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Why Founders Get Outmatched When Selling Their Business with Lewis Schiff

Your Next · 2026-05-24 · 40 min

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Episode notes

Most founders believe that because they built a successful business, they are prepared to sell it. Lewis Schiff believes that assumption can cost them millions. In this episode of Your N.E.X.T., Jerome Myers sits down with Lewis Schiff, Chairman of Birthing of Giants, to unpack why founders are entering one of the most important economic windows of our lifetime. An estimated $80 trillion in wealth is moving from older generations to younger ones, and that capital is looking for places to land. One of those places is founder-led lower middle market businesses. But there is a problem. The founder who built the company may only sell one business in their lifetime. The buyer across the table may buy ten companies a year. That imbalance creates risk. Lewis explains why private equity firms are aggressively pursuing founder-led companies, how professionalization can increase exit value, and why earn-outs often become traps for owners who were not fully prepared before going to market. Jerome and Lewis also explore one of the most important distinctions in the exit conversation: the difference between being an operator and being an owner. Operators make promises and keep promises.

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