Why One Top VC Owns Zero ETH – This Week on Unchained

Good Sunday!

Prediction markets have become one of crypto’s hottest trends. Now they're attracting the attention of federal prosecutors.

Two DOJ cases involving a Google engineer and a U.S. soldier are forcing courts to answer a new question: when does using privileged information on prediction markets cross the line into a crime?

Former SDNY prosecutor Sam Enzer joins Steven Ehrlich to break down the cases and what they could mean for the future of prediction markets.

Meanwhile, one prominent crypto investor has a surprising portfolio position: zero ETH.

Mike Dudas of 6th Man Ventures explains why he’s bearish on Ethereum, why he thinks Hyperliquid could become crypto’s next great cash-flow machine, and the simple framework he uses to decide which tokens are actually worth owning.

Here’s more on what we unpacked this week on Unchained:

• 🔮 Polymarket’s Oracle Problem Is Becoming Impossible to Ignore
  A controversial Strategy market resolution, Circle freezing a $12M DeFi pool, and fresh debate over Solana’s monetary policy all point to the same issue: crypto’s infrastructure keeps breaking at the edge cases. The Uneasy Money crew asks whether Polymarket’s oracle system is becoming a liability at scale.

• 💰 Why Strategy Should Have Sold $2 Billion, Not $2 Million of Bitcoin
  Jeff Dorman argues Strategy’s capital structure is becoming increasingly fragile as dividend obligations grow. He breaks down why all four stakeholder groups may be losing, what the recent Bitcoin sale really signals, and why the market may be underestimating the risks.

• 🦄 Joe Lubin Makes the Bull Case for Ethereum
  As critics pile on Ethereum, Joe Lubin pushes back. The Chopping Block panel debates ETH’s future, the Ethereum Foundation’s brain drain, looming quantum threats, DeFi security concerns, Strategy’s evolving playbook, and the arrival of regulated perpetual futures in the U.S.

• 🤖 The CFTC Opens the Door to True Perps — and Agentic Finance
  The CFTC’s latest ruling could reshape U.S. derivatives markets. Katherine and Jessi unpack what it means for Hyperliquid, while also tackling a new challenge: AI agents that can spend money, place trades, and create legal questions regulators have never faced before.

• 🏛️ Jamie Dimon vs. Brian Armstrong Signals Crypto’s Political Peak
  Strategy’s Bitcoin sale, Anthropic’s trillion-dollar ambitions, and a public clash between JPMorgan’s Jamie Dimon and Coinbase’s Brian Armstrong reveal an industry at a turning point. The Bits + Bips panel explores whether crypto’s political influence is peaking just as the biggest battles begin.

All these episodes are available on Apple Podcasts, Spotify, Fountain, Podcast Addict, Pocket Casts, Amazon Music, or on your favorite podcast platform.

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