Derek and his writing used to be a frequent top page link on HN. When I first started reading them I found them inspirational. As I read more of his writing I got the impression that most of the things he did were presented in the light of “I’m just a simple person that doesn’t need a lot” type of minimalism. However if you look at his “charity” he seems to have just figured out a way to avoid taxation and keep most if not all of his CD Baby exit. Additionally despite using what was the .com boom environment of the late 90s and early 2000s to generate his wealth I believe he has renounced his US citizenship and lives abroad now. I don’t care that he did that really, it just seems that his public persona is a bit of an act and hides a bit of entitlement/petulance.
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.)
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.
“I don’t need a lot” isn’t mutually exclusive with “I don’t want to pay a lot in taxes”. Besides that, he lives in New Zealand where everything costs twice as much. Sounds like your crediting his success solely on being at the right place at the right time. I got news for you - that’s pretty much all success or a component of it. Not to mention, he did build a sustainable business that gave independent artists an outlet to distribute their music. I’d say the guy is a saint.
