092.Will Boland Carlotz

092 | Will Boland | CarLotz |Entrepreneurship Case Study

CarLotz co-founder Will Boland talks about making the leap from investment banking to entrepreneurship, the challenges and benefits of leading a growing company, and what it means to build a life resume.

What you'll hear in today's show:

  • How did Will become an entrepreneur?
  • What was the inspiration for CarLotz?
  • What experience during his work in investment banking gave Will the motivation to become an owner/manager?
  • Will is 2nd generation FI. What did his journey look like?
  • How did Will present and convince his family that it was a good idea to pursue entrepreneurship instead of continuing with his well-paying job?
  • Did Will accumulate significant student loans while completing his undergraduate degree and master’s?
  • What is a life resume, and does Will keep track of his?
  • What role have mentors played in Will’s career?
  • Will has been very open and honest with mentors and co-workers about his specific goals. How does he create an environment at CarLotz to encourage the same from his employees?
  • Why didn’t Will’s mentor want to see his business plan?
  • What was the thought process when Will and his co-founders could only secure small startup investments?
  • What is the advantage of selling a car on consignment?
  • What hiccups did CarLotz overcome in their early days of business?
  • “If you aren’t embarrassed by the first iteration, you’re launching too late.”
  • How does Will encourage employees to share good ideas?
  • Why do pursuing FI and starting a business complement each other well?
  • How did Will and his co-founders create space to share work-place challenges within their partnership?
  • Has Will caught up, financially, to where he’d be if he had continued his job in investment banking?
  • Is he happy with where he’s at?
  • Does CarLotz need to be a financial success in order to keep Will on track to reach financial independence?
  • Why is running Will’s favorite life hack?

Listen to Brad and Jonathan's thoughts about this episode here.

Links mentioned during the show:



“The Tail End” – Wait, But Why?



Your Financial Resilience Toolkit

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5 thoughts on “092 | Will Boland | CarLotz |Entrepreneurship Case Study”

  1. So these are like the guys who call me when I try to sell a car on Craigslist and tell me they can help me sell my car and I ignore all their cars? Well, a knock-off of CarLotz?(since I’m in another state where they aren’t located) Just kidding. Hope his business is doing great!

    Great interview and move by Will to get out on his own taking that risk to start up a business.

    • *calls*, not cars… wow please delete my many replies, I’m a fool and so tired when I’m typing that I’m messing up the very edit of the edit! haha

  2. Great episode. I’d have liked to have learned more on the business structure itself, but I can do that research online. I especially liked the learning as you go approach when they first opened. Very inspiring story.

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