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Growing FreshBooks with Co-Founder & CEO Mike McDerment.

Launching & growing a business with Mike McDerment, the Co-Founder and CEO of FreshBooks, the software for self-employed professionals and small business owners. Mike shares inspirational stories from his early days as a business owner, and how he launched and grew FreshBooks (19:17) while living in his parent’s basement! Mike is an insightful and thoughtful entrepreneur who shares honest opinions and experiences which we can all learn from.

Mike McDermentMike McDerment is the Co-Founder and CEO of FreshBooks, the world’s #1 cloud accounting software for self-employed professionals. In January 2003, Mike was running a four-person design agency and using Microsoft Word to create invoices. One day, he accidentally saved over an old invoice, and that’s when he knew there had to be a better way. Over the next two weeks, he coded up a solution and eventually turned that side project into what is now FreshBooks. To save money, he moved into his parents’ basement for 3 and a half years and completely revamped how he ran his design firm to the point where he only worked 19 days in one year – while generating over $200,000 to bootstrap the company that would become FreshBooks. Today, Mike has grown FreshBooks to nearly 300 people serving more than 10 million users in 160+ countries. To help self-employed professionals set better rates, Mike also co-authored Breaking the Time Barrier, which has been downloaded more than 300,000 times.

Mike lives in Canada.

Growing FreshBooks with Co-Founder & CEO Mike McDerment:

  • What was your initial capital investment for FreshBooks?
  • How long before you were profitable? When did it become your full-time business?
  • “I collect advisors.” Did you leverage advisors and mentors early on or did you learn the value of this later?
  • “Not getting lost in the stuff that does not matter.” How did you determine what does and doesn’t matter in the early days of building your small business
  • What were some of the sacrifices you had to make to start FreshBooks, beyond having to live with your parents.
  • The “saved over the invoice” motivation I can understand with the initial motivator, but I suspect there was more that emerged to keep you focus and motivated to build FreshBooks?
  • Did you know how to code?
  • “Ours is a story of perseverance.” What kept you motivated to persevere? Why did you not give up?
  • How did you decide NOT to pivot your business model?
  • “You need determine how to measure your own success.”
  • Did you have a traditional “Exit Plan” for your business early on?
  • What’s your advice now for others considering starting a side hustle? Of course, it’s different when it’s a side hustle to a small business you own, compared to a corporate job where there are real or perceived conflicts of interest.
  • If you were starting over, what would you do differently?
  • Would you please share your thoughts on embracing Imposter Syndrome and fear as a Founder?
  • What personal skill would you have liked to develop earlier? (Ability to let go or delegate?)
  • Is there a question nobody has asked you yet about launching a small business?


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