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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:

CarLotz Sivers.org “The Tail End” – Wait, But Why? https://www.choosefi.com/092-will-boland-carlotz-and-entrepreneur-case-study/  
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