Also, there are other reasons to sell than "some sucker is willing to pay x". Maybe you are burnt out, want to spend more time with your family, try something new, take some risk off the table.
There is a nugget of truth in much of what 37signals says, but it is always stated in such absolute terms that it becomes off-putting.
Similarly, DHH isn't writing "don't sell your business if you burn out". If you burn out and you can't fix it, do right by your team. DHH is critiquing the notion that you should build to flip, and the notion that there's great honor in doing that repeatedly. It's undeniable that there is a mythology around "serial entrepeneurs" who repeatedly flip companies.
You know what would be incredibly boring? A DHH post that anticipated and acknowledged every special case and every objection. "What if someone offered you $1Tn" is an especially b o r i n g objection. One of the reasons people read DHH's articles and don't read ours is that we write things like "Of course, if someone offers you $100MM, you should blah blah b l a h b l a h", and he doesn't.
It is also OK for him to be wrong. Being wrong --- at least, when you're not writing about password hashing --- does not put a point on your blogging license. The bar is, "is it interesting and does it come from an honest place".
The fact is, nobody is offering 37Signals a trillion dollars with no strings attached. Actual offers would involve non-competes, possibly demands the founders stay on for a year or more, the right to fire employees, the right to raise prices or otherwise make things unpleasant for customers the founders like, and so on.
We can't say "Everyone's soul is for sale at the right price," get a yes, and then come back to reality and pull out a two hundred page term sheet and demand that they consider it since "We've established that they're for sale."
This is roughly akin to asking me if I would work for Microsoft if given a million dollar signing bonus. Does that mean I'm open to working for Micosoft? Or can I stick to my assertion that I'm not interested in working for Micosoft now or in the foreseeable future?
Selling your company only makes sense if you think they can do a better job than you can. Or when you think they’re overvaluing the prospects of your company. That’s either the talk of the meek or a con man (“let’s get these suckers to overpay for this company of questionable value…”).
Of course the trillion dollar number is ridiculous (just trying to make a point) but you can insert whatever number you want. DHH directly says you should only sell if you think the buyer can do better or if they overvalue your company.
As far as selling because you think the buyer can do better goes, does anyone actually do that? How many people are strong enough to build a company to the point where someone wants to buy it and then suddenly turn meek when the offer is on the table?
Selling your company doesn't make you a con man either. Even if someone overpays. If someone overpays, should you offer to give back the difference?
Like I said in my original comment, there is a lot of truth in what 37signals has to say, including this post, but sometimes they stretch it too far.
What's the mission now that there is a computer on every desktop and in every household? Is it as clear? Is it as direct? Will it last for a decade or more? Is it meaningful to every employee?
All I need is someone to answer that question for me and I'll be ready to change my mind.