Built to Sell Radio

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Ep 547 How to Get Your Partners to Buy You Out May 22, 2026

Show notes

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 buyout himself. Three and a half months from the first conversation to the wire hitting his account, $500,000 in cash, no earn-out, no holdback.

In this episode, you discover how to:

Open the conversation with your partners without triggering a defensive reaction or a stall

Anchor your price to a prior valuation event so the number is hard to argue with

Use a deliberately low ask as leverage to get speed, certainty, and 100% cash upfront

Identify which one of your partners is most likely to write the check, and approach them first

Source the cash from a platform partner, franchisor, or custodian who holds the underlying assets

Negotiate a "ceasefire" non-compete that protects the buyers without trapping you

Read inbound acquirer silence as market signal before you push the group toward a full sale

Spot the partner who is too eager to buy, and what that eagerness usually means

Ep 546 $14M Raised, A Car-Changing Exit May 15, 2026

Show notes

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 walks in, looks at the same asset through a different lens, and recognizes a masterpiece.

Dori Yona spent six years and raised $14 million building what he thought was a price protection company for consumers. Earny tracked everything its users bought online and automatically clawed back refunds whenever the price dropped within the retailer's protection window.

The model never quite worked. After two rounds of layoffs, a shutdown plan presented to the board, and a move out of the Santa Monica office, Dori pivoted to selling the one thing the company had in abundance: SKU-level purchase data on 3.5 million users.

That pivot found the acquirer.

To a consumer packaged goods (CPG) giant trying to understand what shoppers were actually putting in their carts during COVID, the data was the prize. The consumer app was almost incidental.

Ep 545 $15M for 15 Employees — How Aaron Leibtag Structured His Pentavere Sale to HealWell May 08, 2026

Show notes

Aaron Leibtag was one of the most popular guests in Built to Sell Radio history. He sold his 15-employee bootstrapped healthcare AI company, Pentavere, for $15 million.

Pentavere built AI to unlock patient data trapped inside PDFs and clinical notes years before large language models existed.

The headline number was $15 million. What it did not reveal was the structure underneath. Part of the consideration was paid in the volatile stock of the acquirer. Aaron and his partners also rolled 49% of their equity into the new entity. Now Aaron returns, and you might be surprised to learn how it all played out.

When it comes time to sell, most business owners want 100% cash at closing. Almost no one gets it. Most deals come with structure, and structure usually comes down to three levers: what currency the buyer pays you in (cash versus stock), how they keep you tied to the future after giving up control (earn-out versus equity roll), and what rights either side has to unwind the relationship later.

Ep 544 Why He Regrets Selling for 3.5X EBITDA May 01, 2026

Show notes

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, then sold to private equity in May 2022.

A year later he wrote a blog post titled "I regret selling my startup" that went viral inside the exited founder community.

Ep 543 From $32M Valuation to Fire Sale — How Ret Taylor Sold Ned After an Apple Update Crushed His Margins and Re-Invented Himself as a Spiritual Guide Apr 24, 2026

Show notes

Ret Taylor spent his entire adult life chasing a number. First it was $30 million. Then $10 million. Then $6 million. Then he sat in a tent at 18,000 feet on Denali with two Arctic storms closing in and realized the number was never the point.

He came down the mountain, sold Ned, his natural remedies company, and now guides people through life transitions on multi-day vision quests in the mountains of Colorado.

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Ep 542 The 15X Multiple That Let Him Walk Away in 12 Months Apr 17, 2026

Show notes

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 bigger pie. Simon Lorenz co-founded Klara, a patient communication platform for medical practices, and raised roughly $32 million across six rounds of outside capital before selling to ModMed at 15 times forward revenue.

The path there was not a clean one. Every funding round was painful. Most of them came down to a single term sheet, take it or leave it, because an early valuation had set an equity story Simon spent years chasing. He hired salespeople he later had to fire. He took on an apparatus he could not easily shut off. And when ModMed's CEO first reached out, Simon almost ignored the email because the company had finally started humming and he was preparing another round.

What turned a distraction into a deal was Simon's willingness to act genuinely uninterested, which pulled ModMed up to a price that made his eyeballs pop out. What let him walk away twelve months after closing was a single clause his lawyer negotiated into the contract.

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Ep 541 Mastering the Deal: 7-Figure Negotiation Mistakes Founders Make When Selling Their Business with MIT's John Richardson, Author of Never Settle Apr 10, 2026

Show notes

Most founders think they're not great negotiators. John Richardson thinks they're wrong. Richardson has spent decades teaching negotiation at MIT's Sloan School of Management and before that at Harvard Law, where he was an associate at the Harvard Negotiation Project and co-authored foundational texts with Roger Fisher and Howard Raiffa. His new book is called Never Settle. In this episode, you discover how to

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Ep 540 From $40K to 8 Figures -- How Murray Kent Sold His Electrical Conduit Business for 6.2x EBITDA Apr 03, 2026

Show notes

Murray Kent had no background in electrical conduit fittings when he paid $40,000 for a four-person business that, as he put it, looked like a bit of a crack den. What he did have was Value Builder's 8 drivers -- pinned to the wall next to his desk as a literal road map for every decision he made.

In this episode of Built to Sell Radio, you discover how to negotiate a clean exit with no earn-out complications and no equity rollover.

You'll learn:

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Ep 539 Deal Collapsed at LOI, Sold for 6x EBITDA Anyway Mar 27, 2026

Show notes

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

Ep 538 How 2 Brothers Bootstrapped AppArmor to a $40M Exit — The Answer That Almost Cost Them $20M Mar 20, 2026

Show notes

David Sinkinson and his brother Chris built AppArmor over eleven years without taking a single dollar from outside investors. They bootstrapped it by running side businesses, plowing the profits back in, and staying lean through long sales cycles and compliance-heavy buyers. By the time they were ready to sell, they had over 250 universities on the platform and roughly $6 million in annual recurring revenue — profitable, with no cap table to split with anyone.

Then an acquirer asked them a simple question, and they answered it. That answer nearly cost them $20 million.

Recorded live at the Value Builder Summit, this is David Sinkinson's second appearance on Built to Sell Radio. This time he goes beyond the mechanics of the deal — into the surprising struggles he faced after the sale, and a take on employee equity that is going to challenge what most founders believe.

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