I have no regrets. I've asked myself a couple of times if it was worth it, and to be honest I can't think of anything else I would have rather been doing at the time. It's not like playing slot machines, hoping someday to hit the jackpot. It's more like an obscure artist trying to find his niche—you do it because this is who you are.

If I never have a big success, I'll die satisfied knowing I was doing what I felt I should be doing. I read a quote from a post on this list some years ago, I wish I could remember the source. But it was something like, "When I look back on my career, I want to say, 'Boy, that was a fun ride!' not 'Boy, I sure felt safe!'"

Even in failure I found a market for the technology I developed and came out slightly ahead through creative licensing. The key: never give up. You really find out about yourself when all you have left is your wits. About the companies: The first closed because I was too young and didn't want to move to where I had to, looking back I should have moved. The other failed due to the industry leaders incompetence that endangered human life causing the government to create unforeseen regulations.

PS: Unfamiliar with the area so if anyone knows an awesome startup in SF looking for a product guru who can literally design and develop anything (mobile, consumer electronics, web apps, etc) please let me know.

Source: http://www.wired.com/wired/archive/15.01/ultraman.html

It'll take me another year or so to pay back all that I owe, and to get to financial break-even; and another year or two to save enough to start my next big project, at worst, but that's not stopping me doing stuff on the side, oh no.

Lessons:

Build a product. I turned out to be awesome at selling an idea, and myself, but got too caught up in that to actually execute on a product. I'm only now turning the work I did over that time into something useful to hopefully recoup some of the money, sweat and tears I poured in.

Follow your instinct. (YMMV. I've learnt over the last two years that my instinct is usually spot on, and spending months convincing myself otherwise is entirely fruitless.)

No experiences are ever wasted. Coming to YC to interview (we didn't get in) was absolutely worth it and was part of the reason I've ended up in the Valley.

Pick a landlord who won't mind if you pay your rent a little late.

Pick advisors who understand your business and who understand business itself. Running a web platform startup I had an advisor who had never started his own company and who didn't understand Twitter (a core part of my technology).

People will evangelise you if you impress them. Do it.

Second startup was a photo sharing startup 3 years later in 2004. We both left our jobs at ClearChannel before we got funding but secured an angel round about 3 months later. That lasted a year and a half before we ran out of money. We made the mistake of rebranding and rewriting the product with the funding (won't do that again). By the time we were ready to market 9 months had gone by and we didn't have a lot of money left.

Currently bootstrapping and looking for when I can leave my day job. We don't have traction yet but I spent 4 weeks hitting the streets and talk to customers (students).

I'm 32 now and after every startup I swear I'm done but I can't not do this. It's in my blood. I apologise to my wife on a regular basis for it. Thankfully she's always been supportive. Two times since we got married 3 years ago and I've looked her in the eyes and said "I think I need to quit my job" twice already.

Hoping the third time is a charm :)

As I learned here, you cannot give in to regret. You have to pick yourself up and resolve not to make the same mistakes.

For the first 2-3 years, we were reasonably well funded (by both Investors and customers) and doing interesting work. I was drawing a reasonable but not optimal salary, and getting paid each month.

After about 3 years, the money was getting tight, on paper, salaries had remained flat, but they weren't being paid regularly or in full. However, we were targeted for acquisition by a major software company, who pulled out (due to having made a different, but unrelated major acquisition). At this point, one of my colleagues had the good sense to call it a day, and go work at a bank.

We spent the next year keeping our heads above water, drawing reduced salary when cash flow allowed, looking for that major company to come back and buy us.

Here is where, in hindsight, the wasted years kicked in. I stuck around looking for the jackpot like a bad gambler, as, I think, did my colleagues. The company was making just enough income that the downfall was a slow bleed, rather than a haemorrhage. We stagnated, I stopped doing anything interesting, and stopped caring. Eventually I left for something more stable. I was not alone in my egress.

Some of my former colleagues are still at it, I believe that with fewer mouths to feed, they are profitable enough, even though they are even more stagnant than before.

There were so many opportunities for me to have left.

- When I realized the business plan basically was formulated around a domain name.

- When a superior said "We don't have to build anything new, what people want is one place to get everything and we'll provide it to them". (Basically a "Don't innovate" directive)

- When the investors sued because they contended they company was trying to steal corporate resources (mostly domain names). (I don't think my boss was, but clearly there was a lack of trust on both sides)

- When a superior asked us to all go onto Digg and "digg down" people who had taken issue with him for trying to purchase wiki.com for 2 million dollars.

Eventually, even the depressed shadow-of-myself left after my boss said "I'm going to make Bittorrent legal! The labels will have to accept it because it will be the same as a swap meet". I realized the writing was on the wall and I had to get out. (This was... after 6 months of not getting paid)

I left about a month after and had a more interesting startup experience at Soundpedia (didn't work out either, but I have zero regrets and loved every minute of it)

I regret that I let my early start on RoR waste away while I was building stuff in PHP and Perl/Mason for them. (ouch) I regret that I didn't have the courage to try to do something on my own, or to go to the states to try working for a more properly managed startup. I regret that I didn't have a more social environment (since I was working remotely). Finally, I regret that I let myself get carried away. It was a classic story of manipulation of a green wild-eyed college kid. Someone posted a while back about the classic pattern of manipulation in an open source project and my experience fit that to a T.

Now when I look back, I can kinda laugh about it all. I learned, moved on, and I gained a lot of skills after doing so. Was I stupid? Hell yes; but it's the kind of stupid you can get away with once in your life.

Would I work for a startup again? Absolutely, even if I had no stake in the business. However, no more remote working, and I won't accept a job where I can't perform excellently.

I've been fortunate to always have a day job that I enjoy, and I've never really sunk big money into any of my side projects, so I'm not in debt.

I look at much of the time I've spent on my projects as time that I would have "wasted" some other way, if I weren't working on them.

Although none of my projects brought me fortune or fame, here's what I got out of them:

* Better coding skills, which has certainly helped me in my day job.

* An assortment of functions and classes that I can re-use in future projects.

* A lot of fun.

Lessons learned, in no particular order, except for the last:

- If you need to explain your app to customers in more than one sentence, or if that sentence contains any four-or-more syllable words, or if any of those words' definitions fail the above two criteria, it will probably fail.

- If you are working on a project to scratch your own itch, confirm that other people have a rash.

- Do not give in to feature creep, unless that feature presents itself immediately and without intervention. For example: Back-end features to improve search results: good. Sliders, filters, color coding, additional search options, menus, extra words, animations, hover effects, etc, will probably only confuse people, unless you are a UX genius, in which case those features will merely go unused.

- People trust their gut instinct on what something does, rather than read instructions, or discover, or wander into unfamiliar territory. Find the design for your product that mimics something people have used to solve a similar problem.

- People are generally incapable of abstraction. If you are the "x of y", that means people need to thoroughly understand x, y, and what it means to abstract one to the other.

- People will exert very little effort into learning something unless the rewards are immediate, have been stated to them by a trusted source, or are made extremely enticing.

- Ideas that require a critical mass of users to be useful are easy to come by, nearly impossible to execute.

- Hope for the best, expect failure.

- Stay the fuck away from anything "meta," or anything involving variables. People like being served things that they pick from a menu, or that people suggest. The most complicated task the average person has to deal with, on any regular basis, is probably choosing multiple toppings for a pizza.

- It is far better to release a crappy implementation of something awesome than it is to release an awesome implementation of something crappy. Awesomeness in the idea is easier and more valuable than awesomeness in the implementation.

- Presentation is much more important than you'd like to believe.

- It is far better to be lucky than any of the above. Yes, you can slightly increase your chances of being "lucky," but don't kid yourself.

Doesn't this conflict with the general sentiment that ideas are near-worthless unless implemented well? Can you elaborate? Are you referring to rapid iterations (i.e. have a 'good idea' for feature x, and launch a crappy implementation, AND THEN iterate until the implementation has evolved to maturity)?

The awesomeness of your idea is like a multiplier. You can easily come up with an idea 10 times as awesome, and any implementation of that will be presumably be 10 times as successful. You can't as easily implement something 10 times better. This is all voodoo mathematics, anyway. You don't have to believe it if you don't want to.

Scratch the "well." Ideas are near worthless unless implemented. "well" helps.

Then I've spent another couple of years on and off, (re)developing an archive management system that may finally become a reality soon, at its 4th iteration and rewrite :)

Anyway these were years well spent; I've learnt a lot.

The first startup story: it ran out of cash, utter failure and sad ending. Basically we had glorious plans of world domination :) but we never had the money to actually make it. The CEO (who brought us 90% of the funding) ended completely broke after burning through € 15 millions in a couple of years. We went through quite a spectacular series of failures :

  * we started the project 6 months to 1 year late. Real work started in 
  March 2000, just before the dotcom bust (Doh).
  * we weren't actually technically qualified to make it through, though we 
  tried hard. The project was too complex and too ambitious from the start, 
  would have needed literally 100s of millions to build.
  * our main partner and support (SGI) wasn't doing too well.
  * our CEO never managed to get any additional funding. Instead of calling 
  a quit after the first year, he kept the sinking boat running, without
  enough resources and people.
  * he literally burnt money : we bought a huge stack of hardware, worth 
  more than half a million euros, without having any resources to even *turn 
  it on*, simply because he *promised to*. We had a huge colo with big iron 
  hardware not even in a runnable state. Sigh...

I'm lucky I just love hacking.

No, I don't regret having dropped Cambridge Univ. internship for a failed startup because at that time it seemed perfectly rational thing to do. I'm happy about the lessons I learnt from that stint and it made for a great groundwork for my future startups.

If a project doesn't fit success criteria I give it about a month before it's pivoted or done.

Regardless, I would never consider these failures, and here's why:

Any venture you do on your own shows initiative and is practice for your programming and business skills - that already places you in the top 1% of software devs. What's the worst that could happen? You build your skills and work for a great company, because any company that fosters entrepreneurial innovation (e.g. Google, Facebook) would LOVE to have you if you built something significant.

So...build a successful business or boost your resume to work for Google/Facebook? Sounds like a win to me.

I think I've spent maybe 12 months total on startups after I should have left them; sometimes it is clear that for team/market (vs. product) reasons, a given startup is doomed. Until that point, it's still a worthwhile experience, as there is a lot to learn, and it's impossible to know it won't be successful -- after, it is a lot harder to stay motivated, even if the day to day tasks can still be educational.

I guess I'd rather produce a technical success that fails for other reasons (unconnected to me, of course :-) than do work that frequently is a failure for reasons much closer to what I do (e.g. impossible projects that are mandated nonetheless because of politics).

I dislike bureaucracy and loathe office politics, so despite their downsides most startups are a better match for me.