Biggest Losers: Altcoins, Gensler, Web3, Strategic BTC Reserve

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. It's a new year, and that means the crew is back with their annual year-end awards and predictions episode.

First up: the 2025 winners and losers. From Trump's meme-coin windfall to Gary Gensler's legacy getting torched, from prediction markets going mainstream to Web3 getting its official eulogy — no one is safe. The team debates the biggest surprises (Circle's shocking IPO run, Ethereum's pivot under new leadership, Zcash's unlikely comeback), the best new mechanisms (ICO 2.0, DATs, federal preemption), and the year's best memes (including the Chopping Block's own tariff factory video).

Then comes the flops and comebacks: AI agents that overpromised, Berachain's fall from grace, and Tether somehow winning again. Finally, the crew reviews how badly their 2025 predictions aged — spoiler: not great — and lays out fresh calls for 2026 including AI-powered hacks, stable-coin-funded AI capex, and equity perps taking over DeFi.

New year, fresh takes, brutal honesty — let's get into it.

Show highlights

🔹 Biggest winner debate — Trump's meme-coin empire, prediction markets going mainstream, and M&A consolidation reshaping the industry.

🔹 Gary Gensler's legacy destroyed — Haseeb declares his SEC tenure the biggest loser as every initiative got reversed.

🔹 Web3 pronounced dead — Tarun writes the epitaph on the "ownership economy" thesis as NFT sentiment hits rock bottom.

🔹 Bitcoin as biggest loser? — Robert's controversial pick: BTC underperformed in a year that should have been its best.

🔹 Circle IPO shocks — From skeptics to $70B market cap, the stablecoin thesis briefly took over Wall Street.

🔹 Ethereum pivot surprise — Vitalik's leadership shake-up and new EF direction restored optimism no one expected.

🔹 DATs dominate mechanism talk — Robert calls them highest "absolute value of impact" — amplifying volatility both ways.

🔹 AI agents flopped hard — From mania to annoyance, the speculative thesis collapsed and sentiment turned hostile.

🔹 2025 predictions reviewed — The team confesses their misses (150K BTC, 5x AI agent caps) with Tom winning at 2/3.

🔹 2026 predictions dropped — AI-generated $100M+ hacks, stable-coin-funded AI capex, and equity perps hitting 20% of DeFi volume.

Hosts:

⭐️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 

Timestamps

00:00 Intro

00:26 Crypto Industry Overview

02:39 Biggest Winners of 2025

07:32 Biggest Losers of 2025

13:29 Biggest Surprises of 2025

22:24 Best New Mechanisms of 2025

28:49 Best Memes of 2025

33:24 Best and Worst Pivots of 2025

39:15 Biggest Flops of 2025

41:31 Biggest Flop of 2025

42:58 Bitcoin's Disappointing Year

45:30 Biggest Comeback Stories of 2025

49:12 Favorite Guests of 2025

52:40 Reflecting on 2025 Predictions

56:33 Predictions for 2026

Disclosures

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