I think the point he's trying to make is that we're all so conditioned to accept institutions without question ("we do it that way because we've ALWAYS done it that way"). This is beaten into us (and creativity beaten OUT OF us) as children, especially through the public schools. Clearly it's not irreverent to innovate, but I can imagine the shock/horror of the mainstream at the "reinvention" of chess.
I work in the Detroit area actually. The handful of one hour contract jobs I've done have been pure maintenance coding (i.e. bug fixes on existing applications, reports modifications, etc.)
The high and low ends vary greatly. I've done little one hour wham-bam-thank-you-ma'am gigs and then I've done projects that run 4-6 months and bring in 5 figures. On average I'd say about $5000. The most I ever brought in on a single project was $24,000. BTW those projects were all done using the .NET Framework. Take THAT, Expensify!
What's wrong with a job at a small or medium sized company? I'm guessing you're very, very young (18-22) to have such a myopic view of things. "The career game is just about spinning the wheel, repeatedly, until you actually win." Wow. Really? How about making things happen for yourself instead of spinning a wheel? There's more opportunities in this world beyond startups and "big" companies. Plenty of mid-sized companies would love to get their hands on a talented individual like you. And not all jobs will suck your soul and drive you to the edge of sanity.
BTW, at 3 years in, you guys aren't "startup"-ing anything. You're playing around at best. Time to get out and get some experience.
Chronicles the build up and ultimate failure of govworks.com in 2000-2001