0106 – Authority Building As A Freelancer w/Jane Portman

Jane Portman profile $100K Freelancing podcast

Jane and Chris talk about building authority as a freelancer in order to generate work, how to enjoy marketing activities, and productized consulting.

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Jane can be found on Twitter, and on the web at uibreakfast.com and tinyreminder.com.


Mastering Ad Presentation
– too broad
– not focused on any certain audience or use case
– didn’t make any money
– it opened doors, just being known as an author

I think we are under-appreciating referrals
– but it’s not THAT magical

Be brave enough to charge higher fees

Wrote a book to build authority
– the most indirect connection
– could send book to clients
– building relationships

Patrick McKenzie – how I became a $500k consultant
– need to bring business value

– big investment

Dennis Field helped make a deal w InVision
– not much money, but tons of credibility

The same skills a software founder uses are similar to the skills a freelancer uses

Productized consulting
– inspired by Nick DiSabato
– reverse-engineered his sales page
– capturing a trend
– started a monthly consulting

– easy to get burnt out
– organizational overhead

Brennan Dunn

Productivity & burnout
– waking up early (IF you can)
– productivity comes in waves
– know your working style
– juggle your obligations in a way that fits your style
* I don’t say I’m shipping on a certain date
* don’t beat yourself up or get stressed out
– productized services; quote a week or two

Leveling up is a complex of different things
– 20% consulting & 80% promoting

The opportunity to turn down work is powerful!

It helps to enjoy the marketing activities
– I like writing articles
– I like podcasting
– I like writing emails

Time & repetition make you better, both technically and as a human being

Ask for help early!

0105 – Controlling The Client Engagement w/Benedikt Deicke

Benedikt Deicke profile $100K Freelancing

Benedikt and Chris talk about strategies for controlling a client engagement, communicating expectations clearly, and talk about their confusion with the idea of trying to niche their freelancing practices

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You can find Benedikt online at http://benediktdeicke.com, and on Twitter.


  1. Disqualify first!
  2. Have a qualification process.
  3. Take control of the engagement.
    – If you aren’t controlling the client engagement, the client is.
  4. No on-site work; it’s bad for your credibility.
  5. Have a good contract.
    – Sets boundaries
    – Sets expectations
  6. Communicate your expectations.
  7. Know your red flag issues.
  8. Don’t be too available.
  9. Say no to bad projects to make room for the good projects.
  10. Build up some financial cushion FIRST, then say “no” more freely.
  11. 5 qualification questions: https://doubleyourfreelancing.com/rate/

0104 – Quoting With Confidence w/Marie Poulin

Maries Poulin profile $100K Freelancing podcast

Marie and Chris talk about quoting freelancing fees with confidence, selling the client an experience to remember, and using coaching to level-up your abilities as a businessperson.

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You can find Marie online at https://weareokidoki.com/, on Twitter, and at MariePoulin.com.


  1. When quoting freelancing fees, quote “healthy” – this offers different value for different clients
    – One might freak, one might not
  2. We go through guided exercises w/clients
  3. We charge enough to be really generous with extras
    – Retainer/monthly deals
    – Barter/free work
    – Word of mouth
  4. Marie Forleo saw a site of mine and it was a big break
    – Role of luck; some random, some self-made
    – Got a lot of traffic
    – Workrate + Hustle = Luck
  5. Hired coaches and mentors to help cope with the increase in business
    – Systems coach
    * What are the pieces and variables in every project?
    – Develop the ability to meet your client where they are
  6. Lead-gen: People find our website (SEO fundamentals in play)
    – Have an idea for a product
    – Don’t know what to do
    – We offer them concierge onboarding
  7. Moving toward an experience enconomy
  8. Value-based pricing when quoting freelancing fees
    – I rarely think hourly
    – Lots of experimenting with rates
    – Experiment to see what sticks with pricing
    – Getting a general sense of level-of-effort
  9. Hybrid consulting-products firm
    – Evergeeen vs hybrid
    – Hybrid allows more customization & fosters greater investment
  10. A lot of quoting freelancing fees boils down to guessing and quoting higher than my fears makes me inclined to

0103 – Make Freelancing Serve Your Own Dreams w/Paul Jarvis

Paul Jarvis profile $100k Freelancing podcast

Chris & Paul discuss freelance marketing to a niche, sustaining your business via recurring work, and designing a business that serves your own dreams and goals, not those of society-at-large.

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You can find Paul online at pjrvs.com, on Twitter, and can also check out his courses Chimp Essentials and Creative Class.


1. 20 years in the business
2. Market wasn’t saturated yet, in the early days
3. Simply being competent would get you recurring work
4. Accidental freelancer
5. Worked at an agency
6. Didn’t like the way the client relationship was treated
7. Pick a narrow niche & do great work to be a persistent blip on a prospects radar
8. Check-up calls to engender recurring work (following up)
9. Started products as a new challenge
10. Waited until products were paying more than freelancing to transition out
11. Small products as a side hustle
12. If you can’t sell the service, you can’t sell the product
13. Don’t live your life or run your business according to someone else’s goals or dreams

0102 – Networking For Projects, And Growing Pains w/Kate Winsor

Kate WInsor profile $100K Freelancing podcast

Kate & Chris talk about networking for projects and, and the growing pains inherent in growing a freelance operation.

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You can find Kate online on Twitter, and houseofwinsor.net.

1. Setting clear expectations
2. Holding boundaries
3. Left/Right Media
4. Creative Mornings (Dallas)
5. World Information Architecture Day (IA is a subdivision of UX)
6. Lots of in-person networking for projects – get business person by person
7. Three Cups of Tea book
8. Unplanned, organic relationship-building
9. Fostering relationships to enable networking for projects
10. Wants to give talks as an authority- and relationship-building service activity
11. Operational issues – when to scale up?
12. Focus on biz dev? No problem.
13. Taxes!
14. Hiring!
15. Managing!
16. “The Struggle Is Real”
17. Jared Spool
18. Business lessons from romance books?
19. “Accidental Business Owner”
20. Might write a book on small business operations for girl-bosses

Also, shout out to Freshbooks in relation to our discussion about how Kate & I do our billing. It’s a great resource for freelancers!

0101: Qualifying (and Disqualifying!) Client Projects w/Bryce Bladon

bryce bladon profile photo $100K Freelancing podcast

Bryce and Chris talk about how to qualify client projects – and disqualify them! – in order to avoid taking on clients from hell.

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You can find Bryce on Twitter and at the Clients From Hell website & podcast. Also, check out his book, Hell To Pay.

Also be sure to check out Christopher’s book, Conquering Client Conflict: How To Handle Difficult Clients, Get More Respect, And Make More Money.


  • “No” is a complete sentence.
  • Stand your ground.
  • Think ahead – know your working values.
  • To qualify clients projects, first disqualify.
  • Diagnose the problem.
  • Decide if this is mutually beneficial (i.e. profitable).
  • Educate! In *their* language.
  • Failing to qualify client projects increases your chances of failure and misery

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