OSF told Krutzky the most surprising thing about markets today is the new generation of traders who have made money consistently through the last two years of a bear market while traditionalists bang their heads wondering why Bitcoin is not higher. He called today's on-chain action a serious opportunity rather than a negative-EV game, pointing to a steady stream of $5 million to $20 million runners every day. His own approach, he said, is to find something mispriced and hold it over three or four weeks while the daily runners die off in a day, because chasing maximum profits every single day is a really tough way to trade.
OSF started trading at 18 with spread betting and penny stocks, and his first buy was UK-listed Provexis on a day it was up 1,700%; he put about £5,000 of savings into it, watched it drop 90%, and never sold — the position is worth roughly £300 to £400 almost 20 years later. After studying maths and economics at the London School of Economics he spent about 10 years at Barclays Capital, seven in the UK and three in New York, where his first year ended with his entire annual P&L wiped out in December on a single trade and the next few years brought four or five defaulting companies in his high-yield and distressed credit book. His 2019 was the first losing year of his career after being short in a market that ground higher, and in 2020 he realized he would have made 10 times more buying the dip than shorting the COVID crash; he was also stopped out of WeWork bonds three days before the whole thing crashed.
After the massive May 2021 crash, OSF put every bit of cash he had into crypto and NFTs, and on the day he quit his Barclays job — admittedly a little drunk — he minted 150 Bored Apes, emptying about $40,000 of ETH from his wallet. He took profits around 0.5 ETH against a 0.08 ETH mint price, then watched the floor run to about 3 ETH, at which point Mando, a previous guest on the show, talked him into buying back in; the pair combined portfolios to co-own about 72 apes and sold the entire position to Machi Big Brother on Blur in February 2022, with the ape coin airdrop alone worth $7-8 million at the time. He called the trade something like a 2,000X, possibly the highest-returning trade ever, but insists he had no idea at the mint that it would become what it did.
OSF argued the best opportunities right now are tokens with cash flows, the model proven by Hyperliquid and by PumpFun, which has now sustained its revenue for over two years. He pointed to Robinhood Chain, whose token trades at roughly a 0.7x multiple while PumpFun trades at three and a half times, because the market only has one month of volumes to judge it on and therefore massively discounts its growth. On a position such as PONS on Robinhood Chain, his invalidation is two weeks of declining revenues and lost market share, and his goal is a re-rating of the multiple from 0.7x toward 2x — the point where he sells, even if it feels like the moment everyone is piling in.
The most underrated narrative in the market, in OSF's view, is Robinhood Chain: the top token, Cash Cat, sits around a $150 million market cap, the next highest is around $50 million, and the rest trade in the $20-30 million range. He estimates only a few hundred active traders are in it, with none of the big crypto CT accounts, VCs, or institutional players involved and maybe Kaleo the only big OG name participating. He thinks just one coin reaching $500 million — not even $1 billion — would trigger an influx of traders, and he expects hindsight posts in two or three months showing coins bought at $20 million caps that made a clean 20X over weeks or months; Solana, by contrast, he finds too saturated to trade with an edge.
OSF said he does not believe he has an edge and that 99% of people do not either, arguing that true edge technically belongs to insiders and cabals holding information no one else has. The best traders instead combine two trainable characteristics — discipline, meaning taking profits and cutting losses consistently, and conviction, holding mispriced ideas in size for months the way Flood reportedly held his Hyperliquid position. He cited the blow-ups of the 'situational awareness' traders who put a few hundred million into AI stocks, noting they had the conviction side but lost out on the discipline side.
OSF runs every trade with four predetermined levels — stop loss, take profit, invalidation, and target — and admitted he still round-trips positions when he abandons them, as recently as last week. He described buying NVIDIA stock yesterday and taking about $30,000 off the table at the open this morning, only to watch it trade higher, and said he now uses Claude to generate scale-out levels and talk through his decisions as a kind of trading coach. After a big round trip in early July he has also cut size, reasoning that putting $100,000 into a stock and keeping $30,000 is better than risking $1 million to chase $300,000.
When losses mount, OSF's prescription is to get flat, take days or a week off, and write the game plan on paper, the habit he carried from Barclays, where a tap on the shoulder meant 'nuke it' and start again the next day. He called greed — taking risk off and then watching the trade go higher — the hardest part of trading to overcome, and he urged beginners to build their own system with stops and take-profits, to trade with a crew rather than solo, and to unlearn the belief that they must own the best-performing coin each day. He also left a question for the next guest, Trader Vain: after making a lot of money, losing a lot in FTX, making it back, and selling Breakout Prop to Kraken, what keeps him in the game from a mental standpoint?