It's tough to pick winners for tech in which to become proficient to expert in this game. A reasonable first order approximation is anything championed by Ubuntu should be dropped like a hot brick.

Mir, Bzr, the phone, the ubuntu desktop the list goes on. At one time they had a policy of not paying for any new development ever, ie contributing nothing back but using and polishing, branding & packaging contributions from their competitors. They got popular by paying Matt Garrett(?) and resourcing him to make suspend work on a bunch of laptops, I recall seeing a photo of a pile of abut 50 by his desk, so Ubuntu worked better than RedHat or debian or whatever else on your laptop, eventually that work found its way back to mainline, it was their edge that drove adoption before it did.

Has any other development they've funded worked out? It must have, right? Has any of it worked well enough to be adopted by their competitors? Eg contribution to the commons, like for example paying for Gnome and GTK+ developer time like RedHat do?

I am biased on this and I want to state that bias clearly so you can adjust for it if you want to. Shuttleworth turned up at LCA one year (Linux conference in Aus/NZ run on the smell of an oily rag by volunteers - a genuine comunity effort) in a private jet and was notably absent from the dinner which usually involves some kind of charity auction and raises a few thousand dollars, no more than that, from the community, most of whom aren't particularly wealthy, for something worthy. Had money for private jet leasing, fuel, pilot wages, landing fees etc etc but $0 for the community charity drive.

Bug #1 in the ubuntu bug tracker was something like "Windows is more popular than linux." They've closed it because Android, which had nothing whatever to do with their efforts.

I have a general dislike for Canonical, and I've been very critical of many things they've done in the past, but I don't think this criticism is fair, for a few reason.

Canonical has pushed a lot of code upstream. They could definitely be better at this, and of the big Linux companies they're among the worst at it, but open source has without a doubt benefited greatly because of Canonical's efforts.

The code they used is also licensed by its authors to allow what they do.

Now that I've defended Canonical, I need to take a shower to try to feel clean again ;-) (just meant to be a light-hearted joke)