Lesson 84: Weaknesses
About the Searcher
One of my weaknesses is my struggle to take care of myself. Jason Jackson, Partner at Futaleufu, said in the ETA Insider Podcast, “I was a very unhealthy CEO: from a physical perspective, I was not eating right and I was not getting enough sleep.” He explained how today he coaches CEOs to be healthy; not only is this better for them and their personal relationships, but they are also better for the business. Maintaining your body, mind, and heart generates more energy and more focus as an operator.
About Entrepreneurship Through Acquisition
The Searcher is the the biggest risk in the business. Acquiring a company as a first-time CEO makes the future of the business unpredictable as the new Operator learns how to do their job. When an investor makes a decision to provide capital for your Search, they need to know you will thrive on this journey. You need to anchor yourself in healthy habits. Your healthy habits will generate the energy and focus necessary to reel in the risks you carry as first-time CEO.
Investing in a first-time CEO is inherently risky. One of the ways to reduce this risk is buying a business with recurring revenue. This week an investor told me he likes recurring revenue because it provides revenue visibility. In other words, the business can predictably make money in the future. Recurring revenue provides a stable base so the CEO can focus on operations and growth rather than scrambling for sales.
A.J. Wasserstein, Senior Lecturer at Yale School of Management, published two articles about recurring revenuet. In 2020, he published “On the Nature of Revenue” and in 2025 he published “Does Recurring Revenue Really Drive Financial Outcomes in Search Fund Acquired Business.” His opinion has evolved to illuminate the value of growing recurring revenue rather than simply acquiring a business with recurring revenue at a higher purchase price.
Research shows businesses with high recurring revenue at acquisition do not deliver superior returns compared to those with low or no recurring revenue. The culprit? Entrepreneurs pay premium EBITDA multiples that offset advantages. The real opportunity lies in increasing recurring revenue during your tenure, not overpaying for it upfront. Again, the CEO must be in top shape to achieve this goal by taking care of themselves and the business.
About the Bigger Picture
My values are to act with love, humility, and wisdom. The first person I need to love when I wake up in the morning is myself. This will allow me to perform my duties on a daily basis. Moreover, this will be an example to other high performing, over-achieving, Type-AAA, “get-it-done” people that you need to take care of yourself. Given the urgency of my need for healthy habits after this first week, I aim to implement tools such as blocking sleep time on my calendar, meal prep, and replacing caffeine with water. These are ways to successfully anchor myself in healthy habits to address the weaknesses of this week.
This is Lesson 84: Weaknesses. Next week is Lesson 85: Celebration.
P.S. I will report back on my sleep and exercise improvements!
