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

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

Author: John Warrillow May 8, 2026 Duration: 48:03

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. 


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: 50

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
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…
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…