I appreciated how he positioned "startups" in the same realm as other "regular" businesses; that's a very honest view because at the end of the day every business (tech startup or Italian restaurant) is judged by the profits they generate by creating value for their customers. Thats what a business does, 1 + 1 = 3, adding valuing. As a business owner you can't escape that law of commerce and expect to survive. Tech startups aren't a special class of business in and of themselves that deserve to be valued higher than other businesses, they're only special if they can grow more efficiently and operate at a higher margin than other businesses.
Most people would take good odds of running a multi-million dollar business over infinitessimally small odds of flipping and retiring. And he's obviously right about the odds: what percentage of YC companies have flipped?
DHH != 37signals
In any case, if you look past the delivery style, his speech contained many good observations.
I met him in Palo Alto on Saturday evening. He was honest, patient in answering people's questions, and very friendly.
It happened with his product, the launch of huddlechat, but that as you know was taken down.