The Hidden Cost of Entrepreneurship

I met my former boss, Nick Fisher, in high school. He was running an entrepreneurship program for high school students called Young Entrepreneurs Business Week. Students in the first year program would spend a week on a college campus and work in teams to run a mock business for a week and present their findings on the last day.

I had gone through the program the previous summer and this second year program was all about investing. We ran mock portfolios for the week and compared two public companies as our core project. My group compared UPS and FedEx. Nick taught this program and I became fascinated by investing. So much so I stayed in contact with Nick in the following years. 

Nick is the portfolio manager at Pilot Wealth Management, a wealth management and advisory firm he co-founded with Jason Lesh. In the years following my time at YEBW, we often met for coffee, generated a long email chain, and had several phone calls. Going into college I started interning for them and had an offer to work for them full time after I graduated. I was incredibly excited and accepted the offer. Being able to work with my mentor, in a job I enjoyed, focusing on a subject matter I was fascinated by, was too good to turn down.

I also started the Think Like an Owner podcast in college. In the fall of my senior year I became fascinated with folks acquiring and operating small companies. Nick encouraged me to create a podcast to meet these investors and operators. I thought it was a great idea and was lucky enough to interview Trish Higgins in Boston on a school trip for the first episode.

Most folks reading this know how the podcast grew from this point. I started with a monthly release cadence and began to attract a (very) small following. A year and a half into the podcast I saw more and more ways it could grow. I started to think about how to work on the podcast full-time so I could spend all my energy making it the best podcast for the SMB world. I decided to take on three sponsors, hire an audio editor (Mathew Passy, he’s awesome), redo my website and cover art (David Bridgeman, also awesome), and become a weekly podcast.

Two days before my wedding in August 2020, in the midst of a global pandemic, I quit my full-time job at Pilot. Going into marriage as an entrepreneur felt incredibly exciting and the podcast improved as a result. Audio quality improved, we found fantastic guests more consistently, and I found new ways to grow the project.

But I soon discovered a hidden cost to becoming an entrepreneur: the loss of daily mentorship. I could still talk with and meet Nick here and there, but we were no longer working on the same projects and goals. We’ve brainstormed many times for one another’s projects, but not being able to do that every day was a cost.

Common advice I received in college was to go work for someone for five to ten years before going off on your own. I scoffed at the idea at the time, but I now see the reasoning behind the advice. Learning from someone who is ten to twenty years ahead of you in life presents a huge amount of learning without the risk of making catastrophic mistakes. Working alongside a mentor can also plug you into a developed professional network, giving you a strong foothold on any venture or opportunity in the future. I’ve made my choice for now, but I am now more aware of the downsides of my choice.

Twitter and the podcast have been great for building new relationships with mentorship elements. But it is still not the same as working together towards the same goals, every day, holding each other accountable, and constantly exchanging ideas and feedback. There are a number of new projects I’m working on that excite me, but they all, for the most part, keep me self-employed. This will be a good forcing mechanism to learn how to build deeper relationships without shared work and goals on a daily basis.

What advice, dear reader, do you have for seeking mentors along your entrepreneurial journey?

Think Like an Owner Sponsors

Live Oak Bank – Live Oak Bank is a seasoned SMB lender providing SBA and conventional financing for search funds, independent sponsors, private equity firms, and individuals looking to acquire lower middle market companies. Live Oak has closed billions of dollars in SBA financing and is actively looking to help more small company investors across the country. If you are in the process of acquiring a company or thinking about starting a search, contact Lisa Forrest or Heather Endresen directly to start a conversation or go to

Hood & Strong, LLP – Hood & Strong is a CPA firm with a long history of working with search funds and private equity firms on diligence, assurance, tax services, and more. Hood & Strong is highly skilled in working with search funds, providing quality of earnings and due diligence services during the search, along with assurance and tax services post-acquisition. They offer a unique way to approach acquisition diligence and manage costs effectively. To learn more about how Hood & Strong can help your search, acquisition, and beyond, please email one of their partners Jerry Zhou at [email protected]

Oberle Risk StrategiesOberle is the leading specialty insurance brokerage catering to search funds and the broader ETA community, providing complimentary due diligence assessments of the target company’s commercial insurance and Employee benefits programs. Over the past decade, August Felker and his team have engaged with hundreds of searchers to provide due diligence and ultimately place the most competitive insurance program at closing. Given August’s experience as a searcher himself, he and his team understand all that goes into buying a business and pride themselves on making the insurance portion of closing seamless and hassle-free.

If you are under LOI, please reach out to August to learn more about how Oberle can help with insurance due diligence at Or reach out to August directly at [email protected].

Interested in sponsoring?

Capital Notes

First, this thread by Patrick O’Shaughnessy on turning 36 and lessons he’s learned through his career was one of the most impactful collections of advice I’ve ever read.

Second, I finally took the time to go through Julian Shapiro’s “What you should be working on” thought exercise. The core of the exercise is to identify the values you care about most in your work. Julian identifies the following values: 

  • Knowledge — Do you become more knowledgeable and skilled from it?
  • Adventure — Do you accrue novel, memorable experiences?
  • Fame — Do you build an audience you can later leverage?
  • Power — Do you acquire resources and connections?
  • Money — Do you increase your financial wealth?
  • Exercising Talent — Do you leverage your skill and creativity?
  • Human Connection — Do you bond with others?

When I reviewed these values and reflected on my own goals, my top three looked like this:

  1. Knowledge: Learning new industries, companies, models, and ways to operate and invest is my top professional value.
  2. Human Connection: I love working with smart and interesting people and place tremendous value on long-term relationships and partnerships with them. I also want to work with professionals I respect, admire, and have a mentor relationship with. 
  3. Exercising Talent: I believe I have become good at building new relationships and creating content.

What is your order of values?

If you found an interesting article, podcast, or interview that I missed, please let me know, I’m always looking for interesting stuff.


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