help them maintain that website, once we’ve parted ways. In that sense, the build it yourself thing really becomes a gateway to awesome accessibility for clients, once they’ve actually bought a website from us.

Chris:                    Wow, okay. You’re kind of geeking out on this, and I love it. I love it. That’s a good sign. That’s a sign you’ve found something you’re passionate about. I think that’s beautiful. Gosh! I’m still so floored by the idea that there’s such a thing as a Squarespace consultant. That’s really cool! I certainly would not have predicted that there was money to be had in that particular niche. How many sites have you worked on?

Kelsey:                 I’m an administrator of 70 different websites at this point. We’ve been doing our Week of the Website process for just about a year and a half now, so it’s been a lot in a pretty short amount of time, but it’s been amazing. The variety of things that we work on from week to week is totally different. Last week it was a nonprofit. The week before that it was a fashion incubator. The week before that it was a hospitality group. Every week it’s something different, which is really fun.

Chris:                    How did you come to occupy this particular space? How did you even identify this as an area of opportunity?

Kelsey:                 Yeah. Before I started Presence Agency, with my business partner, Mallory Ulaszek, I worked for a hospitality group in Chicago here. They ran a bunch of different bars and restaurants around the city, and I was brought on to begin this digital publication for them. My day job … I traveled around the country. I visited different bars and restaurants, talked to them, interviewed their chefs and their bartenders, working with a video team, who made these really cool videos of them making their actual drinks and stuff. Because I was the person who knew about the Internet at this hospitality group, I got asked to help them put together landing pages or minimal websites for new properties that they were opening.

That was my first experience with Squarespace, and that was probably four to four and a half years ago now. That was my first experience with Squarespace. Then, as I worked with them, developing collateral and [inaudible 00:05:49] for their new projects, I was given access to information about what they expected to spend on websites, from the mind of a restaurateur, what they expected that to cost.

Those two pieces of information … Okay, we can build really simple websites using this stuff, and this is what people in this industry expect to pay for websites, and it was less than what anyone in the design industry would say that they charge for websites. There was an opportunity there. My business partner at the time had just come to me a week prior and said, “Hey, I’m looking to get out of the retail business.” She owned multiple boutiques around the city. She was like, “I would be interested in going into business with you.” She kind of like Jedi-minded me into doing it, but I’m happy she did.

A week after that, when we were still just discussing it … We didn’t have a name. We didn’t have a bank account. We had none of that. A friend of ours reached out and said, “Hey, I’ve seen what you’re doing for the hospitality group that you work at, with their websites. Do you know anyone, who is not you, because obviously you work for a competitor, but who has your same skillset that would be able to come and help us redo all of our websites?”

There was one person, who was managing all the websites for their properties, but they were spread over five different CMSs. They were really difficult to use and execute, and that was also something I was seeing, in the hospitality industry especially, was every time someone would open a new restaurant or bar, they would use a completely different backend for the website. Sometimes they were hospitality specific or not, and it was a mess for anyone who had to manage multiple sites. That was kind of the other component of thinking about this. Squarespace has the ability to have a one-manager account for … You can easily pop into multiple websites.

That was kind of when I realized, okay, this could be a really good product, specifically for this type of client. She said, “Hey, let us know if you know anyone who can do this.” I reached out to my business partner and was like, “This opportunity just kind of fell into my lap. What do you think? Should we try for this? Should we pitch this?”

We decided that it was really one of those “nothing ventured, nothing gained” kind of moments, put together a proposal for them, and they ended up becoming our first client. We didn’t end up redoing all of their websites then, but, at this point, they are still, to this day, our best client. We work with them probably four times a year on different projects. That was kind of the moment where we connected that we were able to do something unique.

At that point, we were doing just kind of like a classic agency structure. It was a project that took a couple weeks to get started. It took a couple months to build, and we didn’t like that. It was really frustrating. There was definitely some time before we hit on the Week of the Website process that we use now, but everything that happened at the beginning there really informed the decisions we eventually made to create this structure.

Chris:                    Just to go back a little bit, when you said that you were helping out with the websites for some of these restaurants because a lot of the folks in that industry do not have the requisite skills to set up a website-

Kelsey:                 It’s not the area that they work in, you know? It’s such a different industry, not one that they spend a ton of time doing web stuff in.

Chris:                    A lot of small to medium business owners, they try to expand into these kind of “Oh, I can just DIY it” type skill areas, and they don’t get great results. That’s a huge part of the reason why they turn to people like you and I. What was the average price point that those restaurants were looking to get a website for?

Kelsey:                 I think the general expectation when we talked to people was that it was going to be somewhere between $2500 and $3500, which, if you talk to anyone else in the design or development world, that’s hard to have a designer and then have someone develop the code for it or modify a template. That’s pretty limited. A lot of them ended up like, they would DIY it or they would find someone to do it for them for free, or they would end up finding funding for it somewhere else, but that was not their … They didn’t go into it saying, “I’m here to spend $10,000 per website.” That’s just not the way that restaurants … They just don’t have that kind of margins to be able to do that. I mean, most of them don’t. A lot of them are successful and can do that, and you can always tell. Kudos to them. There are some beautiful restaurant websites in the world. They think like small businesses. They work like small business, and especially when they’re starting, they’re beginning with investment capital that they have to be really conservative with it, because food and all that stuff, so … Anyway, it was different.

To me, that felt like a really underserved … There seemed to be a gap between having someone create like an amazing WordPress website for you and doing it yourself, and this CMS, beginning from templates that could be really easily modified and made beautiful with design and limited development time, seems to actually kind of fit into that space really beautifully.

Chris:                    Okay. Now, I know that the Week of the Website process you’re using right now, I know you didn’t jump immediately to that. Can you tell me a bit more about what your process looked like when you first started doing these sites for the restaurants?

Kelsey:                 You know, it was a really standard agency process. We would meet with the client. We would do a discovery meeting. We would develop concepts for them on Photoshop or present to them a static design, and we would go back and forth. They would say, “We like this. We don’t like this.” Then, once we had nailed down the design, we would start to build it and then they would give us feedback and, ultimately, it was long and slow, and I think a lot of people are comfortable with that, but my personality, both Mallory and I felt like it was just so long. It just dragged out, and it felt like people weren’t that happy. Even though we felt really good about the design, by the time it was done, people had sat with it for so long that they just weren’t excited anymore. They just wanted the project to be over.

Our business was kind of unique in that, within the same very short amount of time that we got hired to build that first website, we also got hired to produce this huge food festival in Chicago and, ultimately, ended up producing more of these festival type events in Chicago and Brooklyn and Miami, and so we were a little divided. We were only taking on a couple of these website projects at a time, because honestly, we just weren’t that excited about them. We happened to be in Brooklyn for a meeting with one of our other clients and just got kind of wild [inaudible 00:12:24] one day and reached out to Squarespace and said, “Hey, we’re going to be in Brooklyn. We’re going to be right by your office. Can we come in and talk to you about the product? Can we come and tell you about our experiences with it with our clients,” thinking we would never hear from them again.

They were like, “Yeah, sure. Come on by.” We sat down with Jeremy Schwartz, who really has taken the lead of all of their Squarespace specialist and developer programs, and they just sat with us, and they asked us questions about what we were doing. We talked to them, told them what we wanted to see, and they told us a little bit about what the future of Squarespace was going to look like for users like us.

In that meeting, hearing about other people doing things with Squarespace in a really unique way, we realized, oh, my God. We were playing by these rules that we thought we had to follow because this was how agencies do it, but this is a different product. This is a different process, and we can create something that feels fun for us to do. It feels exciting for us to do and also hits these other client needs that were really underserved by the way that we’d been doing it before.

I’m actually really grateful we got to do that, because at that moment, I really think back to that meeting, just opened our eyes to the possibility that there was a different way for us to work with clients and still build websites, because, candidly I was like, I don’t want to do this anymore. This isn’t fun. I don’t like it. It sucks. Leaving there, we were like, what if we just did this differently. What if we put some constraints on this, put some limitations on here, lower the price point, and make it fast. We can do this in a week if people are willing to work with us in a different way. I think back on that day very fondly, because it’s a very memorable marker in time of the way that we thought about our business changing.

Chris:                    Now, this is interesting for a number of reasons: number one, and not so much kind of the humorous, gee, I didn’t know there were Squarespace consultants way, but number one, that you identified this as an area of opportunity–you saw the gap; you saw that you’ve got people attempting to DIY things that they’re not particularly well suited for; number two, that they’ve got a certain budget that exists in an underserved market segment; and, number three, that your first thought went to “I can consult around this tool that satisfies both the skill gap and the budget gap.” I think there are a lot of freelancers out there, and maybe I’m coming from a developer bias, being a developer myself, but there are a lot of freelancers out there who would not have concluded, “I can consult around this tool.” They would have said, “I can build a restaurant CMS,” and they would have set out to do that. It would have been a SAS app or it would have been a WordPress theme or something like that.

You started out consultative. You didn’t start out as, “Well, first I was a developer, and then I was a consultant.” You were just doing this already, and you had already identified the opportunity when you launched your business. That’s really cool, because I don’t hear a whole ton of stories like that. That’s a beautiful thing. The way you realized that your process wasn’t working for you … Clearly, it was working for your clients, right? Because they were still hiring you, but you just weren’t enjoying it, and it sounds like you almost walked away, really.

Kelsey:                 I’m a designer. I went to fashion school. I think that thinking about it from the perspective of developing around a tool … I needed other tools to let me build things for people. My fiance, Zack, is a software developer, so he does what appears to be wizard magic to me. I knew that that wasn’t a skill that I had available to me, right? I couldn’t build a CMS. It would have not been worth my time to try and come up with a template I could sell. The real magic behind our process? It has, candidly, nothing to do with Squarespace.

At the end of the day, what we discovered when we started creating this Week of the Website process, which … We start on Monday. We shoot to be completed with the site on Friday. Leading up to the engagement with the client, they get a discovery survey, which I get to look at in advance. My whole goal is to get into their head. When they tell me what they want, what do they really want? When they state their objectives, what is really the most important purpose of this website? What we do for them is that we create this process that is so focused on understanding their needs and making it as easy for them as possible that we jokingly say, “Our product is the process.”

Ultimately, Squarespace is the tool that we use to execute that vision, but we do daily conference calls with them, where they can see my screen, and if they want a color to be different, we just make it different in front of them. That was what we realized we really loved was being able to connect with these clients, to very quickly try to synthesize and understand what it was that they were trying to achieve, try to connect them with some visual information so that they could show us, “Okay, I want it to look like this,” and then lead them through this really, really hyper-collaborative process, so that by Friday they had a website that they were super excited about, they were really proud of, and they had been watching me kind of build in front of them for five days, so that, once they went through the training, they actually had been seeing someone do the things that they were going to need to do to update and market their website in the future.

It just ends up creating this really connected experience with the client, because they have been a part of it. I don’t go away and design things and then show it to them. From the afternoon of their first day on Monday, they have a live link to this site in process, and they can check up on it at any point. They can peek in. We have a way for them to share feedback with us, and that was what we ended up realizing we were really, really good at, was leading people through this kind of project management flow that we, to be honest with you, apply to all different kinds of projects now. Week of the Website is the thing we do most often, but we use this ideology in any production projects we do, any other work outside of Week of the Website, and that was kind of like the coolest part, was discovering what this process allowed us to actually do with our clients.

Chris:                    I like hearing about the process, because you already had the opportunity figured out. Like I said, clearly the clients were happy to hire you, but you weren’t happy with the process. The process that you changed to clearly made you happy. Do you notice that the clients are even happier with the new process or were they just okay to begin with, and they’re still okay now, and they don’t really care about the process?

Kelsey:                 Oh, no, they love it. They love it! You know what? It makes me so happy, because, at the end of the week, they’re kind of blown away. They’re like, “This has been so nice.” People say this to Mallory and I, and we don’t really understand what it means. They’re like, “You’re so nice to work with. You’re so easy to work with.” Mallory and I always laugh at that, because all we do is communicate really well with our clients. We talk to them constantly. We answer their requests. We make changes that they ask for, because I don’t have any ego attached to these websites. I want them to be beautiful. I want them to be really functional. I want people to be happy with them, but I do at least one of these a week, so if someone wants a different color button, they can have a different color button.

I’m not coming in as a designer that’s like, “Well, this really changes my design paradigm.”  We are in the game of making people happy, giving them the website that they want, not the website that we want. We always tell people, “Look, I want you to be happy more than I want to be right.” I don’t have any sense of ownership over these once we leave them, because there’s someone coming the next week. I think that that makes clients feel so heard, that they don’t have to worry about arguing with me over typefaces. Of course, I’m going to give them a great design, and I’m going to encourage them to stick to that great design, but ultimately it’s not mine. I think that thinking is not always the way that people approach this process.

creating a repeatable consulting process quotation
Creating a Repeatable Consulting Process 2/Kelsey Kreiling on the $100K Freelancing podcast

Like I said, there are designers who are incredible and amazing, and that is what they do, but that’s not what we do. That makes clients really excited, because they’re just like, “Oh, okay. I wanted this fixed and you fixed it. Great.” We just don’t have time to sit around. The best clients are the ones who are really engaged with the process. A lot of our clients come back. A ton of our clients send us referrals, even unasked, afterwards because, I don’t want to toot my own horn, but I hope you can hear that when I talk about this, it’s like a parent talking about their child, because it’s such a cool thing to see these clients be happy with it. When we finished, it was like, “Great. The website’s finished. Thank you so much for being done with this.” Now, it’s like, “Wow, this is really fun. I had a great time. It’s so cool to see things happen collaboratively. It feels like such an iterative process. It feels like such a connected process. I love it. I can’t believe I built a website any other way.” That makes us really happy!

Chris:                    With a process like this, I’m wondering how you handle communication. You mentioned that you’re very proactive with communication. You stay on top of it. Are you using any kind of a project management system? Do you try to shoehorn your clients into anything process-wise there? Are you just swapping emails? What’s the marching orders for that?

Kelsey:                 The most important thing for us to remember is that our clients come to us with all levels of Internet proficiency, but most of them, they’re not super Internet savvy people. We definitely ask them to use Google with us. We do everything through Drive. It allows them to upload photos really simply, to use a collaborative document with us for changes and notes. We do daily emails to them, and then we use UberConference to do screen share calls, where they can see my screen, and we can talk about what we’re looking at. We also use Calendly to schedule. We use a little bit of technology to get the to go through this flow with us in project management, but that’s kind of it.

I’ve worked on a lot of different project management software and tools, and I think that works for me, but our whole ethos is meeting the client where they are. As simple as we can keep it, that’s kind of our focus. It’s like, what’s the easiest way for this client to get me the content? Because, I don’t want them to be sitting there going like, “I don’t know how to use Basecamp,” while they’re holding onto all the photos I need.

Chris:                    Right, right. Okay, I want to back up just a little bit. You mentioned that you send a discovery … What did you call it? Discovery, not document; you said questionnaire? Survey?

Kelsey:                 Survey. Yeah, we send them a survey that they fill out. It’s got all different kinds of questions on it: everything from what’s your objective to what are some websites you like or don’t like? We try to keep it pretty simple. Then we talk through all those answers. In that conversation, that really helps us understand what they’re looking for, what their perspective is, that kind of thing. It’s just really to get them … It’s less so for us to get the answers and more so to get them thinking about the kind of things that we’re going to ask them about during our first call on Monday.

Chris:                    I do in-person discovery sessions over here at my consultancy. I know a lot of people do that. There’s sometimes a very, very lightweight intake questionnaire. I’m trying to think right now if I could actually take my initial intake questionnaire and just run with it and start a whole project, and I’m thinking, no. We kind of need that agency style first kickoff meeting to do it. You sound like you’ve figured out a way to kind of dovetail that discovery survey right into hitting the ground running with a really collaborative project. That’s cool!

Kelsey:                 Yeah. Our clients, they are all around the world. We have a lot of clients that are here in Chicago, but I would say, on any given day, that we wouldn’t be able to predict where they are. Sometimes that can get a little tricky with time zones. We worked with someone in Hawaii a couple months ago, and that was a little bit challenging, but we don’t really have the luxury to be able to go in and sit with them, though that is an offering that we’re in the process of putting together, is kind of like an in-office week-long bootcamp, where we really have that level of connectedness with their team, because I think that some people might really like that. The way that it exists now, it’s all over the computer and it’s all over the phone, so we kind of need that survey to do a little bit of that heavy lifting for us, so that we can get into a really good conversation once we start on Monday.

Chris:                    Okay, okay. I want to shift gears here, so instead of talking about what you do when you have a client, I want to back way upstream and talk about how are you getting leads and closing deals? What does that process look like? How are you marketing yourself? What kind of places and via what mediums are you putting Week of the Website and/or Presence Agency out there, and how do you identify the places where you need to be in order to be in front of your ideal client?

Kelsey:                 The first thing for me to note for you is that this is not the right process for everyone. It’s a very personality specific thing. There’s a couple things that we need our clients to be. We need them to be flexible. We need them to be able to make choices. We need them to be kind, because I have to talk to them every day for a week. There’s a lot of pre-vetting that has to happen from our end before we choose to work with a client.

We really focus on very person-to-person based marketing. We’re almost entirely referral based, and we love that, because that means people are typically coming to us via someone else that we know and have worked with. A lot of our clients are very kind to refer us to other people in their industry who need assistance. We always love those, because it also gives us something to start talking about at the beginning, as we get to know each other.

The other thing that we do is we often teach workshops or classes on how to build your own Squarespace site, which sounds a little bit counterintuitive, like why would we teach people how to do what we are trying to convince them to hire us to do. The reality is this person is not my client, but if I teach them the basics of how to get in there and understand the tool and start really building it out themselves, it is very possible that if they get tired and frustrated and realize that it’s not quite as easy as it looks in the Super Bowl commercials, they already have someone to turn to, who is able to help them through that process. We actually created an entirely new offering called Week of the Website Lite for people like that, who already have a Squarespace website, but who want us to come in and, over three days, help push it across the finish line to look like a professional did it for them or to help them answer specific technical questions that they’re struggling with.

Chris:                    You know, I think that’s smart, that you’re catching them. You’re catching them at the very start of the do it yourself, do it with you, do it for you continuum. I think that’s a solid strategy. I do similar things myself with educational marketing around here, where you tell a client, “Oh, so you want to go from A to B? Great. Here’s how you do it.”

Let’s be honest, you know very well most of them will not be able to do it. They’ll make some improvements. Maybe they’ll be happy with that. That’s fine. Maybe you never hear from them, but the ones that are really serious, the ones that undertook to DIY it, not so much because they want to DIY it, but because they’re serious about getting to that place … The ones that are serious, those are the ones that end up calling, in my experience. I wonder if that’s the same with you.

Kelsey:                 Definitely, and not only are they serious, but they also have a familiarity with it that they have a respect for the work that we’re about to do for them, on their behalf, and the speed with which we’ll do it, because that’s what we always say, right? It’s like, “You can build your own website.” Anyone can build a Squarespace site. Anyone. I can teach anyone to build a Squarespace site. The question is how long will it take them and how difficult is it to lead yourself through that process of pulling together the information that you want?

We do a lot of actual content strategizing with them throughout the week. We help them think about what sections do you need? What should be on this page? Those are kind of the intangibles that we offer to people that they can’t get just from one workshop session with us. The other thing that we do is Squarespace has a specialist’s page that they have not updated in years. It is still online, and half of the companies who are on that list are not in business anymore or they are so inundated with requests from being one of the few companies that responds to people on the Squarespace Specialist’s page that they just have too much stuff.

What we did four or five months ago, I think, is we reached out to everyone on that list and said, “Hey, we do this thing. We would love if you will send us clients that you don’t have time for or who have too small of a budget for it or they have too quick of a turnaround time, and, if you do that, we’ll send you a referral [inaudible 00:29:56].” We have developed an amazing, amazing relationship with specifically these two other agencies on the West Coast. One is called The Beauty Shop, run by this amazing woman named Jen, who we ended up working on [inaudible 00:30:14] projects together, and then another studio, called Raygun.

They’d send us projects that aren’t a good fit for them, and it’s been amazing because it has allowed us to also connect more with that community. We’re a part of Jen’s group of designers who do nonprofit work throughout the year. We’re one of her pro bono partners, and that has been both great for us, in terms of finding business and referrals that is essentially pre-cleared by another agency, as well. Then also having this other feel good part of being part of a larger community that has had a marked difference in our experience with referrals, but also just as general company happiness.

Chris:                    Your game is relationships. That’s your entire game, if you’re doing almost all referrals to get work. I’ve heard some people say that if the only way you get work is referrals, then you’re basically leaving your business up to luck. I do not agree with that, speaking as somebody who has invested a lot of time into making and nurturing relationships in order to maintain a steady stream of referral work myself. I don’t think that’s luck at all. I think that is … I hate to use the word “exploiting.” Please understand the context in which I’m using it. I think that that is simply exploiting one’s own efforts at building a network.

I know people who are doing very healthy, six-figure, solo consultancies all off of referrals, all off of relationships, all off of, as you say, person-to-person marketing. That kind of thing is incredibly powerful. I think a lot of the freelancers, who maybe come from the hardcore geeky or technical backgrounds–maybe they’re a little shy or introverted, maybe they’ve just been hard-sold on the golden age of content marketing–they’re maybe not getting out there and doing the person-to-person stuff that really makes money fall from the sky. It’s really interesting to hear about how this is your primary game plan, because it’s huge, and it’s the very oldest and, in my opinion, most effective way of doing business, and yet a lot of us get so caught up in automation when it’s way too early to automate anything, when it’s way to early to be mounting a massive content campaign, that we overlook how much money there is in that person-to-person activities.

Kelsey:                 Yeah, I’m really lucky to be a part of some awesome masterminds with people who are so, so, so good at content marketing, so good at social media, so good at using all of these other techniques to sell their services. You know, there’s definitely things that … I’m going to honest with you. Could we be doing more of that? Absolutely, but the reality is we’re two people, and we have to be very careful about the speed at which we grow, because we can only do so much, and we can only have certain kinds of clients, which it is a very big pool, granted, but it really doesn’t necessarily behoove me to draw in some random person from the Internet, who may not be a good fit for our business.

Do I see the potential for using some more of those automated techniques in the future? Absolutely, but I also think that that is an upcoming stage of our business. Frankly, we always want more business, like I never am going to be like, “You know what? We’ve got too much business. This is a real problem for me.” That’s never going to be a problem for me, but I think that that is still, as we look to the future of our business, that’s definitely something that we see potential for. In the meantime, the quality of and the experience of developing new business from referrals, it also helps us have a connection with those clients in a way that is really helpful.

It’s also nice to know a little bit about what you’re getting before you go into it. Honestly, being able to talk to people about what our process is, because it is so different … It’s hard for people to just read our website and be like, “Oh, I get it.” Its hard for people, without hearing what it’s actually like to spend that week with us, to go like, “Okay, I definitely want to do this.” It’s not cheap. It’s $3000 for a week, and that includes training.

A lot of people might be hearing this podcast going like, “That’s really cheap,” but you also have to understand that it’s a different client. It’s a different perspective. It’s a different mindset, and to them it feels huge. We have to be able to share with them why it’s right or why it fits for them, when they’re looking at Squarespace going, “Oh, I can build this for $18 a month,” and then we go, “Well, it’ll be $3000 if you want to work with us.” They’ve got to get that. They have to understand what the difference between those two things is. That means that when we do things on a referral basis or person-to-person or education based, they can see that it’s not just a website you’re paying for. It’s this whole guided process, where we’re going to help you understand not just what your website’s going to look like at the end of the day, but how it functions, how it works, how you get it to the domain. How do you edit it and use it afterwards? It’s a whole lot more than that. That’s hard to convey sometimes, with some of the more automated marketing methods.

Chris:                    Yeah, I agree. I agree. You bring up an interesting point. I’ve had meetings with restaurant owners locally in my town here, who would get a $3000 quote and would probably tell you to your face, “I will never make that $3000 back from this website. There’s no way I’m spending that money.”

Number one, he would be wrong. The right website would bring in way more than $3000 worth of business within a very short amount of time, but it’s the perspective. It’s not so much the correct or incorrect … It’s the perspective. I find that, on the scale of businesses that have those $2500 or $3000 budgets, they tend to view technical expenditures as pure cost, not as investment. Is that one of the filters that you referred to earlier, when you said you have to pick very particular kinds of clients? Do you find that that’s a constant problem in your attempts to educate prospects in the marketplace about how to view that $3000 expenditure?

Kelsey:                 Well, all of our pricing is super public. It’s right up on our website. I mean, we think of this as kind of a productized service, so, in that vein, it’s a little bit self-selecting, right? Because someone reaches out to us and they say, “Hey, we want to build a website with you. Can you tell us about your pricing?” We go, “Here you go. Here’s the website.”

It’s a little bit self-selecting in that, those people who may be completely price averse, usually if it’s not a person-to-person contact, they’re not making it past that door. For people who get into the conversations with us and still question that pricing, we talk to them about all of those intangible benefits. One of the pieces of feedback that we get from a lot of our clients that I think we’re the most proud of is, “This process has really helped me have a fuller understanding of my business.” Even though that is another intangible thing that … A restaurant is not going to be like, “Wow, I’m glad I spent this amount of money that I feel as if I will never get back, because now I have a fuller understanding of my business.”

That’s not really going to work on a restaurateur, because that’s a money question, in general. That is a whole slew of other factors that need to come into alignment for them to be a right customer, but for people who are starting a business, for people who are realigning a nonprofit, who are trying to build something new or redesign something existing, that ability to go through this process with us and have us ask them questions, not like, “Do you like this color?” But what do you want your clients to understand when you’re talking about X in this section? What do you want them to do once they read this paragraph? What’s the expectation of what comes next? I think that that’s one thing that we probably don’t do as good of a job selling to people is that we’re not just here to put blocks on a page for them and push things around. Anyone can do that.

What we’re actually helping them do is understand their business, have a vision of how clients see them, have a real clear understanding of what message they’re putting forward, and that, especially for small businesses and nonprofits, is really valuable, because we can look at this and go like, “Hey, just looking at this as a user, I think you want me to donate money here, but there’s no button for me to donate.” Those types of things, like helping them understand that value … When we can have a conversation with them, that worry, that question kind of, in a lot of cases, goes away. In a sense, yes, it is one of those filters that we are using, because the price is on the website, but, for me, if someone comes to the table, and they are feeling as if that value doesn’t line up with their expectations, I don’t worry too much about that, because usually by Wednesday, they are seeing just what it is they’re actually getting from the process and they get a website, to boot.

The price … We don’t worry about people who don’t book us at that price, because if they don’t think that that’s an appropriate price, chances are there’s going to be no price that feels right to them. If you’re looking for someone to build you a website, I don’t think that $2000 is going to feel better than three, just thinking about it in general. We always say, if we lose someone on price, that’s okay, because they are now dropping themselves down into this category where they’re going to build their own website, probably in the same way that these agencies who send us these smaller projects don’t worry about losing a $3000 client, because their typical client is 12, something like that. It’s just a matter of mindset.

Chris:                    Something you said earlier struck a chord with me about being very careful how much work you take on, being a team of two. That is so true. Over here, it’s a team of three. I always tell people, no matter how well-oiled your team is, one bad project, one project too many, one project that goes unexpectedly sideways, can completely swamp a small agency. Now, mine is a little weird. There’s a core group of three of us, but I’m plugging mercenaries in and out of projects, depending on skillset and what not, so it may fluctuate, but that’s really true stuff.

It’s good that you’ve got this approach. It’s good that you’re so tailored, because I’ve seen freelancers just keep stuffing coal in the firebox, so to speak, and next thing you know, it’s all out of control. Having these filters in place, kind of deciding ahead of time, these are the kind of clients I want and not those, rather than simply taking anybody who waves a check, that’s where the real power is. The power in freelancing is not so much the ability to set our own hours or any of that other stuff, and it’s not even the ability to choose our own clients. The real power is in being able to say no. No, I won’t do that work. That’s powerful, and that’s healthy, I think. I’m really glad to hear that you’ve got that as part of your vision for the business, that that’s actually a concern and it’s something that you take into account. That’s good.

Kelsey:                 Our life was a huge part of the way that we thought about setting this up. We live and die by our calendar, because we schedule everything. When someone books a week with us, they don’t just book a nebulous time in the future. They book an actual date, and that is so great for Mallory and I, because we’re able to see that schedule come together. She is incredibly good about knowing how much I can take on. Even if I’m like, “No, no, no. Just throw it on the pile. We can do it.” She’ll be like, “No, we need a break. You have to take a floating week.”

She works with me on every project. She does so much of the project management that really helps us succeed. She does 99% of the sales, which is hugely helpful for me. She also really has a good vision for our growth and how fast we should do it. I tend to push us probably faster than we need to go, but it’s really amazing to work with someone who has had businesses grow very quickly before and knows how difficult that can be.

We knew what kind of life we wanted to have when we started this business. I knew there was no way that I could keep working for someone else. I just didn’t know what needed to happen next. I didn’t know what I needed to do, and she wanted the same thing. We are huge travelers, both of us. We love to travel. Her husband and my fiance, we all are always like, “Where can we go? When can we go?”

Sometimes we’re doing these projects from other cities. As long as it has WiFi, that’s okay. We were just in Mexico for my bachelorette party. We were driving through the jungle to Puerto Vallarta Airport, while we were doing one of our discovery calls, and it was awesome. That project was great. We had an awesome time. The client was excited and happy.

We really decided early on that our work needed to support the lives that we wanted to live, because if both of us were only focused on making money, we would be doing this very differently, but our lifestyle, our happiness, the kind of time that we want to spend on this earth is important to us, just as important as building a million websites, and a huge part of that is scheduling and balance. We’re probably getting close to the point where we should start training someone else on how to do this process with us, because I think it is something that can be taught to people. It has to be the right person. It has to be the right type of personality, but we don’t want to rush to that yet. We don’t want to get too much on our plates before we’re ready. We don’t have expectations of being a billion dollar company, because we don’t want the pressure of a billion dollar company, though we would not mind the shopping, just as a point of reference.

Chris:                    Yah.

Kelsey:                 Wouldn’t mind it at all.

Chris:                    Yah, I’m with you there. I’m with you there. I hate to use the term “lifestyle business.” My company’s been referred to as that. I know there are some people that use that label proudly, but I find that it’s usually used as a term … It’s like a condescending, “Oh, what a nice little lifestyle business you have there,” but, you know what? There are a whole lot of us who have businesses designed around our lifestyles, who are taking home a couple hundred grand a year and saying thank you for it and living a fine old time, thank you very much.

Kelsey:                 Let’s be very clear. Having a lifestyle, even having that sentence in your head, is incredibly privileged. To be able to be the kind of person, who’s like, “I have a lifestyle business” … I don’t mind that. I’m proud of that. You know who has a great lifestyle? Gwyneth Paltrow. She has a lifestyle brand. I’ve worked in all different kinds of companies. I’ve worked for a digital agency, a restaurant group. We have both come from a lot of different industries prior to this, and I think that both of us are incredibly grateful to have a lifestyle business.

We have been close to people who have gone through being a part of some of the biggest tech companies in the world, and I’ve got to tell you, the houses are nicer, but I’ve got to say that we have a lot of flexibility. We have a lot of freedom. Could our lifestyle always be better? Sure. Am I going to retire tomorrow? Absolutely not. No way. Not where I want to be yet, but I think that even to consider having a lifestyle is a huge amount of privilege that we have to be aware of, like we have to understand it is a gift that we have to earn for ourselves every day, but I don’t mind being that at all. I don’t mind that.

Chris:                    I’m sure that that’s probably got something to do with the VC funded crowd, like, “Oh, nice lifestyle business. We’re going to be scaling up to a billion.” Yeah, I try to stay away from that, because some folks don’t take too kindly to it, but I like hearing your thoughts on it. I think your thoughts are super, super healthy on the topic. That’s good stuff. We are right about at time, and that’s actually a really cool thing to finish with, that expression of gratitude for the kind of business you have and what you’re able to do with it. That’s good stuff. I think a lot of us probably don’t stop to think about that, and it’s probably healthy to do so.

We can find you on Twitter as KelseyLK, and then we can find you online at weekofthewebsite.com. Where else can the listeners go to keep up with you and your projects online?

Kelsey:                 We have a Presence Agency Facebook page and Presence Agency Instagram, where we also post, not as often as we should. Those are going to be the two: weekofthewebsite.com if you’re interested in learning more about the product; always open to talking to people on Twitter. Anywhere. We’re all over the Internet.

Chris:                    Beautiful. All right. Kelsey, thank you so much for coming on the show. I appreciate you sharing your story. I find it all very interesting and informative. I’m sure the listeners will, too. Thank you.

Kelsey:                 Yeah, thank you so much, Chris. Have a great afternoon.

Chris:                    You, too.

0114 – Long-Term Client Relationships w/Jason Resnick

How to maintain long-term client relationships

Jason and Chris talk about maintaining long-term client relationships, project-based pricing, and how to create a stream of referrals business

Download MP3

You can find Jason on Twitter, online at rezzz.com, or try his paid course, Feast.

$100K Freelancing listeners are invited to try Jason’s free course, Get The Best Clients.


Cablevision out of college, got some good experience

Worked at a variety of projects/startups/technologies

Small money projects to start with

Woken up by https://signalvnoise.com/posts/2219-jason-calacanis-vs-david-heinemeier-hansson-on-this-week-in-startups

Learning to price-anchor

Value-based pricing

Quarterly check-in calls to maintain a long-term relationship w/clients

There are 5 client situations stopping you from earning $100K, right now. Do you know what they are?

Find out who they are and what to do about them with this free 5-part email course.

Full Transcript:

Chris:                    Welcome to another episode of the $100K Freelancing Podcast, I’m your host Christopher Hawkins. Today my co-host is Jason Resnick, WordPress developer long time freelancer. Son of New York and the host of the Live in the Feast podcast and creator of The Feast course for freelancers. Now I must apologize Jason and I got to chatting before we actually started recording, so we’re just going to hit the ground running today. Jason go ahead and finish your thought and we’ll just proceed from there.

Jason:                   I love web development and when I was in college the web was really at an infancy, but I love the instant gratification not the hardcore compiling and all that other stuff. I like the fact that I could write something and refresh and done. I worked full time right out of college doing that, doing web development but I knew that I was going to do, run my own business so to speak.

I had a skill that people didn’t have back then or it was a nice to have skill. People didn’t hire web developers because they needed it, I always looked at it as like having a pool in your backyard; you want a website rather than you need a website. I did the hustle on the side all the while doing full time.

Then when the dot com era imploded in itself in the early 2000s I said, “Hey I have a skill, I have work that I’m doing right now I can run my own business,” and I was sorely mistaken because of all the other business kind of stuff. Inside it two years I went back working full time, I worked for a couple of agencies over the course of next several years. This coming August I’ll be full time for seven years.

Chris:                    That is awesome, that’s bad ass. Now you go all the way back to the late 90s you said?

Jason:                   Yes.

Chris:                    Okay. That’s really cool because the last several episodes that I’ve recorded there seems to be a cluster right around the five year mark with freelancers. I keep talking to people when I say, “How long have you been doing it?” “Four, four and a half years,” and I’ve been waiting. I said, “Okay eventually one of these guys is going to come along and just blow me away in terms of time and industry,” and congratulations my friend you just did it. I love it. Now I don’t have to feel like the old guy in the room for once right?

Jason:                   Yeah. That’s what I always say when people ask me how long I’ve been doing it, I’m like okay this is getting to that age where like where is my gold watch. I have been doing this since the beginning.

Chris:                    You are like I remember a time when a solo web developer could not process credit cards online.

Jason:                   Yeah I do.

Chris:                    People go, “Really,” that’s like saying you remember when cars didn’t have seat belts.

Jason:                   I remember when PayPal came around.

Chris:                    Oh man PayPal yeah. I think I still have my very first amazon.com auto confirmation email archived some place.

Jason:                   Wow.

Chris:                    I remember it was like what was that like 95, 96?

Jason:                   Yeah, probably around there.

Chris:                    I thought that was the most amazing thing ever. Dude I actually printed out one around the office showing people, “Dude look at this, look at this I just made this order and they just emailed me a receipt man. That’s amazing.”

Jason:                   I had a site on GeoCities I was pretty old school.

Chris:                    Oh God I love it that’s so funny, oh man. All right I don’t want to get this too far afield, we can do an entire nostalgia episode.

Jason:                   It’s the eight bit version.

Chris:                    Just about the computing of the 90s yeah the eight bit theme song, yeah that would be great but another day. Here is what I want to know – I also started freelancing on the side of a regular gig. I know before our fore mentioned technical glitch you mentioned that you did some freelancing on the side and your reasoning was really interesting. Can you repeat that now that we’re actually recording?

Jason:                   Yeah. I mean I always did freelancing on the side because I didn’t want to warm somebody else’s seat. I wanted to live the kind of life that I wanted to and for me it’s; family oriented, being able to drop an afternoon because it’s nice out and just go do something outside for four, five hours. That was something that was always internal.

I remember even as a freshman and sophomore in college having this complete blow up fight with my mother to say, “I’m quitting college and I’m going to go out west to San Jose where all this stuff is happening,” which I lost that fight. For me it was always that internal thing that I always wanted to live my life and I knew that I wasn’t going to be able to do that working for somebody else. I always did something on the side having a skill that not a lot of people had at that time.

It was kind of I wouldn’t say easy to get work, but there was plenty of people with ideas right so like the thousand dollar job or $2,000 job was always there. I could always build up the skills that I was learning on the full time job and really go bleeding edge doing the side hustle, learning the new tactics and new skills and stuff like that. That’s why I always did that as part time.

Then God forbid something happen which it did and I didn’t have a job anymore, I had a little bit of a cushion to fall back on. I had clients that I was doing work and I knew at least the very basics of how to get work and doing contracts and waiting in the mail for checks, because at that time that’s what you did. It was what it was and hey now I’m here doing my own thing for seven years full time and I’m able to support my wife, my newborn son living in New York City.

Chris:                    Nice and by the way congratulations on the newborn.

Jason:                   Thank you.

Chris:                    Everybody Jason just had a son. He and his wife have a lovely little baby boy, TJ yes?

Jason:                   Yes, thank you.

Chris:                    Awesome, congrats man that’s a huge moment bravo.

Jason:                   Thank you.

Chris:                    That is why we do it as they say.

Jason:                   Yes it is.

Chris:                    I’m curious you mentioned that you had a cushion way back when you were freelancing on the side of your regular job, I love that. One of the things that I talk to freelancers about is before you go full time have a cushion. Now when you are a young guy though and you’ve got a job with a steady paycheck and you earn that consulting money on the side, were you real disciplined about … Were you stacking chips or were you going, “Awesome now I have money to buy a jet ski and I don’t have to touch my paycheck?”

Jason:                   A little of both. I mean obviously yeah spending cash being a single guy; I was taking vacations, I was buying gadgets, I was doing all that kind of stuff. I had learned that you couldn’t deplete a bank account real quick. The thing is too at that point in time anyway when I was doing a lot of the side hustle, I was taking that $500 project or that thousand dollar project then it should have been a lot more. I felt that, “Hey here is somebody that’s willing to pay me money let them drive the negotiation instead of the other way around.”

It was a lesson learned that I had back then that even $500 or $1,000 extra if I need a new computer there goes that. I just spent four weeks building somebody’s website and I needed a brand new computer there goes that whole entire revenue right out the window.

Chris:                    I know that in my case and it’s probably the same for a lot of freelancers, when you are new to getting money directly from a client rather than a paycheck a thousand dollars in client money seems like, feels like a much bigger deal than a thousand bucks in your paycheck. Possibly because we don’t yet understand how big of a bite Uncle Sam is going to take out of that thousand dollars we get from the client.

It just it feels different, it’s like the first time you sell a product online while you are asleep and you wake up in the morning and you are like, “Oh my God I made 29 bucks,” and that’s like the sweetest $29 that has ever hit your wallet.

Jason:                   Right. That thousand dollars that you like oh that’s a thousand dollars. Now I have a thousand dollars that I didn’t have five minutes ago. Then when you actually look at it from the perspective of owning a business rather than just a hobby like okay 30% you got to put that away so now you are down to $700. How much time did you actually put into the project where you couldn’t do something else? Let’s say there goes another I don’t know 500 bucks and now you are down to 200 bucks you know what I mean?

It’s like, “Wait where did, so I just did all this work for $200,” and that’s a night out on the town, a steak dinner and some drinks. It can be eye opening but it’s a huge adrenaline rush too like you are saying. You get that check like the first time you sell something online or you are like, “Hey how do I make that happen again?”

Chris:                    It’s like a big button that’s wired directly to your dopamine. You just press that and you get that big dopamine spike in your brain and you are like, “Yes we’re doing this again, we’re doing this every day.” Then we realize we’re only pocketing 20% and we are like, “Okay hang on a minute maybe I need to, let’s think through a little bit.” How did you transition out of doing jobs where your pricing did not indicate the true value of the job? How did that light bulb turn on and what did you do about it?

Jason:                   To be honest with you when I really started to look at my business like a business rather than a hobby, I think it was probably when I saw and I don’t know if you remember seeing this. When DHH and Jason Calacanis had that huge disagreement on Jason Calacanis’ TWIST.

DHH went on about revenue is great like you can make a hundred grand, a hundred grand, a hundred grand that’s awesome but what’s the profits. What does that look like at that at the end of the day, like what you take home and stuff like that? That was one point at which I was like, “Hey, wait how I’m I looking at this thousand dollars? What does this really look like? What is my take on what’s my profits?”

Then as I started getting more projects because of what the value that past clients and projects were saying that I was worth I was like, “Hey look I’m I able to affect other people’s businesses in a positive way? How do I correlate that to a price?”

Essentially it took me a long time to get off the hourly, because the thing is that’s easy. It’s easy to look at somebody else that’s been doing this for three years or whatever number of years that you’ve been doing it. They do the same job, what are they charging? They are charging a hundred dollars an hour then I must charge a hundred dollars an hour. That’s the easy win.

The thing to look at that I learned was to be able to price anchor yourself to the value of what you are giving to your client. In other words what I mean by that is e-commerce is easy to do this. If an e-commerce client comes to me and just for the sake of argument they say, “Hey I have $50,000 of revenue last year I’d like to be able to increase that to 100 grand this year by doing x, y and z on the site. I need you to do x, y and z.” If I can deliver that now they are making $50,000 more, even if it takes me two hours to do wouldn’t it be a no-brainer for them to pay me 15 grand to get 50?

That’s why I start looking at how do I price anchor myself to the value of the ROI that I give to a business. When you do that then it’s funny because people are always like, “What’s your hourly rate?” I’m like, “Well if I go to the last project let me see what my effective hourly rate was,” and it’d be like $300 or something like that.

If I say that to somebody they are like, “$300 are you nuts, I’m going to pay you $300 an hour that’s not going to happen,” that’s because it’s all out of context. That for me was as huge game changer and figuring out for my business to be able to build the sustainable freelance business.

Chris:                    Actually there is a lot that there to unpack; number one my friend if it only takes you two hours to optimize a WooCommerce site to the point where you can double the revenue, then you and I need to talk. We need to talk because I need to learn that.

Number two, although with my own business I’ve got some productized consulting stuff that’s flat fee fixed scope. I’m not all in on project based or value based pricing, but I sprinkle little bits of it here and there with the productized stuff. I do know that it’s very important however somebody sets their pricing to even understand their value first.

Like you at some point you realized, “Okay wait a minute when I put my effort into a project it imparts a certain value to the client.” There are a lot of folks out there; competent developers, smart folks, good analysts but they don’t really understand how the transition from I build this thing and then my client receives money happens. They don’t know where the in between part is.

This thing starts running and then my client makes money, but they can’t quite put it together. I suspect that that’s why a lot of folks struggle to either price themselves properly even if it’s hourly or if it’s flat rate or what have you. I think just knowing the business; understanding how a business works, understanding where your widget where it fits into the overall picture of value creation that’s really important.

A lot of freelancers particularly the ones who don’t have a lot of regular job experience, who haven’t had a lot of exposure to businesses large and small tend to struggle with that. At least that’s what imparted to me when I talk to folks every day.

What kind of a process was it for you to just get hip to, “Okay here is how business works and here is how I fit in and this is how the whole value creation chain goes down.” Did that come easy to you or was that something you had to feel around for?

Jason:                   No, it was definitely something I had to feel around for because I could assume what my value is to my clients and I did that for … We all do that, we all say, “Hey my value is way up here,” but what does the client see? How do they understand it and it’s always a lot lower than you think it is. The thing that I wanted to know is I wanted to understand my clients a little bit better like why did they choose to hire me and if they are a recurring client why did they stay with me.

I feel like I couldn’t make this up, like I must have come up with it or read it somewhere. Both like it was I don’t hear a lot of people talking about this though but is to just have a phone call with your clients on a regular basis, I do it quarterly. It’s just a quick 10 or 15 minute phone call and I call them my quarterly temperature calls. It’s just not a technical call at all so leave the projects aside and all that kind of stuff. It’s just a open conversation where I ask, “Hey how is business? How is everything going,” and that’s how I always start it off with.

“Is there anything you are struggling with? Outside of the project itself is there anything you are struggling with,” just so I can get that ball rolling. Then I’ll ask the question, “Why are you still here with me?” Like, “Just to be perfectly frank I just want to know what it is about me and my services that you enjoy or that you like,” or whatever that terminology is.

Often times initially you are going to get like, “Oh we needed this kind of thing,” and it’ll tail back into the project but you have to pull them back out, because you want to know what that hook is. There is a reason why they hired you, they could go and hire any other PHP or WordPress developer or Ruby developer but why did they hire you? Why did you they pay you some money? I wanted to understand that a little bit better because then that’s what you can capitalize on getting other clients.

Similarly at the end I wanted to know what it is that I can be doing better. Because if they have a certain expectation of what I’m doing and I’m completely oblivious to that or maybe it’s something that I don’t offer but they are waiting for, then it gives that opportunity to clear the air and set the expectations back on an even plane and all that kind of stuff.

If it’s something that I can offer maybe I can somehow work that in and then you look like a hero because they have said, “Hey I really need this from you and I don’t think that this is something that you offer or this isn’t something that I’m going to get from you,” or something like that. It could be something really easy and you could loop that into your services not a problem, maybe a little uptake on the price or something like that but they are getting something that they want.

That temperature call there allowed me to see the value to my current clients that I provide in a way that is not my assumption, this is what they are telling me my value is. You can turn that right back around into marketing material for yourself, change up your services page or change up whatever you are tweeting about or whatever it is. That allowed me to see the value of what I was providing to my clients.

Chris:                    That seems to be a practice that a lot of us come to naturally by I guess just from getting beat up enough to realize that we need to do it. I believe [inaudible 00:17:43] calls those strategy calls, I call them a checkup you call it a temperature call. It’s definitely one of those things that appears to be a ‘best practice’ or at least common practice amongst the folks who sustain a career over the long term, that’s smart. I’ve got a concrete example of what happens when you don’t do that, I’ll share this really briefly.

I have a long term client, at the time we’d been working together for about five years and I had been consistently working to maintain and update this old clunky piece of software that a previous consultant had built. We’d been working together regularly, they are constantly calling me, “Hey let’s do this, let’s tune this, let’s add that, let’s change this.” In the absence of having active work to do I didn’t really proactively call them; I didn’t seek them out, I didn’t check up on them much.

Well one day I noticed that they have a new website, a beautiful new website. A big splashy well designed gorgeous new website that I’m sure they allocated a fair amount of budget for. I was like, “That’s awesome that’s good for you guys,” because they’d been stuck in 1998 before that. Then I thought, “Well wait a minute I have been working with these guys for,” you know I’m counting on my fingers, “Almost six years now. I wonder why I didn’t know that they needed a new website or wanted one.”

I began wondering why they didn’t call me and I asked my point of contact and you know what you says Jason, “We didn’t know you did websites.” I thought wait what, they didn’t know how could they know. Because they had had me working on holding this legacy VB6 app together that was basically held together with duct tape and my own ingenuity. It had never occurred to me to talk to them about other parts of their business, to talk to them about, “You need to do this guess what I happen to do that. Here is …”

I just wasn’t doing it and I really felt the burn in that minute. I just so stupid and that’s when I started to change things a bit how I do things around here standard operating procedure. Now I ask loads of questions, I probably annoy my clients. I check in with them and I ask so many questions about; what other parts of the organization does this current project touch, I’ll ping them on email, I’ll call them like with your temperature checks and now it’s very different.

Now it’s very different, now I’m at the point where I don’t even prospect for new clients all that much because I get so much repeat work simply because we are constantly in dialogue, that’s incredibly valuable. I’m glad you brought this subject up because I had to learn that one the hard way. I just got, I didn’t get burned they didn’t do anything wrong, but I basically let a lot of opportunity and a lot of opportunities to help just slip through my fingers just for not knowing any better.

Jason:                   Yeah, I know and that’s the thing too is that that little bit of a check in that you do and you can get recurring work that way and not like monthly recurring but like recurring projects over and over again. That builds up that solid foundation for referrals too and that’s everybody gets referrals. Word of mouth is especially when you are starting out that’s like 100% of your clients.

If you can leverage that exact way that you are getting clients instead of going down another road like ads or something like that that you just go waste time on because you don’t really know what you are doing with that. Leverage what you are good at and figure out a way to do that and those calls like you said it’s proved positive that you keep getting more and more work from the same client over and over again. You don’t have to sell them again because they know that you do good work.

Chris:                    Yeah and that’s a big deal, you mentioned running ads. It seems that freelancers in general struggle with the whole idea of; how do I make leads aware of me? How do I get them to reach out to me? Once they’ve reached out to me how do I close them? That whole chain of marketing and then sales and then you have to execute and manage the work that is difficult for a lot of us.

I’ve found I’m able to skate on a lot of that stuff. Think about it this way, I was talking to somebody I mentor the other day, if you sell each one of your clients just one extra project, they hire you for one project, you do a good job of managing a good relationship. You find out about their other needs, you find out what else your project touches and you sell them one additional project big or small.

Well guess what, you just doubled your business and you didn’t do any advertising. You didn’t write any blog posts, you didn’t do anything, you just worked with what you have in front of you. Now sure you are not going to be able to do that every time, suppose you sold every other client one additional project or even one in every five clients one additional project, that’s a huge difference in your business.

All too often I see the emphasize on how do I get; more clients, more leads, more prospects, more clients, more leads, more prospects. I think back to way back in the day one of those jobs I mentioned before, those crappy jobs you take just to get through college. I worked as a jewelry salesman in a mall.

Jason:                   At one of those kiosks [crosstalk 00:22:36] in the middle?

Chris:                    No, I was in an actual store and I had to wear a suit. It looked from the outside like a pretty cliché job, but it was totally like minimum wage plus commissions if you can make them. I remember I was complaining one time about our product mix I was like, “You know this are all the same wedding sets and the same bands and the same tennis bracelet, this is all the same stuff, are we ever going to get any new products in?”

He goes okay, my manager says, “Hey do you have your contact card on you?” I go, “Yeah,” and I whipped out my contact card and it was all the people that I had called to make appointments with to come in and try to pitch them on something there. He goes, “Okay, have these people seen every product that we have in the store?” “No.” “Great then you have new products all for them,” and I had never thought of it that way before like that client that didn’t know I did websites.

Good God Jason all I had to do is pick up the phone, “Hey guys yeah, project is going great thanks a lot. I really appreciate you being able to help out with this. Hey look, I noticed you are still using a GeoCities site,” and just have that conversation. “Oh, you can help with that?” “Yes I can help with that.” “Well, that’s great. Why don’t we set a meeting and we’ll come in and talk.”

That’s all I had to do is just reach out and maybe I would have gotten the business maybe not. I didn’t even open my mouth because it didn’t occur to me that maybe I just need to put a new product under their nose and see what they think. Just so clueless in the early days but I think we all go through that phase.

Jason:                   The thing is it’s funny too because you always think the grass is greener. I think that that’s why a lot of freelancers or just business in general much rather spend the money on the people that aren’t even customers, those leads, prospects whoever they are might be out there rather than really just putting, “Hey, let’s put some emphases on our current clients and what we can do to serve them better.”

On my fault to that too I’m always looking to see who else is out there, but the same time like you said to be able to have that foundation to get maybe every other client. To get them on the hook for another project that just means that I don’t have to go get another one. I don’t have to get a new client for that because I already have that project and I’m booked up for that.

I’d like to tell a lot of the people that I talk to consulting wise and help coach and stuff like that, is look I have seven clients I don’t have 100 clients, I don’t need 100. I just serve those seven clients to the best of my ability and beyond, I try to exceed their expectations of what I do and they hang around. Just be human about it, don’t be like a call center or something like that where you are just, “Okay this project is done, where is the next one?” Let’s see if how we can serve our own existing clients better.

Chris:                    A lot of this is going to deal with a freelancer’s personal capacity. I know that over here at Cogeian Systems at the peak, I think I’ve had a head count of six maybe eight. I think those last two were kind of on a [inaudible 00:25:35] bit. My point is at one point I had six-ish people, two dozen open client projects at any given time all for different projects.

Now I’ve got a head count of three and I’ve got maybe a dozen client projects open at a time but it’s only for four different clients. It’s a tremendously different mix. The quantity just the sheer number is going to be dictated by head count and personal capacity and things like that. The client to project ratio having that skewed way in favor of having multiple project going per client, that makes a huge difference in task switching. Focus, marketing focus, the actual operations, the actual execution of the work, everything has so much more leverage behind it.

Doing multiple projects for the same client, then it does if every single time you switch your focus from one project to the next, well now you are ramping up a whole new set of contact info, a whole new person that you are sending email to. A whole new style of communication because maybe the contact for this project is a little pre-clear than the one from the other project and so on and so forth.

It is such a high leverage activity to resell stuff to the same clients. It’s so overlooked I imagine because nobody can make money marketing books and courses, teaching people how to sell stuff to the clients they already have. Getting new leads, like that’s a much sexier preposition.

Jason:                   Well that goes back to that grass is greener thing or shiny object. Like, “Hey look, Facebook has ads now.” I remember when that came up and people were like, “We got to jump on that now because the cost per clicks on Google AdWords is a lot higher.” Like you know what I haven’t spent a penny on any ad ever and I have been doing this full time for seven years.

Chris:                    I don’t mean to disparage the idea of getting new leads, as a matter of fact that’s what I want to talk about next. I like doing things in kind of a well-rounded way, it always weirds me out, it weirded me out that I worked for three years without acquiring a single new client I was just only reselling stuff.

Then I know other people, well that’s great if you can do it but I had to build my business up for 10 years before I could, was able to do that. Then I know other people they will email me, “Hey man I need some advice,” and the idea of reselling hasn’t even occurred to them. I’m thinking okay, I’m picturing a pie chart in my head and I’m like, “Okay, so repeat sales and repeat business goes over here.” Some part of that pie chart really needs to be new blood, because if you are not doing that at all clients they fall out eventually.

I’ve had people go out of business, I’ve had people stop working with me, I’ve had people switch to a competitor all sort of stuff you never know what’s going to happen. If you don’t have I think you have to have some kind of a stream of fresh prospects coming in. That’s probably the next thing we should talk about because clearly we are on the same page with; maintain the client relationship, check in with your people, make sure it’s an actual relationship and not just a transaction.

Any of the freelancers out there who are listening to this right now, if you are not doing that it doesn’t take much. Like Jason said, just a phone call every quarter stick your finger in the air see which way the wind is blowing and see if there is an opportunity to offer help. That alone will probably get you some deals.

I want to switch gears now and talk about what you are doing now in terms of getting the fresh leads in the door; the new people, the strangers, the ones who don’t already know you. What is your set up look right now for attracting prospects?

Jason:                   I’m not a sales guy by any stretch of imagination and I’m not one for handing out business cards, in fact I don’t have business cards. I’ve always tried to leverage my own skill sets as a developer. Like I would mention before is to be able to have a solid foundation of things coming in like recurring clients or something like that.

To have new leads coming to me, I learned early on that when you are heads down in client work and you go three weeks without doing anything about thinking about bringing in somebody new, that’s going to hurt a lot more when you actually do need it. Because now you have to kind of ramp up again. You have to be like, “Oh, I have to get myself out there and pound the pavement,” kind of thing.

How do I leverage word of mouth or how do I leverage my skills to be able to attract new clients. Especially starting out even now a lot of what I get from new leads is through social media or looking on communities that I belong to, that kind of a thing.

You could spend hours just in some Reddit thread looking, reading through adding things and all that stuff and then all of a sudden the whole day goes by. You are like, “Oh, I didn’t mean to do that,” or switching Twitter or Craigslist even. People will knock Craigslist but I’ve had a lot of long term clients come from there.

What I did was, I was able to set myself up to kind of be first in line when something was posted. I use things like Zapier and IFTTT to be able to do that. Think a little bit outside the box. Hey, if I’m performing a search on Twitter, how can I automate this in some way so that it’s always going and it’s always doing things while I’m working and still be able to jump in when something appealing comes along?

I got a client through Craigslist and they were online video subscription company and they had clients like PGA, Gander Mountain big brands. I got that through Craigslist because of this system that I set up. I’ve kind of open switched this at this point there is process to be able to use Twitter and Craigslist and stuff.

If anybody is listening you can just go to rezzz.com/100k and you will get right into there and you will get a free bonus as well just by listening to Chris in this awesome podcast. To be able to have people think a little bit outside the box and leverage what their skill set is, I think that gives us a huge advantage as a freelancer to be able to do that because you can’t do that in a corporate job. There is a sales team, there is a sales team there is a marketing team you can’t go outside that box.

Let’s be a little bit more strategic and smart about it, because hey the big companies still use those kind of grassroots ways of finding people. If you can be there in front of them right away, that looks huge on you especially in a professional way.

Chris:                    The general level of quality that you are going to find in place of that Craigslist on average is not going to be as high, it’s a little bit like mining for diamonds. You might have to turn over 40 tons of earth to get a carats worth of jewelry grade diamond. The fact that you are able to automate it and the fact that you are able to kind of separate the good from the bad, that’s good stuff.

Being on Craigslist isn’t always so much an indicator of a low quality client as it is maybe a client who is not technically savvy. That may just mean that there are a better prospect not a worse one. Like you said, you’ve got to automate it because if you were doing that by hand the value add just would not be there.

Jason:                   Believe me before I did all of that I would like, I literally had it in my calendar every Tuesday night from 5 to 8 that’s when I did my lead gen. I mean I had a box called lead gen. every single week on Tuesdays. If they didn’t post during that time let’s say they posted on Wednesday and I didn’t do that again until next week, that was long gone.

I wound up seeing ads from like ESPN and the NFL and things like that I would be like, “Oh, I could have done that I fit this qualifications. They are hiring contractors, how did I miss out on this.” That for me was like my burn like, “I could have gotten this I just wasn’t first in line.”

Like you said Craigslist it is like finding a diamond, but when that diamond posts you want to be right there. Especially if they post on something that you are good at and you know you can do, you want to be first in line.

Chris:                    Right. Now aside from the automated scrapping for lack of a better word to check forward buying signals on Craigslist and Twitter and what not. Are you doing any of the more, I hate to use the word traditional because there is really nothing traditional about online marketing? You know the big thing these days is content marketing or doing live workshops or write these hyper helpful blog posts and then SEO the heck out of them. Are you doing any of that kind of more standard online type stuff?

Jason:                   A little bit I guess. On my services side I do things for e-commerce like just blogging, but it’s more I don’t that at the whole; let me SEO, let me look at that long tail key words and all that kind of stuff. For me that’s just I don’t know, it’s almost always the time for me. The reason why I say that is because I almost use my blog post is like here.

If we are not a good fit, you could just go follow this blog post and do it yourself. I’m still giving value add to maybe a prospect that finds me. A lot of what I do for new leads is warm outreach. It’s not so much that it’s prospects that know me but it’s like; colleagues, vendors, people that I’ve worked with that know what I do and the value that I provide to be able to say, “Hey look.”

By colleague I mean somebody that does exactly the same thing that I do, I never look at them as competition because there is only so many hours in the day. He’s going to have overflow work or I’m going to have overflow work and we could toss work back and forth. Also with vendors too, WooCommerce, subscriptions, affiliate WP this are all things that I work with. I let those companies know, “Hey, look I don’t know if you have a VIP consultant list,” or whatever you want to call it, “For your support team but I just want to throw my name into the hat if you do.”

I get plenty of leads and prospects coming down that route as well and that for me has allowed me not to have to go and buy ads. I do social media, I do all of that kind of stuff to stay out in front of things and to have a face out there. I’ll be honest the value of a blog post I couldn’t tell you what the ROI on that is for me, because I don’t use it in the way that some of the content marketers do.

Chris:                    Now why is that do you think? Is that, is there some black magic to it that you haven’t taken the time to learn. Is one of those things where your other activities are high leverage enough that that one just doesn’t seem to stack up?

Jason:                   I think it goes back to leveraging my skills, I’m not a writer. For me it’s better if somebody know who I am and then reads the blog post because they will be like, “Okay, this is him.” If somebody brand new comes along they will be like, “What the heck.” I throw my sarcasm in there it’s like it’s me when you read it. English is not something that I’m good at if you are looking for like a well written article with commas in the right place and apostrophes used in the right way, this is not me.

I think for me if I can leverage other things, I’ve always been good at the technical aspects but being able to translate business goals into technical aspects. I kind of know that that’s where my sweet spot is.

I can go out and talk to the other companies that I use their software and say, “Hey look, this is what I do.” When they get their customers saying, “Hey, we need this feature built,” and they are never going to build that or it’s not on the road map or something like that they say, “Hey Jason can go build this for you.”

Chris:                    That’s huge, I know that there is a big push these days in marketing circles to get away from relying on referrals, to get away from relying on word of mouth. I think that a strong network is probably the strongest marketing tool that a freelancer can have and I know there are people who disagree with me.

In fact some of the guests that I have scheduled to come on and co-host they’ll probably disagree with me, so we can have a great argument about that in the later episode. There seems to be a definite thrill line with the folks that sustain a career over the long term, there are not doing a bunch of work for strangers all the time. They are pretty steadily drawing from their own community of context.

Sure maybe you developed that community in part by doing a lot of upend marketing, that’s fine I’ll stipulate to then. The fresh complete stranger coming out of nowhere because they read a blog post type leads, those don’t appear to be the biggest component in sustaining a career. At least not from the extent of what I’ve been able to observe and talk about with people.

Jason:                   Yeah. Business is about people to be honest with you and like you said before it’s just, it’s more of a relationship not a transaction. If you want to be sustainable like your best friend you don’t have a best friend for three days, you have a best friend for years. If you want a sustainable business look at it like that just be able to hey look. If you have a best friend for just three days then you are not going to be sustainable.

Chris:                    That was another thing, it was hard for me to learn, it was hard for me to realize. When I moved to the middle of California which is simultaneously the Bible Belt and the Farm Belt I never knew California had either, I grew up in beach towns man. I moved out here and things were very different and people did not take to me.

I was coming from a culture where if you are more competent operator, then I’m going to give you the work because I want it done competently. I come out here and I’m talking to people and they are saying, “Yeah you know my brother in law he screwed up our website so I need you to fix it, but I’m not going to fire him because he is a real good guy. So if you could just fix his work and then I’ll let him go back to maintaining it and then if he breaks it again maybe I’ll call you.”

Here I am let me set the stage Jason, this is a farm town effectively. Here I am, I’m a jackass big city developer and I’m going out prospecting in a suit and tie because I’m like you got to put your best foot forward and it was really off putting to people. I had no idea for about the first six months I was prospecting business. I kept running into scenarios like this, “Like so and so is a real good guy I’m not going to fire him.”

I didn’t quite put it all together. I knew that business was about relationships but the context of those relationships, what those relationships were based on and my professional experience to them had been real transactional and real competency based. I had to get to hip to the more personal side of it real fast because it cost me I don’t know how many jobs I missed out on before I actually got a clue.

Jason:                   Yeah. You can play in the sand box, a lot of people talk about that too. What you do on Twitter you can’t do on Facebook and you can’t do on Reddit and things like that. For the business you kind of have to find where you sweet spot lies. There are clients out there that I would love to land and I know I could do good with them, but maybe just personality wise it’s not a fit. Business is about people and it’s about relationships it’s not two logos talking to each other, it’s two people talking to each other.

Chris:                    Yes, it’s not just two logos talking to each other, I love that. I’m going to let that hang in the air and go ahead and move toward wrap up here. We can find you online as Rezzz that’s three z’s on Twitter. Your primary URL is also rezzz with three z’s .com. You’ve got your rezzz.com $100k course, thank you for that I appreciate you going out of your way and setting something up just for the listeners. Then you are just about ready to launch another course called Feast yes?

Jason:                   Actually we just wrapped up a launch, but yes Feast and actually I will be opening up that to an evergreen model. Definitely listeners if you are interested in Feast and building a sustainable freelance business and stuff like that, check it out.

Chris:                    Fantastic, Jason thanks so much for coming on man. I’ve had my eye on you as a guest for a long time, this is great. I really appreciate you sharing the benefit of your experience and some of your tactics in the way you run your business. It’s really good stuff, thank you.

Jason:                   Thanks Chris appreciate it.

Chris:                    All right, take care brother.

0113 Protect Your Time & Scale Your Business w/Khierstyn Ross

Khierstyn Ross profile on $100K Freelancing

Khierstyn and Chris discuss finding your niche, protecting your time, and learning to scale your business via the power of delegation.

Download MP3

You can find Khierstyn on Twitter, or find her online at crowdfundinguncut.com.


“Gamify how you do things”

* Figure out how to scale
* Figure out what kind of life you want to have, and tailor your business to that
* Do you want to scale your business?
* Does doing client work fit with my goals?
* Change my services to cater to BOTH myself and to my long-term goals
* Consulting for 6 years
* Ran a franchises in college
* Consulted to that company for launching franchises
* Wanted to own a company
* Naturally gave advice to business owners at networking events

Keep yourself in mind!
Can you make money in that niche?
Can you scale your business in that niche?

In London on a visa doing corporate work; quit.
Went to a networking group for some MLM – not for me!
Tried 3-4 per week to try figure out what to do.

Going through the motions – blogging because I was supposed to.

Already tried corporate 2x, could NOT go back.
Spent 14-16 months experimenting w online marketing while helping clients acquired via networking.

Not mapping out what I wanted from the business hindered my progress.

Asked audience to get at the heart of what they need.

Jamie Masters:

* Get on the phone with your list, sell back to them the thing they say they want
* Launching a crowdfunding accelerator

What you need to grow:

* Need to scale your business
* Need to protect your time
* “Clients resist working with my employees”
* “Clients resist working from my course”
* Need to system-ize and delegate the non-client-facing duties

Invested in a project manager:

* Recommended by a friend
* “Asana queen” as COO
* Figure out what systems to build to leverage your time & scale your business

Guest post on Sumo

“Me trying to cater to everyone wasn’t working”

Full Transcript:

Chris:                     Welcome to another episode of the $100k Freelancing Podcast. I’m Christopher Hawkins, your host, and today my co-host is Khierstyn Ross. Khierstyn is a crowd-funding product launch specialist that’s helped creators and entrepreneurs to raise multiple seven figures through Indiegogo and Kickstarter. She’s also the host and founder of the Crowdfunding Uncut Podcast, where she deconstructs what it takes to successfully launch a product online. Khierstyn, very happy to have you on the show.

Khierstyn:           Yeah, I’m so happy to be here. Thanks for hosting.

Chris:                     Yeah it’s good. From the outside, I keep an eye on you, and it looks like your business is doing great.

Khierstyn:           Thank you. It’s funny, because when you’re growing a business, you forget to look backwards and see how far you’ve come in the last twelve months or whatever, so it always seems like it doesn’t move, but in fact you just have bigger problems the further along you go as long as you keep moving. Yeah, it’s nice to take a second and think “Oh yeah, I guess things are going fairly well,” but it never seems that way because I’m very hard on myself. I’m like “Oh no, but because we’re not at like $50 billion in business,” it always feels like you could be better.

Chris:                     Right. Are you one of those folks that has a tendency to not stop and celebrate your wins?

Khierstyn:           How did you know? Yeah that is something I need to intentionally do all the time. Even getting … Whatever you measure your metrics of success are, could be the number of subscribers you have or getting … charging a lot for that next client, or setting boundaries for yourself, I think that we don’t qualify what our success is enough, and I don’t do that. I just look and see … I’ve been doing a better job of it in the last couple months, but I definitely forget to celebrate. That actually sucks because then it means that you never feel happy with your progress because you don’t measure your progress in a certain way to celebrate those wins.

Chris:                     Right, that’s a real psychological hack. I talk to … A lot of the freelancers that I mentor have this problem, and I have this same problem. It’s like it takes one to know one. I looked into my crystal ball and I thought “Gee, I bet Khierstyn does this too. I’ve done the same thing. You make $50K, you’re pissed that you didn’t make $100K. You make the $100K, you’re pissed that you didn’t make $200K. You make $200K, you’re pissed that you didn’t make $400K. We tend to measure ourselves according to the things that we’ve failed to pull off rather than according to the things that we actually shipped or the value that we actually conferred onto the world. It’s tough. I constantly find myself having to encourage younger freelancers to take a minute. Sure, it’s only a $2000 website, that’s cool. Take a minute, acknowledge it, celebrate it, even if it’s as small a celebration as taking yourself to your favorite Mexican restaurant for lunch, do something to acknowledge it.

Khierstyn:           Yeah, I have a friend, you may know the 5-Minute Journal or Productivity Journal.

Chris:                     Yes.

Khierstyn:           With UJ Ramdas. He’s one of my friends here in Toronto, and he has this thing where he manages himself by he does pomodoro tasks, so work for 25 minutes of focus time, take 5 minutes off, and for every pomodoro that he does, he has this bag of candy and nuts, and he rewards himself after every pomodoro, hacking himself kind of like Pavlov’s dog. That’s what he does to measure his success and constantly reward himself for the small wins that a child in him keeps going. It’s really cool.

Chris:                     Right. I was just talking with Josh Doody of Fearless Salary Negotiation about the hedonic treadmill or hedonic adaptation. The tendency of humans to quickly try to return to a state of happiness despite positive or negative changes. That’s why a lot of people fall into a rut, they get an emotional payoff from being the guy that can’t or from being the sad sack story that everybody sympathizes with, but your friend has figured out a clever way to turn that around and get that kind of hedonic rush, that big dopamine rush of reward and pleasure, from things that benefit him, and that’s brilliant. That’s something that’s non-intuitive that a lot of us sometimes do accidentally, sometimes not. Usually we do it the other way around. I’m all for any kind of attempt to hack our own psychology to make our more negative aspects work in a positive way. That’s good stuff.

Khierstyn:           Yeah, I love it. I don’t know what even you call that, personal growth hacking? You just need to become aware of your tendencies and somehow gamify your own how you do things. It’s kind of like if you want to start running in the morning, you will have a better chance of doing it by putting your running shoes by your bed or something so it triggers that aspect of the habit that you want to have versus having to go into the closet or “oh, my running clothes are dirty” or whatever. You planned in advance to gamify yourself so that you create an environment where you’re able to hit your goals and get the reward that you want to.

Chris:                     Yeah, that’s real stuff. That’s real stuff. I think with freelancing, it’s very difficult to do because a lot of things that we do, particularly when it comes to getting clients and particularly when we’re new, it’s just inherently difficult, isolated, non-scalable type stuff that just seems like a slog, but when we make it through the slog and we might some kind of a milestone, again $2000 bucks for a website, even the small stuff. I made ten new contacts today, just something, anything. I got opt-ins on my email list. We’ve got to stop and acknowledge them. It’s really, really important. Otherwise, who’s going to do this if it’s just an endless slog with no moments of pleasure?

Khierstyn:           And you feel like there’s no endgame in sight. That’s what kills me about freelancing, is I love my clients so much, but I don’t want this to be the rest of my life where it’s just constantly looking for that next project, that is not why I’m doing what I’m doing. I want to serve more people. I think that freelancing is a means to an end, but you need to figure out “okay, is this really what I want to be doing long-term,” and if you love being a web designer or launch strategist or whatever, you really need to see how you are going to be able to create your circumstances and your business to cater to the life that you want, which ultimately means figuring our how to scale or change your business so that each of these milestones is progress along the path to bigger and better things for you.

Chris:                     I agree. Do you have a long-term or an over-arching set of goals for your current consulting operation?

Khierstyn:           Yeah, it’s funny because in the last three, four months, I’ve really had to solidify where I want to take this because I have requests from clients to do one thing, but then I need to make sure that that’s in alignment with where I want to go, and looking at … What I do is I help people with launching physical product online, and I love that, so the thing is I need to look at do I want to become an agency where I’m growing the client side of things, or do I want to have a bit more leverage with my time, and answering that question, I know that I only want to work with people … a very small amount of people whose projects I’m super excited about while I’m building the personal brand side. I want to be the author, I want to be the speaker. I want to be the Marie Folio or someone in the marketing space who is an influencer in the startup world, that’s ultimately where I want to be. I just don’t think I can do that by growing full agency side. Having a look at the kind of business I wanted to run, that will help me figure out where I’m going to change my services to cater to people so that I’m still doing what people are asking me to do, but I’m doing it in a way that’s going to serve what I want to do.

Chris:                     Okay, that’s tricky. You’re really trying to strike an interesting balance there. You want to change your services so they still cater to your client base while at the same time still catering to your long-term goals. That sounds to me if I unpack that like you’re in a position where you’re probably going to have to start saying no to clients that you may have previously said yes to, is that right?

Khierstyn:           Yeah, and I am doing that right now.

Chris:                     Nice. Okay, let’s go back just a little bit because I’m looking into my crystal ball and I’m guessing that you did not have quite this clear a set of long-term goals when you started as you do right now. What did the picture look like when you first started consulting?

Khierstyn:           I’ve been consulting for six or seven years. I got my start in consulting because I ran a business in university with a franchise, and when I graduated they asked me to become a startup consultant with them, so I worked across Canada launching new franchises for about four years and it was fantastic. That’s where I started learning how to start a business from scratch. When I discovered Tim Harris’s work a while ago and I realized “Okay, I don’t want to be working under a company consulting for the rest of my life, I want to run a business online and I want to travel and stuff,” so I went traveling and found myself and do what we do. Then I had to figure out how to make money as an entrepreneur, and I kind of realized that I while I would go to networking events, I would just naturally give advice to starting business owners because that’s just what I had naturally done. Then I discovered “Oh, people will pay me to consult their business.” Okay.

Two or three years into that, I was catering to everyone. If you asked me at a networking event what I did, I would say “Oh, I help you get more sales.” And you’re like “What does that mean?” And I didn’t know. I was trying to cater to everybody, which meant my business didn’t do much but pay the bills. It wasn’t until … I was kind of floating by just trying to figure out stuff at that point, and it wasn’t until, I was living in London at this point, it wasn’t until I moved back to Toronto and I got involved with a local startup that ended up being my first Indiegogo campaign, and I just took it on because I’m like “Sure, new product, this looks interesting, I always want to learn new things.” That first product ended up failing. We revisited why it failed, relaunched it, and did $600,000 with the Indiegogo race at that point. I still didn’t want to niche into crowdfunding because I was like “it’s too risky, I don’t want to do this. I don’t like this.” Then I got another contract with a client to launch my second campaign that went really well, then a third, then people just kept coming to me for crowdfunding, then I got really good advice to say “Screw everything else and focus 100%, change the podcast and change everything into being a crowdfunding service provider.”

Chris:                     That’s very interesting.

Khierstyn:           Yeah. You had to, because if you’re a freelancer you’re like “Oh, the number one piece of advice I hear is you need to pick a niche or else you’re not going to be known for anything, but it’s counter-intuitive because people think that if you narrow your scope too much, you’re just saying no to 99% of people out there.” I knew that I had to listen to the advice and niche down fully, because what I was doing before wasn’t working. With my trying to cater to everybody wasn’t working. I quickly became known as the Kickstarter girl, and every time someone would find out that their friend wanted to do a crowdfunding campaign, because I had done Kickstarter, they’re like “Hey, you need to talk to Khierstyn,” so I saw really quickly “Oh crap, maybe what my friend [inaudible 00:12:40] is saying is true that I need to niche everything down because people just keep coming to me for this one thing. I just leap of faith, I did it, and it’s five or six [inaudible 00:12:50] my business in six months by doing that and focusing.

Chris:                     Okay. What I find most interesting about that is with all this advice that we need to choose a niche as consultants, what we don’t talk about very often is that for example in your case, you didn’t choose your niche so much as you accepted the niche that you had already found yourself in even though at first you didn’t really want to be there, and I think a lot of consultants could probably do the same thing if only they could get over their own resistance to the idea that maybe they already have a niche whether they chose it or not.

Khierstyn:           I actually was looking for something because I was giving this advice to a friend where you have to pick a niche, and they’re like “I don’t know how to pick one because I like doing everything,” and I don’t remember what I said, but in terms of picking your niche, it’s finding the balance between what people keep asking from you, it’s finding what you’re most passionate about, and the third thing, what you can get paid the most to do. If you can split all your jobs into the kind of clients you work with, into the kind of jobs you’re doing for them, into even the cost breakdown of how much you could charge or something versus leverage your time versus all that stuff, and find the sweet spot in the middle for that, that’s where you find your niche. I don’t know, if I hated crowdfunding, I don’t recommend anything who was me a year ago, to say “just because everyone wants you to do crowdfunding, you hate it, but you should do it anyways.” You need to keep yourself in mind with what is your endgame with it and make sure that you love designing websites for vets or whatever.

Chris:                     Right. I like the fact that you explicitly call out the one factor, can you make money doing it. I know plenty of people, they get into this business because “Gee, I really love designing websites” or “I really like writing Ad Copy” or “By golly, I just love writing web code,” all right. Then maybe at that other level you say “Gee, I’m really interested in the real estate market,” or “Gosh, I really just love serving attorneys.” Okay, well that’s fine, can you make money doing those things? Will you make money doing those things? I think that’s where a lot of us go off the rails. Sure, you enjoy the actual technical activity you’re doing, but where’s the profit? Can you find the profit? If you can’t, then clearly something needs to change. Maybe it’s you’re niching, maybe it’s your messaging, maybe it’s something else, but it’s often pretty clear that something needs change, and I suspect that a lot of the times we’re either in denial or we just don’t know what to look for, we don’t know what heuristics to use to determine if something needs to change, and if so, what it is.

Khierstyn:           Have you read the book Built to Sell?

Chris:                     I have, yeah.

Khierstyn:           So good. If anyone’s stuck, I recommend reading that book because it’s told like a story of someone who he runs a graphic design agency doing logos, websites, copyright, everything, and going through how he focused his business and systemized it to a point where he made … profitability-wise went up. All that stuff, it’s a great read.

Chris:                     Yeah, it’s good stuff. Really all he did is again, he acknowledged the one thing he was doing that accounted for the vast majority of revenue, which I believe in the book was logos, and systemized. You know what it is? It’s basically [inaudible 00:16:32] consulting at that point.

Khierstyn:           Yes, it is. That’s a good way to see it.

Chris:                     Right? I’ve been experimenting with that a little bit around my shop, because I’m one of those folks, I struggle with niching because I’ve been really successful running a generalist agency, so I look at niching, and I understand all the arguments, I understand why you won’t actually suddenly lose all your business and be turning everybody away. I understand why it would work, but I just don’t have a huge impetus to go hard on it because things have been so successful as a generalist agency, but I know lots of other people, they’ve tried the generalist thing and for whatever reason they haven’t been able to make it work. If things are working well, okay fine. Go get your paper boo boo, don’t mess with it if it’s working. But if you’re struggling, come on, you’ve got to change something. The story in the book was they were starting to struggle, they weren’t enjoying the business, and they figured out that one thing. They kind of were already niched down on logos anyway, that’s where all the money came from.

Khierstyn:           Yeah. I find too that if you’re just starting out finding that sweet spot, you can always add services later, like what’s to say that I’m not going to consult someone on watching a store on Amazon post-Kickstarter. Nothing’s to stop me from that in six to twelve months except my experience doing that, but right now I’m just like “No, I focus on this one phase, and then I know people who I can offload you to.” If you get really, really, really good at one thing, you can once your reputation goes through, then you can add services as things go on.

Chris:                     Yeah, I agree. I want to back up just a little bit and drill down on something you mentioned, that when you went to networking events, you would give advice to anybody and everybody. That actually sounds pretty good. That whole provide value for free early on. Do your networking, get to know people. I’m curious, what kind of networking events were you attending? Number two, is that how you ended up closing your initial state of clients as a new consultant?

Khierstyn:           Yeah, I was on a two-year working visa in the UK, and I was trying to be a normal human being by trying corporate. I didn’t want to do the risky entrepreneur thing anymore, so I got a job working in sales, and after three months I wanted to kill myself. Not actually, maybe I shouldn’t say that, but I just really was hating my life, I didn’t like how I didn’t have a lot of freedom with the company, and after three months I was like “Screw this, I’m quitting.” I had some savings in the bank and I quit my job. I had no idea what I wanted to do or what I can get paid to do. I’m just like “I need to commit to being an entrepreneur 100%,” so the first thing I did was I gave them my resignation and then that night I went to Entrepreneurs in London, which is London’s largest meetup group for entrepreneurs, and I just started talking to people to find out what it was that they were doing. I didn’t have an end goal, I just wanted to hear their businesses and maybe it was something I could get involved with.

It’s funny, that first event I went to, I don’t remember which MLM company was there, but it’s like this one company was doing a massive launch in Europe and there were about six MLM people there and I was like “This is not the event I like.” I ended up checking out a few others, and I would go to three or four events a week to try to meet someone to figure out hopefully they would say something that would prompt some idea in me.

It’s funny because you make it sound like I intentionally would sit down with people and give them free advice and that was an end goal of mine, but I didn’t have … at that point when I was just giving advice, I didn’t even realize that I can get paid to consult. I wasn’t trying to become a consultant, but I had this really annoying tendency of Chris if you come to me and say “Oh, I’ve really wanted to lose weight my whole life or run an IronMan or start a business, but …” and then the excuses come in, it’s my natural inclination to be like “Oh no no, let’s look at this, let’s make a plan because you can do that. You could start here,” and that’s how I naturally dive into conversations with people. Side note, I struggle with people who say they want to do something but don’t actually take action or want to take action because I just have this tendency to do whatever. That’s just how I was.

I would hear these entrepreneurs struggling with “I don’t know how to get clients,” and because I knew how to do that, I’m like “Oh, what if you” whatever it was. Eventually, a couple people came back and they’re like “So you used to do this, right? Would I be able to hire you?” At that point I was like “But I don’t know how to be a consultant,” then I realized that I did because I consulted a franchise so why can’t I just apply the same system and skills that I learned there to other companies. That was a turning point for me, and then here we are.

Chris:                     Nice. Intentionally or not, you ended up building a network of people to whom you were a known quantity. You built trust, you build rapport, you developed relationships, and lo and behold, these people came back and ended up hiring you. I think that that is pretty indicative of how most of us really get clients when we start out. A lot of freelancers are out there, they’re like “Dude, I have to get my social media game on point and I have to blog and I have to set up an automated marketing funnel and this and that,” and I’m always telling them “No you don’t, it’s day one. What you need are relationships.” I always get looked at like I just sprouted this second head, but when we’re starting out especially, that’s where all the stuff flows from. Nobody starts consulting in a vacuum.

Khierstyn:           If you want to go online, I struggled with this, there is this guy, this egotistical … he’s this 20-year-old entrepreneur that hated me so much in the UK, he’s named Stewart [Mayland 00:23:06], he’s really successful for his age, but his ego is ridiculous and he would just tear me apart on social media when I first got started.

Chris:                     Really?

Khierstyn:           Yeah. Not crowdfunding, this is before crowdfunding, this is when I had my brand, when I had no idea what I was talking … I just didn’t know what message I was trying to convey. I just thought “I need to go through the motions of writing a blog post because that’s what I’m supposed to do according to these gurus.” The thing is when you’re just getting started and you don’t really know what your specialty is or what people want to hire you for, how are you supposed to have a blog content strategy? It’s weird, because you just like “I don’t get it, what are you trying to say? It’s great that you taught sales people, you apparently are a business strategist, not a sales coach, I don’t understand.” He had a great point, and it wasn’t until … I didn’t do much on the podcasting side really until crowdfunding and then finally I was like “I get it, this is what people want, this is what I love,” then it took off for me there because I had a content message that was in alignment with the work that I was already getting paid to do.

Chris:                     Okay, now that’s huge. I want to unpack that a little bit. Number one, you were primarily unsure of what exactly you wanted, number two you were unsure of how to communicate that, number three it sounds like you had some clients, you had some traction, but I’m guessing that you would not characterize yourself as killing it at that point. What was it that kept you in? Especially when you’re facing this withering criticism who has apparently “made it,” what is it that kept you in, what kept you moving forward, what stopped you from just calling time of death and slinking back to a corporate job?

Khierstyn:           Because I tried the corporate side twice and I knew that after only lasting for three months, I couldn’t do it. I had to figure it out. I think it was the decision to just quit my job and risk going in debt. I just had to commit to myself because I am an entrepreneur at spirit and I think I’m completely unemployable. I had to make it work. Yeah, maybe the Stewart thing, had I not had major success offline and seen how to run a real business and have impacted hundreds of entrepreneurs that way, maybe if I didn’t have that experience, and I’m just going online, I would’ve let his criticism get to me, but I knew that I knew how to run a business and even if everything crashed and burned online, I’d just figure it out.

Chris:                     Right. How long did it take before you got those … rather, between the time when you got those ad hoc clients from your networking activities and when you started doing crowdfunding and making it work, was there a long span of time in between those two?

Khierstyn:           I think it was like 14 to 16 months.

Chris:                     Okay. During those 14 to 16 months, did you continue to rely on networking and on exploiting your own network to find work, or did you experiment with the other either scalable or non-scalable marketing techniques to bring potential clients into your … I hate the word funnel, it’s just annoying, but I guess that’s what it is.

Khierstyn:           In this 14 to 16 months is when I was experimenting online. I got all of my business from networking while I learned the online side. Again, it’s really hard to sell something if you don’t know what your audience wants and you don’t even know what you’re doing to help clients because I was literally doing everything. I was helping a company build an offline sales team, I was helping an app get sales remotely, I was advising on funnel strategy, it was all over the place. I don’t know, it’s really embarrassing what I started off online as because it was really just learning as I went.

Chris:                     Yeah, that’s interesting. I’m curious, were you earning fairly well during this time when you were experimenting online but you were working with your clients you’d acquired via networking? I know a lot of freelancers who primarily go into online marketing because they feel like they have to, but I know more than one person who’s earning 100 grand a year simply via work that they acquired through their network.

Khierstyn:           Yeah, I was making enough to pay the bills and live comfortably, but it wasn’t by any means what I wanted, and I think that had I … I don’t know why I didn’t choose to stay offline, but I think if I had committed to offline and getting business through word of mouth and all that. I’d have a very different business to what I have today, but it’s because I wanted to go online that I think I cut my income a little bit because I wanted to make sure I had the time to spend building that.

Chris:                     Right, that’s smart. It sounds like, I don’t know if you could’ve articulated at the time, but it sounds like you were conducting your business in accordance with some of the goals that you shared earlier with me in the show, and again I don’t know if you could’ve articulated those goals at the time, but you clearly were working in service of something bigger than what was right in front of you.

Khierstyn:           Yeah, I think too one thing that hindered my progress back then is I didn’t sit down and really map out where I wanted the business to go I’m just like “Oh, I’m living in another country, I’m living comfortably, paying the bills and whatever,” but I wanted to go online, I didn’t sit down and really commit to what that would look like or how that would change my life. I think what’s really changed is because I got traction … It’s almost like because I got a lot of traction in the Kickstarter space, that’s what really forced me to take it seriously and set the goals and figure out what I want my empire to look like, but because I didn’t get traction in one area before, I didn’t really take it seriously so I just lived comfortable if that makes sense.

Chris:                     Yeah, that absolutely makes sense. It’s very easy to get caught in the zone of being comfortable enough, but still you went through … you walked through the desert for 14 to 16 months trying to make your online presence work, trying to make your online marketing message work, and it sounds like you eventually got it. Do you remember the first moment, the first online marketing activity, the first bit of online messaging that you put out into the world that clearly connected?

Khierstyn:           I think there wasn’t one specific moment. With the podcast, I think as soon as I … It was a couple moments. As soon as I changed from entrepreneur and cut to crowdfunding and my audience definitely got cut in half, but my audience went from trying to be a [inaudible 00:30:37] to a very niche hyper-focused crowd, and I started to see major engagement when I became one of only a handful of players in a very big space for one. Secondly, I finally got my opt-in or my lead magnet that people wanted that started getting really good conversions was my checklist that I created because Nathan Chan of Foundr Magazine begged me to make it, and finally that’s the one time I was like “You know what, instead of guessing what my audience wants, why don’t I ask them or take feedback from a question or something and just do it.” That checklist, I’ve received so much feedback from it. I think the moment for me is really understanding the power of listening to your audience and giving them what they ask for. That’s been a bit of a game-changer for me with how I do stuff.

Chris:                     Right, that’s powerful. I had a recent experience that was very similar to that. Before I started this podcast, I’d been blogging for about 10 years, had built up a bit of a mailing list, and very similar to what you did, I read a survey. Straight up, it’s boring, it’s old-school, but hey surveys are powerful and they still work and that’s why people still do them. I went right down the numbers, what are your pains, what are you worried about, are you this or that, are you thinking about this or the other, and that group of answers really informed the way I do my coaching now. It really informed the decision to even launch this podcast, it informed a lot of things on the marketing to other freelancers side of the house. If anybody out there has got even a little bit of an audience, a little bit of quiet deal flow happening, a little bit of a following, engage those people, talk to them, ask them questions.

I think a lot of the time, Khierstyn, we’re afraid to ask questions for whatever reason, whether it’s introverted geek tendencies or insecurity or imposter syndrome, I think that the folks who invest in our work, I think they love when we ask them questions. I think they’re happy to fill us in on what’s troubling them because once we have a little bit of trust built up, they know damn well that we’re probably going to find a solution to whatever’s ailing them.

Khierstyn:           Yeah, I agree. It’s funny we’re having this conversation now because up until Sunday, so like five days ago, I had resisted getting on the phone with anyone because I’m like “No, I have to protect my time because I’m not getting anything else done.” I am going through this chicken-egg scenario where I want to scale my practice and I don’t know how to do that. I kept guessing at what kind of offers my list wanted, so I pitched one. It tanked. I asked them why and then I realized that there was a bit of a combination of an offer that I wanted to do. I was at a Mastermind last week and I asked “How do I survey my audience to pull out what they need?”

Jaimie Masters being in the crowd, she was [Johnny Duance’s 00:33:49] mentor and Grant Cardone’s and stuff, and she was like “Don’t do surveys, I have a program that you can use to get your list on the phone, validate, and sell back to them something that they specifically want.” I was like “All right, whatever.” I went through the course, I decided to bite the bullet and get on the phone with people. I had about 35 people come back to me saying “Yes, I would like a phone call to talk about this program and give you my feedback.”

I got on the phone, I told them “I’m not looking to sell you, but if I think it’s a fit, we will set up another phone call.” I dug into “What are your big frustrations, what are some resources you’ve gone into online, and where do you feel online,” blah blah blah, and all that stuff. At the end I was like “Do you want to hear about the program if I think it’s a fit?” I was like “Here it is, and here’s the price” and they were like “Okay.” I tore out some objections from them and I said “Do you want to set up another call to actually go through this and see if it’s a fit?” Now I’ve done that and I’m actually launching a crowdfunding accelerator because of this, because it was exactly what people wanted and I’ve sold like 25% of it in the last two days just from doing this. I would say this is by far my most successful launch, and it’s actually something people want.

I really wish I got on the phone with people sooner because it’s amazing how much money you’re leaving on the table by … you don’t know how many people on your list want to work with you but they just haven’t reached out yet. It’s been a bit of a game-changer I think.

Chris:                     That’s huge, and congratulations for that because again, a lot of us, for whatever reason, we’re really averse to talking to the people that we hope to sell to. Once these people are already in our orbit, they’re already on your mailing list, maybe they’ve already bought something from you, the trust is there and we just need to acknowledge it and act on it in ways that can hopefully work out to be a win-win, so that’s good. Congratulations for that, that’s a strong move.

Khierstyn:           Thank you.

Chris:                     I want to talk a little bit about … There are a couple of things that you mentioned that I want to drill down on. Number one is when you talked about you want to grow your practice, you’re not sure how, it sounds as though launching this accelerator is one way to do that. The other thing that you mentioned was protecting your time. I think those two things are linked. The wanting to grow in scale and protecting your time, I think those two are linked maybe moreso than maybe one would think just by hearing us talk about it. Do you have any sense that you’ve been successful that you may have boxed yourself in, that your client list would resist the idea of you scaling up and hiring people to work with/under you, do you think there’s any chance that your clients would say “No no no, I only want to work with you, Khierstyn, directly you?”

Khierstyn:           Yes, that is exactly what happened. They’re like “You know …” because when I tried to sell a course, the difference between the accelerator and the course is the one-on-one time now. The course I was like “I can make a six-week video series you can work through at your own pace” and everyone came back and was like “It’s not the price, I just really need someone who I can send my video script to and get feedback on it,” which is me. As part of me hearing objections, this is why I don’t think I’ll be able to do a high-level flagship course and why I need to do a high-level accelerator because what people are really paying for is the ability to get tailored campaign advice from me. I’ve had to integrate that into the accelerator and the conversations I’ve been having because that came up with every person who’s like “I really want to work with you, but my big concern is getting lost in some big membership group. I don’t want that, I want you.” It’s like trying to get creative with how much of your time you’re going to give versus being able to scale that in some group setting.

Chris:                     Yeah. I had a feeling that may be the case, number one because I’ve been there and number two because that’s a big part of what I do is I go into my clients’ businesses and I just kind of look at them with the x-ray vision and I find the pieces that are working in contradiction to one another and where the processes are broken down and they say “Oh, I bet this is this” and there we go. So that is a [concern 00:38:26]. Number two, knowing that, and it sounds like you’re already aware of that, this is more in the vein of both protecting your time, have you identified any parts of the process, clearly not the client-facing parts, but any parts of the process internally, operationally, where you can break pieces off of the process and delegate those while maintaining your client-facing duties.

Khierstyn:           Yeah, it’s about systemizing as much as possible. I need to look at value I bring to the table and I can’t outsource to someone, and that’s any sort of advice. That’s where I’m having problems scaling myself because a launch has so many parts. A launch has a video story where it has to be looked at, a launch has copywriting that needs to be positioned properly, a launch has all these things. That’s been the cog for me, so I’m in the middle of … in a perfect world in a couple months, I think I’m going to be getting a creative director who will be able to look at things that don’t rely heavily on Kickstarter strategy but would be like looking at the copy and making sure that it checks certain boxes.

think there are two phases of agency. One is the advising and one is the doing. We can split that off by saying, if part of the advising and say copywriting, I can systemize what kind of documents need to be written for clients and what the outline of that document for copy looks like. Then I can make sure that every time we have a new launch, I can say “Copywriter, here are the documents in the systems, go write it,” but what I would ultimately like to do is have a creative director to then be able to look over that and protect the quality because right now I’m doing both advising and I’m doing the quality control, and something has to give there in the future.

Chris:                     Yeah, that’s tough. I’m in a spot similar to that myself. I’ve got a team of two that are assisting me, so no code gets shipped out of this place unless I cast my eyes on it and vouch for it before it goes to the client, and that’s cool while the team is just three, but back in the day the team was much bigger, and I’m trying to build back up to that and I’m very rapidly getting to the point where it’s not going to be sustainable. So, I feel your pain on that. I’m curious, do you have any particular strategies in mind for managing that whole process? Do you have any particular tools that you like to turn to for managing projects? You mentioned pomodoro earlier that your friend uses, are you a fan of that, what kind of hacks do you use internally? Maybe not with your clients, but just internally to manage your own work especially now as you contemplate bringing on help?

Khierstyn:           I’ve invested in a project manager, which she manages me basically. She was recommended to me by a really good friend who said “She’s the Asana queen, you need her” and I was like “Okay, I don’t need Asana but whatever.” Then I brought her into my business and I really needed to look at what I badly needed to be able to move my business forward and I need someone who can basically figure out what my problems are and figure out what systems have to be built to leverage me better, because that’s my big problem right now is leverage. So, figure out what systems we need to build to save time and leverage, build the systems, then implement and manage. That was a combination I badly needed, and I needed someone really competent who I can trust as a COO or something.

I found her and started working with her and she’s been a major help. Some of the hacks we use are Asana to manage everything. What I’m now doing is I’m theming the week, like we’re on a big systems push right now, so systems are like “What does our sales system look like to make sure we’re getting the right people on the funnel. What does the content system look like, what does the client onboarding system look like?” All these things just to … We’re just increasing quality across the board, so we can’t just say we’re going to attack all this at once, we need to say “Okay, week one we’re doing this” and at the beginning of the week “Here are the five things you’re doing throughout the week to do it,” then we action those in Asana and the next week we say “How did we do, are we down that check? Let’s move on to the next thing.” I think it’s planning, it’s breaking down the system, then it’s using Asana and time management and productivity stuff to actually do it.

Chris:                     Okay. What about the other side of that, not the internally-facing things, but the client-facing work that you do? Do you use any particular tools to interact with your clients to manage the client-end of the engagement or is that all phone calls and email?

Khierstyn:           It’s a bit everywhere right now. I have a … because I don’t work with a ton of clients, I keep a friend approach. We have a chat on … we’ll have a client chat discussion room on Skype for random questions throughout the week. I got them on Asana so they can see a high level of each project and then we get them interacting with anything that they need to do for deliverables. Internally I use Slack. I guess to answer your question, it’s a combination between Skype for quick stuff, email for anything that doesn’t require a major response but agreements or graphics or whatever, then I just keep Asana for the project timeline, and then a shared Google Drive for any collaterals or whatever that we need to be sharing.

Chris:                     Okay, it sounds like a lot of collaboration tools on the client end of things but not a lot of automation tools, is that right?

Khierstyn:           Not yet, literally doing that now because I can’t skill without it. I know this is your podcast, but what is your favorite automation tool?

Chris:                     I’ve got to say that so far it’s Drip. I started out on MailChimp and I moved to ConvertKit, and both of those served their role in my business’s growth, now I am on Drip. It sounds super simple because it’s just “Okay, you’re automating email, big deal,” but for client onboarding, being able to pull somebody in through a form and send them through some kind of an automation workflow, that’s huge. Having somebody on the list and being able to drip out certain kinds of information to them according to the certain set of parameters, that’s huge. That saves I don’t know how much time, it’s got to be hours per week because it saves me from having to click through and analyze and formulate responses to emails that happen in every single client project. A lot of the stuff gets to happen by rote now, and I’m only looped into the system when human intervention is needed, and that’s big because at a certain point, maybe you’re stuffing everything at a Basecamp, maybe you’re stuffing everything into FogBugz or BugTracker.net, what have you, but at a certain point a human being has to interface with all that stuff and there are so many things in a project that a human being doesn’t necessarily need to be in on, at least not on both sides.

Drip is my go-to these days for managing anything that’s either client-facing or mailing-list-facing. For project management stuff internally, not so much automation but more collaboration. I guess it’s kind of the opposite of how you’re doing things. I’ve got most of my automation facing the clients and most of my collaboration facing inwardly toward my team.

Khierstyn:           Yeah, that’s cool because most of my automation right now is through ActiveCampaign with my list, but I don’t do any … I have zero client onboarding process apart from a checklist from things you need to get from a client, so I’m literally building that as we go. I’ll definitely check out Drip because there are a lot of automations that we could take humans out of, which would be nice.

Chris:                     Yeah, I love Drip. They were just rolling out automations back when I was on MailChimp, but as nice of a service as MailChimp is, I just didn’t have that much confidence in it. I’ve met Rob Walling in person, he used to live just up the road a ways here. We met at some of the local tech events. I trust him, I got to see close-up what he was doing with his operation, and when the time came I felt really good about what they were doing over there at Drip. Now they were acquired by Leadpages, so they’re all out in Minneapolis right now and they’ve got the resources of Leadpages behind them, so I feel very, very good about the long-term future of keeping my stuff on drip.

Khierstyn:           Yeah, that’s cool. I’ll definitely check them out, so thanks for the plug.

Chris:                     Yeah no problem, no problem. Good tools are hard to come by sometimes.

Khierstyn:           I know.

Chris:                     We’re moving toward wrap-up here, we are about at time. I want to make sure that everybody can follow you online if they want to. I’ve got you on Twitter @khierstynross and your primary URL is crowdfundinguncut.com where you can grab the exact strategies Khierstyn has used to crowdfund over $1.5 million. You know what? You might need to update that headline, I’m sure you’ve got to be way over that by now.

Khierstyn:           I’m just saying multiple seven figures because technically some of the campaigns are in demand, which means they are continuously raising money, so I like the $1.5 mil, but that’s powerful, I think I’m going to change it to multiple seven figures, but I need a clickbaity title.

Chris:                     No shame in that, no shame in that. I love clickbait as much as the next guy. Is there anyplace else online … Oh, your Crowdfunding Uncut podcast, is that also available on crowdfundinguncut.com?

Khierstyn:           Yeah. Just click on the podcast or you can go to crowdfundinguncut.com/blog and you’ll find it there.

Chris:                     Fantastic, is there anyplace else online that listeners can keep up with you and your projects?

Khierstyn:           No, I’m doing the odd guest posts here and there, I have one coming up in Sumo soon, but no I think crowdfundinguncut.com is the main hub right now. I just like to keep it simple under that brand, but in the future I’m sure I’m going to be adding a personal site and all that stuff.

Chris:                     Fantastic. Okay, well Khierstyn, thank you so much for sharing your story with everybody and I love the tips and operational strategy stuff, that’s really valuable and I’m thankful for that because a lot of us just gloss right over that, so thank you for sharing with us today.

Khierstyn:           Yeah, no worries. Thanks for having me.

0112 Simplified Client Acquisition and Positioning w/Kai Davis

Kai Davis profile on $100K Freelancing - how to get freelancing clients as a developer, designer, marketer, etc

Kai and Chris talk about how to get freelancing clients as a developer, designer, marketer, etc, putting your message in front of them, generating referrals, positioning and re-positioning your business, and more!

Download MP3

You can find Kai online on Twitter, at DoubleYourAudience.com, and at KaiDavis.com.


Started out building WordPress sites:

  • Market position was “if you have money, I will build a site for you”

Brochure sites are pretty far from the money:

  • Moved into traffic; it’s closer to the money

Created own niche position:

  • Outreach consultant

Don’t think about the immediate sale; think 3 sales ahead

How to get freelancing clients as a developer, designer, marketer, etc:

  • “strategy calls”
  • “check-ins”
  • “follow-ups”
  • ask a lot of questions


  • tickler file to manage follow-ups
  • recurring work and follow-ups

Traffic is not the most important metric for a consultant to focus on:

  • # of leads generated (client flow) is the most important metric

How to get the right eyeballs:

  • understand your positioning
  • philip morgan
  • positioningcrashcourse.com
  • target market + expensive problem
  • where to find that target market
  • makes all of your contetn-marketing and outreach easierHow to get freelancing clients as a developer, designer, marketer, etc – answer these questions:
  • Who is your ideal customer?
  • What problem are you solving for them?
  • Where do these people already hang out?
  • be proactive
  • reach out to them where they are

Positioning for consulting is similar to positioning a product.

Changing positioning might take a year:

  • like a cross-fade between 2 tracks
  • slow ramp-down, slow ramp-up
  • had a false start; launch a sales page, nobody buys, big deal
  • positioning is just a marketing channel; it’s not permanent
  • minimized risk by changing gradually

You might not need positioning:

  • it’s a force-multiplier
  • if your business is happy, healthy and profitable, don’t change anything

The Three R’s: referrals, relationships, recurring work

  • that’s how Christopher has built his business

“Reputational Positioning”:

  • known for a particular problem w/o a vertical

How to reverse-engineering your positioning:

  • look at your body of work & score each project 1-10
  • how fun/how lucrative/how enjoyable is the industry
  • see what pops out
  • also talk w clients
    • “what was the highlight of this project?”
  • what words do they use to describe you?

You can brute-force your positioning (it’s hard!):

  • research the problems, test the positioning
  • put up a landing page
  • test a couple of client projects

Are you generating referrals? Are you closing sales? If so, keep going:

  • are people engaging?
  • are leads coming in through these channels?
  • reach out to 10-15 contacts, send e-mail, ask for referrals to market/problem/etc

How to get freelancing clients as a developer, designer, marketer, etc with your new positioning? 1st email previous clients who match the positioning:

  • ask for a call; get the benefit of the last project
    • testimonial (more clients/more employees/more leads)
    • refine our positioning around that
  • referral-based strategy is the most powerful sign that your positioning is appropriate

2nd revise the messaging on your website: * home page update/landing page/etc for that position * 500 words, add a strong cta * have conversations

Timing matters!

  • Right position + right target market + wrong time = no sales

For help with how to get freelancing clients as a developer, designer, marketer, etc, visit freeoutreachcourse.com

Full Transcript:

Chris:                    And welcome back to another episode of the $100K Freelancing podcast. I’m Christopher Hawkins, your host, and today’s co-host is my pal, outreach consultant Kai Davis. Kai, how the heck are you?

Kai:                        Hey folks. Hey Chris. Glad to be here, excited to be on the show. Yeah, excited to be here.

Chris:                    You know, it’s a little odd introducing you, because I’m not completely convinced that “outreach consultant” adequately covers all the different things you do.

Kai:                        Well thank you so much. It’s an odd title for sure, and I picked it primarily because of positioning. I wanted to have a phrase that was unique, that was memorable. I was just coming out of the search engine optimization space and people were like, “SEO, I know what that is. That’s Black Hat stuff.” So I wanted a phrase that I could own and really create positioning around, and so I intentionally picked outreach consultant, and people often follow up with like, “What the heck is that?” That I find provokes a conversation and lets me get into the types of problems I solve, the types of outcomes I help my clients achieve, which it may or may not be directly within the outreach sending more email space. But yeah, it’s a title I picked and it’s gotten me at least this far.

Chris:                    Okay. I’m dying to know, have you ever explained to somebody what you mean by outreach consultant, and then had them kind of nod their head and say, “Oh, soooo…SEO?”

Kai:                        No, thankfully. The way I got into outreach consulting was I was doing SEO and link building projects for e-commerce clients, and I just was not enjoying them. I stared looking around at big lists of different link building strategies and I saw a couple people say, “You know, the thing that’s going to displace traditional link building the next two to five years, is going to be essentially, digital public relations. People doing outreach on behalf of their clients, building relationships, finding opportunities to provide value to an audience, to a community, to a site, to a site owner, and then using those relationships to generate links.”

Hey, this is a perfect example. I appeared on your podcast. There’s going to be a link involved in that, so I jumped onto outreach consulting as my positioning to help my clients earn more links and get more traffic, and when I framed it as, “Well hey, I’m an outreach consultant, which means I work in digital public relations. I help people promote their best product and services to an audience of their dream buyers, or target customers.” People are like, “I want to promote my stuff to an audience of my dream customers. Tell me more.”

Chris:                    Right. Now you’ve clearly given this a lot of thought. I have to ask, did you get your start in the game in this SEO space?

Kai:                        Actually as a consultant I started out doing WordPress website development. My positioning back then was … I say it jokingly, but it honestly was this, “If you have money I will build you a website.” And there was no positioning, there was no thought into expense problem. It was as commoditized as possible. I just built WordPress websites for people, and a couple years into that I started thinking about it and said, “Well hey, I want to always have my business be moving closer to where the money is in their business.” One way to figure out where the money is is to identify where they’re having challenges, or problems, or spending money and not seeing results.

So as I grew my client list, as I worked with more people, I just always made a point of asking, “What other types of consultants have you invested in recently? What problems are you experiencing in your business? What’s the highest priority right now?” I discovered for a majority of my clients, it was getting more traffic, or earning links to their site. As I discovered that I said, “Okay so, websites, let’s say they’re pretty far from the money. You could have a site, but it’s not honestly that difficult to have a site, but getting more traffic to the site, that’s an interesting challenge.”

I realized that was a little closer to the money, a more valuable problem to be solving, and reoriented my positioning to focus on that. Throughout my consulting career it’s always been an iterative process of discovering where that expensive problem is, or what a new expensive problem to solve for my target market is, and saying, “Well do I have enough knowledge already to solve that problem?” If not, “What study do I need to develop that knowledge? To learn what I need to know.” Or if I do have enough knowledge, “Okay, great. Let’s move forward and start testing the waters with a new service offering, or a new positioning statement, to target this new aspect of the market, or this new market entirely, and see how it works for my business.” I think just by thinking about, “Well where is the money being spent in the business?” Or, “Where is that expensive problem they’re willing to spend a thousand, ten thousand, tens of thousands of dollars to solve?” It alerts you to opportunities to grow you business and focus on new areas to make money in.

Chris:                    That’s strong stuff. I talk to a lot of freelancers about being aware of the position they occupy in the value chain in their client’s business, because a lot of us, especially starting out, we don’t think to ask that. That, “If you have money, I will build something for you.” That is the way we all get started, every single one of us, and frankly there’s a lot of money to be made with that approach, if a person is capable of fostering enough relationships, and getting enough clients to repeat that kind of engagement.

But what you’re doing right now I often talk to freelancers about, because I find that A, as you said, you get closer to the money, you can charge better rates, you get more respect, you’re held in higher in esteem, you’re less micromanaged, so on and so forth. I also find that it seems to foster recurring work a lot more so than the one-off, “If you have money, I will build something for you.” type of engagement’s doing. That’s pretty powerful.

Kai:                        I completely, completely agree. It plays very well into follow up or building a relationship with that client. I think Alan Weiss said it very well. “When you’re a consultant, and engaged on a project, or talking up a prospect, you don’t want to think about the sale that’s immediately in front of you. You want to think of the third, the fourth, the fifth transaction, the fifth project with this client.” And this first project, well this is an opportunity to build that relationship to get to that third, forth, and fifth project, and by focusing on … We might frame it as value-based questions, or just questions about their business, “How does your business run? How do you make money? What keeps you up at night?” You demonstrate an interest in that high level aspect of their business. Is it succeeding or failing? If it’s failing, how so? If it’s succeeding, what could be done better?

And when it comes time to put together a proposal, or pitch your services for this project, re circle back a couple months later and say, “Hey, how is business growing? You mentioned this upcoming product launch, how did that go?” It takes a couple seconds on the front end to collect that information, but it allows you to demonstrate a knowledge and an interest in their business that begets future work. “Oh, this is the consultant we had a great experience with. Oh, they emailed us at the right time and mentioned that big project we’re stressing about. Let’s see if they could help.”

Chris:                    Yeah. That’s hugely powerful. Be present and be curious. I’ve been to known to ask clients questions about their business almost to the point of annoyance, almost. Truth be told I’ve probably crossed the line once or twice, but I find that that’s a really fantastic way to A, figure out where you are on the value chain, if you don’t already know, because if you don’t know that’s kind of a problem on its own, and also to find out what else is going on in the business. I’ve talked to a lot of other freelancers who have a natural process for this. Matt Inglot calls them strategy calls, Jason Resnick calls them check-ins, I call it following up, so on and so forth. Do you have a specific method of doing that, or is it just a constant effort toward being present?

Kai:                        I’d say some of both. It’s a constant effort towards being present in the sense that if a client has a newsletter or a Twitter feed, I’ll subscribe and glance at the newsletters as they come out. They release a case study, if they release some article, I’ll be like, “Oh, hey. That was awesome.” And spend a few seconds just to respond back and show, “Hey, I’m still present.” Beyond that, I find that having a systematic, and persistent, and polite follow up strategy in place, and you can definitely start with something super simple on this, helps me get that future work, and helps continue building that relationship.

One very small and simple example of this is, I use a CRM, a contact management software, called Pipedrive, and so for every deal, there’s a person associated with it, at the end of a project, or even once they’ve paid and that project kicks off, I just set a reminder three months out, “Hey, email a follow up and check in with them.” So three months pass by, I might have forgotten about it by then, “I worked on a project with that client?” But the software is smart enough, it will remember for me and it’s like, “Hey, yo, Kai, you need to email a follow up with that person and just send a quick check in. ‘Hey, how’s business going? Anything I could do to help you grow?'”

By offloading that need to remember it to a piece of software, be it a contact management tool, be it an outreach tool like ReplyApp or something else, you make it easier to follow up on a consistent schedule, without needing to remember, “Oh, I worked with 30 clients this year, so I need to be managing 30 different follow up campaigns at the same time.” That can be mind melting. By delegating it to a program, I find it easier to remember who to follow up with, and when is the most appropriate time.

Chris:                    That’s nice. That reminds me of … I’m dating myself here. Back in the 90’s where I worked as a telemarketer. We had a tickler file. This effectively sounds like a 2017, probably Saas, appified version of a tickler file, yes?

Kai:                        Entirely. Entirely.

Chris:                    Okay. I love it, I love it. God, I can’t believe I just dated myself. Yes, I was old enough to be a telemarketer in the 90’s, yes I was enough of a scumbag to be a telemarketer in the 90’s, leave me alone. We all have our past.

I want to loop back around the traffic issue. It’s really interesting that you mentioned that specifically as being a more expensive, or rather, more valuable problem to solve. For two reasons, number one, when it comes to content marketing, the number one thing I hear from younger freelancers … Heck, not even younger freelancers, freelancers in general, is I’m writing all this stuff and no one is reading it, and I don’t know how to get people to read it. And number two, it makes me figure that traffic was probably a problem that you had solved for yourself right off the bat. Am I correct there?

Kai:                        Yes, very much so. In fact, I sort of take a controversial view to traffic, that traffic isn’t for a freelancer or a consultant, traffic is not the most important metric to be focused on. If you’re selling a product, if you’re running a Saas, if you’re selling an e-book, then traffic becomes I think a key performance indicator for you site, but for most consultants I think a more valuable metric to focus on is number of leads generated. It might be that, you write a great post, it goes viral, it’s the number one post on Hacker News for three months straight, and you get a million visitors to your site, but if not one of those visitors converts into a prospect for your business, or opts in say, to your email list to get more information, to learn more about your process, did you really accomplish anything aside from blowing up your hosting bills for the month?

I argue that the more important thing to focus on, more important than traffic, is client flow. It might be, you only get ten visitors a month … Or ten visitors a day to your site, if that, but every day or two you get another lead coming through, it doesn’t matter that you have low traffic. You have a very nice lead flow that you’re then able to close into projects. So I don’t think traffic is necessarily the number one metric to focus on for a consultant or a freelancer. More important is, “Am I consistently getting new leads contacting me?”

Chris:                    Okay. This is good stuff. Number one, I like controversy, it’s good for ratings. Number two, I have actually had that thing you describe happen. I had an article of mine blow up a little bit on Hacker News, I got 16,000 or 18,000 visits in a single day, but again, that wasn’t my audience. It may have been my audience, but that was not my target customer, my ideal customer. No leads, no nothing. All I got was a bunch of nasty comments and a bad taste in my mouth. You can’t run a consulting business on a bunch of nasty comments. Here’s the question: If client flow, lead flow, leads generated, is the more important currency than traffic, what can we do when we’re putting out content out in the world, when we’re demonstrating our expertise, to make sure that the right eye balls hit our material, rather than simply enough eyeballs hit our material?

Kai:                        Good question. I think first and foremost is understanding your positioning as a freelancer or consultant. I have to give a shout out to Philip Morgan, author of the position manual and creator of his free outreach course at FreeOutreachCourse.com … not free outreach course, PositioningCrashCourse.com. Accidentally plugged my own course, I’m so sorry! PositioningCrashCourse.com, that teachers the fundamentals of position, because positioning really breaks down to the target market you want to work with, let’s say it’s realtors, and the expensive problem you’re solving for that. That might be getting more clients, or getting more viewings of a house, or closing more house sales. Whatever that it, you need to understand who that target market is and what that expensive problem is, so you can understand where to find that target market.

If you don’t know who your target market is, you can do content creation, you can do guest posting, you can appear on podcasts, but do you know if you’re appearing on the right one? I think first and foremost, it starts with fundamentally understanding your positioning in the market. Who do you serve, and what outcomes do you help them generate? Once you have those in place, it becomes dramatically easier to say, “Okay, where does this audience already hang out online? Are there podcasts they listen to? Content and authority sites they read? Email lists they subscribe to? Conferences they attend? Twitter authorities, or Twitter lists that they’re apart of?” Whatever it may be, if we want to get the right eyeballs on our content, the right eyeballs being people who are in need of the service we offer, first and foremost we need to understand who that is, and what problem we’re solving for the.

Second, we need to start looking at the market and saying, “Well, where do these people already hang out? Where do they already spend their time online?” If we just wait for them to stumble onto one of our articles, well chances are it’s going to take a little bit of time. By being proactive, by doing outreach, contacting people, building relationships and seeing if you can convert those relationships into means to be present in front of our audience, then it becomes more likely we’re able to get that article in front of the right people. It might be orders of magnitudes different in traffic. You got 16,000 plus visitors off of the Hacker News post, but they weren’t your target market. It might be through outreach and relationship building.

We got a guest article published and there’s a hundred readers of that article, but of those hundred readers, 10 say, “Oh my gosh. I am ready to hire you today Chris, to solve this problem for my business. How do we get started?” So it’s not that we had tens of thousands of more visitors, it’s that we were in front of the right audience segment at the right time to demonstrate our expertise, and that all comes down to positioning.

Chris:                    Right, and frankly, 10 good prospects, 10 good leads, that sounds much better than 15,000 angry Hackers. Any day of the week, I will take those odds anytime you want to give them to me.

Kai:                        Heck yeah.

Chris:                    Yeah, I mean that’s really what it boils down to. We’ve got to find our people. I observed something while you were talking about this. This advice that you’re giving, it sounds remarkably like the advice that is given to start up founders as well, when it comes to marketing a product. I’ve often complained in the past, back when I was trying to be mister start up guy, I often complained that the marketing skills required to move product were very different than the marketing skills required to keep a consulting agency open, but in this particular way I find they’re super, super similar. Is this maybe the place where those two worlds meet?

Kai:                        I think it is. I dislike some aspects of startup culture, but what I do like in start up or product culture is a focus on, “Hey, let’s validate our understanding of our market before we build the thing, or before we do a lot of content creation.” And that’s something I’m trying to bring over to the freelancer space. Before we write a dozen articles, before we launch a new service offering, before we invest thousands of dollars in a new website, or revamp our messaging, do we understand who our target customer is? Do we understand what problem we’re solving for them? And okay, great, now that we’ve answered those two questions and hopefully we said yes to both of them, now we’re able to move forward with the product creation. In this case for a consultancy, that product creation might be our own messaging, our website, the service offerings we have available, but I think that validation that we see present in product creation worlds, bootstrap worlds, start up worlds, is very applicable to freelancers and consultants in that it helps us identify and validate the problem we need to solve.

Chris:                    Now you’ve clearly got this problem figured out for yourself, you mentioned doing WP websites, the old, “If you have a check, I will come.” type business model. You moved into dealing with traffic, and then you ended up as an outreach consultant. Was there a transitional stage between the, “Now I’m going to work on traffic.” and, “Now I’m an outreach consultant.” stage? What I’m curious is, can you kind of demonstrate for us … It’s clear that you did not immediately jump to your proper positioning, you evolved into it, and I think a lot of freelancers are probably number one, confused by positioning. I speak to people all the time who are confused by positioning.

Number two, you have the people like me who conceptually get positioning, but look at their own business and say, “Man, I’ve been really successful without doing any of that, so maybe I don’t need to bother.” And number three, when they actually sit down with say, a copy of Philip Morgan’s book – which is excellent, by the way, I’m on my second rereading because I was a poor student the first time and I didn’t actually do any of the work – they think they have to jump immediately to their final positioning, right? I’m not sure that’s even possible. What is your experience been like? Can you fill in some of the gaps in how you arrived at your own positioning?

Kai:                        Absolutely. In every single case, whenever I’ve switched positioning for my business, it’s been a year long … I use this metaphor even though I’ve never worked in the music industry, like a cross-fade between two tracks, so I start off 100% focused on let’s say, I’ll make WordPress websites for you, or I’ll help you get more traffic. And then I want to bring in my new positioning. I don’t burn the burn the boats, shut everything down, and then switch. I slowly transition, so I’m still getting client inquiries and leads from the old positioning, and I’ll still accept them. I might have a slightly higher bar for accepting them as client. A fewer number of red flags will make me say, “Hey you know what, I’m not the right consultant to help you with this.” But I’ll accept clients from that pervious positioning, that previous marketing channel, while I’m slowly ramping up the marketing for my new positioning. Establishing a new placement in the minds of my customers in the market.

I found that that gradual transition between the two positionings works the best, because it allows me to slowly and carefully experiment with the new positioning. There’s been a number of false starts on my side where I say, “Hey you know what, this expensive problem seems like the one to target.” So I’ll launch a sales page, I’ll put some material together, and nobody buys bupkis, in which case I’m able to say, “Okay. Test failed. Let’s move onto the next idea and see what we could have succeed there.”

When I do start to see some initial success, I remind myself that positioning is nothing more than a marketing chip. It’s saying, “I work best with this type of client to solve this type of problem.” We could always adjust that, we could always change it. Positioning is not permanent and not forever, so I do a slow fade between the two, where I’ll still have field marketing channels, landing pages, sales pages up, and people could come in and say, “Hey I want to work for you.” And it might be positioning that I slowly started fading out a year ago, but I still have those marketing channels in place to accept those clients. Meanwhile, I’m building up new marketing channels in line with my new positioning to bring in new clients who match that positioning. Finding podcasts they listen to, article sites they read, mailing lists they read, finding ways to reach that community and say, “Hey, new positioning. If you experience this problem and you’re in this target market, I could help you solve it this way.”

I found that by doing the slow fade between the two. It minimizes the risk, because if there was a false start, or I head off in the wrong direction, I still have all my old business assets, and all my old positioning, and all my old marketing channels still running, still bringing in leads, while I’m experimenting with something, and it might be a false start, in which case I say, “Okay, great. Let’s go back to the big ol’ list of possible positions, or possible expensive problems, and try number two, or number three on the list.” And just slowly, iteratively work my way through them. Am I explaining that well?

Chris:                    Kai, in this moment, you are my favorite human being who has ever existed. I want to say to everyone listening right now, this … Rewind the last couple minutes, rewind, listen and … Now I’m really dating myself. Rewind. Good God. Listen to the last couple of minutes again. You do not go to bed Monday night with positioning A and wake up Tuesday with positioning B. It is very, very easy though Kai, for the folks who are reading all the … And there’s tons of positioning type information out there in the marketplace now, it’s being aimed at us, it’s very easy to believe that if you do not wake up Tuesday morning fully entrenched in positioning B, you have failed and you are a bad freelancer.

I really appreciate you laying this out. Number one, the cross-fade metaphor is fantastic, being an audio geek, but the slow ramp down and the slow ramp up taking place at the same time, taking a year, thank you for laying that out there, because that’s not always evident from the material that’s available. I think a lot of the time people feel like they have to pull this off within a quarter, or else they’ve screwed it up. It’s very humanizing to hear that that’s not actually the case.

Kai:                        Absolutely. Jumping back to the point you had raised earlier in the question about how a number of freelancers and consultants look at the idea of positioning and say, “Well hey, I’ve already built a successful six figure business,” or a “business that supports my lifestyle. Why do I need this positioning thing?” Maybe you don’t. I mean, if we want to get meta, the reason we’re consultants and independent business owners is to live the life we want. If you’re making enough money as a consultant with undifferentiated positioning, you have steady client flow, you like the projects you’re working on, and you say, “Hey, you know what, I like my business the way it is.” And the business is supporting the lifestyle you want? There’s no need to rearrange the deck chairs on the titanic. If you’re happy, that’s wonderful. You have won. You have succeeded at business. You might be able to make more money, or get more clients with a more refined positioning, but if you’re not looking for either of those outcomes, there might not be a need to even monkey around with positioning in the first place.

I recently had a consulting call with a seven figure company that has a positioning statement that boils down to basically, “We make websites if you need one.” And I’m like, “How many people are on your team?” And it’s in the hundreds, and they nailed it. They focus very much on relationship marketing, referral based marketing, and ongoing projects with clients, and so it’s been very successful for them. They’re now starting to evaluate, “Well, can we become more successful with a more refined positioning statement? But they built a very successful, fantastic company on the basis of not really having a positioning statement. I think positioning is valuable. It’s what I think of as a force multiplier for a consultant or a freelancer. It lets you have more of an impact with less force, but if you’re happy with your business the way it is, there’s not necessarily a reason to say, “I need to redo my positioning today.”

Chris:                    You know, that’s really interesting. This is almost like a therapy session for my own business, because the three things you just named, referrals, relationships, and recurring work, the three R’s, that in a nutshell spells out how my business has been able to operate for the last 15 years. Although I have to admit, I may have had a positioning early on without realizing it. My agency was known as the fix it company, right. Your developer dropped the ball on you, your developer disappeared over night, which is a surprisingly and distressingly common scenario, they deliver broken work, “Hey, I know. Call these guys. They’re really good at picking up broken projects and turning them into something.” Maybe that’s positioning, maybe it’s not, but that’s certainly a reputation that we’ve had early on. You know what the funny thing is Kai, as much business as that brought in the door, and there’s a ton of fix it business out there, I resented the fact that that’s what we were known for. Isn’t that funny?

Kai:                        Mm-hmm, I hear you on that. Sometimes there is that internal push against like, “I don’t like the thing I’m known for.” I experienced that first hand in search engine optimization. I remember somebody came to my website, subscribed to my list, read a couple of my emails, applied to work with me. We get on the call and the first thing the person says to me is, “There’s two types of businesses I hate.” And I’m like, “Okay.” “Lawyers, and search engine optimization consultants.” The punchline to the joke is my dad’s a lawyer, and I’m doing SEO at the time, and I’m like, “Why do you start the call this way? I don’t understand. Why do you want to hire me? This is very confusing.”

It was actually at that moment when I realized, I wanted to refine my positioning to avoid those types of scenarios. That I disliked somebody having a preconceived notion of what SEO is, what SEO … You know, it’s $300, you get some back links, it’ll work. I know a guy. He’ll help you out. I disliked that framing of positioning and wanted to rebel against it, and move against it, which is why I flipped over to outreach. Similar to how you were receiving a lot of work, but not necessarily happy with what you were known for within the market place, or what those types of jobs ended up being.

Chris:                    I agree. Number one, that’s really funny, speaking as a guy who once considered going to law school, that’s really funny. Everybody has a … I’m trying to keep the show clean. Everybody has a jerk attorney joke, or you know, “That SOB lawyer.” Nobody has a outreach consultant joke. Nobody has a, “That SOB outreach consultant, all he did was get me on a bunch of podcasts.” Nobody has that story. That’s really funny the way lawyers are just universally reviled like that.

Kai:                        What’s that quote, I think from one of the Henry plays from Shakespeare, “First thing we do, let’s kill all the lawyers.”


Chris:                    “Kill all the lawyers.” Yes, that’s funny. And number two, you’re right. I really did resent what I was known for. Although I have to admit, one of the coolest moment in my career came when one of my clients referred to me as, “the Winston Wolf of software development.” I was like, “Man, that’s going on the website today.”

Kai:                        That is wonderful.

Chris:                    Yeah, and I didn’t even have to wear a tuxedo.

Kai:                        You could!

Chris:                    Yeah, I felt like I was getting away with something. It was great.

Kai:                        I think you’re right though, we often think, and I often advocate positioning as being a focus on a market vertical, and a specific problem. Dentists who need more clients, attorneys who need more leads, whatever it may be, but that, since focusing on a vertical is often easier for people who want to get started with positioning … I talk with people who say, “I figured out my positioning. I’m working with, wait for it, B2B businesses.” And I’m like, “That is a very wide range my friend. Perhaps we could narrow the scope.”

Chris:                    Yeah. That’s, like… every business.

Kai:                        Every business! I think focusing on a vertical could help, but often times you could develop what we could think of as reputational positioning. “I am the guy,” or “We are the guys who will fix it when it’s broken. Don’t worry about it, we have it covered. We’re the Winston Wolf of website development.” Being known for solving that expensive problem, even if you don’t have it attached to a specific market segment, can work incredibly well as positioning. You get referrals, you create those referable moments. If one of your clients hears one of their friends saying, “Oh man, our developer went on an unexpected six week vacation. The site’s starting to go down, we’re going to lose money.” “I know who you need to call. You need to call Chris. He’s the Winston Wolf of helping people in this situation.” I think that is in itself positioning, it’s just a different form in flavor of the more common positioning we see advocated.

Chris:                    Right. Right, and it was completely unintentional. In fact, I was unaware that my little firm had that positioning for a few years. It wasn’t until a few people had mentioned it to me, and it kept coming up, that I said, “Oh, so when you guys talk about us out there in the business community, that’s what you talk about us for?” I had no idea.

Here’s what I want to ask you: Let’s say, my typical listener is a freelancer who’s got some clients, they’re got some traction, they don’t feel like they’re killing it, and as the name of the show implies, they have not reached that six figure income mark yet. Some of these folks are trying to experiment with the positioning. Some of them share with me their frustrations. Some of them have even asked if it’s possible to reverse engineer a positioning. That is, as in the case with my firm, I was known for a thing, was unaware of it, was made aware of it, did not like it. It was completely unintentional, I didn’t intentionally create that positioning. Is it possible to look at your existing body of work and figure out a positioning that you either already have, or that perhaps you should have? Is it something you need to talk to client about? Is it something that you can really have control over, or is how we’re perceived by the market place largely defined by our client interactions?

Kai:                        That’s a great question. I think it is 100% possible to reverse engineer your positioning, and there’s a couple different ways you could do it. Through looking at your previous body of work, through client interactions, through client conversations. When it comes to looking at your previous body of work, what I often advocate is, look through and start scoring projects and clients. I use a simple three score method where I just list every project or every client I worked with in the last or two, and I score it from one to ten on, “How fun was it to work with this project? How lucrative is it to work on these types of projects?” And, “How much do I personally enjoy working with this type of industry?” I’ll just sum up the one to ten scores and sort them by that master summation column and be like, “Oh, what comes at the top?”

It’s interesting to see what might pop out. You might be like, “Oh wow. I didn’t realize that I really enjoyed this type of project that was the most financially lucrative for me. Let me try niche-ing down on that.” And so we could definitely reverse engineer positioning by looking at our previous body of work and cherry picking specific clients or types of projects and saying, “You know what, we’ve got this larger Venn diagram, this larger circle of all projects I’ve worked on, but we’ve got this sub set of projects I loved working on. Let’s focus on those and see what happens.” So you could definitely reverse engineer a position that way.

I think talking with clients is another option. I advocate follow up with clients after a project, and a month or so down the line, one great question to ask in a follow up email, or a follow up sequence is, “Hey, I’m just curious. In your own words, what was the best part?” Or, “What was the highlight of working on this project?” Or, “How did this project help your company improve?” And just let them type as much or as little as they want, or say as much or as little as they want if you’re on the phone with them, and hear the words they use to describe you. Since as you discovered, your clients may already have you slotted into a specific positioning in their mind, you just don’t know it yet.

By opening the door to that conversation, it becomes much easier to be like, “Oh wow. Three of the five clients I talked to described me as ‘The guys to call when everything is falling apart.’ Huh. That’s interesting. Do I want to continue with that? Do I want to try to reset it and reposition myself?” If anything, it’s data that you’re able to incorporate into your thinking about positioning.

The third and final thing I’ll say about reverse engineering positioning is, I think it is possible to brute force reverse engineer a positioning statement, or a positioning for your business. It is probably the hardest of the modes or modalities of positioning, but it can be successful. In my own case, when I made that jump from WordPress developer to, “I’m going to do search engine optimization for e-commerce stores.” I have yet to do a search engine optimization project, and I have yet to work with an e-commerce client, but I thought it would be a strong positioning to pick because I looked at the market place and said, “Okay, of the clients I’ve worked with, or the clients I can work with, who would be the most enjoyable?” And I was doing a lot of reading about e-commerce and Shopify and saying, “Oh wow, seems like these people are investing a lot of money in their businesses. Okay. There’s some cash flow set up here, I want to set up my business next to that cash flow.”

Then I started reading about the types of problems they were experiencing, going onto forums, reading discussions groups, seeing the different articles and tutorials posted, and there was a lot around, “How do I get more traffic to my store?” I said, “Okay, great. Here’s a positioning I could test. If you own a e-commerce store, I will help you get more traffic.” I was able to put that positioning out into the market, contact a couple store owners, engage in conversations with them, close the first of many clients in the e-commerce space and discover, “Oh wow. This is a valuable problem to solve.” But it involved a lot of self study and researching on my part. I think I read six or seven different books on search engine optimization and link building, a number of different guides and articles on the process, a number of different guides and articles specifically about e-commerce stores and traffic, because I knew coming into this new positioning I was at a knowledge deficit compared to other people in the market, and the action I needed to take was study as much as I could.

Honestly, we aren’t talking that much. Five to seven books, five to seven articles, a couple weeks of work at this to understand, “Okay, what exactly do I need to do here to solve this problem?” So there’s a number of different ways we could sort of reverse engineer or back our way into a positioning rather than say, “Hey I’m going to take a stab in the dark at something new out there.” We could look at our own body of work, we could talk to clients and see what they already hear and see us as in the market, or we could say, “Well, I’m going to pick a new target market based on different signs that I see, and I’m going to see what expensive problem they’re experiencing through market research.” And that will become the positioning, that test.

Chris:                    Now the brute forcing of a positioning, I’m guessing that’s probably a good candidate for the kind of processes you were talking about earlier where maybe you need to let it take a year and very slowly, slowly ease into it?

Kai:                        Mm-hmm (affirmative). Absolutely. I think that’s definitely the case where you want to test as much as possible, and I typically advocate setting up a separate landing page on your site. Maybe it’s like “kaidavis.com/e-commerce”, and people are able to go there and see, “Oh, this is the e-commerce stuff her does.” The front page talks about different things that might still be a more generic positioning statement, but I’m starting to test my positioning through that one off page. I think there’s a number of different activities you could take to test that positioning, but even when it’s more of a let’s say, safe but or small adjustment in your positioning, I think taking some time and approaching it slowly and cautiously and saying, “This is a multi month process.”

Just like starting advertising, you don’t start advertising on Facebook and instantly your campaign is a success, you start advertising on Facebook, collect data, synthesize all that data, make changes, and repeat, and it’s that same methodology I think when it comes to revisiting our positioning or revisiting our marketing at large, as a consultant or freelancer.

Chris:                    Okay, so here’s my question: Once you embark on this process, this process of either, “Oh look, it turns out I have a positioning, now I need to just behave like it.” Or, whether you’re trying to brute force your way into right now, or whether you’re trying to very slowly do your cross-fade technique, how long of a period should it take? How long into the process can you get? How do you gauge whether or not you’re seeing enough of a result to continue to invest in switching to that positioning? What are the signals that tell you, “You know, maybe I shouldn’t spend the rest of the year on this. Maybe I should switch to something else right now.” After one quarter or two quarters, or what have you. How do you gauge whether to continue?

Kai:                        I think it’s a combination of looking to see if you’re generating referrals, if people are responding to your positioning statement, if new clients are coming out of the woodwork and saying, “Oh we didn’t know you did this. We’re that exact type of company and we need help with that.” It’s a lot of business quantitative figures like that. Are we seeing leads come through these new channels? Are we seeing inquiries for these new types of projects? Are we seeing people seek us out for our new reputation, or our new positioning? Often times what I recommend is trying to generate referable moments. It might be, we choose a new position for our business, and we say, “Okay great, we need to go out there and see how the market reacts to this.” What I advocate is making a list of 10 to 15 business owners, colleagues, past clients, people you’ve worked with, people you know, people you’re friends with, and just sending them a simple email.

You want to create referrals from this email, so you basically say something like, “Hey. Just a quick update. Hope you’re doing well. Wanted to let you know, I’m changing the positioning for my business. I’m focusing in on,” Or, “I’m experimenting with focusing in on ‘new target market’ and helping them achieve ‘specific outcome’ by solving ‘expensive problem’. I’m curious though, I’m doing market research on this and want to make sure I’m focusing on the right things. Do you know of anybody who works in ‘target market’ experiencing ‘problem’ that you could connect me with? If so, I deeply appreciate that referral. If not, not a worry, still love you, hope you have a wonderful weekend.”

We send out these outreach emails to people we already know. Warm contacts. We’re looking to generate referrals from them or response from them saying, “Oh, yeah. I know three people who are exactly like that. Let me make sure it’s okay to introduce you two, and I’ll go ahead and introduce you two.” So by trying to generate referable moments like that, we’re able to increase the number of people coming in, the number of people exposed to our new positioning, and get more validation that, “Oh, hey, this is a valuable thing to focus on.”

Chris:                    Nice. I like that a lot. I like that a lot. Let’s continue … [inaudible 00:36:45] a case study with the freelancer I described earlier. Little bit of traffic, making some money, has some clients, is not intentionally moving into a particular positioning, and is not yet earning six figure, so suppose they look at their body of work, they go through the exercises that you describe, and they discover, “Oh look, apparently I’m the karate school web design guy.” Or, “Look, apparently I’m the blue collar HVAC repair WordPress site guy.” Whatever positioning a person discovers that they may already have in the marketplace, intentional or not. If a freelancer chooses a positioning, right, whether it’s one that they’ve accidentally backed into or whether it’s one that as you said, they want to brute force, “I’m going to move all my marketing into position to support positioning X.” They’ve never done this before. What’s the very first thing they need to start doing in order to proactively establish that positioning? Take that ground and hold it in the marketplace.

Kai:                        I think, say the first and most important and most valuable thing you could do is, especially if you’ve looked at your previous body of work and you’re picking your positioning based off of that, email the pervious clients, or call out the previous clients who match that position, who are in that industry, who own HVAC businesses, or whatever that positioning may be, and say, “Hey, it was wonderful to work on that project with you. What I’d love to do is just set up a quick 10 minute call, see how things are going,” and here in your own words, “the benefit this project helped your business achieve.”

The goal is just to learn in the client’s own words, what outcome this project helped them achieve, and that I feel fully informs our positioning statement, because then we’re able to say, “Okay, so I specialize in helping HVAC companies get websites that get leads.” What outcome did that have for their business? “Oh, it helped them get more clients, it helped them hire three new employees because they got more deals, it helped them get more traffic and get more phone calls.” We want to discover, in their own words what the outcome generated is, and from that we’re able to refine our positioning, or say, “Hey, you know what, I’m specializing with companies like yours. I’m wondering, do you know two or three people I Should contact who are in your network, who you would trust, who you think I would be a good fit for, that would be a good person for me to talk with?”

Reaching out to past clients, or reaching out to colleagues or acquaintances from more of a referral based strategy is I think the number one most important action to take. It lets you easily validate the position if people come back and are like, “I don’t quite understand what you do.” You aren’t explaining it clearly enough. If people say, “Hey, I could think of three people I should introduce you to.” That’s a very good early sign that your positioning is resonate with the market, it’s coherent with the pains and problems that target market is experiencing, and aligns with the needs that they have.

Chris:                    Very nice, very nice. What would be second?

Kai:                        Second after that outreach I’d say is starting to revise the messaging on your website. So we’ve picked positioning, we’ve done a round of essentially, market research outreach. Does what we’re offering actually match up with what people want to buy? Okay, it does. Let’s either update our home page or create a specific sub page on our site speaking directly to that target market. Our homepage might still be, “We make websites for people that need them.” But on this particular HVAC page it might be like, “if you own an HVAC business and you’re struggling to get more leads and phone calls from your website, let us show you how to double your number of clients.” whatever it may be, and have that specific page talking about the pains they’re experiencing, problems you could help them solve, and the outcomes they achieve when they work with you.

By doing that, it becomes dramatically easier to direct that traffic, direct those leads, direct those prospects to a page that speaks directly to them. We’ve essentially done the minimum necessary to update our position by creating this new page, and we’re only honestly talking 500 to 1,000 words maximum. Include a call to action at the bottom, “Schedule a time here. Contact me through this forum. Email me here.” Then as we engage in conversations with people are either in the industry or could provide referrals in the industry, we have a specific page we could send them to that speaks directly to them and their market. I think that next step is a first round revision of your messaging. Not a full on content rescaling, update all the pages, but let’s just target one page first and update the messaging on that page to be more coherent with the target market, and move forward that way.

Chris:                    So by this time in the process we’ve already taken some reasonably serious, or maybe I should say, earnest steps to not only change our messaging, but to get that new messaging out in front of the people that it was intended to address.

Kai:                        And specifically explain, “This is what I’ll be able to do for you. This is how I’ll be able to help you. This is the outcome your business will achieve.” And it allows you to test the water of position. By this point, we’re honestly, the work we’ve done is look at our past clients, see if any stand out as being in industries we want to focus on, picked one of those industries or picked a separate industry, done a little bit of market research, reaching out to people we know in that industry, or people who could refer us to people in that industry, have a couple conversations with people in that industry to say, “Hey, what keeps you up at night? What’s the biggest issue you’re having right now? What’s the latest thing you paid a consultant to help you with?”

Then we fold that information into a single page on our site that just specifically says, “If you’re in this industry experiencing this problem, this is how I could help you.” By being able to share that with clients or prospects in our target market as they come in, we’re easily able to communicate, “Hey, we’re specializing in this. Our entire site might not yet show it yet, but you know what, it always takes a while to update sites, but this is what we’re specializing in, and this is how we could help you.” And after two, three, four months you’re like, “Well, no leads and no conversions and I actually don’t really like this target market at all, they’re all ninnypoos.” Well, then you could say, “Okay, all I really put on the line here was writing one new page of my site.”

We practiced a ton of what I call meta skills along the way. Improving our positioning, doing market research, having conversations with people, and writing a sales page. All of those are skills that will apply next time you test a new position, or the time after that, or the time after that. We are practicing valuable business skills throughout this exercise, so eve if this attempt at positioning does not perfectly work, that’s fine, you are going to become a better business owner by taking the time to experiment in this way. If that attempt in positioning does not work, it doesn’t mean you are a bad business owner, or you somehow have failed, it just means hey, you tested a marketing channel. That’s all that positioning really needs to break down to be. A single marketing channel, and that one didn’t work.

Just like we can look around and identify people who tried Facebook ads and were like, “Nope. That one did not produce a return on investment for me.” Or people who tried search engine optimization and said, “Hey, you know what, SEO is not the game for me to get clients or traffic.” A particular position is just a marketing channel. It’s like having a big billboard that says, “If you’re this type of person, I will help you solve this problem. Sometimes we pick a particular target market and a particular problem that people don’t need help solving yet. I worked with a coaching student about a year ago who picked a fabulous target market, one that routinely hires consultants for six figure plus engagements, and a very, very, very necessary expensive problem.

But as the student moved forward with market research, what he discovered was this was an incredible expensive problem, it would be costing people in his target market hundreds of thousands of dollars per business if they did not work on it, however, the government deadline to fully implement a solution to this problem was not for three years and nobody gave a fig at this point.

Chris:                    Wow, that’s kind of a heartbreaking example of the sometimes make or break role of timing in any kind of a marketing effort in freelancing. Even something small or something as big as repositioning.

Kai:                        He was perfectly positioned to move on it and he was like, “Well, nobody really wants to spend money for two and half years, what do I do?” And I’m like, is there another problem that target market is experiencing? Can we sort of hedge your bets that way? And he ended up finding another expensive problem within the same target market, so when it came time 6 months or 12 months before that government deadline, he’d be able to start ramping up the positioning, and ramping up the marketing, and saying, “Hey, you know we’re 11 months away from this big ol deadline that’s going to effect your business. If you want to get ahead of the game, if you want to make sure you aren’t in trouble or aren’t dealing with issues when this deadline hits, we better start talking now.” But sometimes you do get to that market research point and discover, “Oh, the market does not yet have a need for the service I’m offering.”

Chris:                    Right, so whether your friend was correct or incorrect about his market positioning change, it really doesn’t matter unless he’s also doing this change at the time the market is ready to accept it?

Kai:                        Perfectly put.

Chris:                    As if repositioning isn’t tough enough, now we’re just telling stories that are going to create anxiety. My goodness. But all the said, we’re going to need to move towards wrap up. Kai, I know that people can find you on Twitter as @kaisdavis, and also at doubleyouraudience.com. Where else out on the internet can the listeners keep up with you and your projects?

Kai:                        That’s a great question. If the listeners go to kaidavis.com, they could sign up for my daily newsletter. Every day I email out a tip about freelancing or consulting as it applies to us as business owners. How do get more clients, how to refine your positioning, how to build a better business. So if you go to kaidavis.com you’ll be able to sign up for my daily marketing tip for freelancers or consultants. You could also go to freeoutreachcourse.com. I’ve written two books about outreach, emailing clients or audience owners, building relationships with them and turning those relationships into opportunities for you and your business. If you want to learn more about the process of outreach, just go to freeoutreachcourse.com, and you’ll be able to sign up for a free five day, five part lesson.

Chris:                    That’s a generous offer. Kai, thank you so much for coming on the show. I appreciate it.

Kai:                        Hey, thank you so much for having me, and I hope the listeners enjoy this episode.

0111 – Authority Building & Qualifying Clients w/Sarah Jackson (Part 2)

Sarah Jackson on the $100K Freelancing podcast

Sarah and Chris discuss how to build your freelancing authority, how to qualify freelancing clients, and how to communicate with a client. Part 2 of a 2-part interview.

Download MP3

You can follow Sarah on Twitter, and find her work online at Office of Sarah.


Build your freelancing authority on purpose:

  • Cherry-picking portfolio pieces
  • Only your best work
  • Only work similar to what you want to do
  • Only work that you can do profitably

Impart faith in the client’s mind that you can do the work:

  • Show that you’ve done it once, the client will believe you can do it again

Loss-leader strategy?

  • Show your least-expensive work to get clients in the door
  • Runs the risk of attracting penny-pinching clients
  • Ignores professional quality-of-life issues

If the client wants YOU then the price is not an obstacle:

  • Sometimes there’s no factor that explains why you fit w a client
  • Pricing send a signal
  • Pricing positions both you AND your clients

“I have no low-bid. If I did that, I would starve.”

Cost is a factor, but shouldn’t be the factor, bounded by the potential ROI of the project.

A lack of understand of value and ROI can lead to a cost-first focus and a lack of the client being committed to working with YOU specifically.

Qualifying clients:

  • It’s a common struggle
  • Educating the client on the process & where the value resides
  • It’s part of your job to educate on the process & the value


  • Hyper focus on cost or speed is a red flag
  • Expecting quality out of line w budget or cost is a red flag
  • Unrealistic timelines are another red flag

Immovable rule – the decision-maker HAS to be in the room when I’m presenting design or making decisions:

  • “When I’m not dealing with the decision-maker, that’s when projects go haywire”
  • One of the best ways to get design work approved is to have the decision-maker in the room.
  • It avoids turning a project into playing a game of “telephone”.

Trying to communicate experience via proxy does not work:

  • Some contacts lack the ability to articulate your feedback to their boss
  • You have to make sure your contributions aren’t mis-represented by the non-decision-makers to the decision-makers
  • Some contacts lack the inclination to appear lacking in authority

Some contacts will actively misrepresent how much authority they have over your freelancing project:

  • We want to presume goodwill
  • Sometimes our trust is not rewarded

How to determine if you’re talking to the real decision-maker:

  • Authorized to sign deals in general
  • Authorized to sign THIS deal
  • Authorized to approve payment
  • Authorized to veto this project?

You have to be very careful here:

  • You have to discover the real decision-maker, AND
  • You have to also respect the non-decision-maker point-of-contact, AND
  • You have to turn non-decision-maker stakeholders into allies, AND

If you don’t like interacting with people you will have a difficult time in freelancing.

The Freelancing Continuum (Contracting <—> Freelancing <—> Consulting)

If you’re not facing the clients yourself, you’re dependent on a middle-man of some kind to give you work.

Getting closer to the money helps create stronger clients relationships, and charge more for your work.

Finding the sweet spot:

  • Sarah likes striking a balance between being a strategic consultant and a technical pair of hands
  • Helps create a blend of work
  • Keep you technically satisfied as well as positioned for healthy fees

Difficult to find the client before all the important decisions are made?

  • This is a marketing problem
  • Nobody likes doing useless work:
  • Getting in on the strategy allows you to ensure your work truly benefits the client

Don’t let the client tell you what thing they need:

  • Client should tell you their desired outcomes
  • You should tell the client what thing they need

Sometimes the client won’t listen:

  • How much time do they have?
  • How much patience do they have?
  • Are they resistant to your help?
  • This might end up being a one-time project

Recurring work:

  • The goal is always to have a long-term relationship with a client
  • The simplest thing to do is listen and ask “why”
  • This often leads to strategic discussions that create more and better work

You don’t have to be interested in turning every client into repeat work:

  • Sometimes you see yourself becoming part of the client team
  • Sometimes projects are just projects and that’s the end of it

Chris once got called out for disinterest on a client project early in his career.

Our role is as much to signal the health of and confidence in the project as it is to execute on the project.

How to combat apathy about projects:

  • Make sure you stay connected and inspired
  • Always have a side project
  • Stay active in professional groups
  • Practice “professional self-care”

0110 – Growth, Delegating and Networking w/Sarah Jackson (Part 1)

Sarah Jackson profile on the $100K Freelancing podcast

Sarah and Chris discuss the dangers of growing a freelancing practice, what and when to delegate, and the power of networking to get clients.

Download MP3

You can follow Sarah on Twitter, and find her work online at Office of Sarah.


Currently going back to school & doing less client work.

Build-a-team of go-to contractors.

The dangers of growth!

  • Big for the sake of big
  • Is more headcount really what you want?
  • Regulatory burden of abigger business w/employees

Good growth gives you:

  • Better clients
  • Better pay
  • Better professional quality-of-life

Edmondton is a unique city for entrepreneurs:

  • Very flat, open, cultural hierarchy
  • Big DIY ethos

Project mgmt is hard!

Jokingly talked about being horrible to our assistants.

Technical domain-work is what I enjoy:

  • Don’t want to stuck doing a job I hate
  • Outsourced the things I hated most (made a list)
  • Got a bookkeppers first
    Focusing on what you’re good at vs focusing on what you enjoy
  • Stretch assignment vs outsourcing specialties

Sometimes hard to remember to bill for everything.

Never start work without a contract!

Remember to address scope changes in quote.

To get clients:

  • Commitment to high-quality work
  • Lots of referral & network business
  • Personal projects for gaining clients

“I’m generally doing a few ridiculous things in my day”

Building credibility w/personal projects:

  • They can serve as a calling card
  • Accidental calling card: Jennifer Wilde (book about peanut butter* kid’s book)

How the book helped with credibility/authority:

  • Billed as an illustrator & writer
  • Fostered variety in work
  • Thinks the mixture is a benefit to clients & a strength
  • Got a university client contract
  • Won work that was totally unrelated to children’s books

Merely having professional artifacts like books can help establish credibility.

0109 – Beginner Marketing Wins/Matt Inglot

Matt Inglot profile $100K Freelancing podcast

Matt and Chris talk about beginner marketing wins for new freelancers, why content marketing is NOT a beginner move, how to make sure you’re connecting with decision-makers, and getting repeat work

Download MP3

You can follow Matt on Twitter and at Freelance Transformation.

To hear another conversation between Matt & Chris, listen to Episode 72 of the Freelance Transformation podcast.


Content marketing is not for beginners!

Non-scalable activities that offer feedback are for beginners. These are beginner marketing wins.

Getting started vs scaling:

  • Content marketing = scaling move
  • Not much feedback; if an ad doesn’t work, I don’t know how far off I am

Starter activities should optimize for feedback:

  • 1 on 1 talk
  • Start with your own network
  • Pitch intros as a research project, not as a sales pitch
  • Nobody wants to subject their friends to a sales pitch
  • Have those convos to determine if the problem you want to solve is a real problem
  • Events, cold outreach

The keep your network growing prescription:

  • Chamber meetings
  • good for small biz
  • Not many enterprise-level decision makers
  • Meetups
  • Local events
  • User groups
  • Conferences specific to the industry you’re targeting

Must have people skills in order to break in to the conversation.

Get to the decision-maker.

Don’t expect a sale right away:

  • Pivot; can you get contact info? Can you send them email?

Once you have clients from your network, how do you sustain a practice

You have to be selling something that CAN be a recurring/repeat sale:

  • Look at your pricing & profitablity
  • Look at the kind of sale you’re making
  • Repeat vs one-off work
  • Can you climb the value ladder (ex. go from logo > branding > brand strategy)?

Strategy calls:

  • Check in w clients once per quarter
  • Act like the expert you are
  • Have a regular dialogue w clients
  • How can I support you & create value?
  • You CANNOT wait for the client to call
  • Get each client on a call once x quarter
  • Evaluate goals & results
  • http://freelancetransformation.com/strategy-calls

Beginner marketing wins are usually non-scalable activities.