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Egads. There is nothing wrong with selling. Imagine this scenario: You sell your first company, perhaps you've bootstrapped it and perhaps you sell it for 8 digits. Then you can create a second company (yes, people, it IS possible to create TWO companies unless your fist company was a fluke and you're unable to come up with a second company idea). Starting a second company with serious money in the bank gives one a level of freedom you cannot possibly imagine today. The 37Signals gurus always express their ideas relative to having only a single company in one's lifetime (because that's what they know). I've started and sold two companies to date and I couldn't be happier with the outcome (that's an understatement). I am having more fun than I ever had in my life and had I not sold, I would have never met my fiance -- she's the true passion in my life and startups don't hold a candle to her!

And my next company will be something wayyy out there -- probably so far out that I can't get funding because it's too risky. The only reason I can do that is because I sold my first two companies very early on and I have just enough financial wiggle room to where I can, for now, take some risks. I see companies like 37Signals making safe, predictable product bets and leaning on their brand and existing customer base for income, and that's fine. But the world needs risk takers, too. And taking risk requires capital and if that means selling a couple of companies before they turn into empires, then count me in! If I were to do it all over, I wouldn't change a thing.




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