Summary

The highest-conviction setup is conditional: Jonah calls GBTC “the best trade” for getting ahead of a potential BlackRock ETF approval, while Avi says to sell the approval euphoria rather than chase it. Jonah argues that crypto lacks sufficient accessible capital, gateways, and risk appetite to pre-position fully for the potential flows. He puts approval at a 75% chance, estimates perhaps $3 billion-$4 billion of inflows, and cautions that he does not know BTC’s path, adding, “I don’t think it’s a buy right now.” Avi expects GBTC exits and front-running to offset some flows and says the net effect is uncertain near term but positive over a longer period.
Jonah bought ETH/BTC around 0.0662 after ETH sentiment deteriorated from June 28-30 while its price stopped falling; the episode’s BTC timestamp was stated only as “.064.” Avi’s event playbook is to expect BTC euphoria and ETH panic at approval, buy ETH on a post-approval dip roughly a month later, then pivot and sell roughly a week afterward.
The tactical sell does not negate the structural bull case, but the hosts frame it differently. Avi calls BTC and ETH megatrend assets in a multidecade uptrend. Jonah sees Bitcoin approaching institutionalization and believes the coming months could solidify a base for a “crazy run” in 2024 and 2025. Avi expects sideways trading after the ETF event until the Q1 2024 halving approaches.
The DeFi rally looks more like an ownership squeeze than a fundamental renaissance. Avi argues the assets were “horrifically under-owned,” with almost no speculative holders left; Jonah’s alternative framing is a bear-market bounce after more than a year of fire sales, with FTX not helping. In reflexive crypto markets, Avi favors leaders over laggards because “you almost never make as much money buying the laggard.”
NFTs may be emerging from their trough of disillusionment as art, status goods, and ownership infrastructure. Jonah compares profile-picture projects to fashion brands and separates Fidenzas, Squiggles, Punks, and Rocks as a different category. Avi expects a crypto wealth effect, increasing attention from the traditional art world, and broader deployments from Nike, Starbucks, artists, DJs, and athletes. Jonah’s sharper use case is on-chain certificates of authenticity and gallery-friendly NFT custody.
Their worst trades produced the episode’s durable risk rule: a valid thesis does not excuse ignoring changed information or a vanished edge. Avi kept buying upside calls after Bitcoin’s 2019 run from $3,000 to $14,000 because earlier gains made him feel “really good at this”; Jonah stayed max-long crude in 2018 after the Iran-sanctions premise changed. The corrective is blunt: “When everybody’s panicking, you buy; when everybody’s euphoric, you sell.”

Deep dive

1. Winning trades become dangerous when the original edge disappears

Avi’s defining mistake followed a spectacular 2019 run: after Bitcoin rose from $3,000 to $14,000, repeated purchases of mispriced upside options had grown his account rapidly. By the top, the inefficiency had vanished—volatility was trading “100 points higher in my mind”—but recency bias told him, “I’m really good at this,” so he maintained heavy call exposure and “took an absolute beating.”
The missed exit was especially instructive. During the fast drop from roughly $14,000 to $12,000, volatility spiked so sharply that his calls lost only 5%-6% despite spot falling 10%-15%. He read that resilience as permission to stay long; Avi now treats a massive short-term crypto volatility spike as a “99% hit-rate sell,” with the signal even better near month-end. Jonah suggests modeling a one-day, two- or three-standard-deviation move in volatility as a sell signal.
Jonah’s scar came from the opposite lesson applied too rigidly. After repeatedly taking 10%-50% profits in Facebook, Bitcoin, and, to some extent, crude—then watching those positions rise much further—he resolved to ride trends. In 2018 he was max-long crude as supply tightened, but failed to adapt when Trump softened Iran sanctions amid concern that high gasoline prices could damage presidencies in an election year.
The loss took roughly 18 months to recover. Jonah’s resulting test is whether price reflects a genuine technological or market unlock, such as vastly broader access through an ETF, or merely the peak of a hype cycle where existing participants now find the asset unattractive. At $30,000, miners might be financing their businesses by selling, while an imminent ETF-driven influx of capital would argue against selling.

2. History supplies the pattern library for bubbles and technological commodities

Avi credits studying history with making him the most money. Great traders appear intuitive because they have absorbed years of charts, balance sheets, and prior episodes—the market equivalent of wrestling muscle memory: “You do certain things in certain situations, and you just know to do those things.”
His reading list starts with John Steele Gordon’s The Great Game, whose Wall Street anecdotes include a trader deliberately dropping a buy list so club members would purchase the stocks he wanted to sell. George Soros’s The Alchemy of Finance is Avi’s “best book in the world” for playing bubbles and understanding reflexivity. He also recommends Bernard Baruch’s autobiography, which follows the trader’s pivot into politics and role as an adviser to FDR.
Jonah adds Daniel Yergin’s The Prize, a 1,000-page, 150-year history of crude oil. His analogy is that a commodity is “tradable technology”: early oil was debated as either a miraculous replacement for whale oil or useless black tar, while Yale scientists worked on refining it into kerosene. Crypto builders are attempting a comparable transformation around a deceptively simple question: “Does the world need a publicly owned spreadsheet?”

3. DeFi’s rally is an under-ownership squeeze, not yet a new thesis

Avi sees no clear fundamental change behind the DeFi 1.0 pumps. These assets had almost no speculative ownership; the remaining sellers were largely existing holders receiving inflation and selling. When traders realized they had zero DeFi exposure, the result was effectively “a massive short squeeze.”
Jonah’s pushback—worth keeping—is that a 150% BCH rebound can still be a blip inside a larger downtrend after the asset class had been fire-sold for more than a year, with FTX not helping. Avi also mentions speculation that the SEC was being told by the Biden administration to loosen up on crypto, but says, “I have no insight into that.”
BCH, in Avi’s view, is “a very tightly controlled asset,” making sharp moves easier to manufacture, though he avoids a direct accusation. LTC then tends to follow as traders seek a secondary expression. His repeated lesson is that crypto crowds into winners: a laggard may offer a one-to-three-day convergence trade of 10%-20%, but the leader usually continues outperforming.
The market snapshot included GRT, BitDAO’s rebrand to Mantle DAO, FRAX, Maker, and Blur; Avi also saw Bybit as a winner amid Binance’s issues. Jonah later speculates that DeFi may have rallied after the SEC came after Coinbase: traders expected DeFi to get “absolutely nuked,” but since nothing had happened, price was rising again. He presents that only as a possible explanation.

4. NFTs are shifting from profile-picture fashion to durable ownership rails

Jonah distinguishes community-driven profile-picture projects from Fidenzas, Squiggles, Punks, and Rocks. The former behave like Gucci, Prada, Versace, or American Eagle: their value depends on teams and communities that “wax and wane in potency,” rather than functioning like Picasso or Damien Hirst.
Avi’s first bullish mechanism is the wealth effect. If crypto rises, holders will want to display gains through “gaudy things in the digital world”—Rocks, Fidenzas, Squiggles, and other expensive NFTs—while broader cultural acceptance makes that display increasingly legible.
The second signal is traditional-art attention: Avi’s New York art-world contacts now monitor NFTs, and a Pace gallery near the London office in Mayfair was exhibiting them. The third is expansion beyond art through Nike.Swoosh, Starbucks, and Fan3, a platform in which the hosts invested that is helping artists issue NFTs at greater scale. Avi says DJs are lined up to issue NFTs granting access to conferences and music, with athletes also lined up.
Jonah locates the deeper use case in authentication. Paper certificates for physical art can be forged or lost, and even registered deeds remain a headache. He proposes a paired business: on-chain certificates for traditional art, plus a gallery-friendly service that lets collectors buy and custody NFTs through familiar signatures and DocuSign rather than MetaMask. For custody, he says he would prefer Chase to a startup or Microsoft.

5. The ETF trade separates pre-positioning, event euphoria, and ETH catch-up

The episode’s BTC timestamp was stated only as “.064.” Jonah said he had changed his view over the prior two weeks, gotten longer ETH/BTC, bought ETH and other alts, and later specified an ETH/BTC purchase around 0.0662. From June 28-30, ETH sentiment became steadily worse while price stayed flat—his preferred divergence, because “everybody hated it, but the price was flat.”
Jonah’s GBTC thesis rests on market structure: traditional capital can pre-hedge widely anticipated events, but crypto lacks enough accessible money, gateways, and risk appetite to fully front-run a BlackRock approval. Anyone able to buy spot BTC or GBTC can therefore position ahead of what he sees as a fundamental mispricing. He lists long GBTC, ETH, Stacks, and BTC upside among his favorite trades, while also noting that he does not know where BTC goes and saying, “I don’t think it’s a buy right now.”
Jonah estimates that an ETF could bring a few billion dollars of flows, perhaps $3 billion-$4 billion, but thinks outright GBTC holders could redeem, drain the trust of Bitcoin, and exit once able. Avi expects some time between approval and redemption, believes flows will be partly offset and front-run, and says he does not know the net amount; over a longer period, he expects the effect to be positive for BTC.
Avi’s event model resembles the futures ETF approval: BTC tops effectively on approval, ETH runs afterward and catches up sharply, both eventually top, and the market moves sideways until Q1 2024, when the halving approaches.
That produces a nimble sequence rather than passive chasing: Avi calls the ETF a sale, expects BTC euphoria and ETH panic at approval, then says to buy ETH on a dip about a month in, pivot, and sell everything roughly a week later before waiting for the halving. Separately, Avi calls BTC and ETH megatrend assets in a multidecade uptrend; Jonah’s earlier Facebook and Bitcoin profit-taking provides the caution against prematurely selling a genuine long-term trend.

Crypto Is Entering A Paradigm Shift The Bear Case for Risk Assets | 1000x