Jeff Bezos is letting his charities do something radical – whatever they want
vox.com
vox.com
Perhaps the most important thing Bezos could bring (aside, of course, from money) is a sense for finding people who know things. That's the true talent of a great CEO, being able to assess sincerity, intelligence, creativity, and the ability to manage people. Writing hundreds of pages of grant proposals is probably less effective than being able to tell a good story, which contains the crucial hints about how you assess what's important, how well you communicate, and how you think about the people you'll need.
There's a good chance many -- perhaps most -- of these will fail anyway. Homelessness will remain hard. But it could well end up being very cost-effective to let creative and industrious people try things, even if some fail. That's very Silicon Valley, at least in myth. I have no idea how much of that myth is real and how much was just lucky executives in the right place at the right time.