I've come close to starting new startups a couple times, but I always pull back because I don't want four years of my life to be consumed by random schleps. I know this business well enough to know you can't do it half-heartedly. What makes a good startup founder so dangerous is his willingness to endure infinite schleps.
There is a bit of a problem with retirement, though. Like a lot of people, I like to work. And one of the many weird little problems you discover when you get rich is that a lot of the interesting people you'd like to work with are not rich. They need to work at something that pays the bills. Which means if you want to have them as colleagues, you have to work at something that pays the bills too, even though you don't need to. I think this is what drives a lot of serial entrepreneurs, actually.
That's why I love working on Y Combinator so much. It's an excuse to work on something interesting with people I like.
This was my reason for not starting a startup for most of my twenties. Like a lot of people that age, I valued freedom most of all. I was reluctant to do anything that required a commitment of more than a few months. Nor would I have wanted to do anything that completely took over my life the way a startup does. And that's fine. If you want to spend your time travelling around, or playing in a band, or whatever, that's a perfectly legitimate reason not to start a company.
If you start a startup that succeeds, it's going to consume at least three or four years. (If it fails, you'll be done a lot quicker.) So you shouldn't do it if you're not ready for commitments on that scale. Be aware, though, that if you get a regular job, you'll probably end up working there for as long as a startup would take, and you'll find you have much less spare time than you might expect. So if you're ready to clip on that ID badge and go to that orientation session, you may also be ready to start that startup.
I'm told there are people who need structure in their lives. This seems to be a nice way of saying they need someone to tell them what to do. I believe such people exist. There's plenty of empirical evidence: armies, religious cults, and so on. They may even be the majority.
If you're one of these people, you probably shouldn't start a startup. In fact, you probably shouldn't even go to work for one. In a good startup, you don't get told what to do very much. There may be one person whose job title is CEO, but till the company has about twelve people no one should be telling anyone what to do. That's too inefficient. Each person should just do what they need to without anyone telling them.
If that sounds like a recipe for chaos, think about a soccer team. Eleven people manage to work together in quite complicated ways, and yet only in occasional emergencies does anyone tell anyone else what to do. A reporter once asked David Beckham if there were any language problems at Real Madrid, since the players were from about eight different countries. He said it was never an issue, because everyone was so good they never had to talk. They all just did the right thing.
How do you tell if you're independent-minded enough to start a startup? If you'd bristle at the suggestion that you aren't, then you probably are.
Perhaps some people are deterred from starting startups because they don't like the uncertainty. If you go to work for Microsoft, you can predict fairly accurately what the next few years will be like—all too accurately, in fact. If you start a startup, anything might happen.
Well, if you're troubled by uncertainty, I can solve that problem for you: if you start a startup, it will probably fail. Seriously, though, this is not a bad way to think about the whole experience. Hope for the best, but expect the worst. In the worst case, it will at least be interesting. In the best case you might get rich.
No one will blame you if the startup tanks, so long as you made a serious effort. There may once have been a time when employers would regard that as a mark against you, but they wouldn't now. I asked managers at big companies, and they all said they'd prefer to hire someone who'd tried to start a startup and failed over someone who'd spent the same time working at a big company.
Nor will investors hold it against you, as long as you didn't fail out of laziness or incurable stupidity. I'm told there's a lot of stigma attached to failing in other places—in Europe, for example. Not here. In America, companies, like practically everything else, are disposable.
One reason people who've been out in the world for a year or two make better founders than people straight from college is that they know what they're avoiding. If their startup fails, they'll have to get a job, and they know how much jobs suck.
If you've had summer jobs in college, you may think you know what jobs are like, but you probably don't. Summer jobs at technology companies are not real jobs. If you get a summer job as a waiter, that's a real job. Then you have to carry your weight. But software companies don't hire students for the summer as a source of cheap labor. They do it in the hope of recruiting them when they graduate. So while they're happy if you produce, they don't expect you to.
That will change if you get a real job after you graduate. Then you'll have to earn your keep. And since most of what big companies do is boring, you're going to have to work on boring stuff. Easy, compared to college, but boring. At first it may seem cool to get paid for doing easy stuff, after paying to do hard stuff in college. But that wears off after a few months. Eventually it gets demoralizing to work on dumb stuff, even if it's easy and you get paid a lot.
And that's not the worst of it. The thing that really sucks about having a regular job is the expectation that you're supposed to be there at certain times. Even Google is afflicted with this, apparently. And what this means, as everyone who's had a regular job can tell you, is that there are going to be times when you have absolutely no desire to work on anything, and you're going to have to go to work anyway and sit in front of your screen and pretend to. To someone who likes work, as most good hackers do, this is torture.
In a startup, you skip all that. There's no concept of office hours in most startups. Work and life just get mixed together. But the good thing about that is that no one minds if you have a life at work. In a startup you can do whatever you want most of the time. If you're a founder, what you want to do most of the time is work. But you never have to pretend to.
If you took a nap in your office in a big company, it would seem unprofessional. But if you're starting a startup and you fall asleep in the middle of the day, your cofounders will just assume you were tired.
A significant number of would-be startup founders are probably dissuaded from doing it by their parents. I'm not going to say you shouldn't listen to them. Families are entitled to their own traditions, and who am I to argue with them? But I will give you a couple reasons why a safe career might not be what your parents really want for you.
One is that parents tend to be more conservative for their kids than they would be for themselves. This is actually a rational response to their situation. Parents end up sharing more of their kids' ill fortune than good fortune. Most parents don't mind this; it's part of the job; but it does tend to make them excessively conservative. And erring on the side of conservatism is still erring. In almost everything, reward is proportionate to risk. So by protecting their kids from risk, parents are, without realizing it, also protecting them from rewards. If they saw that, they'd want you to take more risks.