Built to Sell Radio

A lot of owners are losing sleep over AI right now. They watch search traffic erode, they see competitors automating, and they wonder if the business they spent twenty years building is quietly becoming obsolete. 

Jaryd Krause sees it differently. He's a buyer. And when he looks at a 20-year-old company run by an owner who is "scared of AI and selling because of it," he sees an acquisition opportunity, not a write-off. 

Krause has been acquiring online businesses since 2014.

When Sean Kernan wanted out of the financial advisor support business he co-founded in Dallas, he didn't shop it to outside acquirers, and he didn't wait for his five partners to make him an offer. He engineered the buyout himself. Three and a half months from the first conversation to the wire hitting his account, $500,000 in cash, no earn-out, no holdback. 

In this episode, you discover how to: 

Open the conversation with your partners without triggering a defensive reaction or a stall 


Anchor your price to a prior valuation event so the number is hard to argue with 


Use a deliberately low ask as leverage to get speed, certainty, and 100% cash upfront 


Identify which one of your partners is most likely to write the check, and approach them first 


Source the cash from a platform partner, franchisor, or custodian who holds the underlying assets 


Negotiate a "ceasefire" non-compete that protects the buyers without trapping you 


Read inbound acquirer silence as market signal before you push the group toward a full sale 


Spot the partner who is too eager to buy, and what that eagerness usually means

There's an old idea in M&A called the Rembrandt in the attic. A company owns something valuable — a brand, a patent, a customer list, a data set — and nobody inside the business sees it for what it is. The right acquirer walks in, looks at the same asset through a different lens, and recognizes a masterpiece. 

Dori Yona spent six years and raised $14 million building what he thought was a price protection company for consumers. Earny tracked everything its users bought online and automatically clawed back refunds whenever the price dropped within the retailer's protection window. 

The model never quite worked. After two rounds of layoffs, a shutdown plan presented to the board, and a move out of the Santa Monica office, Dori pivoted to selling the one thing the company had in abundance: SKU-level purchase data on 3.5 million users. 

That pivot found the acquirer. 

To a consumer packaged goods (CPG) giant trying to understand what shoppers were actually putting in their carts during COVID, the data was the prize. The consumer app was almost incidental.

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.