I don't think his speech was that great. Loud and arrogant doesn't make for a great speech. He kept stressing the ease of settling for the middle and just asking people to pay for your services. He used the analogy of us paying for cars but I think there's one huge difference. There is a huge barrier of entry into the car business which ultimately results in us having to pay what we pay, but I'm the web world, your product can be copied on the fly, look begged and be free, and that's why people want to horde the masses, something he criticized, so they can offer a free service and yet monetize using advertisements.
It happened with his product, the launch of huddlechat, but that as you know was taken down.
It's not a zero sum game, you can make money selling stuff that also given away for free elsewhere. Putting out a free version of Basecamp won't kill Basecamp, the market is big enough for everyone to live. As far as most businesses are concerned, $25 a month is free, it's pocket change. If your app solves one of their problems for that price, they'll pay it gladly rather than deal with hosting or maintaining their own free version, or using someone else's free version because most real business folk don't trust free.
I think you've missed the point. The point is not to settle for the middle, the point is that there are real everyday problems that need solving, and there's real success that can naturally come from solving those problems, overtime. You can't force success or simply will it.
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.
"His product" is Basecamp, not Campfire; a tiny fraction of their revenue comes from Campfire.
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?
Ok, but the point that the economics of information goods are often quite different from physical products is a valid one. That said, the idea that you should look for markets that aren't winner take all, where you could have a sustainable, mid-sized business, is a good one.
There's been an open source "copy" of Basecamp for quite a while now, but I don't see 37signals going out of business. Turns out companies are quite happy to pay a real company real money for a real service, rather than mess around playing with free alternatives that may or may not deliver.
It happened with his product, the launch of huddlechat, but that as you know was taken down.