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Welcome to The Chopping Block — where crypto insiders Haseeb Qureshi, Tom Schmidt, Tarun Chitra, and Robert Leshner chop it up about the latest in crypto.
This episode kicks off with major news: Dragonfly just closed their $650 million Fund IV, making them one of the largest crypto VCs not through growth, but because others have downsized. The timing feels surreal — they keep raising right when markets dump, creating the biggest gap between institutional optimism and retail sentiment Haseeb has ever seen.
But money flowing in contrasts sharply with talent flowing out. Kyle Samani left Multicoin, Arianna Simpson departed A16z Crypto, and several other crypto veterans are moving on. The crew unpacks what this “great resignation” means for an industry that feels like it’s shifted from pioneer phase to settler phase.
Then they dive into the OpenClaw saga — the viral AI coding assistant that got acquired by OpenAI, but not before its creator almost deleted it due to harassment from crypto Twitter demanding he launch a token. This leads to a deep discussion on X402 payment standards and why AI agents might prefer crypto over credit cards.
Finally, they debate Polymarket’s controversial 5-minute Bitcoin betting markets and the brewing legal battle between federal and state regulation of prediction markets. Let’s get into it.
Hosts:
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- Haseeb Qureshi, Managing Partner at Dragonfly
- Robert Leshner, CEO & Co-founder of Superstate
- Tarun Chitra, Managing Partner at Robot Ventures
- Tom Schmidt, General Partner at Dragonfly

