featured image for podcast episodeWill Boland | CarLotz |Entrepreneurship Case Study

Will Boland | CarLotz |Entrepreneurship Case Study
Episode 092

Episode Guide

Designing your future involves navigating challenges and making calculated risks, as demonstrated by Will, who transitioned from a lucrative financial career to entrepreneurship. His story showcases stepping outside comfort zones and the importance of mentorship in shaping paths. Will's journey to founding CarLotz illustrates practical insights in pursuing business, focusing on learning from failures, and adapting to customer needs. The conversation with Jonathan Mendonsa and Brad Barrett emphasizes how aligning passion with work can redefine success, paving the way for a fulfilling life rich in experiences, rather than mere financial metrics. Key takeaways stress the essence of authenticity, the value of taking action despite fear of failure, and how mentorship fosters growth in both professional and personal domains.

Episode Timestamps

Embrace Entrepreneurship: The Journey to Designing Your Future

Transitioning from a stable career to entrepreneurship is a bold move. Will Boland's story illustrates how following a passion while managing risks brings value not just in business but in life itself. If you are contemplating taking that leap, consider the insights and lessons derived from Will's experiences, which are especially relevant for anyone in the financial independence (FI) community.

The Power of Taking Calculated Risks

Entrepreneurship is not reserved for those with the most innovative ideas; it thrives on those unafraid to take risks. Will’s transition from investment banking to co-founding Carlotz, a consignment store for cars, demonstrates that success comes from action rather than sheer brilliance of concept. Recognize that the biggest risk may often be not taking one at all. Reflect on your current situation: what calculated risk can you take today to align your career with your values?

Focus on Incremental Steps

One of the crucial lessons from Will's journey is to focus on the steps rather than the big picture. Whether planning for a business start-up or changing careers, emphasize small, actionable tasks over overwhelming end goals. Each step contributes to your larger vision, maintaining motivation and clarity along your journey.

Building a Life Resume

In a time when traditional resumes dominate our career narratives, consider building a "life resume." This concept emphasizes valuing your experiences, relationships, and personal achievements—much more than just professional milestones.

Define Your Values

Spend time identifying what truly matters to you. Will emphasizes the importance of pursuing interests beyond mere professional achievements. Set goals that encompass your values and passions, and consider them while designing your career path.

  • Action Step: Create a list of personal values and milestones you'd like to achieve in life that contribute to a broader sense of fulfillment beyond your career.

Leverage Mentorship

Effective mentorship can profoundly impact your entrepreneurial journey. Will's experience underscores the value of transparency with mentors about your goals. When you articulate your ambitions clearly, you can cultivate invaluable support and guidance.

Be Open and Honest

Will's relationship with his mentor allowed him to gain insights that were crucial for initiating his own business. Don't hesitate to seek advice and maintain open communication about your aspirations. As you navigate your entrepreneurial path, consider how sharing your goals with a trusted mentor can enhance your experience and strategy.

  • Action Step: Identify a mentor in your field. Schedule regular check-ins to discuss your progress and seek feedback on your goals.

Embracing Imperfection in Launching

In the startup realm, pursuing perfection can lead to missed opportunities. Will's approach highlights that launching even an imperfect business is better than waiting until everything feels "just right."

Iterate as You Go

Reflect on Will's mantra: "If you're not embarrassed by the first iteration, you're launching too late." Embrace the idea that feedback and experience in front of real customers are invaluable in refining and improving your concept.

  • Action Step: Start with a minimal viable product or service. Don't wait for everything to be perfect—get something out there and learn through doing.

Risk Management and Financial Independence

Understanding and managing financial risk is essential in entrepreneurship. While Will's decision to take a pay cut might seem daunting, it was part of a well-considered strategy to gain control over his future.

Assess Your Financial Buffer

Before making significant changes, analyze your finances. Determine how much runway you have to explore your venture without jeopardizing your family's financial wellbeing. Will and his wife created a financial plan that afforded him the time to establish Carlotz without immediate financial pressure.

  • Action Step: Calculate your monthly expenses and savings. Create a funding plan that will support you during your entrepreneurial pursuit.

Balancing Family Life and Business

Navigating the complexities of creating a business while maintaining family life can be challenging. A conscious decision to prioritize family is crucial to avoid burnout and maintain a sense of balance.

Design Your Schedule

Will opted to keep his family and business life in harmony. This consciousness about how he allocates his time allows him to partake in significant family moments without the burden of work obligations.

  • Action Step: Reflect on your current commitments. How can you design your schedule to create a more balanced life? List priority moments you don’t want to miss out on and allocate time for them.

Conclusion: Start Designing Your Future Today

Will Boland's story emphasizes that entrepreneurship is a journey worth embarking on, one that is aligned with personal values and authentic goals. By focusing on the steps you take, embracing imperfection, leveraging mentorship, and maintaining a work-family balance, you can design the future you desire.

Now is the time to evaluate what steps you can take towards creating a fulfilling life. The journey may be challenging, but the rewards in personal growth and fulfillment are undeniably worth it.

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.

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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.

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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