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 533 Inside the Mind of an Acquirer: The Anatomy of a Failed Deal [not-audio_url] [/not-audio_url]

Duration: 1:00:08
This episode is part of our Inside the Mind of an Acquirer series, and it unpacks the ETA (Entrepreneurship Through Acquisition) wave now flooding the market. For business owners, ETA is a double-edged sword. On the upsi…
Ep 532 Is Your Business Worth More Dead or Alive? [not-audio_url] [/not-audio_url]

Duration: 57:11
We often think of a "successful exit" as handing over the keys to a perfectly oiled machine—a business that is growing, profitable, and operationally sound. But what happens when the machine starts to sputter? What if th…
Ep 531 The #1 M&A Mistake Founders Make with Nick Katz [not-audio_url] [/not-audio_url]

Duration: 45:00
acasa helps people run a shared home without the usual friction. It started as a simple way for housemates to track and split rent, bills, and groceries, then added payments and utility setup so households could manage r…
Ep 530 $40M for a Big Fish in a Small Pond [not-audio_url] [/not-audio_url]

Duration: 57:12
Nick Telson-Sillett and his co-founder built what you could call "OpenTable for bars and nightclubs" in the UK. Instead of chasing the US (the move most founders are told to make), they went big fish, small pond: dominat…
Ep 528  The Dirty Businesses that Create Quiet Millionaires [not-audio_url] [/not-audio_url]

Duration: 1:02:40
Some of the richest founders don't run trendy companies. They run dirty ones. The kind of work you'd never brag about at a dinner party, but that quietly throws off real money because it's hard, risky, and most people wo…
Ep 527 How to Avoid an Earn-Out (Even in a Service Business) [not-audio_url] [/not-audio_url]

Duration: 1:34:18
Most business owners hit a fork in the road. Stay "on the tools" and keep making great money. Or start feathering back your personal involvement so the business can grow beyond you. In this episode of Built to Sell Radio…
Ep 526 Best of 2025: 4 Moments That Change How You Exit [not-audio_url] [/not-audio_url]

Duration: 36:48
Built to Sell Radio just dropped a year-end special that pulls the strongest moments from 2025 into one episode. Across four formats (Exit Story, Inside the Mind of an Acquirer, Mastering the Deal, and After the Deal), y…