To answer your question directly: It felt absolutely terrible. I had no idea on how to gain control of the wild horse that had left the stable unsaddled, with a jockey that was about as unprepared as could be. We did the best we could. We missed critical time-slots, dealt with all kinds of trouble as good as we could all the time knowing that we could - and should - do better.
Being CEO of such a company (at the peak > 20 employees on two continents) was more responsibility than I had bargained for. It took away time from those dearest to me, it stressed me out beyond belief and it gave me more experience in a few years than I'd built up in the decade before, both in a business sense and in a technology sense.
It made me weary of people, when you're having that level of success (newspaper cover photographs, TV appearances, the works) business wise you gain the attention of a lot of nice people, but also of a lot of not-so-nice people. They can be extremely hard to tell apart.
Suddenly you're responsible for two orders of magnitude more money than you've ever dealt with in your life. You worry more about your ability to pay your employees than you worry about your own health.
I could go on like that for a bit. Let's just leave it at if it wasn't planned that you were founder of a popular start-up it can wreck your life really well. Better make it something that you're aiming for consciously, then at least you will be somewhat prepared for the journey.
I would definitely not want to go through such a period of hyper growth without a means to control it again, I'm all for controlling the situation and maybe ending up a bit less successful than to end up investing too much of my most precious resource (time) into a company. Any company.
The price on other fronts is too high, which of course is a personal feeling but it is definitely where I stand today. That doesn't mean that I wouldn't want to be part of a success story, it means that I no longer want to be in an out-of-control situation and that I'll work really hard to maintain control, even if that's at the expense of some growth. I think in the longer term that that benefits everybody.
Although I'm not successful yet, I can relate strongly with something you wrote (as a CEO):
> You worry more about your ability to pay your employees than you worry about your own health.
When you are the CEO of a business - any business, you have ton of worries. I can only think that when you become 'popular' or 'successful', these worries just increase and you somehow dont have the time to savor the moment.
People in the popular state tend to have the challenges of handling fame; when pushed into the spotlight, managing one's image becomes a challenge (among the others of a business).
People in the successful state tend to have a slightly different set of pressures; past success doesn't guarantee future success, so maintaining business growth and product development sit on your mind.
Of course, there are folks at the intersection of these two groups, and you can imagine that they have both sets of pressures, and perhaps some new ones as well.
Also. One of the advantages of Silicon Valley being an insular bubble at times is that however successful you might be, there's someone within a few square miles who has accomplished more. It's easy to get constantly humbled.
For every Drew Houston there's a Mark Pincus and for every Mark Pincus there's a Bill Campbell.
Obviously take everything I say here as just my own personal experience and my company is very very very early. But these are just some personal notes & thoughts.
You still feel insanely stressed because there's even more at stake now.
You still wonder if you're working on the right thing.
I dunno. Things don't really change much honestly.
So yes, thinking it through once or twice is a good idea, and something most people don't do.
Assuming intelligence is "an adaptation… To say that intelligence is a particular instance of biological adaptation is thus to suppose that it is essentially an organization and that its function is to structure the universe just as the organism structures its immediate environment" I do not see a best way to "leverage the group intelligence" than helping community members to adapt.
I did not ask for "the veritable answer in a haystack", but for some experiences and suggestions regarding how to proceed.
"no one the community knows the answer"
I also find it difficult to believe a community of entrepreneurs, like HN is, does not possess the right knowledge to give its 2cents on this.
It will affect everyone differently. But I imagine the folks that see ongoing success are the ones best realizing what worked and what didn't and continue to execute on successful concepts while scratching stuff as it becomes less effective.