[tptacek]

I really don't think I need to cite a study that 5 years of time is a lot to give up on a company that goes nowhere. It happens! It's normal! And very painful. Which is why getting to a decisive resolution in 6 months is often a gift.

You will make more money, and probably work on equivalently interesting problems, working any other job than at a startup you cofounded that limps for years before winding down. It's really hard to see what upside you're finding here. I don't say this often, but this isn't a place I see leaving at "reasonable disagreement".

[apgwoz]

> I really don't think I need to cite a study that 5 years of time is a lot to give up on a company that goes nowhere.

I think your problem is that you have one definition of success for a startup and that’s to become a unicorn.

> working any other job than at a startup you cofounded that limps for years before winding down.

Not everyone starts a startup to become a billionaire, and not everyone seeks to _make more money_.

But aside from that, the way you’re going to _make more money_ in another job is by working at a large company that can pay you more money. That large company has lots of people and lots of jobs that are specialized… because? Lots of people are there to do them. If I work on a team in a large company, I very likely have a narrow focus and I am not “solving interesting problems” on average.

[tptacek]

You keep saying stuff like this, but I'm asking a simple question. How have you personally benefited from spending years at a startup that failed, so much so that you were better off at the doomed startup than in any other place in the industry? I'm looking for some kind of relatable experience.

[apgwoz]

You haven’t asked a question before now…

I’ve worked at a few “unsuccessful,” but long term startups. Bought, but kind of for parts. The 2 yo startup I closed down was the most enjoyable and most rewarding from a learning perspective. The longer term, but unsuccessful, ones were also enjoyable and great learning experiences.

The two larger company experiences had me much more pigeonholed, even as a principal engineer / architect, and exposed me to far less of the important aspects of running a company or product, generally, but I made money. Often it was not enjoyable, and certainly leadership did not always enjoy my questioning of their actions and decisions.

[tptacek]

During what "era" did these startups wind down? Pre- or post- first Internet bubble? How old were you at the time? Maybe a failed startup is a great experience when you're 23, and not so much when you're 38?

(I've worked in startups my entire career, and been a founder of five, one serious acquisition, two going concerns, and two failures, one fast one slow; the long failure, circa 2001, was not a valuable experience in any way.)

[apgwoz]

I started working at startups in 2009… in my late 20s.

If you’re not already financially stable at 60 and hoping to win the startup lottery to retire… well…

So yeah, obviously age plays some role here.

I didn’t go work at startups because I thought I was gonna get rich. I worked at startups because I expected to learn waaaaay more than at Big Co, and have wayyyy more fun while doing it. This panned out.

Money has never been my motivation in computing—interesting problems are.

It wasn’t until I turned 42 that I realized I did it all backwards, though. I should have started by working at Big Co and saved/invested every penny to seek early retirement, and then do whatever I wanted with no financial pressure, later.

I could have stayed at a Big Co for 4+ more years and racked up more RSUs, and bonuses, but my job became boring, and I started to resent it. What can I say?

Curious about the 2001 failure… but am guessing the amount of free money in the dotcom boom led to you trying to build something not well thought out or with ang real hope for viability. (not throwing shade, but lots of mud was thrown and very little stuck)

It happens! It’s OK!

[tptacek]

I don't understand this "startup lottery" stuff. I've been on HN since roughly 2007 and for most of those 18 years I've been a bootstrapping evangelist. My most successful exit to date was a bootstrapped company. I'm just saying: there's no romance or great reward to working in a failing startup. If you have a clear signal that your startup is failing, you've been given a gift from the heavens: the ability to see into the future, see yourself wasting years, and then navigate around those years.

2001 was the beginning of the "nuclear winter" for startups. I think part of this is that I'm just older than you? (I have no idea how old you are, but "how did your startup fail in 2001" is an odd question).

Were you a founder at any of these startups you're talking about? If you're just talking about being an employee, that's totally different. It's often (maybe even usually) reasonable for employees to value their equity at ε. That being the case: you can absolutely choose roles based solely on base comp, how interesting the work is, and how it looks on your resume.

Finally: if you try to factor money out of entrepreneurship discussions, you get to very funny places. We're in one of them now! It is strictly better for a startup to fail at 6 months in than it is for it to fail at 5 years in.