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When's the "right" time to sell? I like how Marshall explains it. His family is now set for life. Could he have gone bigger? Maybe! But at some point, it's enough. A lot of founders look back and think, I should've sold then. But they saw the possibility of getting more, so they kept pushing. Ironically, you don't want to get to the top of that hill and *then* sell. You'll get the most for the business in a sale when it's *still growing*.
Built my bootstrapped business to $52M, sold a controlling stake to PE, and now an advisor. Founder of Somewhere.com (formerly Shepherd).
I was making over $500k per month personally before I sold my business. Some months? $600K+. Profits were growing. Compounding fast. Then the acquisition offers started rolling in. And I found myself facing one of the hardest decisions of my life. $500K/month is life-changing cash flow. That kind of money, invested well, turns into generational wealth. So why would I even consider selling? Because I realized there were only two types of regret I could face: 1. Regret of Greed – "I sold too early, and this could have been a billion-dollar company." 2. Regret of Loss – "I held on too long, and the business went to zero." Which would hurt more? Regret of Greed? That’s just "I could have done better." Regret of Loss? That’s "I had an opportunity to secure my family’s future, and I threw it away." One stings. The other destroys you. So I made my choice. I signed the deal. We sold for $52,000,000. Life-changing money for me, my wife, and our two kids. No regrets. I still own a minority stake. The business is thriving. Maybe one day, I'll feel the Regret of Greed. But I’ll never feel the Regret of Loss with this. And that’s why I made the right call. Would you have sold or held on?
