Ask HN: how many years have you "wasted" on failed startups? And any regrets?

Were you referring to this quote? "Life is not a journey to the grave with the intention to arrive safely in a pretty and well-preserved body, but rather to skid in broadside, thoroughly used up, totally worn out, and loudly proclaiming: Wow!! What a ride!"

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

You are an artist. You think of ideas, and you turn them into software others can interact with. You are always in the process of creation. There is not one second wasted, so long as your goal is to create. Painters do not look back at the last 100 canvases and ask "How many hours have I wasted?". They just paint. So paint, or should I say "Code".

Have been doings tons and tons of side-projects hoping them to fly. I will tell you a story. When I was in college, I got an offer from Cambridge University for paid internship (800 pounds per month + travel -- that's a lot for a student). But I was so enthusiastic about startups (thanks to HN!) that I declined that offer and started a so-called startup of recruiting people through social networks. We had a fancy tag-line "infiltrating social networks' and I distinctly remember having day-dreams of dominating the recruiting space with that idea. Needless to say, two months of summer and lot of naivety doesn't translate into success.

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.

2-3 years on Searching.com/Searching.ca. I definitely regret a wide swath of it, mostly not being more daring and trying out more things. They had me (a junior programmer albeit with a College degree) building out large parts of their infrastructure, then switching things at the drop of a dime. (picked up some good skills in the aftermath)

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 think the quote is from Tom Preston-Werner's post "How I Turned Down $300,000 from Microsoft to go Full-Time on GitHub" http://tom.preston-werner.com/2008/10/18/how-i-turned-down-3...