Ep 499 After the Deal: The Hidden Cost of Generational Wealth

Ep 499 After the Deal: The Hidden Cost of Generational Wealth

Author: John Warrillow June 20, 2025 Duration: 49:54

You've built a valuable company. Maybe you're even thinking about selling. But what happens after the wire hits? 
 
In this episode of Built to Sell Radio, Alex Bean, co-founder of Divvy, shares what it felt like to sell his company for $2.5 billion—and why the real challenges began after the deal closed. 
 
This conversation will help you think more strategically about what you're really building—and how to avoid the regrets that often follow a big payday.


For any entrepreneur, the idea of selling the company they've built is both a daunting prospect and a potential pinnacle of success. Built to Sell Radio, hosted by John Warrillow, steps into that complex space with a clear, practical focus. This isn't about abstract theory; it's a weekly conversation grounded in real experience. Every episode features a different founder who has recently navigated the sale of their business. The discussion goes straight to the heart of the matter: understanding the personal and strategic reasons behind the decision to sell. Listeners get an honest breakdown of what worked, from preparation and valuation to negotiation, and perhaps more importantly, the unforeseen pitfalls and mistakes made along the way. It’s that candid post-mortem, the lessons learned in the trenches of a transaction, that provides unparalleled value. By compiling these firsthand accounts, the podcast builds a comprehensive library of exit strategies and cautionary tales. Tuning in feels like gaining access to a private mastermind, where seasoned entrepreneurs share the unvarnished truth about cashing in their life's work. If you're contemplating your own eventual exit, this series offers the nuanced, peer-to-peer insights you need to think like a buyer, protect your interests, and ultimately, build a business that is truly desirable. Built to Sell Radio serves as an essential guide, transforming the opaque process of selling a business into a clearer, more manageable journey.
Author: Language: English Episodes: 100

Built to Sell Radio
Podcast Episodes
Ep 542 The 15X Multiple That Let Him Walk Away in 12 Months [not-audio_url] [/not-audio_url]

Duration: 1:08:04
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Ep 539 Deal Collapsed at LOI, Sold for 6x EBITDA Anyway [not-audio_url] [/not-audio_url]

Duration: 45:42
Jay Richards spent five months deep in an acquisition process. He had a letter of intent. He had mentally checked out. He was planning what came next. Then issues surfaced in diligence and the deal collapsed. This week o…
Ep 537 Why this $5M Business Sold for $25M [not-audio_url] [/not-audio_url]

Duration: 1:06:38
When Sharon Gillenwater built Boardroom Insiders, she was doing something nobody else wanted to do: manually researching the personal work styles, business initiatives, and habits of Fortune 500 executives so that enterp…
Ep 534 Why a "short list" of acquirers may be a trap [not-audio_url] [/not-audio_url]

Duration: 58:17
Andrew McConnell built a SaaS company that helped vacation rental managers price homes like airlines using dynamic pricing based on demand. He eventually successfully exited, but not before learning the hard way that bui…