The Buyback Dilemma: Sell Crypto to Repurchase Shares?

The Chopping Block unpacks crypto’s DATpocalypse — NAVs collapsing, volumes drying up, and consolidation on the horizon. Plus: Vitalik sparks a wave of quantum panic, what Q-Day really means for Bitcoin and smart-contract chains, and why “qubits per share” might become the next great crypto meme.

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 opens with the DATpocalypse: almost every DAT is now below NAV, volumes have collapsed outside Bitmine and MicroStrategy, and the market is finally confronting what happens when issuances outrun demand. We get into consolidation talk, preferred-share experiments, capital-structure pivots, and whether any DAT should actually be selling crypto to buy back shares at a discount.

Then we shift into quantum mania. Vitalik’s “2028” comment lit up Q-Day fears, and we separate genuine hardware progress from pure panic. We discuss why post-quantum upgrades are simple for Bitcoin but brutal for stateful chains, and how hype alone could trigger a wave of “quantum-resistant” speculation. And yes — the running gag: DATs using quantum machines to steal Satoshi’s coins.

Tough markets, weird narratives, and institutions quietly holding the line. Let’s get into it.

Show highlights

🔹 DATpocalypse — Most DATs now trade below NAV; Bitmine and MicroStrategy dominate the only real volume.

🔹 Supply & Demand — Issuances outpaced buyers; M/NAV compresses toward 1 across the entire class.

🔹 Consolidation watch — Sub-scale DATs may merge to form multi-billion-dollar vehicles that can compete.

🔹 New financing era — Preferreds, debt, and MicroStrategy-style capital engineering become the next playbook.

🔹 Buyback dilemma — Trading at 0.5× NAV suggests selling crypto to buy shares—if liquidity exists.

🔹 Retail gone, institutions steady — Tokens follow the 4-year retail cycle; equity deals reflect institutional conviction.

🔹 Token vs equity split — Depressed token markets contrast with mega equity raises like Kraken’s $20B round.

🔹 AI distraction — Retail rotates into Nvidia/AI stocks, starving page-2 tokens of attention.

🔹 Quantum mania — Vitalik’s “2028” comment triggers Q-Day fears, despite quantum still being far from breaking ECC.

🔹 Post-quantum headaches — Bitcoin is easy to migrate; Ethereum/Solana transitions will be complex and messy.

🔹 Q-Day = Y2K energy — Expect years of hype and “quantum-resistant” pumps before reality catches up.

🔹 Qubits-per-share meme — DATs running quantum computers to steal Satoshi coins becomes the episode’s running gag.

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 

⁠Disclosures

Timestamps

00:00 Intro 

01:14 BTC Breaks Down

02:52 DATpocalypse Begins

05:01 DAT Playbooks & Buybacks

20:48 Equity Boom, Token Bust

28:00 Retail vs. Institutions

34:01 Quantum Panic Hits Crypto

41:45 Post-Quantum Problems

46:32 Road to Q-Day & Y2K Vibes

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