Ep 539 Deal Collapsed at LOI, Sold for 6x EBITDA Anyway

Ep 539 Deal Collapsed at LOI, Sold for 6x EBITDA Anyway

Author: John Warrillow March 27, 2026 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 on Built to Sell Radio, Jay walks John Warrillow through the full story of selling Imagen Insights, a qualitative research platform with clients like Visa, Google, and Amazon, and how you discover how to navigate two very different acquisition conversations and come out the other side with a deal you are genuinely happy with. 

You'll learn why: 

  • an LOI means far less than you think, and how problems in your books can kill a deal 

  • founders who shop their company can signal desperation, and what Jay did instead 

  • the eventual buyer valued the business on EBITDA instead of revenue, and why that worked in Jay's favor 

  • Jay accepted an earn-out worth more than half the deal, and why he was comfortable with it 

  • handing out equity without vesting created a problem at the worst possible moment 

  • a long-standing accountant relationship does not guarantee clean books, and how this nearly killed the deal 

  • the moment the DocuSign came through did not bring relief, but a flood of new ideas


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 548 Inside the Mind of an Acquirer: The Threat and Curse of AI [not-audio_url] [/not-audio_url]

Duration: 42:05
A lot of owners are losing sleep over AI right now. They watch search traffic erode, they see competitors automating, and they wonder if the business they spent twenty years building is quietly becoming obsolete. Jaryd K…
Ep 547 How to Get Your Partners to Buy You Out [not-audio_url] [/not-audio_url]

Duration: 47:05
When Sean Kernan wanted out of the financial advisor support business he co-founded in Dallas, he didn't shop it to outside acquirers, and he didn't wait for his five partners to make him an offer. He engineered the buyo…
Ep 546 $14M Raised, A Car-Changing Exit [not-audio_url] [/not-audio_url]

Duration: 47:47
There's an old idea in M&A called the Rembrandt in the attic. A company owns something valuable — a brand, a patent, a customer list, a data set — and nobody inside the business sees it for what it is. The right acquirer…
Ep 544 Why He Regrets Selling for 3.5X EBITDA [not-audio_url] [/not-audio_url]

Duration: 48:56
Boris Berenberg bootstrapped Atlas Authority, an Atlassian partner that resold Jira and Confluence to mid-market companies and built apps on top of the platform, to high seven figures in revenue with 18% net margins, the…
Ep 542 The 15X Multiple That Let Him Walk Away in 12 Months [not-audio_url] [/not-audio_url]

Duration: 1:08:04
At some point every founder needs to ask a simple question: is it better to own a big slice of a small pie, or a smaller slice of a bigger pie? In this week's episode, we hear from someone who chose a smaller slice of a…