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Both Magnatune (http://magnatune.com) and BookMooch (http://bookmooch.com) are bootstrapped by me.

The hardest things for me are:

1) sometimes you come up with an idea that would make money at a certain scale (in my case, lots of shoutcast radio stations of Magnatune's music) but you can't do it because you don't have the money

2) I have to put a lot more time into making the software I write efficient and scalable, because I can't afford to buy lots of machines when the site grows. So, for instance, I tend to avoid doing a lot of SQL queries, which might be handy, because scaling that requires lots of SQL server machines.

3) In the old days (10 years ago, when I self-funded Lyris, which eventually became a success) a big problem I had was getting licenses to technology (C++ libraries, database servers) but these days open source replaces all that.

4) doing without employees. That's both a benefit in the near-term, as I have to learn how to do everything lean and well, but a disadvantage if there are rote tasks to do now as we scale. With BookMooch, I've managed to get volunteers to do those rote tasks, but with Magnatune, I got 3 not-very-well-paid part timers.

- John Buckman




Well whaddya know! I attended Magnatune's workshop presentation at WikiMania; nice to see the founder here.




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