I'm only going off of what I heard in his interviews, and talks throughout the years, and I admit I'm def a bit of a fanboy of his. But regarding the charity,

I'm only going off of what I heard in his interviews, and talks throughout the years, and I admit I'm def a bit of a fanboy of his. But regarding the charity, from reading your comment I thought maybe this was another case of don't seek your heroes. Here's what he says about it: “Independent Musicians Charitable Remainder Unitrust.” When I die, all of its assets will go to music education. But while I’m alive, it pays out 5% of its value per year to me. (Note: 5% is the minimum allowed by law. It’s still too much. I would have preferred 1%, but oh well. I’m free to use it to start new businesses to help people, or whatever.) The trust has 8.8M in assets. http://www.nonprofitfacts.com/WA/Independent-Musicians-Charitable-Remainder-Tr-Derek-Sivers-Ttee.html http://www.nonprofitfacts.com/WA/Independent-Musicians-Chari... I really don't see a problem with 400k/year tbh, and if you believe him, 100k a year. And I wouldn't define "giving up the assets on death" as "keeping" either. The dude says on interviews that he lives in a house with pretty much no furniture, and has an empty fridge. He himself knows it's fucking nuts and doesn't prescribe it to anyone. It's just his weird schtick and it seems to be genuine to me. Could this be a huge act to play up a persona? Maybe. But the guy's been pretty consistent throughout the years and appears to practice what he preaches. Any interaction I've had with him has been totally consistent as well.