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

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.