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Ask HN: Founders whose startups have failed, where did life take you afterwards?

235 points| windowshopping | 11 years ago | reply

172 comments

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[+] jfb|11 years ago|reply
I ran out of gas and left my cofounder; divorced; worked a succession of small startup jobs, some better than others; ended up back at Apple. I have ideas that I cannot express at Apple and so may end up taking another whack at the piñata, now that a) I am not in the throes of a crumbling personal relationship and b) I've gone round the carousel once, so I have some idea how the world works.

I regret the way I left my startup, but at the time I was under an abominable amount of pressure outside work, and I just sort of shot out sideways, like a watermelon seed being squeezed between thumb and forefinger. I do not regret leaving Apple to do the startup, not in the least.

[+] rdl|11 years ago|reply
I don't think it is possible to do with more than two of work stress; personal life stress; physical safety or health stress simultaneously. One at a time is ideal, but most startups have work stress and physical stress (due to time) simultaneously.

You don't have to be single and childless to do a startup successfully, but if you have family life or interpersonal relationships, they have to be good ones, or at least low stress ones.

[+] rayleoni|11 years ago|reply
Can you give a few quick takeaways from your experiences concerning 'how the world works?'
[+] buro9|11 years ago|reply
Might be too soon to answer, my startup ( http://microco.sm/ ) just failed. As someone else put it: insufficient growth, ran out of runway. But at times I wonder whether it's because myself and my co-founder were of like skills and we didn't have a strong enough sales function. Whatever, we failed.

I've had ~10 opportunities presented to me since announcing we'd failed. They ranged from dev position through to CTO position, but ultimately I sent an email to CloudFlare and have joined their team.

A startup failing is traumatic. Aside from the emotional trauma it may lead you to doubt your own competency. I shine at product dev, and coding for that, so sought a place to do that. To regain confidence in myself.

I also wanted regular(ish) hours and salary, to build able to rebuild some stability. I'm getting married in a month's time and most of the cost of that will be on credit card (founding a startup empties your coffers). So it was important for me to be earning and giving our marriage a good start.

I may, in a few years, find that I want to return to the fray. But for the foreseeable future I feel deeply happy that I've joined a great team working on some hard problems, and that for myself I get stability out of it.

A startup is a ship at sea in a storm, I wanted to experience a boat in harbour for a while.

[+] eps|11 years ago|reply
Have you at all looked at selling microcosm as a upscale managed forum service? "Build a community" sounds like a far larger and less doable task than "host your forum with us".
[+] Udo|11 years ago|reply
In the early 2000s with a few friends together I founded and ran a web development startup in Germany. Because I had been consulting for advertising agencies since high school, building a service company for agencies seemed like the natural thing to do. Afterall, it was the kind of customers I understood well, and my cofounders were enthusiastic about the concept, too.

Despite doing every single conceivable thing wrong, we lasted a few years before dramatic failure ultimately hit. I learned the insidious thing about initial (modest) success is you become conditioned to underestimate the scope and probability of failure that can topple you in the future.

One of my cofounders, who had always hated the startup part of our endeavor, and who wanted us to become a respectable German company as soon as possible, he was the first one to bail. And in hindsight he was absolutely correct about choosing the right moment to quit. It took me a few more months of pouring my own money in and taking on debt until I realized how absolutely screwed we were.

Let me tell you: failing, in Germany, with your own money and in debt... it's pretty bad. Here, culturally most of your relationships are built on a sense of success and respectability. You lose all that in an instant. Customers and business partners wouldn't even take my call when I wanted to do a last farewell chat, even though we didn't owe them any money or anything like that. The disappointment coming from my family and friends was just complete and total, though they tried to be nice about it. The failure of my company now meant that I as a person was also a failure.

After going down with the ship I went for a full time job, eventually sold a side project/company for a bit of independence, and did this for a few years, then transitioned to freelance software development.

I have to say after the startup - even considering the horrible parts towards the end - after the startup there is a bleakness to a "normal" lifestyle I could never quite shake off. Recently I've also gotten some very unpleasant nudges from life which made me realize time spent on things is irrevocably wasted if they're not important to me.

So I'm going into the fray again. In fact I'm working on a prototype right now.

[+] k__|11 years ago|reply
Can't blame you.

I know a bunch of german companies who did everything wrong, but still operate for years.

Many of my friends worked for so called "web agencies" who build shitty typo3 pages en masse. Most of the people working there were interns.

I worked at a academic spin off. They had good tech but bad UX. They worked on for about 14 years and didn't make any money. Somehow the founders were good at raising money from investors. So the bills always got paid.

[+] Swizec|11 years ago|reply
> after the startup there is a bleakness to a "normal" lifestyle I could never quite shake off

"Running a company would make you perfect for any conceivable job were it not for the fact you'll never want one again."

Not sure where I read that, but it sounds true. I am being gently pushed into job life by circumstance after 5 or 6 years of independent life (startup ~2 years, school ~1 year, freelancing ~2 years) and getting hired, even just talking about the possibility of a job job, feels like losing.

But alas, freelancers do not get visas so I will just have to suck it up.

[+] appreneur|11 years ago|reply
Failed, job, startup -success...gave up company because of co- founder,started again.. startup- success...amazing journey first 3 years...next 4 years hell with business partner.

I have failed in the year 2011 after 7 long years at my bootstrapped company. My business partner didn't want me around, I was pretty emotional after so many years, I felt it's time to accept fate n move forward.

Broke up with my gf, I quit my company(gave my 67% to partner if he split debt). So I pretty much walked out with million dollars debt and nothing on hand, life was tough.

I started again,my small business was ok, my burn rate was low,I was ramen profitable ...burning $2000 per month but all customers money, hired employees fired lazy ones.

I just couldn't cope with debt sold my house, my car, my dads house , my aunts house, fortunately n unfortunately I am from india, here people threaten with dire consequences and people give all their life earnings for loved ones. So all the assests cleared about 500k usd dollars.

I earned 200k usd doing consulting, mobile apps, web apps, sentiment analysis ,paid 60k usd salaries. Now I have another 200,000 usd to clear on track to clear it but ....something beautiful happened , I married my gf after 3 years of break, my ex-business partner wants to do business with me again since he saw how I came out of rat hole,...

.I just have one thing to say "don't give up and hang in there with logic and common sense"

I feel I will succeed financially in 2015 , Our product is coming beautifully...then perhaps I can write a book...till then I have midnight oil to burn..

[+] swombat|11 years ago|reply
How did you end up with $1m of personal debt? That seems like an epic disaster, worth telling the tale to allow others to avoid making that sort of mistake.

For my part, in 2 failed businesses I never went more than £10k or so into personal debt.

[+] wushupork|11 years ago|reply
Congrats on coming out of failure. I would love to learn more about what worked and what didn't work. What sort of pitfalls you had, lessons learned, etc
[+] seunosewa|11 years ago|reply
Why did you break up with your girlfriend initially and what motivated both of you to come back together?
[+] BIackSwan|11 years ago|reply
Failed at a bootstrapped startup (http://shoutt.me/) earlier this year after a painful 2 years. Learnt a lot and failed a lot - in practically everything - marketing, sales, growth, tech, operations. Lost a fair bit of money too. Failed because the product was wrong and it took us 2 years to accept it.

Succeeded in one thing - found the right co founders.

In 2 months started working on the another idea (https://doctorc.in) with the same co founders - moved to India. Got funded this August. Could execute infinitely better on this one because of all the lessons learnt in Shoutt. The experience of failure of the first startup is paying off now in the second one.

I wouldn't have it any other way.

[+] prezjordan|11 years ago|reply
Shoutt was a great idea. I'm not sure why all startups like this fail to take off - Vark, Jelly, etc. Is it a timing thing? I mean everyone has a smartphone now, right? So how come it never works out?

Wishing you and your team the best of luck with the new venture!

[+] StandardFuture|11 years ago|reply
I honestly believe that you have the single most important thing for a startup (a true 'just starting out' startup). The right co-founders (co-founding team).

It's the one thing out of all the other things that you listed that cannot be learned. It is dependent on pure and simple luck. So, I have hopes for you guys if you have that plus a plethora of lessons learned. Good luck! Even though you may not even need it. ;)

[+] joshmn|11 years ago|reply
Had a startup (rather, small company that was established in the hosting space), sold it when I was 19. Took that money, paid out employees, and tried to start something new and fresh.

That failed. Had a co-founder that wasn't dedicated. Had some tech that I could sell and did sell, but I still considered it a failure because I never hit the mark I wanted.

Consulted, took some jobs with startups here and there. Those startups failed for some reason or another so I went back to consulting.

I'm now consulting and lending myself out to people/businesses with ideas, usually spending about 30 hours a week doing so. I spend another 10 volunteering and tutoring, and another 20 whipping up ideas of my own and seeing if I can find something that I'm confident enough to run with.

My plan is to keep on trying. I have a book of ideas that I want to execute. I'm mostly just waiting for the right idea and the right front-end guy. I'll usually crank out an MVP and never release it because I fear it failing (and I'm not a popularizer); sooner or later, though, I'm confident something will stick when I find the right people to execute with (or they find me)

[+] StandardFuture|11 years ago|reply
You should publish your book of ideas as a GitHub repo and submit it here. It might help you find a perfect cofounder for one of your ideas, etc. Or just get general feedback. :)
[+] kiraken|11 years ago|reply
I'm a pretty decent front-end developer and looking for a back end developer as well :) my email is [email protected] Contact me if you wanna talk it through
[+] mrfusion|11 years ago|reply
What do you mean about not being a popularizer?
[+] kolinko|11 years ago|reply
During the past 10 years I tried launching startups a few times, failed most of the times within 6-12 months. After each failure I spent 3-6 months trying some more relaxing things (public speaking, dancing, standup comedy), and then got back to doing startups again and again.

Right now I'm quite tired of all that, but fortunately the past micro-startup & investments brought in around $300k which would be enough to live comfortably for ~5 years in Poland.

Right now I'm 30 years old, and the plan is to keep on trying. What changed during the past 10 years is that I'm no longer striving to go all in with a financed business and spend 70-hour workweeks. I don't want to build a billion-dollar business. Instead, I want to build something much smaller which will allow me to have personal life as well.

[+] aerovistae|11 years ago|reply
In what universe is stand-up comedy relaxing??? My god I would be nervous.
[+] notahuman|11 years ago|reply
Wow, honestly i want a similar life just like you.
[+] staunch|11 years ago|reply
After a previous failure, my co-founder (and co-brother) and I are moving to the bay area this month, from LA. We're keeping our expenses low and plan to drive for Uber part-time as a way of avoiding day jobs.

Even though I'm married and have a newborn, we're sharing a place and living like (healthy) college students. We've both turned down huge salaries to work together indefinitely.

I love creating products for people. I love solving problems and I love writing code. The stress of a startup feels like a small price to pay to create something great. And I really want to create something great.

[+] kartikkumar|11 years ago|reply
Doing a startup with a sibling, that's always intrigued me. I've thought about talking to my brother about it a few times. Just feels like it might be incurring too much risk to the personal relationship. What is your experience of that aspect of doing a startup like?

Kudos got knowing what you want and going for it.

[+] nostrademons|11 years ago|reply
http://diffle-history.blogspot.com/2008/12/aftermath.html

Spent 5+ years at Google after that, worked on a bunch of cool projects, finessed my technical skills, learned how to push through difficult projects until completion, rebuilt my confidence, and recently left to try again. We'll see how it works out this time.

[+] dennisgorelik|11 years ago|reply
Did you notice that your blog is full of SEO-spam comments?
[+] meelooo|11 years ago|reply
I tried and "failed" a couple of times in the last 14 years. Having a family pushed me to decide to settle down for some time. I started working as a software engineer at Apple a week ago. The itch is still there though ;-).
[+] monksy|11 years ago|reply
Where do you think you went wrong and who do you think you can avoid that in the future?
[+] sirbetsalot|11 years ago|reply
Started a startup in Vancouver using Machine learning to automate the sports betting odds generating stack. Got two cofounders one MBA (yah i know) and a fundraiser, both failed badly as I did all the code. ended up doing 40% of the fundraising. fired the MBA for incompetence, 4 coders I had all left when other co founder did a deal where the term sheet was pulled last second. packed up left the company to the fundraiser and used all 12 man years of work to bet on sports. Now a successful sports gambler, completely financially free. Single most deadly killer to startups is a bad cofounder.
[+] marketmaker|11 years ago|reply
I have a question for you:

How did you navigate the line between "I should just make money off of my own product and forget customers" vs "I should focus on the product and acquire customers"? Since there's an opportunity cost to doing both, I'm curious to understand how you navigated things with that kind of "fork in the road", so to speak.

[+] notastartup|11 years ago|reply
im in vancouver too. interesting you are in to sports gambling are the odds anything like poker? you should write an article on it.
[+] nicwest|11 years ago|reply
I got a job where I just get to write code, go home at regular time, and get paid every month. it's awesome.
[+] tomasien|11 years ago|reply
I kept creating stuff, learned to code, ended up being on the front page of the website that taught me to code, made a website that was in Time Magazine, and started another startup that is now well funded and growing rapidly.

Just keep making stuff, stay afloat, and manage your mood - stay healthy, stay happy, but PRODUCE AND PUBLISH LOTS OF WORK!

[+] dont_pm_me|11 years ago|reply
i worked at a startup with a couple of failed founders -- basically you grab the next best engineering job you can find and lick your wounds until you're either ready to start again or give up completely
[+] blrgeek|11 years ago|reply
Startup failed (early employee).

Did my own startup; growth was insufficient. Ran out of runway (7yrs of doing startups).

Looked around & got a position as a Product Manager in AdTech, since I didn't want to get back into a dev role, and wanted to move more into the prod/mktg side.

Since then moved into an accelerator working with early-stage startups on mktg/prod.

Life's been much better than I expected when I failed.

[+] jeremyriney|11 years ago|reply
I went and lived in a monastery for a little over a year. Then started something new. Couldn't stay away for long.
[+] kartikkumar|11 years ago|reply
Wow, where was that? Sounds like a fascinating experience. Did you cut off from tech altogether for that period?
[+] infinitone|11 years ago|reply
Intrigued. Do tell more.
[+] unclebucknasty|11 years ago|reply
Another startup. And another, until it worked.

Here's a question that is less frequently asked: to founders whose startups met with moderate success wherein it turned into a lifestyle business that could be sustained indefinitely, but never appeared to be reaching the life-changing initial vision, what did you do?

We focus a lot on success and failure as binary concepts, but I think there are a ton of businesses that meet with some success, but fall well short of the initial goal.

[+] aaronbrethorst|11 years ago|reply
I consulted for a couple years, joined someone else's startup, consulted again, and am currently very much enjoying a real 9-5 job with a great salary, decent benefits, excellent coworkers, and the best work-life balance I've ever enjoyed.

I may not have won the startup lottery, but I've never been happier.

[+] jkent|11 years ago|reply
In the late 90s, I started a cloud-type hosting provider, with an angel round $100k+, dropping out of university. The dotcom crash happened and raising more money became near impossible. I was inexperienced and tried to do everything myself, and hired the wrong people.

I morphed it in to a web development business that did OK, then worked out it was easier working for someone else (got my life-work balance better) - in a VC-backed startup that ultimately got acquired.

I left to finish my degree. Got confused for a year and did a bit of sales. Then another startup that I couldn't get off the ground (services marketplace) - perhaps insanely ambitious.

Then I trained as a teacher (forgot that), teaching inner city kids how to add up.

I now work at Google in partnerships, where I am largely happy, married, get to travel a lot - and occasionally still 'get the itch' ...

[+] raminassemi|11 years ago|reply
Someone should start a blog interviewing failed startup founders and letting them tell their stories and share their lessons, really in-depth. Maybe even bring in other people for multiple perspectives.
[+] mdparker89|11 years ago|reply
The problem is these lessons are, for the most part, already out there. Unfortunately, some things you just have to go through to really learn. All of the mistakes I made were ones I read about. It just took me a while to recognize that my mistakes were the same as the ones I read about.

That said, if somebody did start that blog I would definitely read it.

[+] jbkkd|11 years ago|reply
I'm up for this.

Founders, if you're willing to share your experience on a blog, hit me up. My email is on my profile. Anonymity guaranteed.

I'm not sure about what the format will be yet, but I'm thinking of interviews which will be transcribed, with the audio as an option. I'm open to other suggestions.