David Heinemeier Hansson at Startup School 08

I haven't read the book that some others have been recommending, but it looks good (I respect a lot of the people who gave it favorable reviews on its website). Aside from that, I'd say you should do some research on others who've successfully followed this path. They exist -- they're just less likely to show up in tech news, which is heavily influenced by investors (who only care about big wins) and bloggers (who only care about big news). Take a look at the early blog posts from Balsamiq's Peldi, anything by Patrick Mackenzie, the Wufoo guys, Gary Vaynerchuck, or anything from the 37Signals guys. This talk by DHH never fails to motivate me: [VIDEO]

Have you already watched DHH's "How to Make Money Online" presentation ( [VIDEO] )? If not, watch it ASAP. If you go down the bootstrapping road, you must have profits coming in, to fund and further the development of your product. Sooner or later you will have to make money and since you don't seem to have a lot of funds laying around, the sooner the better. Moreover, have you validated your idea(s) (included the previous, failed attempts to excute them and build a viable business)? Are you sure that there are enough people out there with the burning desire to throw money at you for this app to make it worth the hustle? (assuming you want to sell your app, which would be the best and most simple way to make money) As PG says, the worst mistake one can make trying to build a company is building something THEY think is NEEDED by their customers and not what the market actually needs. Listen to your audience. Do the people need an iphone app to "truly define us"? Creating a kickstarter campaign was a good move, by the response you'll get you'll understand if you are solving a real problem or not. To expose more people to your app (and validate it or not with a wider set of data) you can use an adwords\facebook voucher and create a campaign (just search for them). Link to your homepage, track how many visitors opt in vs how many of them just land and bounce away, not interested. Ask questions on Answers sites, open threads on forums your ideal customer hangs out, the more eyebal

Reading the ending hits closer to home and made me more sad than expected! Andrew Welch was uneasy about the idea of scaling up, especially when they could survive as they were just fine off their utility products Way back in the day, YC always said not to worry about competitors raising tons of money (not sure if that's still the rec). The 2008 DHH boostrapping talk during Startup School is still one of the most influential videos on my career as a founder. But that path is increasingly less popular! [VIDEO] Lastly, for all the bolo comments out there, I remember the huge transition from modems to school ethernet that made it playable - it was honestly one of the reasons I was looking forward to dorm life!

Nice collection but this one with David Heinemeier Hansson on bootstrapping a profitable startup is definitely missing: [VIDEO]

The other answers aren't wrong, but I think listening to 37Signals Partner DHH from Startup School would speak best: [VIDEO] Almost more than their products, they're known for their very vocal broadcasting against the standard startup focus of investments, valuations, exits, etc... Their books "Getting Real" and "Rework" represent their bootstrapping, sustainable-business values - they're not timid in speaking out against the nonsense of the modern startup conventional wisdom. Personally, I think it's a very refreshing and empowering voice for entrepreneurs. It's not without controversy though, so dig in to their content for yourself to make your own judgement. (FWIW - "Getting Real" is a free PDF out there somewhere. I recommend it, though others may or may not.)

"Not every important idea is a huge world-changing event. Sometimes building a small company that makes a big difference to a small number of people is more important." Totally agree. DHH actually gave a talk about this subject at Start-Up School back in 2008. Definitely worth watching [VIDEO]

There is more to business than startups. If you can program, then you can bootstrap a "lifestyle" business. I don't love that term, but people know what it means. You can make a business that doesn't depend on traction and scale. Find a prosaic need, and serve it. Could start with consulting, or products. Start small, stay small by Rob Walling is an excellent primer, as is the four hour workweek. The latter glosses over how much effort is actually required to make a "muse", but the mindset is spot on. I'm currently doing this. I'll never get a $10 million payout, but I've built good revenue streams and have complete freedom of time. And I did it without knowing programming. You've basically got a superpower in the internet world. You can program AND you have a baseline of entrepreneurial knowledge. Just shift out of startup mode. As long as you've got enough money or time that you can work on something new without starving, it's not THAT hard to make a business that gives you freedom. (No guaranteed success, but the odds are significantly better than in a startup. This talk by DHH is a good overview) [VIDEO]

Cold email is a hit and miss approach. Just go talk to people face to face. Initially it seems like a non-scalable approach but it works wonders. The silicon valley, VC preached mantra of hyper scale is what muddles the minds of most entrepreneurs. Everyone starts thinking of million of users rather than 100s of users. There is a very interesting presentation at YC startup school 2008: [VIDEO] You will recognise the speaker :)