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This is my experience with bootstrapping as well.

The technical platform problems around bootstrapping have gotten much easier, due to Heroku, AWS and all the services out there (Papertrail, Exceptional, New Relic, etc.)

Unfortunately relatively little work has been done on the "requires that you be a stubborn bastard" problem.

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1) Creating any business is hard, unless you sell blue meth. 2) Creating two businesses is even harder (bootstrapping + consulting to make a living). 3) Technical hurdles are getting easier but rarely does the best product win. Marketing is hugely more important that product, although I wish that wasn't true.

I suspect you'll find even the meth business is tricky. Indeed, I believe there's a popular TV series about it.

Serously, Breaking Bad is an excellent primer on entrepreneurship. It covers everything: distribution, marketing, negotiation, finding business partners, scaling, exit strategies...

Similar experience, and pretty much reflects what most bootstrappers I know said, too.

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