>With regards to the new knowledge that 20k customers is possible, that just gives you something to shoot for next, right?

Well, yes. Mostly I'm just amazed how they did that so quickly. That is admirable. But, I guess most of my growth has been in mad dashes, too... mad dashes followed by lulls where subscriptions keep pace with cancellations. I can see how it'd be possible to keep up those mad dashes, if your automation was better to start with, and if your support was better, and the marketing. All these are things I can improve; but it's admirable how they absolutely nailed all those things in such a short period of time.

>I'd suggest, as the Slicehost guys did, "automating the "%#)(% out of everything" and then focusing on customer acquisition as your primary job

Yeah. This. I mean, I make the excuse that I'm too busy 'shooting alligators' but you really have to set aside time to drain the swamp (and let's be honest here, I've started a bunch of different projects... time that would have been better spent on draining the swamp by automating more of this stuff.) I did actually make a lot of progress automating the killing of old accounts the night you wrote that. (It's still a manual process, but I wrote some scripts that took it from being an all-day thing to clear out everyone to it being a 10 minute thing to clear out everyone.)

>More broadly: philosophically, if we consider ourselves failures for not doing things other people have done, then we'll all be failures essentially all of the time. That strikes me as an unhappy bit of philosophy to adopt then.

The balance between arrogance and considering oneself a failure is a tricky one. I mean, I know that the only thing that has come close to destroying me was that confidence. (Well, after getting out of school. That's a long story; but there certainly were plenty of strong voices saying that I can't do it then; they were all, of course, trying to get me to put in the effort to get into a reasonable college, the upshot, of course, being that nearly everyone told me I was going to work at 7-11 if I didn't go to college, and it was obvious that I wasn't going to do so. I think a lot of my arrogance is innate, but a lot of it also comes from just how easy the real world was for me, compared to school.)

But yeah, PG wrote about confidence in a way that I related to, perhaps better than anyone else I've read:

"But you should treat your optimism the way you'd treat the core of a nuclear reactor: as a source of power that's also very dangerous. You have to build a shield around it, or it will fry you."

That line, really, is why I got interested in his writing and in this community. I've gotten burned badly, several times, by raising the control rods too much. I know that for most people I know, their big mistakes usually have to do with hitting the metaphorical SCRAM button before the reactor even gets warm, but for me? The big problems have always been that over-reach; the over confidence.

Of course, Graham goes on to say:

"The shielding of a reactor is not uniform; the reactor would be useless if it were. It's pierced in a few places to let pipes in. An optimism shield has to be pierced too. I think the place to draw the line is between what you expect of yourself, and what you expect of other people. It's ok to be optimistic about what you can do, but assume the worst about machines and other people."

which, of course, I believe is Very Bad Advice if you are a flawed individual. Self-doubt is essential to survival. Personally, I like the control-rod metaphor. When things get too hot? you lower the rods and let things cool down. Need more power? raise the rods.

But always be aware that while having no power is a problem, it's easier to clean up after a SCRAM than a meltdown.

Of course, much like how it may be best for the military to select fighter pilots with irrational levels of confidence, I can see how it would be best for an investor to select founders with irrational levels of confidence. If they try hard and fail? eh, well, there's always another one waiting on the sidelines. And in both cases, there's a supervisor that tries to make sure they don't get in too much trouble.

When it's just you, well, you've gotta consider the consequences of failure. And sometimes the consequences are small; if you have a corporation, and the credit is all in the corp's name? sure, take big risks and fold it if you screw up. But, make damn sure ahead of time that is possible.

Those mistakes (of overconfidence in cases where the consequences of failure were non-zero) have cost me years. And nearly all of the strategic mistakes I make now are attributable to the same source. Most of my tactical mistakes are attributable to, well, my brain not functioning normally. whatever you want to call it; attention deficit disorder; being lazy, having difficulty focusing? whatever you want to call it. It does respond fairly well to a battery of only moderately unpleasant medications, so I can't complain too much. - but the thing is, I know that about myself. It had a lot to do with why I didn't do well in school. I should be able to include this margin for error in my planning; but no. that confidence takes what I can do on the days that everything is just right and plans using that; forgetting that even with medication, I get maybe three of those days a week, when I'm really paying attention to all the inputs, working out, eating right and sleeping well; Otherwise, three of those days a month is a more realistic estimate. And I really am effective on those days; even if I planned for three of those effective days a month, I seem to still meet bay area sysadmin standards, so with half a decade, I ought to be able to come up with what is maybe ten days of good solid work on this problem.

I mean, I personally think that the biggest thing holding prgmr.com back the most right now is the automation, and I think the primary thing holding that back is that I've been spending my good days on other projects... that yeah, are interesting and might be worth something at some point in the future, but ultimately should take a backseat to the butter and guns.