092 | Will Boland | CarLotz and Entrepreneur Case Study

092 | 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.

• 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?

For more information, visit the show notes at https://ChooseFI.com/092