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by kyro 4387 days ago
Can someone provide insight on life after a failed startup, in terms of career prospects? Often depression can make you feel as if you're failing on all fronts, that nothing will get better in the foreseeable future. Most of the time that really isn't true. You're often stuck in a temporary rut that your mind drastically exaggerates. But for a founder who's going through a dark time and whose startup ultimately fails, is it easy to pick yourself up again? Can you realistically transition into a more stable job where you'll have more energy to improve your life? I've heard from quite a few that the years spent on a failed startup do not improve your career options, and for a founder that may find themselves depressed running a company, I can't imagine such poor prospects lending any hope.
6 comments

It's hard to "provide insight" because it's different for everybody. My story is in the last two posts here:

http://diffle-history.blogspot.com/

Basically, I sucked it up, felt depressed and aimless for about 3 months, and then went and got a job at Google and moved out to California. Had a very successful 5+ year career there where I generally felt that my startup experience was an advantage, although there were definitely a few moments where I thought "I wish I'd joined Google in 2005 instead of wasting 4 years with this startup dream." Such is life though - I remember talking to a Google coworker (who later become a 2-time YC founder with a successful exit) who said "Dude, pretty much everyone at Google wishes they joined 4 years earlier." Now gearing up to try it all again.

I suspect that a major factor that accounted for that was that I founded my startup thinking it was an experiment and not a goal - I needed to know, myself, what I was capable of. If the answer was "Not founding a company, apparently", well, then I had my answer, and I could be happy in a regular company. If the answer was "You're rich now", well, so much the better. At no point did I feel I had to get rich, or that it was my destiny, or that I was worthless if I didn't succeed.

I've also seen some of the posts you mention that describe how years spent on a failed startup do not improve their career options, and the thing that's jumped out about most of them is that the founders there founded a company to escape having a real job, and then continued working on it long past the point where it would be rational to quit and do something else. Of course that'll hurt your prospects - you are losing time that can be spent developing skills and working on projects that actually will have an impact, and it also shows that you're not entirely rational. I also know a number of startup founders who tried it, realized their business concept was flawed (or in some, it was even successful but they just didn't want to do it anymore), and then went to work for Google. You typically don't hear about them on Hacker News, however, because they close that chapter of their life and feel no need to dwell on it and no bitterness to it, and so they don't post.

Yes, it's easy to pick yourself up again. As major life events go, the failure of a startup is not one of the harder ones to metabolize (but it sure feels like it is in the middle of it).

Here's something I wrote a few months ago that covers the same ground:

https://news.ycombinator.com/item?id=7140231#up_7140423

Just from empirical observation, healthy people will naturally adjust to new circumstances, even terrible ones. It's the time spent transitioning between states that makes us depressed. Otherwise, we'd never be able to overcome the loss of a loved one, a bad diagnosis, bankruptcy, etc. This is why it's important to have someone to talk to so you can get through this period of downtime, and if you notice a friend struggling, go the extra mile to help take her mind off whatever she's going through to avoid something like suicide which, sadly, happened to someone close to me.

On the flip side, this probably explains why the extremely wealthy are usually not happier than the not so wealthy - they've mentally adjusted to their new state.

So if you find yourself depressed and can't talk to anyone, you can at least count on time to heal your wound.

I'll chime in with my experience. I'm in an emerging market in the middle east (Saudi).

I'm the founder of one of the very few funded Internet companies in the country. Spent the last 24 months fundraising with little luck. My God what a brutal time it's been.

When the company ran out of money, I talked with our leading investor about my need for temporary employment (we were talking with a couple of VCs at the time and I didn't want to commit before hearing from them). He ran an Internet company as well, and I worked with them for a while.

I did that for about six months till I knew the investments were not coming. After that I polished my resume and started contacting people and companies about possible full time jobs.

The first question that came to my mind was about which type position to apply for. Before starting the company, I was a software engineer - so I could always fall back on that. But the years I spent working on the startup forced me to be a generalist. It really worried me to think I wasn't sure what sort of position I should be seeking.

It came down to three main options,

1- managing a software product team (which aligns well with my passion for building things) at a software company.

2- working with investment companies interested in Internet/tech investment. What helped me in this area was that I did my homework when we were discussing the term sheet for our seed investment. And that I blogged and spoke about the experience (Arabic content about the topic is very rare, aside from general entrepreneurship hype).

3- working in digital marketing. This drew upon our experience with digital marketing our product. This was my least favorite option, but it had the most market demand.

One of the things that really helped me in this job hunt was that I was visible to the local industry in my attempts to promote the company. I spoke at events about lessons learned, I blogged about the various experiences... Etc.

I think the best way to do well after failure is to be intellectually honest with yourself.

Polonius said it best "To thine own self be true."

As an engineer, in Seattle and the Bay Area, you will always have access to jobs.

For non-technical founders, you will have had gained valuable experience that will make you significantly more attractive.

You often have to wear multiple hats, manage your time, focus on what matters, and you gain a lot of experience in finance, shipping product, dealing with investors, dealing with customers, all of which is harder to get if you have a specific role at a larger organization.

Now, there are startups, and there are startups. If you quit your job and tinker at something for a few months to a few years and never really do anything to show for it (ship an MVP, hire an employee or two, raise or attempt to raise money), then, I imagine you didn't really learn anything, but if you were able to do those things, you will have gained real world applicable experience.

Being a founder, was the 2nd best thing that I could have ever done to my career.

My start-up didn't fail, but I ended up leaving because I was slowing it down.

My role now is basically a founder working for a late stage organization. I use lean methodology and entrepreneurship thinking to build new services to explore untapped market opportunities. Instead of raising funding with investors, my company will fund the growth of the service into a full fledged business unit.

(You know, Polonius was meant as a figure of mockery, so I'm not sure it makes sense to go around quoting his ironic sayings....!)
Honestly, and this is all my personal experience so not really generalizable, but finally admitting that my old startup had failed and we were going to shut it down was like getting released from a prison. Instantly you no longer have to worry about the thing you spent all your time worrying about and you can re-balance. It's pretty liberating in all honesty.

Just make sure you have people around to support you and also to use all that new found mental capacity on.