But the most important thing I learned, and which I used in both Viaweb and Y Combinator, is that the low end eats the high end: that it's good to be the "entry level" option, even though that will be less prestigious, because if you're not, someone else will be, and will squash you against the ceiling. Which in turn means that prestige is a danger sign.

(If you're curious why my site looks so old-fashioned, it's because it's still made with this software. It may look clunky today, but in 1996 it was the last word in slick.)

If we'd been a startup I was advising at Y Combinator, I would have said: Stop being so stressed out, because you're doing fine. You're growing 7x a year. Just don't hire too many more people and you'll soon be profitable, and then you'll control your own destiny.

Now when I talk to founders who are leaving after selling their companies, my advice is always the same: take a vacation. That's what I should have done, just gone off somewhere and done nothing for a month or two, but the idea never occurred to me.

One of the most conspicuous patterns I've noticed in my life is how well it has worked, for me at least, to work on things that weren't prestigious. Still life has always been the least prestigious form of painting. Viaweb and Y Combinator both seemed lame when we started them.

It's not that unprestigious types of work are good per se. But when you find yourself drawn to some kind of work despite its current lack of prestige, it's a sign both that there's something real to be discovered there, and that you have the right kind of motives. Impure motives are a big danger for the ambitious. If anything is going to lead you astray, it will be the desire to impress people. So while working on things that aren't prestigious doesn't guarantee you're on the right track, it at least guarantees you're not on the most common type of wrong one.

One of my tricks for writing essays had always been to give talks. The prospect of having to stand up in front of a group of people and tell them something that wouldn't waste their time was a great spur to the imagination. When the Harvard Computer Society, the undergrad computer club, asked me to give a talk, I decided I would tell them how to start a startup. Maybe they'd be able to avoid the worst of the mistakes we'd made.

We'd use the building I owned in Cambridge as our headquarters. We'd all have dinner there once a week — on tuesdays, since I was already cooking for the thursday diners on thursdays — and after dinner we'd bring in experts on startups to give talks.

being part of a batch was better for the startups too. It solved one of the biggest problems faced by founders: the isolation. Now you not only had colleagues, but colleagues who understood the problems you were facing and could tell you how they were solving them.

To test this new Arc, I wrote Hacker News in it. It was originally meant to be a news aggregator for startup founders and was called Startup News, but after a few months I got tired of reading about nothing but startups. Plus it wasn't startup founders we wanted to reach. It was future startup founders. So I changed the name to Hacker News and the topic to whatever engaged one's intellectual curiosity.

YC was different from other kinds of work I've done. Instead of deciding for myself what to work on, the problems came to me. Every 6 months there was a new batch of startups, and their problems, whatever they were, became our problems. It was very engaging work, because their problems were quite varied, and the good founders were very effective. If you were trying to learn the most you could about startups in the shortest possible time, you couldn't have picked a better way to do it.

Kevin Hale once said about companies: "No one works harder than the boss." He meant it both descriptively and prescriptively, and it was the second part that scared me. I wanted YC to be good, so if how hard I worked set the upper bound on how hard everyone else worked, I'd better work very hard.

we wanted YC to last for a long time, and to do that it couldn't be controlled by the founders. So if Sam said yes, we'd let him reorganize YC. Robert and I would retire, and Jessica and Trevor would become ordinary partners

attention is a zero sum game. If you can choose what to work on, and you choose a project that's not the best one (or at least a good one) for you, then it's getting in the way of another project that is. And at 50 there was some opportunity cost to screwing around