[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.

[apgwoz]

> I don't understand this "startup lottery" stuff.

What’s not to understand? There’s a whole class of people that start a startup hoping for it to be the next big thing and they get their golden ticket to billionairedom. There’s also a whole class of non-founders that will join early stage companies at their riskiest stage hoping for the lottery payout. I’m not sure what there is to misunderstand about this?

> 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.

I don’t think I’ve said anything that negates this statement? If after 6 months you have absolutely no customers and you’ve tried everything, then clearly you don’t stick around for 5 years trying. I’ve never said that. This is way different than “we’ve found some success and after 5 years, hired people, just never figured out how to take it to the next level and so we’re shutting down.”

But you can’t make a general statement that there’s no “romance or reward” because people have a whole lot of reasons for doing what they’re doing. That’s been my big disagreement here. As always the answer is “it depends.” You’ve not cited some study that says differently… so… shrug.

> (I have no idea how old you are, but "how did your startup fail in 2001" is an odd question).

I _guess_ I asked that question, but not really. I asked what your startup was, and made an assumption that the amount of “free money” available may have doomed it from the start. Maybe VCs bet on something that obviously (in retrospect) couldn’t succeed … like Pets.com, or the wide variety of “we’ll just burn all this cash paying people to drive a pack of gum from the upper east side to wall st… in the middle of rush hour… and hope we figure out a way to scale it later!!!!!” startups that existed.

> Were you a founder …

I’m not sure why this actually matters? There are plenty of founders who start a company… almost accidentally… because a project they built became bigger than side-project, who aren’t necessarily motivated by a potential unicorn status. The people who benefit most from “try something for 3mo and hope it fails fast!!!” are (I’m going to make a guess because I doubt there’s a citable study out there!) the people most likely looking to win the startup lottery. In that case, the more chances to “scratch off the ticket” the better.

But, I still maintain that it’d be better for those people to have the experience of being a longer term founder for 5 years to gain more experience, see and adapt to more problems… etc, than to start and kill, start and kill, over and over again. In a fast cycles, you can test one or two hypotheses against a very targetted customer base. But you could totally be looking for a great white shark in a lake, which makes absolutely no sense.

> Finally: if you try to factor money out of entrepreneurship discussions, you get to very funny places.

Funny, when I brought money into it before:

> Yeah, you're missing my point. Given most startups fail, the question isn't "at the end of the day do you still get a paycheck for your failed startup", it's "how much of your life did you burn on that failed startup".

This will be my last reply. We don’t agree, and that’s fine. :)

[tptacek]

Yeah, I think I understand the perspective mismatch now. Thanks!