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?
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JP Morgan Reserve cards
In order for credit card coverage to kick in you need to: decline rental company collision waiver, be the primary driver of the rental vehicle, and pay for the card in full with the card that offers the insurance protection.
Does your primary car insurance actually provide rental car insurance?
An email from Shari who recently made huge adjustments in her investments strategies, and realized that her son is 4th Generation FI.
Chris talks about his “Family Bank”.
How and why did Chris get this started?
What are the logistics of how the loans and “accounts” work?
Why does Chris’ family opt to use the Family Bank as opposed using traditional mortgage loans?
What impact does the Family Bank have on Chris’ investment strategy?
The first step toward the family bank is having transparent conversations about money.
What does Shane Mason, CPA/CFP, think of the family bank?
Does Shane consider the family bank an investment comparable to bonds?
Does the Family Bank need to be considered a business?
Interest income is always a taxable income.
Might the IRS have an issue with taking a loan from oneself?
Robert, from The College Investor, talks about his lucrative job as a Target store manager, building his blog into a highly profitable side hustle, his relationship with frugality, and the keys to success in a retail interview.
What you'll hear discussed on today's show
How did Robert end up where he is now – side hustler for life, and founder of The College Investor blog.
What was Robert’s original business?
How did Robert progress from collecting carts at Target, for the first 17 years of his career?
What is Robert’s experience with tuition reimbursement, and does he generally recommend that to students?
What were the steps that led to store manager?
What’s the key to being a successful retail manager?
Does it make a difference where an employee’s college degree?
Why are many young adults “over-educated and under-experienced”?
As a hiring manager, what did Robert look for during interview?
Are you friendly?
Are you nice?
Can you look me in the eyes?
Can you have a conversation with me?
What inspired Robert to start The College Investor?
How does Robert feel about his first blog posts?
When and why did The College Investor evolve from just an investment blog, to address college loans, personal finance, etc.
How did The College Investor get to 2.4 million unique viewers per month?
What role did does consistency play in the blog’s success?
Networking and connecting with other financial bloggers had a big influence on Robert, educating him and building partnerships.
Does Robert consider himself frugal?
Why does Robert focus more on income than frugality in his pursuit of FI?
What factors did Robert consider before he left his job at Target?
Why doesn’t Robert own a car?
Maxing out your company 401k contributions is different from contributing whatever your employer will match.
Don Wettrick, CEO and co-founder of StartEdUp Innovation program, and a current high school teach, talks about the cultivating innovation and creativity in the classroom, harnessing a learner’s internal motivation, and giving students opportunities to solve problems they’re passionate about.
What you'll hear from Don Wettrick:
Why and how did Don create an Innovation course at his school, and ultimately the StartEdUp Innovation program?
What was challenging about getting his students involved during the early stages, when it was just extra time during his class?
When do students lose their curiosity or learning?
How much does a reward really motivate students?
What would the process look like to develop and nurture internally motivated learners through elementary school?
What’s the difference between creativity and imagination?
How can a parent help their child be more innovative outside of school?
What does Don recommend as a good consumption v. production ratio?
How does changing consumption habits – how much, and what – impact the way Don’s students and own children think?
How does building community within a cohort of “creators” impact a student’s relationship?
Does participation in Don’s high school class impact his students other grades?
How do mastery, autonomy and purpose mix together best?
What does it look like to be in Don’s Innovation Class?
6-7 weeks of class
Basics of innovation
How to think creatively
Building a professional social media presence
Remainder of class is “open source learning”
Volunteer with struggling non-profits, to see problems close up
Statewide student “Pitch” competition
Helping struggling local businesses
What sort of projects have his students build?
What story do you tell yourself, about yourself?
Is there a difference between improvement and new opportunity?
How would Don hope to integrate innovation development into schools in his 10-year dream?