The Wisdom Wall

10 quotable lessons, heuristics and mental models. Every one is playable at the moment it was said. No fortune cookies allowed.

Everyone Chamath Palihapitiya (240)David Sacks (207)David Friedberg (189)Jason Calacanis (47)Brad Gerstner (16)Gavin Baker (13)Bill Gurley (13)Tucker Carlson (10)Naval Ravikant (10)Nate Silver (10)Ray Dalio (9)Sergey Brin (8)Travis Kalanick (7)Shyam Sankar (7) Best Newest Oldest

“I just don't think that like politics teaches people to think critically and it's like, yeah, part of that is like, they're not thinking probabilistically, but it's more like people just want to see their kind of priors confirmed.”

Nate Silver, May 30, 2022

“One thing that people in Silicon Valley get right for all their faults and self-servingness in some ways, right, They kind of get the orders of magnitudes, right? They understand scale, um, and social media and the daily news cycle really collapses that, right? So some extremely important problem and some trivial…”

Nate Silver, May 30, 2022

“in VC, I mean, you might want to find a founder or a sector or a company that's undervalued by the market, but eventually you want that sector to grow. You want to attract more talent. You want to attract future fundraising rounds. So you kind of are more being Ahead of the curve by, um, by half a year to a year.”

Nate Silver, May 30, 2022

“the most successful gamblers don't actually care that much about money.”

Nate Silver, May 30, 2022

“Almost every election now is a change election.”

Nate Silver, Jun 29, 2026

“They're, they're almost perfectly correlated. So if the odds of Democrats winning the Senate, but not the House are like, are like one percent, if you go to Kalshi or Polymarket, whatever else, they have to be like around one percent. So conditional on Democrats winning the Senate, they'll almost certainly have Won the…”

Nate Silver, Jun 29, 2026

“Really obvious one is that successful gamblers think probabilistically. It's not just a matter of understanding probability, but being comfortable with uncertainty, being willing to take bets on an uncertain basis.”

Nate Silver, May 30, 2022

“successful gamblers are contrarian, at least to some degree. And again, I'm kind of repeating myself a little bit, but there's, there's no edge if someone, if everyone does the same thing in the same way.”

Nate Silver, May 30, 2022

“I think people can, in matters that happen only occasionally, like a presidential election, people think, well, my gut is that so-and-so will win. You don't have enough practice at forecasting elections to really, for that to be very useful, right?”

Nate Silver, May 30, 2022

“in poker is basically like, you know, three states, right? Super rich, somewhat rich, and dead broke, like not a lot in between.”

Nate Silver, May 30, 2022
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