Most entrepreneurs focus on how to sell their business. But what happens after the check clears?
Michael Sonnenfeldt sold two companies before the age of 43, making him wealthy beyond his expectations. But he quickly realized something most founders don’t: The skills that make you a great entrepreneur don’t necessarily make you a great investor.
That realization led him to create Tiger 21, a private network for ultra-high-net-worth individuals—people with at least $20 million in investable assets. Over the past 25 years, Sonnenfeldt has seen the best and worst investment decisions wealthy founders make after selling their businesses.
In this episode of Built to Sell Radio, you’ll discover:
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The biggest investing mistake entrepreneurs make after selling.
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Why angel investing is more of a hobby than a serious strategy for building wealth.
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How the ultra-wealthy structure their portfolios to preserve capital.
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The hidden emotional challenge of living off your investments.
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What “sticker shock” really means after an exit.
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How to strike the right balance between risk-on and risk-off investing.
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Why some founders struggle with spending their wealth after a lifetime of discipline.
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How ultra-wealthy parents think about raising kids that aren’t spoiled by money.
Whether you’re thinking about selling or just curious about how the ultra-wealthy manage their money, this episode offers a rare glimpse into what happens after the deal.
Quote of the Week
When you sell your business, the market tells you you’re a genius. That’s when you’re most dangerous.
Deals
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Pintail Completions, a provider of wireline services to the oilfield industry in the Permian Basin, has been acquired by RPC, Inc. (NYSE: RES) for approximately $245 million. Pintail generated $409 million in revenue in 2024, with the acquisition price reflecting a revenue multiple of approximately 0.60 times.
