Ep 507 After the Deal: Why Adam Rossi Wanted to Undo His Exit
Release Date: 08/15/2025
Ep 543 From $32M Valuation to Fire Sale — How Ret Taylor Sold Ned After an Apple Update Crushed His Margins and Re-Invented Himself as a Spiritual Guide
Built to Sell Radio
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.
info_outline
Ep 542 The 15X Multiple That Let Him Walk Away in 12 Months
Built to Sell Radio
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...
info_outline
Ep 541 Mastering the Deal: 7-Figure Negotiation Mistakes Founders Make When Selling Their Business with MIT's John Richardson, Author of Never Settle
Built to Sell Radio
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 use a "best guess" about a buyer's motivations to get them talking, even when they're deliberately keeping their cards...
info_outline
Ep 540 From $40K to 8 Figures -- How Murray Kent Sold His Electrical Conduit Business for 6.2x EBITDA
Built to Sell Radio
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: Why posting the eight drivers next to your desk changes the decisions you make every day How Murray...
info_outline
Ep 539 Deal Collapsed at LOI, Sold for 6x EBITDA Anyway
Built to Sell Radio
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. ...
info_outline
Ep 538 How 2 Brothers Bootstrapped AppArmor to a $40M Exit — The Answer That Almost Cost Them $20M
Built to Sell Radio
David Sinkinson and his brother Chris built AppArmor over eleven years without taking a single dollar from outside investors. They bootstrapped it by running side businesses, plowing the profits back in, and staying lean through long sales cycles and compliance-heavy buyers. By the time they were ready to sell, they had over 250 universities on the platform and roughly $6 million in annual recurring revenue — profitable, with no cap table to split with anyone. Then an acquirer asked them a simple question, and they answered it. That answer nearly cost them $20...
info_outline
Ep 537 Why this $5M Business Sold for $25M
Built to Sell Radio
When Sharon Gillenwater built Boardroom Insiders, she was doing something nobody else wanted to do: manually researching the personal work styles, business initiatives, and habits of Fortune 500 executives so that enterprise sales teams could finally get a meeting with the C-suite. It was hard, painstaking work — and that was exactly the point. After more than a decade of bootstrapping, consulting on the side to fund payroll, and raising just $275,000 from three people she knew personally, Sharon sold Boardroom Insiders to London-based public...
info_outline
Ep 536 Mastering the Deal: 3 Types of Sellers, 3 Very Different Deals — Which One Are You?
Built to Sell Radio
Most founders approach a sale with one goal: get the highest price possible. But Mark Ferrer argues that focusing only on price can lead to the wrong deal, the wrong partner, and a painful transition after closing. In this episode of Built to Sell Radio, John Warrillow talks with Ferrer about what he has learned after moving from founder to buyer, and why every owner needs to know whether they are a transactional, transitional, or transformative seller before they go to market. In this episode, you discover how to identify your seller type before a buyer does it...
info_outline
Ep 535 Inside the Mind of an Acquirer: When Your Buyer Is Risking Their House
Built to Sell Radio
Most business owners assume their buyer will be a private equity group or a strategic acquirer. But if you run a smaller business in a niche category, the person most likely to buy you is an individual — someone who likes what you've built, can see a path to improve it, and is willing to put their own name on the line to finance the deal. This week on Built to Sell Radio, Joe Soelberg joins the Inside the Mind of an Acquirer series to pull back the curtain on what that kind of buyer actually looks like — and what it means for you as a seller. Listen and you discover how...
info_outline
Ep 534 Why a “short list” of acquirers may be a trap
Built to Sell Radio
Andrew McConnell built a SaaS company that helped vacation rental managers price homes like airlines using dynamic pricing based on demand. He eventually successfully exited, but not before learning the hard way that building a company and selling one require two entirely different skill sets. In this episode of Built to Sell Radio, Andrew walks through the pivot that saved his business, why his VC backers stayed on board, and the exact moment he realized that a "short buyer list" is a dangerous trap for founders. Listen in to discover how to: ...
info_outlineAdam Rossi built a 250-employee software company serving law enforcement and intelligence agencies. They routinely beat Lockheed Martin in head-to-head bids.
Then a banker came back with five acquisition offers — each at the “absurd” number Adam and his wife had thrown out as a hypothetical. The winning bid came from SRA International, a publicly traded defense contractor, for a price that created generational wealth for his family. Adam took all cash and walked away with no earn-out.
But as Adam discovered, the hard part wasn’t negotiating the deal — it was figuring out what to do after it closed.