Most of the people I knew in the late 90s "new media" sphere are no longer involved in Web development or Internet media at all.. and certainly wouldn't be hanging around forums for those kinds of people. Their stories are stuck with them in their new roles as bank managers, fashion journalists, and mechanics (the founders of Boo.com, for example, are now a fashion designer and an investment advisor).
I doubt the strongest "failed and never got back on the saddle" stories would come from asking on HN. People who died in the entrepreneurial space are most likely not here.
Update: An idea, perhaps, would be to find people from famous Internet companies or "up and coming" lists and track down where they ended up.
When I left the company I started, I intended to start another one almost immediately. But then I didn't. Partially this was because of assorted conceptual and administrative issues, but partially it was because I realized how burned out I was. I'd been living this thing for five years, breathing life into it as part of a very small team, starting with literally no budget. Business is hard, and it was often soul-destroying - I discovered that other people were considerably more cut-throat than I was willing to be, and consistently underestimated how low people could go. And on top of the business itself, I was up to my eyeballs in code most of the time. Over time, I lost perspective. Within a space of a couple of months, though, two immediate family members were told they were seriously ill, and my sister became long-term disabled, and I was snapped back to reality.
It wasn't that entrepreneurship wasn't for me, as such, I don't think. It was that the specific kind of entrepreneurship I was living didn't fit my hopes or goals, and was eclipsing everything else in my life in a very negative way. I didn't think I could fit the care-giving that would potentially be required with the demands of the job. They're still going strong, but I wanted to live a different kind of life, closer to what Tony Stubblebine writes about on his blog. (Tony's the smartest guy I know on the topic.) That was always my intention, but we diverged.
It's certainly positively affected my career. Since leaving, I've spoken at Harvard, been published by IBM and have worked in a bunch of really interesting situations, with fantastic people, on a consultancy basis. Before the startup, I was a ground-level developer, so that's a win. But I'll certainly start a company again, at some point, if only because I'm the kind of person who loves to make things, and to do things on my own terms.
I'd ask yourself carefully if it's entrepreneurship that's not for you, or the situations you've been in.
(By the way, my family's health situation is vastly improved - but I think the thought experiment of what would happen if you needed to be a care-giver is a good one.)
Look, for every 100 people that venture into entrepreneurship, less than 10 make it, that is why there is so much money to be made. You should be proud of your effort, the only time you should be pissed at yourself is if you didn't commit 100%, in the long run we are all dead!
In the trading industry, they say that only 5% of traders are successful and of that 5% only 1% make enough to call themselves wealthy.....that is why George Soros can make $500mill a year or $1bill in the 1992 British pound trade, or Ken Griffith buying a $60mill dollar painting and giving it to a museum. Many traders will say that number is higher but you find many traders who hover around that break even point unable to make the leap.
Look at the sporting industry, how many kids want to be star athletes and how many make it, then when u look at those that make it to college level, more drop off unable to make the leap. Then of those that go pro, there will only be a handful that will be stars, like Kobe.
So i guess its not about just making it, its about making the leap from borderline success to real success that separates the men from the boys. Since if u are just borderline you will never be happy and you will eventually burn out.
Ok, just kidding.
I knew it was the right move when I realized I was learning 5 times as much in the startup.
Nothing matters more to your career than the development of your brain.
And if you're not excited by what you're learning, if its become stale and dreary, make a change.
Not all learning is technical. I didn't even mention that specifically. You can learn marketing, sales, leadership skills, project management, customer relations and qualities like tenacity and creativity at startups.
If you meant corporate life by 'career', my startup experience landed me in better and better jobs.
I've been an entrepreneur for most of my life. Aside from a brief stint at IBM where mostly people looked at me funny for two years, I've done ridiculously financially risky things just because I enjoy taking risks and seeing if I can make them come out. I'm like a compulsive gambler who bets the rent every month, except I place longer-term bets than the craps table, and I've beat the house more than half the time.
I published my first piece of code at 7, and it was for a TRS-80. Like most risk addicts, the #1 predictor of getting hooked is early success. Even if you're predisposed to being an adrenaline junkie, if you hurt yourself trying the first few times, you're done. Needless to say, the heroin of early success has a particularly acute effect on a 7 year old.
I tried a lot of stuff over time, some of it way out of my league, some not worth trying, some just dumb, and some a bad fit for the exigent circumstances of life and market. Those were the losers, and I've been kicked in the balls hard many times by betting on losing ideas, bad plans, lousy partners, conniving vendors, bad customers, and, more than anything, my own personal triumph of hope over cold, hard experience.
I also have just enough successes to keep me hooked. But on average, I'm not a whole lot better off financially than many of my 9-to-5er friends. My years where I turned over a lot of personal income are offset by the years when I don't, for sure. So for me, it just isn't about wealth. It's about the one place where I have the 9-to-5ers beat: that where they say, "Wouldn't it be cool if somebody..." I live my life being able to say, "Isn't it cool that I did?" But that's not the life for everybody. Most folks need the sense of security and uniform societal justification that being one more cog in the machine brings. I've never personally valued or had either.
So I totally blew a startup project I was working on for over a year. All but abandoned it a couple months ago. It was just too complex to fund, and it was a regulatory nightmare. I personally lost most of my net worth on the miscalculation. Oops. (On the bright side, I didn't lose anybody else's money, so I came out with as many friends as I went in with.)
And, of course, it flamed out at the height of the biggest recession in generations, so I was left fairly idle. I moped. I piddled. I taught myself to cook. I toyed with other backburner ideas I've let simmer for a long time. I did a fair bit of nothing and pretended it wasn't awful and painful and embarrassing and deflating and demoralizing. I'd trot out Michael Jordan's, "I've missed more than 9000 shots..." quote in my head and try to ignore that he was Michael Jordan and I wasn't.
The other day, I was talking with a recruiter friend of mine, and he said that it would be easy to get me a real job (gasp, choke). Suggested that I join his big company, do something simple, and let them pay for grad school in some subject area that I enjoy but doesn't necessarily have any commercial value. Get paid to hang with folks and just think for a few years. So I considered it. I even began the application process.
Then, I talked to a line manager at the company my recruiter friend works for (because I do my homework), and the guy related to me how much trouble they have managing the line because they have very weak procedures and no training on the line as to how they'd develop procedures.
My response was: "Well heck, I've been wanting to do some Android development, and you guys all have Android phones. I'll just build you an app to support your line management. I'll learn Android on a non-trivial project, and you'll get to know me."
The point (and I do have one) is that even my personal risk management behaviors are colored by entrepreneurial behaviors. I'm thinking of taking a 35-hour per week job to pay me to go hang out at a school and pay the rent, and I somehow manage to turn my job interview into new development and a mini-enterprise applications project. It's just who I am now.
I have a lot of respect for people who walk away from the startup game and go act like normies - I know tons of 'em, and I know that almost all of them miss the exhilaration and the sense that every time they come to work, they have a chance to move the needle. I can't seem to let myself give up that rush, and I really don't want to. I have no problem picking up high-paying work when I need it, but that's a function of having cultivated skills that have value no matter what kind of job I take - startup or secure (consulting, of course). I'm confident that if push came to shove and I needed to walk away, I could. I have a steady stream of job offers to prove it.
Churchill said that success is going from failure to failure without loss of enthusiasm. Of course, he won his war, so he would say that. And forums like HN are rich in first-attempt winners because there's an audience for them. So they've been as immunized to failure as a published 7-year-old. If you get into startups and totally flame out, assuming you can tolerate failure like a fully-formed adult (seriously, be sure you can), you might end up taking a pay cut if you decide to leave for higher ground. You might end up leaving for something deadly boring. But any losses you incur will probably be temporary, relatively minor, and non-fatal.
Or maybe you'll get hooked, and your life will just stay interesting. If you live by the Chinese curse, "May you live in interesting times," then don't do it. If you think that's a blessing and not a curse, go for it.
If you don't mind me asking, what would you have done instead?
I have failed w/two different startups, one very recent. The first time it was great for my career in monetary terms. The second - I don't know what will happen, but I don't regret doing it.
Working on a failed startup is draining. Your whole life is tied up in it, and if the company fails it seems like a phantom limb for awhile.
To directly answer your question - past entrepreneurship should be a big plus to any company worth working for.
You know you want to try something else, why not another startup?
Sure some things change. I can't be as reckless or risky now as I was when I was 20. Perhaps this IS my last attempt, but I doubt it. If it is I hope I can find just as much joy in something equally as productive as entrepreneurship.
One thing it did for me is that for a while, I was hesitant just jumping into any idea, because I know now how much it can take out of you (years of work before you know it).
Saying that, most careers are dead. Obviously in some areas there will always be a direct path of experience where a true career will exist, but the days where you went from junior to intermediate to senior to manager to vp etc are dying fast, especially with companies people who frequent HN are likely to want to work with. Do you want to take a job where they say you didn't do two years as senior developer or marketing assistant etc so you can't have the job?
More and more companies are starting to recognize the experience gained in the field and it is easier than ever to move between fields and jump "stages". Not all companies are like that yet, in fact maybe most aren't yet, but as they lose good candidates to companies that are then they will change.
So I wouldn't worry about what happens if everything fails, if you're willing to try the life of an entrepreneur then survival post that is going to be easy.
But that life is definitely sustainable. You might not have the biggest house and nicest car, but you should definitely be able to live an OK life. It gets more difficult as you have dependants, but some things will work, some things wont, and overall you just kind of hope it works out in the long run. There are no guarantees, but I don't know many people who pursue that life and end up on the street.
I wouldn't say I live a truly cutting edge entrepreneurial life but in 20 years of "adulthood" I have never had a "real job", I've gotten married, two kids, nice house in a leafy part of London. I drive a Mazda rather than a Ferrari so I'm definitely not where I'd like to be, but life is pretty good.
Don't worry about the future too much and just go for it, things will work out.
If you define your success by something that you have been unsuccessful at for years, it seems to me you will get depressed sooner or later.
PS: To me, Gagarin did not restart - was central idea of the animation.
Personally I pay a lot of attention to stories on HN when they mention failure (complete and not just cosmetic how we failed and then won type stories).
There are a couple solutions to this:
1) Invest more of your wages in low risk investments to offset the monetary risk of a startup.
2) Work full-time or as a contractor whilst also working 20% of the time on your own startup to try to gain traction which would lower the risk. Though if that succeeds, you should be then reinvesting your time in another startup. It's a vicious cycle :)
Go find something you enjoy doing, and then find people willing to pay for it. Enjoy your life. Don't go searching for the next big thing.
Then, when you least expect it, you will have an itch that needs scratching, that might be of value to other people, and you will be rested and ready to try again.
I'm just starting my second year of college, and trying to figure out where I want my life to go. I think I was born to do startups but need to know what I can fall back to. There's a very low success rate but because of statistical bias we hear mostly from those who succeed. I want to hear the other side of the story to find out what it's really like.
The one problem I've had is that some jobs are literally beneath you once you've started a company - people can be afraid to hire you. But that's not really an obstacle as much as a platform.
I've failed at majority of the things I've done, but I can always try again. The biggest problem with me was that I took problems as problems to be dealt with, but in fact they were teachers to be learned from. It's something really, really clichéd but the subtle meaning in it is something that takes frustratingly long to grasp. I think that it derives directly from the fact that I cannot change my environment, but I can always change myself.
No one ever is, but you can always make a choice.
But after I put in a couple years as an employee -- where I learned a lot and paid off my debt -- I quit again. Cuz life's too short to make crap, which is inevitably what happens if you work for somebody else.
How about that?
What do you think you will learn from hearing stories of people who gave up?
As I explained further down, my hope is to learn more about the risks of entrepreneurship to inform my decision about what to do with my life. I don't want to go into this naively.
I know this is hard to grasp, because it's counter-intuitive, but it's true.
My entrepreneurship approach is extremely low risk. (That sob story above was from consulting. Anyone can get taken by a conman.) It's a SaaS we built in our part time.
My business is growing 15-20% in revenue each month; even if we didn't touch it again, it'd earn more than $120k in the next 12 mos, but since we are working on it, by the end of 12 mos I expect our outlook to be greater than half a million for the year ahead of that.
See, I'm not worrying about "externalities." I'm not looking for funding or partners. I'm not trying to get somebody other than my customers to approve of what I'm doing and pat me on the head. I'm not trying to get bought (in part because I've seen how miserable people are after their startups are bought, they become employees again, watch BigCo destroy everything they've built.)
The only thing I'm gambling with is my time, and honestly, I've wasted more time sitting on my ass being sorry for myself than I would have wasted on this product if it fell apart tomorrow.
It will all work out if your are persistent.