Mike Cannon-Brookes wrote a post about the perennial Open Source debate. If you haven't read that, read it first or this will be way out of context.
Probably the best response you'll see to open source has come from Apple. Open Source does infrastructure very, very well. Take the infrastructure, and build something on top of it that Open Source doesn't do well at all - a consumer operating system, populated with fantastic, original applications.
IBM's done the same. It's not supporting Linux just because it likes penguins. It's using it as a cheap platform to stick really big expensive things like DB2 and Websphere on top of.
JIRA's another good example. An open-source base (WebWork, OFBiz, and it can run on the major open-source appservers), topped with a slick user-interface, and very responsive support.
Open source is great for commoditising things that deserve to be commoditised - the implementations of standards and protocols, areas of computing where innovation has slowed or stopped, and the building of tools that can be used to build other tools.
Even Microsoft recognise the value of open source, which is why you'll find the BSD license reproduced in your Windows 2000 licence booklet.
Dave Winer is a trifle disingenuous, because even Userland benefits from programmers working for free. Radio may not itself be open, but Userland has a very liberal policy on allowing people to post patches for it or add-ons based on Radio code. Because there's no competing Radio clone, everyone who creates and distributes a free add-on for Radio (under the open-source principle that it's easier to share than to hoard) is improving the Radio application, and making it more valuable to Dave Winer.
Closed source vendors could also learn a lot from open source. They're mostly Cluetrain-style lessons. The first lesson would be "Don't lie to your customers". Keep an open bug database. Let people know early what you're working on, and when their pet problem is likely to be fixed. Don't just shovel new releases into the trough under a cloud of hype.
Maybe if they'd learn that lesson, there'd be a lot less crap released.