Ep 548 Inside the Mind of an Acquirer: The Threat and Curse of AI

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. 

Ret Taylor spent his entire adult life chasing a number. First it was $30 million. Then $10 million. Then $6 million. Then he sat in a tent at 18,000 feet on Denali with two Arctic storms closing in and realized the number was never the point.  He came down the mountain, sold Ned, his natural remedies company, and now guides people through life transitions on multi-day vision quests in the mountains of Colorado.   Subscribe to our weekly newsletter: https://builttosell.com/subscribe/ Curious what your business is worth? Find out now

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 bigger pie. Simon Lorenz co-founded Klara, a patient communication platform for medical practices, and raised roughly $32 million across six rounds of outside capital before selling to ModMed at 15 times forward revenue.  The path there was not a clean one. Every funding round was painful. Most of them came down to a single term sheet, take it or leave it, because an early valuation had set an equity story Simon spent years chasing. He hired salespeople he later had to fire. He took on an apparatus he could not easily shut off. And when ModMed's CEO first reached out, Simon almost ignored the email because the company had finally started humming and he was preparing another round.  What turned a distraction into a deal was Simon's willingness to act genuinely uninterested, which pulled ModMed up to a price that made his eyeballs pop out. What let him walk away twelve months after closing was a single clause his lawyer negotiated into the contract.    Subscribe to our weekly newsletter: https://builttosell.com/subscribe/ Curious what your business is worth? Find out now

Most founders think they're not great negotiators. John Richardson thinks they're wrong. Richardson has spent decades teaching negotiation at MIT's Sloan School of Management and before that at Harvard Law, where he was an associate at the Harvard Negotiation Project and co-authored foundational texts with Roger Fisher and Howard Raiffa. His new book is called Never Settle. In this episode, you discover how to    Subscribe to our weekly newsletter: https://builttosell.com/subscribe/ Curious what your business is worth? Find out now

Murray Kent had no background in electrical conduit fittings when he paid $40,000 for a four-person business that, as he put it, looked like a bit of a crack den. What he did have was Value Builder's 8 drivers -- pinned to the wall next to his desk as a literal road map for every decision he made.  In this episode of Built to Sell Radio, you discover how to negotiate a clean exit with no earn-out complications and no equity rollover.  You'll learn:    Subscribe to our weekly newsletter: https://builttosell.com/subscribe/ Curious what your business is worth? Find out now

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 on Built to Sell Radio, Jay walks John Warrillow through the full story of selling Imagen Insights, a qualitative research platform with clients like Visa, Google, and Amazon, and how you discover how to navigate two very different acquisition conversations and come out the other side with a deal you are genuinely happy with.  You'll learn why:  an LOI means far less than you think, and how problems in your books can kill a deal  founders who shop their company can signal desperation, and what Jay did instead  the eventual buyer valued the business on EBITDA instead of revenue, and why that worked in Jay's favor  Jay accepted an earn-out worth more than half the deal, and why he was comfortable with it  handing out equity without vesting created a problem at the worst possible moment  a long-standing accountant relationship does not guarantee clean books, and how this nearly killed the deal  the moment the DocuSign came through did not bring relief, but a flood of new ideas