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The Exit Paradox

14 min

How Great Entrepreneurs Exit Their Companies on Top

Golden Hook & Introduction

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Mark: Alright Michelle, here's a scary number for every business owner out there. Of all the companies that get put up for sale, what percentage do you think actually sell? Michelle: Oh, that's a tough one. I'd guess it's a grind. Maybe 50%? It's tough out there, you have to find the right buyer, the right price... Mark: Try 20 percent. Four out of five businesses listed for sale walk away with nothing. And that's the good news. Michelle: Wait, that's the good news? How is that possibly the good news? That sounds like a catastrophe. Mark: Because it points to the huge, overlooked problem that Bo Burlingham tackles in his book, Finish Big: How Great Entrepreneurs Exit Their Companies on Top. Burlingham, who's been a long-time editor at Inc. magazine, noticed that our entire culture is obsessed with the startup story—the garage, the hustle, the billion-dollar valuation. But almost no one talks about the most important deal of an entrepreneur's life: the end. Michelle: That’s so true. We celebrate the beginning and the middle, but the exit is treated like this secret, shameful event. Or it’s just a headline with a number, and we assume everyone lived happily ever after. Mark: Exactly. And as that 80% failure rate shows, most don't. Burlingham argues that exiting isn't an event; it's the final, critical phase of your journey. And how you navigate it defines your entire legacy.

The Exit Paradox: Why Planning to Sell Makes You a Better Owner

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Michelle: Okay, so if 80% of businesses that try to sell fail to do so, what's the fundamental problem? Are the businesses just not good enough? Mark: That's the fascinating paradox the book opens with. The problem isn't always that the business is "bad." The problem is that it wasn't built to be sellable. And Burlingham's first big insight is that the process of making your company sellable is the very thing that makes it a fantastic company to own. Michelle: Hold on, that sounds like a riddle. The secret to keeping your business is to get it ready to be sold? Mark: Precisely. Because it forces you to stop thinking like an emotional, attached founder and start thinking like a cold, rational buyer. A buyer doesn't care about your blood, sweat, and tears. They care about one thing: predictable future cash flow. They want a machine that runs without you. Michelle: I see. So it forces you to fix all the things you've been ignoring because, well, it's your baby and you can overlook its flaws. Mark: Exactly. The book gives this perfect example with a guy named Ray Pagano, who owned a company called Videolarm. He'd been running it for decades, it was doing fine, about $10 million in sales. But it was completely dependent on him. He was the heart and soul, which sounds great, but it's a huge liability. Michelle: Right, if Ray gets hit by a bus, the company gets hit by a bus. Mark: You got it. So in 2004, at 61, he decides he wants to think about an exit. He starts the process of getting the company ready for a sale. And this is where the magic happens. He doesn't just clean up the books; he fundamentally transforms the business. Michelle: Okay, so what did he actually do? What does this preparation look like in the real world? Mark: He did a few brilliant things. First, he introduced something called "phantom stock." He gave his key employees a stake in the company's future success. If the company sold for a high price, they'd get a big payout. Suddenly, they weren't just employees; they were thinking like owners. Michelle: Phantom stock, I like the name. It's like giving them the upside of ownership without the complicated legal structure. It aligns everyone's incentives. Mark: Perfectly. Then, he did something that terrifies most owners: he implemented open-book management. He started sharing the company's financials with everyone. He taught them what the numbers meant, how their work impacted the bottom line. Michelle: Wow. Most founders guard their numbers like a state secret. Weren't people scared when they saw the real costs or a slow month? Mark: Initially, yes. There was skepticism. But it created a culture of accountability and trust. People started coming up with ideas to save money or boost sales because they could see the direct impact. They held an off-site meeting, and for the first time, the managers—not Ray—created the annual plan. He was building a company that could thrive without him. Michelle: He was making himself redundant, which is the hardest thing for a founder to do. So what was the result of all this? Mark: The result was staggering. The company's performance and profitability shot through the roof. Before he started this process, he got a tentative offer that valued the company at a certain price. After a few years of these changes, he sold Videolarm to a company called Moog Inc. for $45 million—four times the initial valuation. Michelle: Four times! That's incredible. Mark: And here's the kicker. Pagano's biggest regret? He told the author, "I really just wish I’d done it sooner." The process of preparing for the sale made his company so much better and his life so much less stressful that he wished he'd started on day one. That's the exit paradox: build your business as if you'll own it forever, but could sell it tomorrow.

The Identity Crisis: Who Are You If Not Your Business?

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Michelle: Okay, so Ray Pagano's story is the dream scenario. You build a great company, you make it sellable, you get a fantastic payout, and your employees are happy. You've won the game. But as you hinted earlier, that's not always the end of the story, is it? Mark: Not even close. In fact, for many entrepreneurs, the financial win is the beginning of a profound personal crisis. This is the second major theme of the book: Who are you if not your business? Michelle: The identity crisis. I can see that. For so many founders, the company isn't just a job; it's their name, their social life, their purpose. It's everything. Mark: And when you sell it, you sell all of that, too. The book tells the absolutely gut-wrenching story of Bruce Leech, who founded a company called CrossCom National. He built it up over two decades to $70 million in sales. But he was burned out, his marriage had failed, he was exhausted. Michelle: The classic founder burnout story. Selling seems like the only escape hatch. Mark: It did to him. He got into a deal with a private equity firm. He had doubts the night before signing, a gut feeling that something was wrong, but he felt pressured and went through with it. He sold a majority stake and became instantly, independently wealthy. Michelle: The dream, right? Mark: The nightmare. He said, and this quote is haunting, "I really hadn’t thought about my life after the sale... it was a huge void for me." He had the money, but he had no purpose. He'd go to social events, and people would ask, "What do you do?" He no longer had an answer. He felt insignificant, irrelevant. He had exited his business but he hadn't planned his own next chapter. Michelle: Wow, that's terrifying. To get everything you thought you wanted and just feel empty. It’s the dark side of the entrepreneurial dream. Isn't this the trap our whole culture pushes founders into? Your work is your life, your company is your identity. Mark: It is. And Burlingham argues that the happiest exits come from entrepreneurs who untangle their identity from their business before they sell. They have an answer to the question, "What's next?" It might be starting another venture, philanthropy, travel, or mentoring. The what doesn't matter as much as the having a what. Michelle: So what's the antidote to becoming Bruce Leech? How do you avoid that void? Mark: The book offers a powerful mindset shift through another entrepreneur, Michael LeMonier. After getting fired from a job early in his career, he had an epiphany. He said, "It showed me how wrong I was having all of my ego tied up in my work." From that day on, he viewed the businesses he built not as his life's work, but as investments. Michelle: That's a huge mental shift. He detached his self-worth from the company's balance sheet. Mark: Exactly. He was still passionate and worked hard, but he saw the business as a vehicle, not a destination. It was a tool to create a great life, not the life itself. This "investor mindset" allowed him to buy, build, and sell companies successfully without the emotional turmoil and identity crisis that plagued Bruce Leech. He knew who he was, with or without the CEO title. Michelle: It makes you ask a really fundamental question: Are you building a business, or is the business building you? If you don't decide, the business will decide for you, and you might not like the person it turns you into. Mark: That's the core of it. Self-awareness isn't a soft skill in entrepreneurship; it's the ultimate strategic advantage, especially when it comes to the end.

The Human Factor: Deal or No Deal, It's About People

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Mark: And that self-awareness, that sense of purpose beyond the money, leads directly to the book's third, and perhaps most important, theme: the human factor. A good exit isn't just about the price you get or what you do next. It's about how you treat the people who helped you get there. Michelle: The people part. Your employees, your partners, even your successor. This is where it gets really messy and emotional. Mark: Incredibly. And the standard advice from lawyers and brokers is often terrible here. They tell you, "Keep the sale a secret. Don't tell anyone until the ink is dry. It's too risky." Michelle: Right, because you don't want employees to panic and leave, or competitors to find out. It makes logical sense, but it feels... wrong. Mark: It feels wrong because it often is. The book tells the story of Jack Altschuler, who sold his company, Maram Corp. He followed his advisors' advice and kept it a total secret. The day the deal closed, he called his employees into a room and announced it. He said their reaction was "just awful." His loyal office manager, who had been with him for years, felt utterly betrayed. Years later, Altschuler was still filled with regret. He got his money, but he damaged relationships he cherished. Michelle: That's heartbreaking. You spend years building a "family" culture, and then in the most important moment, you treat them like they're just assets on a spreadsheet. Mark: And that's why the most sophisticated entrepreneurs, the ones who truly "finish big," reject that advice. They understand that transparency and loyalty are a two-way street. This brings us to one of the most brilliant case studies in the book: the sale of Stonyfield Farm. Michelle: Oh, the organic yogurt company! I love their products. I assume this is a more positive story. Mark: It's a masterclass in how to exit with integrity. The founder, Gary Hirshberg, had built this amazing company with a powerful mission-driven culture. But he had hundreds of early investors—friends, family—who needed a return. He had to sell. Michelle: A classic dilemma. How do you cash out without selling out? Mark: He was terrified of being bought by a big, soulless corporation that would strip-mine the brand and fire everyone. So he didn't just look for the highest bidder; he went looking for the right partner. He ended up in talks with Danone, the French food giant. Michelle: A giant corporation. That sounds like exactly what he was afraid of. Mark: On the surface, yes. But Hirshberg did his homework. He spent time with their CEO, Franck Riboud, and realized they genuinely respected Stonyfield's mission and wanted to learn from it, not just own it. But he didn't just take their word for it. He structured an incredibly clever deal. Michelle: Hold on, he sold a majority stake to Danone but somehow kept control? How is that even possible? That sounds like a fantasy for most founders. Mark: It's not a fantasy if you have leverage and you know what to ask for. Here’s what he did: Danone would buy a 40% stake initially, with an agreement to buy more later. But Hirshberg and his team remained in charge of the board and day-to-day operations. The deal had a crucial clause: a two-year trial period. Danone had to prove they were good partners. They had to help Stonyfield grow and hit certain targets without interfering with its culture. If they failed, the deal could be unwound. Michelle: A trial period for your own acquisition! That's genius. It's like dating before you get married. He forced them to earn his trust. Mark: Exactly. And they did. Danone provided resources and distribution that helped Stonyfield explode in growth, but they respected the boundaries. The partnership was so successful that Hirshberg eventually felt comfortable selling them the rest of the company. He got a great price for his investors, protected his employees, and preserved the company's soul. He knew his buyer.

Synthesis & Takeaways

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Michelle: It’s amazing how these three ideas are so interconnected. You can't really do one without the others. Mark: That's the ultimate takeaway from Finish Big. It all connects. You start by building a sellable company, like Ray Pagano did. That discipline makes the business stronger, which gives you the leverage to be picky about your exit. Michelle: And because you've done the internal work to know who you are without the business, like Michael LeMonier, you're not desperate. You can walk away from a bad deal, like Norm Brodsky did in the book's introduction, because your identity isn't on the line. Mark: And that freedom allows you to focus on the human element—to find a buyer like Danone who respects your legacy, and to treat your people with the dignity they deserve. The final line on your entrepreneurial report card isn't the price. It's how you managed the entire journey, especially the end. Michelle: It really makes you ask, what game are you actually playing? Are you building a financial asset, a personal identity, or a community? The book suggests you have to be intentional about all three, or one will inevitably sabotage the others. Mark: That’s a perfect way to put it. It’s a holistic view of the entrepreneurial lifecycle. Michelle: So for anyone listening who runs something—a business, a team, even just a personal project—I think the question the book leaves you with is powerful: What would you do differently if you knew you had to hand it over to someone else tomorrow? Mark: A question worth thinking about long before you ever have to. It might just be the key to building something that truly lasts. We'd love to hear your thoughts on this. What does "finishing big" mean to you? Let us know on our social channels. Michelle: This is Aibrary, signing off.

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