PODCAST · business
Built to Sell Radio
by John Warrillow
Built to Sell Radio is a weekly podcast for business owners interested in selling a business. Each week, we ask an entrepreneur who has recently sold a business why they decided to sell their business, what they did right and what mistakes they made through the process of exiting their business. Built to Sell Radio is the ultimate insider's guide to approaching the most important financial transaction of your life.
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Ep 552: What to Know Before Selling to an ETA Buyer | Built to Sell Radio
What do you need to know before selling your business to an ETA buyer? Most owners have received the email. It usually starts with something flattering: "I love what you've built…" Then comes the ask: a quick call to learn more about your business. Increasingly, those emails are coming from ETA buyers — entrepreneurs using entrepreneurship through acquisition as their path into business ownership. Instead of starting a company from scratch, they look to buy an existing business and run it themselves. In this episode of Built to Sell Radio, John Warrillow talks with Will Smith, host of Acquiring Minds, one of the leading podcasts covering entrepreneurship through acquisition. Will has interviewed hundreds of ETA buyers and brings rare insight into how they think, how they finance deals, and where deals fall apart. What You'll Learn in This Episode Whether you're actively considering selling your business or just exploring your options, this conversation covers what every owner should understand before entertaining an offer from an ETA buyer: How to tell the difference between a funded searcher and a self-funded buyer — and why it matters for your deal structure Why some ETA buyers use heavy debt to acquire a business — and what that means for you as a seller How to spot the hidden risk in a seller note — a key piece of most ETA transactions How to evaluate whether a young buyer has the leadership experience to run your company after you exit How to protect your employees from a buyer who may not fit your culture Better questions to ask before signing a letter of intent (LOI) with an ETA buyer How to judge whether a buyer can actually close — not just sign Are ETA Buyers Right for Your Business? ETA buyers can be a great fit for owners of profitable niche businesses that may not attract private equity or a strategic acquirer. They're often motivated, passionate, and willing to pay fair value for the right business. But they come with real risks. A buyer may need your financing — in the form of a seller note — to get the deal done. They may still need to raise money after you sign an LOI. And they may look great on paper but struggle to lead the team you've built over years. That's why this conversation is worth your time. Before you take the next call from someone who says they "love what you've built," listen to this episode. About Will Smith Will Smith is the host of Acquiring Minds, a podcast dedicated to entrepreneurship through acquisition. He has interviewed hundreds of search fund entrepreneurs and self-funded searchers, making him one of the most knowledgeable voices on the ETA buyer landscape. About Built to Sell Radio Built to Sell Radio is hosted by John Warrillow, author of Built to Sell: Creating a Business That Can Thrive Without You. Each week, John interviews business owners who have navigated the process of selling their company — sharing what worked, what didn't, and what every owner should know before they sell. Keywords: ETA buyer, entrepreneurship through acquisition, selling your business, search fund, seller note, business acquisition, how to sell a business, Built to Sell Radio, Will Smith Acquiring Minds, exit strategy, business exit planning
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Ep 551 Cameron Passmore Sold Half an $8 Billion Firm—Then Acquired 5 More Businesses
Knowing what kind of seller you are turns out to be one of the most important things you can figure out before you ever take a meeting with a potential acquirer. There are three: the transactional seller who wants the money and the door, the transitional seller who wants to land the plane, and the transformational seller who sells to go bigger. Cameron Passmore built one of the largest independent wealth management firms in Canada, roughly 3,000 families and about $8 billion under management, and owned half of it. Most founders in that seat cash out and leave. Cameron sold to OneDigital at 60, and has no intention of going anywhere. He rolled 40% of the deal into equity, and now uses OneDigital's capital, deal expertise, and acquisition currency to buy other firms. He has acquired five and roughly doubled the business in under two years.
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Ep 550 The One Phrase That Can Ruin a $10 Million Business Sale
"When I sell the company, then I'll be happy." Psychotherapist Jo Swann says that one phrase is the most reliable predictor of a miserable exit. She would know. She made her money in the 90s, retired to an oceanfront apartment in Borneo, and fell straight into an existential crisis. In this episode of Built to Sell Radio, part of our popular After the Deal series, Swann explains why the trap survives the wire transfer
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Ep 549 How a $105 Million Business Sale Revealed the Second Most Important Number in an LOI
Every founder fixates on the multiple. Tim Hellebrand will tell you the (second) most important number on a letter of intent is the one almost nobody understands until it is too late: working capital. When Tim and his four brothers took their $105 million family appliance business to market, six letters of intent came back, and the spread between the lowest and the highest was 60 percent. Most of that gap had nothing to do with the multiple. Don's Appliances ran on a mountain of inventory, refrigerators and ranges and washers sitting across two distribution centers, and every buyer had a different view of how much of that had to stay locked in the company on closing day. Whatever stayed in was money the brothers did not get to take home. Tim assumed they would simply get their inventory money back. That is not how it works.
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Ep 548 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.
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Ep 547 How to Get Your Partners to Buy You Out
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
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Ep 546 $14M Raised, A Car-Changing Exit
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.
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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.
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Ep 544 Why He Regrets Selling for 3.5X EBITDA
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.
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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
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
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Ep 542 The 15X Multiple That Let Him Walk Away in 12 Months
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
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Ep 541 Mastering the Deal: 7-Figure Negotiation Mistakes Founders Make When Selling Their Business with MIT's John Richardson, Author of Never Settle
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
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Ep 540 From $40K to 8 Figures -- How Murray Kent Sold His Electrical Conduit Business for 6.2x EBITDA
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
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Ep 539 Deal Collapsed at LOI, Sold for 6x EBITDA Anyway
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
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Ep 538 How 2 Brothers Bootstrapped AppArmor to a $40M Exit — The Answer That Almost Cost Them $20M
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 million. Recorded live at the Value Builder Summit, this is David Sinkinson's second appearance on Built to Sell Radio. This time he goes beyond the mechanics of the deal — into the surprising struggles he faced after the sale, and a take on employee equity that is going to challenge what most founders believe.
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Ep 537 Why this $5M Business Sold for $25M
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 company EuroMoney for $25 million — all cash at close, no earn-out. In this episode, you discover how to build and sell a business where customers love you so much they follow you from company to company. You'll learn: Why a cold call from a PE firm offering $48 million was actually the worst thing that could have happened to Sharon — and what she did instead The one overheard side conversation that changed her negotiation posture entirely and helped her push from a $17–20M offer to $25M Why Sharon insisted on all cash at close — and why her angel investor told her a lower number in cash beats a higher number with strings attached What convertible notes look like after a decade — and why her investors converted their notes just six months before the sale Why Sharon cried on her birthday, the day she was quietly walked out of the company she had spent 13 years building How she watched the acquirer run Boardroom Insiders into the ground, tried to buy it back — and then decided to rebuild from scratch anyway The land-and-expand growth strategy that took Boardroom Insiders from zero to $5 million ARR without ever cracking the demand generation problem
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Ep 536 Mastering the Deal: 3 Types of Sellers, 3 Very Different Deals — Which One Are You?
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 for you. You'll learn: Why a transactional founder who insists they just want the money often turns out to be something else entirely — and why getting that wrong poisons the deal What a buyer learns about you when they ask whether you would sell to your biggest competitor for the same price Why the multiple is just the starting point, and how cash at closing, seller financing, and rolled equity can swing the real outcome by more than most founders expect How Mark lost 8 to 14 percent of his own deal proceeds not because of bad faith, but because he did not ask the right questions about his rolled equity Why pushing for agreement after a sale closes is the fastest way to destroy a partnership — and what to focus on instead What working capital and normalized earnings actually mean, and why founders who gloss over both almost always regret it How to clarify the role you want after closing before it becomes the source of tension no one saw coming
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Ep 535 Inside the Mind of an Acquirer: When Your Buyer Is Risking Their House
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 to: spot the tells of a real buyer versus "capital partners" theater pressure-test proof of funds without turning it adversarial use a seller note as a credibility filter, not just a concession understand why individual buyers consistently misread the cash down, seller note, bank structure and how to use that to your advantage ask questions that surface risk early, before lawyers get involved
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Ep 534 Why a "short list" of acquirers may be a trap
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: Spot the "hidden ceiling" in a business that looks like it's doubling—right up until it isn't. Move a cap table from a failed bet into a new one without lighting your professional relationships on fire. Understand liquidation preference in plain English (and why it can erase a founder's take-home pay at exit). See why a banker's real value isn't just managing the process—it's forcing pressure and widening the field of potential acquirers Avoid the "I can sell this myself" mindset that often results in a year of free research for buyers and zero leverage for you.
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Ep 533 Inside the Mind of an Acquirer: The Anatomy of a Failed Deal
This episode is part of our Inside the Mind of an Acquirer series, and it unpacks the ETA (Entrepreneurship Through Acquisition) wave now flooding the market. For business owners, ETA is a double-edged sword. On the upside, more buyers courting you means more choice, more urgency, and more liquidity. On the downside, many ETA buyers are first-timers who lean on heavy leverage and seller financing. If they misread your business or hit a snag they can't handle, the part of the deal you financed can quickly become the part you never collect.
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Ep 532 Is Your Business Worth More Dead or Alive?
We often think of a "successful exit" as handing over the keys to a perfectly oiled machine—a business that is growing, profitable, and operationally sound. But what happens when the machine starts to sputter? What if the margins are too thin, the operations are exhausting, and you are simply burned out? It is easy to assume that a broken business model means a worthless company. But as this week's guest on Built to Sell Radio proves, sometimes the individual parts are worth more than the whole. Meet Jason Patel. Jason built Transitions Education, a college counseling marketplace. On the surface, it looked great: upper six-figure revenue and a noble mission. But under the hood, customer acquisition costs were eating his margins, and he was carrying $250,000 in personal debt to keep it afloat. He was ready to walk away. He assumed he had zero leverage. Then, a "Micro Private Equity" firm reached out. They didn't want his headaches. They didn't want his operations. They didn't even want his business model. They wanted his "parts." Specifically, they wanted his SEO ranking, his blog traffic, and his 5-star reputation. They realized they could strip away the expensive service delivery and plug his high-performing marketing assets into their own portfolio. In this episode, Jason breaks down how he structured an asset sale that allowed him to: Sell the high-value "parts" (marketing assets) without the operational baggage. Avoid a grueling earn-out (because the buyer didn't need him to run the company). Pay off his debt and fund his next venture. If you feel like your business model is grinding you down, this episode will open your eyes to the hidden value sitting on your balance sheet right now.
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Ep 531 The #1 M&A Mistake Founders Make with Nick Katz
acasa helps people run a shared home without the usual friction. It started as a simple way for housemates to track and split rent, bills, and groceries, then added payments and utility setup so households could manage recurring bills in one place. When Nick Katz tried to sell acasa on his own, the downside wasn't just a slow process. It created a setup where buyers had the leverage: they could keep asking for information, keep "exploring," and never commit to an LOI.
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Ep 530 $40M for a Big Fish in a Small Pond
Nick Telson-Sillett and his co-founder built what you could call "OpenTable for bars and nightclubs" in the UK. Instead of chasing the US (the move most founders are told to make), they went big fish, small pond: dominate their home market first. That focus helped them build DesignMyNight into a business that sold for more than $40M. In this episode of Built to Sell Radio, Nick shares what happened, so you discover how to: Turn one clear customer frustration into a business idea you can explain fast Choose focus over hype when everyone tells you to chase the biggest market Set a "financial freedom" number and use it to make cleaner decisions Run a sale process without tipping off competitors too early Negotiate an earn-out tied to revenue so the targets stay in your control Plan for the morning after the deal, when your identity gets reset
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Ep 529 The Personal Brand Trap and how to slash a 3-Year Earn-Out to 9 Months Without Giving Up Value
The fastest way to make a service company unsellable is building it around a personal brand. When clients hire you—because of your reputation, your name, and your specific expertise—you haven't built a business; you've built a high-paying job. And as Gavin Bell realized, you can't sell a reputation. Gavin was known as the "Facebook Ads Guy" in the UK. He was making good money, but he knew that to build a sellable asset, he had to fire himself as the face of the company. He rebranded his firm from "Gavin Bell" to "Yatter," productized his service, and systematically removed himself from sales and delivery. The result? He sold Yatter to a larger agency, Velstar, in a deal that closed just one minute before a major tax deadline. In this episode of Built to Sell Radio, Gavin breaks down exactly how he made the switch.
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Ep 528 The Dirty Businesses that Create Quiet Millionaires
Some of the richest founders don't run trendy companies. They run dirty ones. The kind of work you'd never brag about at a dinner party, but that quietly throws off real money because it's hard, risky, and most people won't do it. This Built to Sell Radio episode follows Shenar Wood, who built an underground power business by taking on personal risk, earning trust job by job, and eventually selling when he hit a ceiling that had nothing to do with demand, you discover how to: Recognize the hidden ceiling that has nothing to do with demand and everything to do with your balance sheet Stop confusing "more revenue" with "more value" when margin and risk aren't improving Build a reputation flywheel where customers feed you better work because they trust how you operate Separate assets from value so you don't overestimate what a buyer will pay for "stuff" Fix the financial story before a buyer forces an expensive cleanup under pressure Negotiate earn-out terms so the buyer can't hit your results by moving costs onto your books Decide when it's smarter to sell now than grind for years just to add a rounding error to valuation
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Ep 527 How to Avoid an Earn-Out (Even in a Service Business)
Most business owners hit a fork in the road. Stay "on the tools" and keep making great money. Or start feathering back your personal involvement so the business can grow beyond you. In this episode of Built to Sell Radio, Dr. Michael Filosi walks through how he made that shift in a dental practice, without jeopardizing cash flow. He didn't rip the band-aid off. He reduced his patient days one day at a time while the practice added clinicians and transitioned patients carefully. Over a few years, his billings went from roughly 43% of revenue to single digits, and he only went to zero once the business was already producing most of his take-home income. In this episode, you discover how to Spot the "capped upside" moment when your time becomes the constraint Feather back from four days on the tools to three, then two, then zero Time each reduction using numbers, not hope Transition customers off the owner without breaking trust Remove key-person risk by ensuring no one producer dominates revenue Keep cash flow steady while you trade personal production for enterprise value The result: Filosi sold his practice and collected 100% of his cash at closing, which is almost unheard of in dentistry.
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Ep 526 Best of 2025: 4 Moments That Change How You Exit
Built to Sell Radio just dropped a year-end special that pulls the strongest moments from 2025 into one episode. Across four formats (Exit Story, Inside the Mind of an Acquirer, Mastering the Deal, and After the Deal), you discover how to Choose exit value over lifestyle income before comfort caps valuation Spot the "founder-dependent" trap that scares off serious buyers See how buyers price risk, not just revenue and EBITDA Use imperfections as leverage instead of liabilities Build leverage before a first offer quietly sets your ceiling Create real alternatives so negotiations stop feeling one-sided Prepare for the identity shift that hits after the wire clears
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Ep 525 How to Know When to Get Out: What to do when Shopify threatens, Selling vs. hiring a CEO. A controlled process instead of massive auction and getting your cash up front.
If you're feeling a little queasy about the pace of change, you're not alone. AI is accelerating competition in almost every market, and it's making some business models feel irrelevant almost overnight. In this episode of Built to Sell Radio, John Warrillow talks with Ryan O'Leary, who saw a similar wave coming in payments when Shopify started bundling merchant processing into its plans. O'Leary chose to sell before the shift crushed margins, structuring a deal that put most of his cash in hand up front. In this episode, you discover how to • Decide whether to raise capital, hire a CEO, roll equity, or sell • Spot the early signals that a platform is about to "bundle" you into irrelevance • Run a tight sale process with a short target list and still generate multiple LOIs fast • Negotiate for deal structure that protects you, not just a higher multiple • Limit earnout risk by keeping the earnout short and the rules hard to game • Separate emotion from the numbers so you can negotiate clean • Keep your team aligned through the transition by sharing upside, including the earnout
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Ep 524 3 Non-Negotiables to Walk Away Clean, Turn Your Expertise into Recurring Revenue, and Avoiding a Deal-Killing Clause.
Most experts who start a practice or studio end up trapped by their own success. The schedule is packed, the waitlist is long, but every dollar still depends on them showing up. In this week's episode of Built to Sell Radio, John talks to a physical therapist who turned a fully booked, owner-dependent practice into a boutique fitness business with recurring revenue, a second-in-command, and a clean exit on her terms. After a first deal collapsed on closing day thanks to a last-minute bank clause, she went back to market with three non-negotiables and still got a seven-figure outcome.
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Ep 523 15 x EBITDA for a Service Firm
In this episode of Built to Sell Radio, John Warrillow sits down with Ujwal Arkalgud, who built the same company twice. Chapter one was a classic problem: a profitable, founder-heavy services firm with impressive EBITDA but a ceiling on valuation. Chapter two began when he turned that service into a productized offering, transformed how customers bought his work, and ultimately sold for more than 15x EBITDA — roughly three times the offer he received as a simple service provider.
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Ep 522 The difference between 4x vs.8x EBITDA, Customer Concentration Discounts, PE Re-trades with Eric Wiklendt on this special edition of Inside the Mind of an Acquirer
For many owners, private equity feels like a black box: a buyer shows up with a multiple, some debt, and a term sheet, and it is hard to tell whether you are getting a fair shake or being set up for a painful re-trade later. In this Inside the Mind of an Acquirer episode of Built to Sell Radio, John Warrillow sits down with Speyside Equity managing director Eric Wiklendt.
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Ep 521 10x Outcome Selling Tiny to Private Equity and how to make the 'Cruise vs Double Down' Decision
Andrew Roberts spent two decades turning a bootstrapped family company from Brisbane into one of the most widely used text editors on the web, then faced the hardest call of his career: keep a comfortable, profitable business or push for a bigger exit with venture capital and private equity in the mix.
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Ep 520 How Chris Hutchins convinced Google to buy Milk—and Wealthfront to acquire Grove—despite not generating much revenue (and no EBITDA)
A strategic acquirer is a company buying to advance its own roadmap, distribution, or capabilities—unlike financial buyers (private equity, family offices) who buy primarily for cash flow. To a strategic, value may sit in what you've built, not what you've earned. Chris Hutchins' story makes the point. He co-founded Milk, acquired by Google, and later founded Grove, acquired by Wealthfront. Both saw assets they could plug in—product, team, IP—even when revenue and EBITDA weren't impressive. If you want a strategic acquirer to pay for what you've built rather than how much money you make, this episode of Built to Sell Radio is for you. You'll discover how to: • Define and prioritize the assets a strategic may value now (team, product, customer list, roadmap, even your lease) • Reframe your pitch so a distribution-rich buyer may see an immediate lift from your assets • Run a fast, momentum-led process that invites quick noes and surfaces real interest • Split assets across buyers when it improves the overall outcome • Protect employees and customers while you move quickly toward a decision If a strategic exit is on your radar, this playbook helps you create options when EBITDA won't carry the deal.
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Ep 519 How to Avoid the Unforced Errors That Can Wipe Out Your Equity
Spencer Dennis was an elite golfer whose playing career ended with spine surgery in his teens. He became a tour-level coach, running high-performance programs for juniors, college players, and pros. Managing parents, trainers, and recruiters through texts and email was chaos, so he built CoachNow to guide athletes between sessions. CoachNow caught on quickly with busy coaches. Then a run of decisions—turning off revenue under "grow fast" advice, stacking convertibles and preferences, and accepting stock-for-stock deals—left Spencer with little to show for a product customers loved. This is a cautionary tale for any owner negotiating with "sophisticated" investors.
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Ep 518 Growth Equity, Control, and When Rolling Equity Fails — John Ruffolo (Inside the Mind of an Acquirer)
If you're considering your endgame, you're probably looking at private equity. Most PE firms use a familiar formula: buy a majority stake and ask the owner to "roll equity"—re-invest part of the proceeds—into the newco they're building. The downside: you become a minority shareholder in a business you no longer control. There's another path: growth equity, which lets you take chips off the table via a secondary while maintaining control. That's the business John Ruffolo is in as Founder & Managing Partner at Maverix Private Equity (he also founded OMERS Ventures).
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Ep 517 The Surprising Truth of a 9-Figure Exit — and How Not to Lose $23 Million (After the Deal)
If you've ever noticed those ads inside a mobile game, you have Zain Jaffer to thank. He co-founded Vungle and helped popularize rewarded video ads—the ones that revive your character or hand you in-app currency after you watch. In this Built to Sell Radio episode, Zain explains how he rode the smartphone wave to a $780M all-cash exit to Blackstone—and why he personally took home more than $100M. Then he gets candid about what came next.
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Ep 516 How Joyride Fetched 7x Revenue for a Business Selling Abandoned Cars (Exit Story)
Most cities have a problem: what to do with cars that get towed and never picked up. They pile up in impound lots—taking up space and tying up cash. Stan Markuze helped solve that problem by co-founding Joyride Auto, an online auction platform where repair shops, scrap dealers, and car enthusiasts can buy those abandoned vehicles directly from the lot. In this episode, Stan shares how he and his co-founders built a cash-flow-positive business that turned a clunky, paper-based process into a digital marketplace—and sold it to a private-equity firm for seven times revenue in just two years.
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Ep 515 Inside the Mind of an Acquirer with Valtech's Randy Woods
After a 23-year journey building Non-Linear Creations into a marketing giant with more than 120 employees, Randy Woods sold it in 2017 to Valtech. Valtech is a distinguished digital agency offering marketing, digital technology, and business transformation consulting services. Post-sale, Woods now serves as the SVP of Strategic Growth Opportunity at Valtech, a role dedicated to identifying potential acquisitions for the business. In the latest installment of Built to Sell Radio's Inside the Mind of an Acquirer series, we sit down with Woods to discuss how to: Make your company irresistible to an acquirer. Leverage a "put option" to cover your downside. Understand the factors that influence how acquirers value businesses. Target potential acquirers who would see your company as a strategic addition. Avoid deal breakers during negotiations with potential acquirers.
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Ep 514 Why the Old Private Equity Playbook is Dead - Inside the Mind of an Acquirer with Lee McCabe
Today's episode of Built to Sell Radio is part of our Inside the Mind of an Acquirer series. John Warrillow interviews Lee McCabe, a former Meta and Alibaba executive turned private equity investor—now an advisor helping PE firms modernize how they create value. McCabe argues the old model of buying cheap, piling on debt, and hoping for multiple expansion is over. Interest rates are up, LPs are demanding more, and the firms that win will need to act more like operators than bankers. If you're planning to sell, and private equity is your natural buyer, you'll want to hear this.
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Ep 513 Exit Story: How Dave Sifry Lost $100 Million, Lessons from Starting 9 Companies, the Dangers of Raising Money, and Why He's Doing It Differently with Warmstart
Dave Sifry has founded nine companies, including Technorati and Linuxcare, raising more than $170 million along the way. In this episode of Built to Sell Radio, he reveals how he went from being worth more than $100 million on paper to watching that value disappear — and what he'd do differently if he had the chance again. Despite those scars, Sifry has built an extraordinary career. He has founded nine companies and today is founder and CEO of Warmstart, a platform that helps entrepreneurs turn old contacts into new business.
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Ep 512 Exit Story: Selling iLab for 6× ARR, Choosing Strategic Over PE, and Life After an Eight-Figure Exit
In 2006, Tad Fallows and two friends spotted a problem inside Harvard's cancer labs: researchers were spending more time managing freezers, fruit flies, and mice than actually doing research. They built iLab, a SaaS tool for universities and hospitals, bootstrapped it to high–7-figure ARR, and eventually sold to Agilent Technologies for roughly six times revenue. But the journey wasn't smooth. Cash was often razor-thin with 75 employees on payroll, and an early inbound offer at 3× ARR forced Tad and his partners to decide: take the deal, or gamble on building more value.
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Ep 511 Exit Story: Why Ronan Berder Walked Away from Techstars and Sold Wiredcraft for 67 Million Euros
Ronan Berder built Wiredcraft to 140 people, then sold to Publicis for a reported 67 million euros. This Exit Story traces the moment he walked away from Techstars and a product dream to double down on services—and why that decision paid off.
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Ep 510 Mastering the Deal: Earn-outs, Equity Rolls & Seller Notes—Risk or Reward?
Most owners want 100% cash at closing. Most acquirers want the opposite—they try to hold back as much as possible and tie it to future results. That tug-of-war defines the negotiation. In this week's episode of Built to Sell Radio, you discover how to turn common transition structures from potential pitfalls into opportunities for upside.
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Ep 509 Mastering the Deal: 4 Buyer Types — Private Equity, Strategics, Hybrids & Acquisition Entrepreneurs
What happens when it's time to sell? Every acquirer looks at your business differently. In this special episode of Built to Sell Radio, John Warrillow breaks down the four most common buyer profiles and explains how each thinks about acquiring a company. Along the way, you'll hear clips from past guests from our Inside the Mind of an Acquirer series.
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Ep 508 Exit Story: The Surprising Math Behind a $100 Million Exit
Dan Berger built Social Tables into a SaaS success story with $20M in recurring revenue and more than 6,000 customers. He sold the business for $100 million. But after raising $27M in venture funding and navigating liquidation preferences, his personal payout was just under $20M. In this week's episode of Built to Sell Radio, Dan reveals the surprising math behind his deal and shares the emotional highs and lows of walking away from his company.
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Ep 507 After the Deal: Why Adam Rossi Wanted to Undo His Exit
Adam 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.
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Ep 506 Exit Story: $50 Million Was His Number—Here's How Josh Payne Got There
Unlike most tech founders, Josh Payne never dreamed of a billion-dollar valuation. His goal was simpler—and harder. He wanted his equity stake to be worth $50 million. To get there, he skipped the usual playbook. No blitzscaling. No VC treadmill. He raised a small seed round, built a profitable company, and avoided dilution. By the time he sold StackCommerce, Payne still owned 75%—and hit his number.
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Ep 505 Inside the Mind of an Acquirer: Why David Hauser Walked Away After a $175M Exit to Become a Disciplined Buyer
Most founders measure success by the price they get for their company. David Hauser did that—he built Grasshopper to $30M Annual Recurring Revenue (ARR) and sold it for $175M – almost 6 times revenue. He and his partner owned the majority of the shares so the deal was life-changing for Hauser. But what makes this interview different is what Hauser did next: he crossed the table to become an investor and now acquires businesses through Durable Capital. It's a study in contrasts. As a founder, Hauser chased growth. As an investor, he's ruthlessly disciplined. He mocks the PE herd chasing home services roll-ups and avoids auction-driven deals. Drawing on his experience founding Grasshopper and Mark Cuban-backed Chargify, he outmaneuvers ETA buyers and first-time acquirers with quiet, direct, close-ready offers. This is a rare window into how someone who's built and sold a business thinks about buying one—and what makes a deal attractive from the other side.
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Ep 504 Exit Story: One Founder's War with Private Equity—and the $500M Ending
After selling When Rich Galgano was 25, he left a sales job in wire distribution to start Windy City Wire. Within nine months, he was doing over $1 million in sales—while fighting a lawsuit from his former employer. Fast forward 30 years, and Galgano had built the dominant low-voltage cable distributor in the U.S., sold it for just under half a billion dollars, and stayed on as CEO.
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Ep 503 How to Land an 8-Figure Deal Without Running the Business Day to Day
When Ryan Atkinson sold CORE Resources to 24 Seven, it wasn't his first exit. After selling Redwood Global in 2014, Ryan played a different role in his next venture—injecting $2 million of his own capital while his partner ran the business day-to-day. The model worked. They grew CORE Resources into a go-to firm for specialized technology talent solutions and ultimately sold the company to 24 Seven—one of the largest privately held marketing, creative, and digital talent firms in North America—in an eight-figure exit. In this week's episode of Built to Sell Radio, Ryan shares how they structured the deal, avoided resentment, and nearly lost the sale in the final hours.
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ABOUT THIS SHOW
Built to Sell Radio is a weekly podcast for business owners interested in selling a business. Each week, we ask an entrepreneur who has recently sold a business why they decided to sell their business, what they did right and what mistakes they made through the process of exiting their business. Built to Sell Radio is the ultimate insider's guide to approaching the most important financial transaction of your life.
HOSTED BY
John Warrillow
CATEGORIES
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