The Ledger

Every statement that passed quotation and attribution checks. Mix any filter with any other: certainty 1/5, debate potential 5/5, or both at once.

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why aren't all 12 resolved? a statement only gets an assessment when the public record can support or contradict it. opinions and what-ifs never can, and 0 checkable ones are still open, waiting for their date. predictions held up or didn't; assertions are supported or contradicted. on every card: ▮▮▮▮▮ certainty · ▮▮▮▮▮ debate potential. speakers are clickable

Disclosure
Ferriss deliberately alienates 10% of his audience to preserve his authenticity
“So I will deliberately kind of routinely get rid of like 10% of my audience by just being unapologetically brazenly myself, showcasing the things that I would not be inclined to showcase otherwise, and I find that, at least for me, that has helped to keep off-…”
Tim Ferriss Oct 31, 2025 ▶ 10:34 20VC: Tim Ferriss: Why I Walked Away From Angel Investing After Uber | How I Accidentally Lost $150 Million | Money Fixed My Problems—Then Made Me Miserable
Disclosure
Ferriss: Viral video clips with 100M+ views drove zero podcast growth
“I've had clips, shorts, that have exceeded a hundred million views. The branding of the show is there. It's clearly an interview on my podcast. There's a link to the full episode, and the impact on the long-form episode has been imperceptible. You look at the …”
Tim Ferriss Oct 31, 2025 ▶ 13:04 20VC: Tim Ferriss: Why I Walked Away From Angel Investing After Uber | How I Accidentally Lost $150 Million | Money Fixed My Problems—Then Made Me Miserable
Disclosure
Ferriss treated his initial $120K angel investing budget as non-refundable tuition
“Why don't I take what I would have spent on tuition, a 120 K for two years, something like that. And that would have been sunk cost. I pay out of pocket. And what's the hope with business school, what you learn and the connections you make, make it worth it th…”
Tim Ferriss Oct 31, 2025 ▶ 44:27 20VC: Tim Ferriss: Why I Walked Away From Angel Investing After Uber | How I Accidentally Lost $150 Million | Money Fixed My Problems—Then Made Me Miserable
Disclosure
Ferriss estimates 70% to 80% of his wealth came from angel investing
“I would say, like, maybe it's 70% angel investing, could be 80, 20% podcast, 10% books.”
Tim Ferriss Oct 31, 2025 ▶ 27:48 20VC: Tim Ferriss: Why I Walked Away From Angel Investing After Uber | How I Accidentally Lost $150 Million | Money Fixed My Problems—Then Made Me Miserable
Disclosure
Ferriss lost $50K of his initial $120K angel budget on one startup
“So I have a 120 K for two years. I go in, I think one of my earliest investments, I was like, I'm putting in 50 K. And Mike was like, you sure you want to do that? And I was like, oh man, yeah. Yeah. This is really incredible. No, I just, I see the upside pote…”
Tim Ferriss Oct 31, 2025 ▶ 45:36 20VC: Tim Ferriss: Why I Walked Away From Angel Investing After Uber | How I Accidentally Lost $150 Million | Money Fixed My Problems—Then Made Me Miserable
Disclosure
Ferriss became an advisor to Shopify when it had roughly 12 employees
“I talked to a couple of people who were doing advising, and I figured out how to begin stepping into advising, and ultimately, with Shopify becoming an advisor when they had whatever it was, 10 or 12 employees, and then becoming an advisor at Uber.”
Tim Ferriss Oct 31, 2025 ▶ 46:12 20VC: Tim Ferriss: Why I Walked Away From Angel Investing After Uber | How I Accidentally Lost $150 Million | Money Fixed My Problems—Then Made Me Miserable
Disclosure
Ferriss was one of the first three advisors to Uber
“We're trading emails and that becomes Uber cab LLC. And I become one of the first three advisors.”
Tim Ferriss Oct 31, 2025 ▶ 47:18 20VC: Tim Ferriss: Why I Walked Away From Angel Investing After Uber | How I Accidentally Lost $150 Million | Money Fixed My Problems—Then Made Me Miserable
Disclosure
Ferriss: Selling Shopify shares immediately after IPO lockup cost him $150 million
“Shopify could have been just as big, but I sold a lot of my Shopify as soon as lockup expired because I had no experience with public markets. Yeah, you're holding your face. I mean, that would have been, that was a hundred and fifty million dollar mistake or …”
Tim Ferriss Oct 31, 2025 ▶ 48:28 20VC: Tim Ferriss: Why I Walked Away From Angel Investing After Uber | How I Accidentally Lost $150 Million | Money Fixed My Problems—Then Made Me Miserable
Disclosure
Ferriss invested in SV Angel primarily to receive Silicon Valley intelligence reports
“But the reason I invested 25 or fifty-k, whatever it was, in SV Angel, and their approach, I mean, it ended up being pretty smart on a lot of levels, was because I got a report card on pretty much everything in the Valley regularly. And that allowed me to go h…”
Tim Ferriss Oct 31, 2025 ▶ 54:14 20VC: Tim Ferriss: Why I Walked Away From Angel Investing After Uber | How I Accidentally Lost $150 Million | Money Fixed My Problems—Then Made Me Miserable
Disclosure
Ferriss completely stopped angel investing in 2015 to double down on podcasting
“So I stopped in 2015, which also allowed me to double and triple down on the podcast, which was born of the burnout of the four hour chef.”
Tim Ferriss Oct 31, 2025 ▶ 1:02:00 20VC: Tim Ferriss: Why I Walked Away From Angel Investing After Uber | How I Accidentally Lost $150 Million | Money Fixed My Problems—Then Made Me Miserable
Disclosure
Ferriss set an early goal to match his annual salary monthly
“I wanted to make as much per month as I was previously making per year. So at my startup job out of college in Silicon Valley, Shortly thereafter, keep in mind, this was 2000. The company imploded, everybody got fired. And I started my own company. I was like,…”
Tim Ferriss Oct 31, 2025 ▶ 21:32 20VC: Tim Ferriss: Why I Walked Away From Angel Investing After Uber | How I Accidentally Lost $150 Million | Money Fixed My Problems—Then Made Me Miserable
Disclosure
Ferriss held his Duolingo stock post-IPO to avoid repeating past selling mistakes
“Duolingo I held on to because I try to learn from my past mistakes”
Tim Ferriss Oct 31, 2025 ▶ 50:00 20VC: Tim Ferriss: Why I Walked Away From Angel Investing After Uber | How I Accidentally Lost $150 Million | Money Fixed My Problems—Then Made Me Miserable
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