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.

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.

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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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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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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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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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

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.

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 enterprise sales teams could finally get a meeting with the C-suite. It was hard, painstaking work — and that was exactly the point.

After more than a decade of bootstrapping, consulting on the side to fund payroll, and raising just $275,000 from three people she knew personally, Sharon sold Boardroom Insiders to London-based public company EuroMoney for $25 million — all cash at close, no earn-out. In this episode, you discover how to build and sell a business where customers love you so much they follow you from company to company.

You'll learn:

• Why a cold call from a PE firm offering $48 million was actually the worst thing that could have happened to Sharon — and what she did instead

• The one overheard side conversation that changed her negotiation posture entirely and helped her push from a $17–20M offer to $25M

• Why Sharon insisted on all cash at close — and why her angel investor told her a lower number in cash beats a higher number with strings attached

• What convertible notes look like after a decade — and why her investors converted their notes just six months before the sale

• Why Sharon cried on her birthday, the day she was quietly walked out of the company she had spent 13 years building

• How she watched the acquirer run Boardroom Insiders into the ground, tried to buy it back — and then decided to rebuild from scratch anyway

• The land-and-expand growth strategy that took Boardroom Insiders from zero to $5 million ARR without ever cracking the demand generation problem

Most founders approach a sale with one goal: get the highest price possible. But Mark Ferrer argues that focusing only on price can lead to the wrong deal, the wrong partner, and a painful transition after closing.

In this episode of Built to Sell Radio, John Warrillow talks with Ferrer about what he has learned after moving from founder to buyer, and why every owner needs to know whether they are a transactional, transitional, or transformative seller before they go to market. In this episode, you discover how to identify your seller type before a buyer does it for you.

You'll learn:

• Why a transactional founder who insists they just want the money often turns out to be something else entirely — and why getting that wrong poisons the deal

• What a buyer learns about you when they ask whether you would sell to your biggest competitor for the same price

• Why the multiple is just the starting point, and how cash at closing, seller financing, and rolled equity can swing the real outcome by more than most founders expect

• How Mark lost 8 to 14 percent of his own deal proceeds not because of bad faith, but because he did not ask the right questions about his rolled equity

• Why pushing for agreement after a sale closes is the fastest way to destroy a partnership — and what to focus on instead

• What working capital and normalized earnings actually mean, and why founders who gloss over both almost always regret it

• How to clarify the role you want after closing before it becomes the source of tension no one saw coming

Most business owners assume their buyer will be a private equity group or a strategic acquirer. But if you run a smaller business in a niche category, the person most likely to buy you is an individual — someone who likes what you've built, can see a path to improve it, and is willing to put their own name on the line to finance the deal.

This week on Built to Sell Radio, Joe Soelberg joins the Inside the Mind of an Acquirer series to pull back the curtain on what that kind of buyer actually looks like — and what it means for you as a seller. Listen and you discover how to:

• spot the tells of a real buyer versus "capital partners" theater

• pressure-test proof of funds without turning it adversarial

• use a seller note as a credibility filter, not just a concession

• understand why individual buyers consistently misread the cash down, seller note, bank structure and how to use that to your advantage

• ask questions that surface risk early, before lawyers get involved