“Don’t F*ck It Up": Les Trachtman on Avoiding Post-Close Founder Succession Mistakes
Thu Feb 05 2026
This episode is brought to you by Boulay, the industry standard for Quality of Earnings, tax, and audit services, serving search fund entrepreneurs for 20+ years
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This episode is brought to you by Oberle Risk Strategies: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses
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When assuming the leadership role of a company that was previously held by its original Founder, new CEOs are often surprised at how difficult it can be to properly manage that relationship. A non-functional relationship between the incoming and outgoing owners can divide the employee base, create confusion about who to approach with problems and opportunities, and can limit critical transfers of knowledge and relationships that incoming CEOs typically require.
Incoming owners often themselves in a bit of an awkward position during their first few months on the job: On one hand, they've likely just spent many months slogging through a protracted purchase process with the seller that was likely filled with contentious negotiations and several emotional disagreements. Yet on the other hand, almost immediately upon the closing of that acquisition, new CEOs will likely find themselves meaningfully in need of the help, knowledge and experience that only the person from whom they purchased the business can provide. In other words: Upon closing, what the seller wants from the buyer (mostly transaction proceeds) has already been received. What the buyer wants of the seller (help, knowledge transfer, introductions, and so on), hasn’t even yet begun.
To help us better understand how to manage this critical hand off process, I was joined this week by Les Trachtman, Author of “Don't F**k It Up: How Founders and Their Successors Can Avoid the Clichés That Inhibit Growth”. Les is a seasoned entrepreneur, educator, and author with over four decades of entrepreneurial experience. He is also an adjunct instructor at the Johns Hopkins University Carey Business School, and is a frequent guest lecturer at Harvard Business School, MIT and other academic institutions, where he often talks to students about the unappreciated nuances of Founder succession.
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This episode is brought to you by Boulay, the industry standard for Quality of Earnings, tax, and audit services, serving search fund entrepreneurs for 20+ years * This episode is brought to you by Oberle Risk Strategies: Insurance Broker and Insurance Due Diligence Provider for Search Funds and Other Small-to-Medium-Sized Businesses * When assuming the leadership role of a company that was previously held by its original Founder, new CEOs are often surprised at how difficult it can be to properly manage that relationship. A non-functional relationship between the incoming and outgoing owners can divide the employee base, create confusion about who to approach with problems and opportunities, and can limit critical transfers of knowledge and relationships that incoming CEOs typically require. Incoming owners often themselves in a bit of an awkward position during their first few months on the job: On one hand, they've likely just spent many months slogging through a protracted purchase process with the seller that was likely filled with contentious negotiations and several emotional disagreements. Yet on the other hand, almost immediately upon the closing of that acquisition, new CEOs will likely find themselves meaningfully in need of the help, knowledge and experience that only the person from whom they purchased the business can provide. In other words: Upon closing, what the seller wants from the buyer (mostly transaction proceeds) has already been received. What the buyer wants of the seller (help, knowledge transfer, introductions, and so on), hasn’t even yet begun. To help us better understand how to manage this critical hand off process, I was joined this week by Les Trachtman, Author of “Don't F**k It Up: How Founders and Their Successors Can Avoid the Clichés That Inhibit Growth”. Les is a seasoned entrepreneur, educator, and author with over four decades of entrepreneurial experience. He is also an adjunct instructor at the Johns Hopkins University Carey Business School, and is a frequent guest lecturer at Harvard Business School, MIT and other academic institutions, where he often talks to students about the unappreciated nuances of Founder succession.