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We need more posts like this. The nuts and bolts of bootstrapping. Too many articles talking about what to do at step 43, need more about steps 2-5.

Speaking of, has anybody had success with rather than dumping the 9-5 and jumping straight into your startup, tried going contractor for a while and use the down time to work on the start-up?




I'm trying that approach, with a little more incrementalism thrown in for good measure. Too soon to tell if it'll work, but at least contracting is paying the bills (plus padding), and still leaving me some time to build out a couple projects on the side.

I started contracting in March when my last startup ran past its runway and focused exclusively on that for four months. In July, I had some free time, so I started writing a handful of very simple iPhone apps to learn a few things:

- Can I build an iOS app in a single day that will make money? (A: maybe, but too soon to tell)

- What are the most effective strategies for monetizing an iOS app with advertising?

- How do some of the new iOS 4.0 frameworks work? (especially SMS and iAd)

Demand for my contracting services has grown sufficiently over the past five months that I'm planning on raising my rates this Fall, with the intention of taking on fewer clients while maintaining my same level of income.

The free time I have will be spent on building out a suite of web and mobile applications. I don't expect to strike it rich on any of them, but with a couple moderate successes and maybe one home run I'll be able to further ratchet up my consulting rates, ratchet down the hours, and make up any discrepancy with quasi-passive income from the apps I've built.

The final goal, of course, is to be able to transition entirely to living off income from products already in-market so I can focus on bigger and bigger projects.

We'll see what happens, but—regardless—it's better than getting a salary.


I didn't find the article particularly helpful actually. Didn't learn anything new. But maybe in the sense of the author pushing his own opinion/bias it was useful: if you trust him, it makes decisionmaking earier. Things like "Use Quickbooks", "Do the Delaware Dance" are just opinion.


I agree. He makes it sound like a Delaware C corp a no-brainer, but it's a lot more complex than that. Delaware is geared toward larger companies but and is great if you plan to get acquired. the legal system in Delaware is very favorable to corporations. I don't think it's right for every business, or every businessperson.




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