17 Lessons on the Psychology of Being a Searcher and CEO

In The Trenches

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During my ~10 years as a searcher and CEO, I had an endless number of commercial problems and opportunities that required my attention at any given time. However, it was often the personal considerations that kept me up at night: I rarely lost sleep over whether to raise prices by 5% or 15%, but instead was kept awake by the idea that even asking the question suggested that I didn’t truly know what I was doing. I wasn’t anxious about what mix of equity and debt to include in a letter of intent, but was instead anxious about the prospect of not finding a company to acquire at all after spending two years in pursuit of one.

For this reason, I thought it might be helpful to compile some of the lessons that I’ve learned over the years that cover the “human side” of acquisition entrepreneurship. I hope at least one of them provides you with a reason to reflect on your own situation, and perhaps make a change for the better in the process.