Welcome to The Chopping Block, where crypto insiders Tom Schmidt, Tarun Chitra, and Robert Leshner chop it up about the latest in crypto. This week Rob Hadick of Dragonfly sits in for Haseeb as part of a podcast host swap.
Tom walks through Black October, 48 hours in which top-severity vulnerabilities dropped across PHP, Node, Railway, and more, and Tarun runs down the rest of the damage, from Linux kernel exploits to Finland shutting down its internet services. Robert argues the blast radius was small for the worst day the web has had, Tarun says crypto was ironically ready first and closed source is the less safe bet, and he explains why defenders had to patch with open source models. Then banks start blocking AI agents: Robert says anything that can click a button terrifies them, Tarun reads Bernie Sanders’ call to pause AI, and Rob asks what happened to Occupy Wall Street. Finally, Joe Weisenthal comes around on Hyperliquid, Tom is outed as the onion futures guy, and the hosts weigh a rumored $2.5 billion Visa deal for Fireblocks, 2021’s bubble valuations, and where an AI financial crisis would start.
Listen to the episode on Apple Podcasts, Spotify, Pods, Fountain, Podcast Addict, Pocket Casts, Amazon Music, or on your favorite podcast platform.
Show highlights
🔹 Rob Hadick guest-hosts as part of a host swap with Empire’s Weekly Roundup, and Tarun says the hosts are finally free of the dictatorship of Haseeb.
🔹 Black October: in 48 hours, critical vulnerabilities hit PHP, Node, and Railway, Cloudflare saw millions of exploit attempts, and European governments took sites offline.
🔹 Tarun adds Linux kernel exploits with no responsible disclosure, a QUIC zero day, a GitLab flaw, and a Chinese state-aligned agent caught exploiting the CVEs in the wild.
🔹 Robert calls it the doomsday batch of security vulnerabilities, and says not that much broke.
🔹 Tarun says crypto was ironically prepared first, and that closed source is the less safe bet because every binary can now be reverse engineered.
🔹 Defenders tried to patch with Claude and got blocked, so open source models were the only way to rotate keys fast, the same reason AI trading agents took off.
🔹 JPMorgan, Wells Fargo, Bank of America, Schwab, and Citi are restricting AI agents in customer accounts, after a month of talk about an agentic bank run.
🔹 Robert says banks took a decade to accept read-only Plaid, so anything that can click a button is 10 times as terrifying, and the friction is deliberate.
🔹 Bernie Sanders wants to pause AI to protect your bank account. Robert says he drew the exact opposite conclusion he should have.
🔹 Tarun says everything is crypto now: banks can’t tell you from your agent, and that is the point.
🔹 Robert would short health insurance companies, the industry AI should hurt most.
🔹 Joe Weisenthal comes around on Hyperliquid 11 years after blockchain, not Bitcoin. Tom points out that Hyperliquid is not TradFi in any way.
🔹 Visa is rumored to be buying Fireblocks for about $2.5 billion, down from an $8 billion valuation. Robert says January 2022 prices were bubble prices.
🔹 Character.ai burned $16 in compute for every dollar of revenue, and Tarun maps the duration mismatch where an AI financial crisis would start.
Hosts
⭐️Rob Hadick, General Partner at Dragonfly
⭐️Tom Schmidt, General Partner at Dragonfly
⭐️Tarun Chitra, Managing Partner at Robot Ventures
⭐️Robert Leshner, Founder & CEO of Superstate
