Close this search box.

Ep. 255: De-Risking the Move to Self-Employment with Matt Baker

My guest today is Matt Baker. He’s the VP of Corporate Strategy and International Expansion at FreshBooks, which makes accounting, bookkeeping and invoicing software to help service providers get paid faster and save time on tedious administrative tasks.

Matt’s also super passionate about helping entrepreneurs mitigate the risks associated with going from side hustle to self employed.

I’m super pumped to have him on the show – even though we both graduated from colleges that have a huge football rivalry (Go Buckeyes!) – to share some of his insights with you because he’s in the unique position at Freshbooks to have access to a lot of data about challenges faced by people who are self-employed, and what prevents people who really, really want to quit their day jobs and have the freedom, flexibility and financial independence that comes with working for yourself from making the leap.

Today we’re talking about:

  • What’s stopping the 20 million Americans who say they want to be self-employed but aren’t taking the leap.
  • A low-risk way to start your business so that you don’t have to jump without a safety net.
  • How to figure out if you are charging too little, and what to do instead.
  • The difference between value-based billing and time-based billing, and which one Matt advises side hustlers use.
  • Matt’s best advice for you if you want to make the jump to self-employed.
  • Matt’s best advice for how you can create a sustainable, long-term business.

My favorite quotes from Matt:

  • “You don’t want to price on surviving, you want to price on thriving.”
  • “You have to know how to go out and find your own clients.”

Resources mentioned in this episode:

Connect with Matt:

Freshbooks Website




Matt Baker is a money strategist and business coach who’s passionate about helping entrepreneurs solve their most challenging problems. As VP of Corporate Strategy and International Expansion at FreshBooks, Matt is helping millions of self-employed pro’s grow their businesses and get paid faster.

As a reformed management consultant and ex-Google strategist, Matt loves asking the tough questions that lead to tipping points in business. When he’s not helping businesses grow, you’ll find him teaching a Change Management course at UC Berkeley or giving back via his seat as a board member at the Next Step Learning Center, an adult literacy program based in Oakland.