Caitlin Ostroff
speaker
397 appearances
3 recordings
2 series
first heard Feb 2026
last heard 6 Jul
Caitlin Ostroff’s voice in public audio — every appearance, attributed to the second.
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recordings per month · last 12 monthsRecordings per month over the last 12 months — 3 in all, peaking in Jul 2026 with 2.
Appearances
I don't know what the odds are right now, but the last time I looked, it was like a 95% chance that he won't return, which implied like a 5% chance that he will.
So take the election, for example, the 2024 presidential election.
The polls were very close between Donald Trump and Kamala Harris, with the slight exception of on Polymarket, where the people who were putting down money were betting more than the polls that Donald Trump would win.
And so that was kind of one of the major inflection points where you saw prediction market be more accurate than traditional polls.
Right, exactly.
It is, and I've seen a couple of those too.
And again, this is, it's betting.
Like, unless you are trading with information that isn't public and you are more certain of the outcome, it is a gamble.
So there was one user who started making all of these very correct bets on when strikes would start to happen and when a ceasefire would be called.
And so because of that, people online were quick to latch onto this and be like, this person is doing really, really well at, you know, this sensitive market.
Like, whether Israel will strike Iran is something not many people should know about, but they might know something that the rest of us don't.
The most recent one, major one, was the ousting of Nicolas Maduro in Venezuela, where, you know, I woke up after New Year's to see that all of a sudden this account had made $400,000 off of betting when Maduro would be ousted.
And you could see the bets leading up to the strikes.
You know, those happened at 2 a.m., and you could see bets being placed right up until about 11 p.m.
the night before.
Hmm.
And they were just, you know, doing more and more of these chunks of bets that this would happen.
Wow.
And so those were kind of the ones that stuck out for us where we were like, we can't say for sure if it's people trading on non-public information, but it looks really kind of... It's hard to imagine.
The odds of someone guessing that correctly and then doubling down in the three hours, like, leading up to... To the actual moment.
Showing 321–340 of 397 · page 17 of 20
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