08 May Built to Sell: $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.
In this week’s episode of Built to Sell Radio, you discover how to:
Negotiate the right to sell your acquirer’s stock immediately instead of accepting a hold period
Use an equity roll instead of an earn-out to stay aligned with the buyer
Structure a buyer-side call option with a fixed-price floor that increases over time
Add a multiple-of-gross-profit kicker so you participate when the business outperforms
Position professional services revenue as strategic, not lower quality
Push back on lockups, vesting, and other clauses using the “reasonable expectation at time of bargain” principle
Decide when stock may be more valuable than cash in a public-company acquisition
