How many people have worked on their own startup in the valley for 5+ years and had nothing come of it? Before I made the leap to working on a startup full time, I searched for a while for an example where 5 or more years resulted in complete failure but I couldn't find one. Not a single data point among hundreds that I read about/heard about anecdotally. I'm very curious, anyone care to share an example where they worked on their startup for 5+ years and it resulted in failure?

I can give you two I know about personally. An ISP that couldn't afford the transition to a post dial-up world, sold its user base off for a pittance. Not really worth the six years.

The other was a fairly niche data processing startup in a several billion dollar niche. 10 years in and they missed the boat migrating their front end to the browser and moving their back end off of windows.

Couldn't even sell off the source code in the end.

The companies failed, but did the founders end up worse off than if they had been random engineers at Microsoft?

I guess define "worse off". But I would say in both cases they ended up about the same...but I will grant they learned lots of intangibles from the experiences.

How did the end up about the same? Were they paying themselves the same salaries they would have been getting at Microsoft the whole time? Were they living more frugally than they would have been had they been working at Microsoft?

I think in terms of the kind of job position they could get going into a Microsoft after their startup, they ended up about the same as if they had been at Microsoft the whole time.

So it wasn't wasted time in that respect, and they'll be bringing in unique and different skills that they probably wouldn't have developed had they been at MS the whole time.

But...there's things like the lower pay they probably had while doing their business, and the intensity of running a failing business is very very hard mentally and physically.

Near the end, one of the guys shut down...hard...now that he's moved on he's recovering. But I think that kind of experience trails along with you for a long while.

One way to tell- if you asked them, would they say that they should have spent their time doing something else? What do you think they would say? (Or if you could just ask them, that would be even better!)

I think that's very dependent on the person and how they internalized the experience. One of them I know thinks that it was wasted years off of his life. Another feels like they learned more in those years than they did in the rest of their career combined, and it's armed them to be more effective in future endeavors.

Observational bias. The ones that failed you will be far more hard pressed to find 'data points'(dym information?) on.

Yes, I know there's a strong selection bias in who I hear about. That's why I'm extremely curious to find even one data point on the other side. If you have one, please share!

I don't have any, but I do wonder if this is another reason why there's a bias towards younger founders (or at least the perception of one). You start a company at 25 after a few years of unfulfilling work, put your nose to the grindstone for 5 years, and, in this unusually terrible hypothetical, end up with nothing but lost time and opportunity.

But hey, you're 30. There's time for a comeback. There's no age limit on making a comeback, but I don't think it would be an outrageous claim to say that bouncing back at 30 is easier than bouncing back at 50. Of course, as is the case in most things, attitude matters. A lot. You can look at your 5 year struggle as a massive loss, or as an incomparable learning experience, and that could be the deciding factor in how successful your next venture is.

I feel in a lot of ways that starting over at 50 must be easier than starting over at 30. At 30 you possibly have kids, a spouse, and are just getting started in a mortgage. At 50 the kids are off to college, the house should be paid off or close to it, and now you have many peers in the same situation as you (ie, access to capital). It's no wonder the avg age for entrepreneurs is mid 40s

Yes, in the real world outside of the sexy tech startup scene, most entrepreneurs are over 40, often over 50.

In a lot of ways, I feel that my own path has had that trajectory.

Thanks for sharing that. Do you think you could have better spent your time elsewhere outside of tech startups?

Not entirely. I wished I was able to shorten the time I spent at various stages learning some of the hard-earned lessons.

It took me seven years and two failed startups (one of them through YC) before I finally had a hit (the Ruby on Rails Tutorial). I think part of what made it work was intentionally taking a medium risk for a medium reward. My first two startups were all-or-nothing (which turned out to be nothing), whereas the Rails Tutorial, even had it "failed", would still have produced a five-figure annual income stream. (It succeeded, so it's six.)

This has its own sets of biases. Working on a startup with nothing coming of it only works until you're tapped out. How many founders do you know would just remain broke when they run out of money vs doing the rational thing which is getting a job or whatever to get back to supporting life's basic necessities?

Ang Lee was, even after 5 years of failure. I have heard of quite a few people in other industries (namely entertainment and art) that just failed to make it and would have been better served having spent that time pursuing something else. I've never heard of an example in tech startups though.

I would love to run a controlled experiment. Unfortunately we can't force people to do anything, so we never really can eliminate people's choices as a confounding variable.

I can give you one data point from my own experience. We committed to creating a company for two years no matter what happened. After a year and a half, there's no question it was the right choice. If I had chosen to do something else like high frequency trading, programming at a large company, or grad school, the likely outcome would not be on the same level as where we're at now. Even our worst case scenario, selling for a talent acquisition, ends up ahead of those other options.

> would have been better served having spent that time pursuing something else

This is just the gamble that success requires. It's easy to say that objectively they may have been better doing something else in retrospect, but perhaps they felt some satisfaction trying. In any event, it's impossible to know whether someone is going to succeed in advance, or remain unsuccessful.

It appears the decision to persevere, like the decision to "give up", cannot be made rationally. I'd love to be shown otherwise though.

Genuine question, how do you know when to continue/slog and when to stop?

When you run out of passion, or will.

Agreed. If you don't do things for yourself first, and measure success with an internal yardstick, you'll run out of steam.

But as long as you like it and want to do it, lack of success should be easier to take.

Yep, well put. I was thinking this too which sort of made it all the more 'tragic' - though perhaps that isn't a good word as this story isn't tragic...but it almost certainly could have been!

Good for Ang Lee!