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Key Takeaways
- After watching a once-thriving business lose momentum as markets changed, I learned a hard truth: Company value is based on a buyer’s confidence in the future, not a founder’s belief in what’s possible.
- The best time to sell is often when you don’t want to — because that’s usually when your company is worth the most.
There are moments in every entrepreneur’s life that seem permanent while you’re living them. You convince yourself you’ve finally crossed some invisible finish line — that all the years of uncertainty, sleepless nights and wondering whether payroll would clear have finally given way to something durable. For me, that moment arrived during Covid.
The world had changed almost overnight, and so had our business. Real estate agents suddenly couldn’t meet clients in person, hold open houses or spend their weekends driving buyers from one property to another. Almost overnight, the service we had spent years building became one of the safest and most effective ways for agents to continue growing their businesses.
Demand exploded. We were opening offices faster than I ever imagined possible. Money was coming in faster than we could deploy it. Investors wanted to invest. Employees wanted to join. It felt like every decision we made worked.
When you’re in a season like that, it’s hard to imagine it ever ending. I certainly didn’t.
The future I was betting on
People occasionally approached us about buying the company, and I barely entertained the conversations. Looking back, some of those offers were extraordinary. At the time, they didn’t feel extraordinary at all because I wasn’t comparing them to what the business was worth. I was comparing them to what I believed it would eventually become.
That’s an important distinction.
I wasn’t building a company to sell. I was building something I genuinely believed my children might one day inherit. Maybe even my grandchildren after them. I had fallen into the same trap I now see so many founders fall into: I assumed my business would be one of the rare exceptions that would survive generation after generation. History says very few companies actually do, but entrepreneurs don’t build companies by thinking statistically. We build them by believing our story will be different.
Mine wasn’t.
As the world slowly returned to normal, something changed that I didn’t fully appreciate at first. Nothing collapsed overnight. Revenue didn’t suddenly disappear. We still had customers. We still had talented people. We still had investors who believed in us enough to continue putting money into the business.
From the inside, it never felt like we were standing on the edge of a cliff. It felt more like we were driving into a headwind that would eventually pass. The problem was that the market had changed in ways we couldn’t simply outwork.
During Covid, we weren’t just a good solution. In many ways, we were the solution. We helped real estate professionals generate leads, find buyers and continue selling homes without putting themselves or their clients at risk. Once the world reopened, that advantage slowly disappeared. We weren’t solving the same urgent problem anymore, yet we were still operating the company that had been built for that extraordinary moment in history.
Like many founders, I responded the only way I knew how. Grow. Launch something new. Hire more people. Build more technology. Open another office. Keep moving.
Entrepreneurs are conditioned to believe that growth solves almost every problem. Most of the time that’s true. This time it wasn’t.
When growth stops creating value
What I didn’t understand then — but understand completely now — is that there comes a point when growth stops creating value and starts disguising problems. Every new initiative gave me another reason to believe the turnaround was just around the corner. Every round of funding reinforced that belief. Investors continued supporting the company because they believed, as I did, that we could navigate the transition.
Investor confidence can be intoxicating. It can also be misleading.
I eventually learned that investors and buyers evaluate businesses through completely different lenses. Investors had spent years getting to know us. They knew our leadership team, understood our strategy and believed we could execute it. Buyers don’t have that luxury. Buyers don’t care how difficult the journey has been or how many obstacles you’ve already overcome. They aren’t buying your past. They’re deciding whether your future is more attractive than every other opportunity competing for their capital.
By the time I truly understood that difference, the conversation had already changed. The offers stopped reflecting where the company had been and started reflecting where buyers believed it was going.
I can still remember realizing that the business could absolutely become successful again. I believed that then, and I still believe it now. But getting there would have required dismantling much of what we had built, rebuilding our technology, restructuring the organization and spending several years growing slowly with little or no profit.
In other words, we weren’t really running an established company anymore. We were preparing to become a startup again. Years earlier, I would have embraced that challenge without hesitation. This time, I couldn’t.
The lesson that changed how I build
Eventually, there was a meeting that every founder hopes never happens. Not because the company had failed, but because everyone in the room had reached the same conclusion at the same time. We no longer wanted to spend years rebuilding what we had already built once before. We weren’t walking away because it was impossible. We were walking away because we had reached the end of the journey we wanted to take.
Looking back, I don’t regret building that company. I don’t regret believing in it. What I regret is believing there would always be more time.
I assumed that as long as the business remained profitable — or at least capable of becoming profitable again — its value would eventually recover. I couldn’t have been more wrong. Value isn’t determined by how optimistic the founder feels. It’s determined by how much confidence someone else has in the road ahead.
That lesson changed the way I’ve approached every business since.
I’ve now bought and sold dozens of companies, and I have never repeated that mistake. I still build with ambition. I still believe in long-term growth. But I also understand that every company, no matter how successful it becomes, is likely headed toward one of three outcomes: It will be sold, it will close or someone else will eventually inherit the responsibility of deciding its future.
That’s why every founder needs an exit strategy long before they think they’ll ever need one. Not because you plan to sell. Because one day you’ll have the opportunity to — and the market won’t care whether you’re emotionally ready.
The hardest lesson I ever learned in business is also the simplest: The best time to sell a company is usually the moment when selling feels completely unnecessary.
Key Takeaways
- After watching a once-thriving business lose momentum as markets changed, I learned a hard truth: Company value is based on a buyer’s confidence in the future, not a founder’s belief in what’s possible.
- The best time to sell is often when you don’t want to — because that’s usually when your company is worth the most.
There are moments in every entrepreneur’s life that seem permanent while you’re living them. You convince yourself you’ve finally crossed some invisible finish line — that all the years of uncertainty, sleepless nights and wondering whether payroll would clear have finally given way to something durable. For me, that moment arrived during Covid.
The world had changed almost overnight, and so had our business. Real estate agents suddenly couldn’t meet clients in person, hold open houses or spend their weekends driving buyers from one property to another. Almost overnight, the service we had spent years building became one of the safest and most effective ways for agents to continue growing their businesses.
Demand exploded. We were opening offices faster than I ever imagined possible. Money was coming in faster than we could deploy it. Investors wanted to invest. Employees wanted to join. It felt like every decision we made worked.