Why MSTR Should Have Sold $2 Billion Instead of $2 Million of Bitcoin

Steve Sosnick on the ratchet effect in equities, the AI bandwidth parallel, Kevin Warsh’s impossible first week, and why crypto is the unsexy trade right now. --- Thank you to our sponsor! Coinbase: Get 20% off the first year of your Coinbase One annual plan at coinbase.com/unchained. Heads up! If you haven’t yet, be sure to subscribe to Bits + Bips, since the show will migrate there in a few weeks. Follow us on ⁠⁠⁠⁠⁠⁠⁠⁠Apple Podcasts⁠⁠⁠⁠⁠⁠⁠⁠, ⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠, ⁠⁠⁠⁠⁠⁠⁠⁠Spotify⁠⁠⁠⁠⁠⁠⁠⁠, ⁠⁠⁠⁠⁠⁠⁠⁠X⁠⁠⁠⁠⁠⁠⁠⁠, ⁠⁠⁠⁠⁠⁠⁠⁠Unchained⁠⁠⁠⁠⁠⁠⁠⁠ and wherever you get your podcasts. ---- Equities are near all-time highs, the Fed’s preferred inflation gauge just hit a multi-year peak, Iran ceasefire talks are producing a familiar ratchet effect in markets, and Bitcoin is quietly underperforming tech stocks on a nine-month volatility low. Steve Sosnick, chief strategist at Interactive Brokers, joins Steve Ehrlich to map what’s actually driving these unique market dynamics. They cover the two vulnerabilities that could change things, the uncomfortable parallel between today’s AI capex and the 1999 bandwidth buildout, what $120 billion in money market inflows says about where retail cash is actually sitting, the challenge Kevin Warsh faces walking into an already-skeptical FOMC, and why crypto is currently losing the competition for momentum-chasing money to AI stocks, upcoming IPOs, and even a memory chip ETF. Host: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Steve Ehrlich, Head of Research at SharpLink and Host of Bits + Bips: The Interview Guest: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Steve Sosnick — Chief Strategist at Interactive Brokers Learn more about your ad choices. Visit megaphone.fm/adchoices

Circle froze $12M in a DeFi pool on a Friday court order, trapping users who had nothing to do with the dispute. . Polymarket couldn't resolve a Strategy market. And MegaETH's apps are defecting. Nothing is simple. ======================================================== Thank you to our sponsors! Multichain Advisors: Get help navigating TGEs, go‑to‑market, BD and partnerships, capital markets advisory, PR, media placements, KOL activations and more at https://multichainadv.com. ======================================================== Strategy sold 32 Bitcoin before the May 31 deadline. It just didn't disclose it until June 1 — and that one-day gap is why a $50M Polymarket market resolved "no," even though Strategy's own 8-K shows the sale happened inside the window.Kain Warwick, Luca Netz, and Taylor Monahan trace why Polymarket keeps writing resolution criteria that break under edge cases, and why handing oracle duties to UMA is a liability for a $20 billion platform. They also get into the third proposal to cut Solana's staking inflation, and what it would take to spark an "ultrasound money" moment for SOL. The most consequential story is Circle. A Friday-afternoon ex-parte court order froze a $12M commingled USDC pool all weekend, trapping innocent users' funds inside the Zama privacy protocol. Taylor’s warning: Circle's policy of complying with any court order without retaining a final say creates a replicable attack template for any pool with USDC exposure. The episode closes on MegaETH and Monad: Kain on whether the "Mega Mafia" approach was adverse selection from the start, and Luca on what chains actually owe their builders. Host: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Kain Warwick⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠, Founder of Infinex and Synthetix ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Taylor Monahan⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠, Security Expert ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Luca Netz⁠⁠⁠⁠⁠⁠⁠⁠, CEO of Pudgy Penguins Learn more about your ad choices. Visit megaphone.fm/adchoices

Mike Dudas holds zero ETH and sees Hyperliquid as crypto's Tether moment. He also has a clear framework for what makes a token worth buying. ======================================================== Thank you to our sponsor! Fidelity: Explore crypto careers and make the decision that could change your future at https://crypto.fidelitycareers.com ======================================================== Strategy sold 32 Bitcoin, worth just $2.5 million, and the market didn't miss it. For Mike Dudas, Managing Partner at 6th Man Ventures, the sale broke the "never sell" promise that sustained the company's premium. He doesn't see how the narrative gets rebuilt. Dudas applies the same unsentimental read to the rest of the L1 landscape. His firm holds zero ETH — five years of contradictory narratives have left the market unable to value it. In his view, Solana's decline is simpler: memecoin activity peaked and hasn't recovered. Hyperliquid, in his view, is closer to Tether than a competing L1: the no-KYC international market is enormous, and asset quality is the moat. His framework for tokens worth owning: programmatic buybacks and consistent communication from leadership. On AI, he argues agentic trading will far outpace agentic payments — Visa, Mastercard, and Stripe are moving too fast for new entrants to displace them. Host: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Laura Shin⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠, Host / Unchained Guests: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Mike Dudas - Managing Partner of 6th Man Ventures - Learn more about your ad choices. Visit megaphone.fm/adchoices

Jeff Dorman on why Strategy's four stakeholder classes are all losing, and why Saylor should have sold $2B of Bitcoin at once instead of $2.5M. ======================================================== Thank you to our sponsor! Fidelity: Explore opportunities at https://crypto.fidelitycareers.com ======================================================== Strategy’s late-May Bitcoin sale has turned a long-running investor concern into a sharper question: how sustainable is the company’s capital structure if its Bitcoin accumulation strategy now comes with large cash obligations? Jeff Dorman, chief investment officer at Arca, joins Laura Shin to discuss why the sale changed his view of the risks around Strategy. After months of pushing back on fears of forced selling, Dorman says the company’s preferred-share financing has altered the analysis. He points to roughly $15 billion in preferred shares carrying 10% to 12% dividend rates, which he estimates could mean about $1.7 billion in annual cash obligations for a company without operating revenue. Dorman also breaks down the stakeholder groups shaping Strategy’s choices, the tradeoffs each path may create, and the Polymarket dispute over whether Strategy sold Bitcoin in May. Host: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Laura Shin⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠, Host / Unchained Guests: ⁠⁠⁠⁠⁠⁠⁠⁠⁠Jeff Dorman - Chief Investment Officer at Arca - https://x.com/jdorman81 Learn more about your ad choices. Visit megaphone.fm/adchoices

Joe Lubin makes the bull case for Ethereum amid a sea of bearishness. The panel dissects Saylor selling Bitcoin for the first time in four years, the meaning behind 9 senior EF departures, Justin Drake's Q-Day call (50% by 2032), Manuel Araoz declaring all of DeFi unsafe, the ThorChain hack fallout, the Zama/Overnight Finance USDC freeze saga, and the CFTC greenlighting the first US perpetual futures product. 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 week Joe Lubin is stepping in to make the bull case for ETH on what he admits is a tough day to be bullish. We open on Strategy's first Bitcoin sale in four years and whether the STRC preferred stock structure is "an algorithmic stablecoin with too many steps," as Tarun puts it. Joe pivots to pitching Ether DATs, then we get into the Ethereum Foundation's brain drain -- nine researchers gone, CROPS as the new mandate, and a mysterious new developer organization taking shape behind the scenes. The episode's meatiest block covers DeFi security: Justin Drake warns Q-Day is 50% likely by 2032, Manuel Araoz says all of DeFi is unsafe, ThorChain's been offline for two weeks post-hack, and the panel debates whether we're entering a rough 12-24 months where attackers outrun defenders. We close on Hyperliquid's all-time highs and the CFTC opening the door to US perps.  Listen to the episode on Apple Podcasts, Spotify, Pods, Fountain, Podcast Addict, Pocket Casts, Amazon Music, or on your favorite podcast platform. Show highlights 🔹 Strategy sold 32 BTC for the first time in four years as STRC falls below $100 par – Tarun calls it "an algorithmic stablecoin with too many steps" 🔹 Joe Lubin pitches Ether DATs as a safer model than Strategy – ~3% staking yield, no leverage, and "permanent capital" for the ecosystem 🔹 Nine senior Ethereum Foundation members departed in 2026 including Tim Beiko and Barnabe Monnot as Vitalik reframes EF around CROPS mandate 🔹 Joe reveals SharpLink, BitMine, and ConsenSys in talks to become Ethereum's "decentralized commercialization engines" – "there's only one foundation" but new nodes are forming 🔹 Justin Drake puts Q-Day at 50% by 2032 and calls NIST's 2035 timeline "a joke" after Google's quantum circuit breakthrough 🔹 Crowdsourced reverse engineering of Google's withheld quantum circuit improved results 12-13% using LLMs as a grinding tool 🔹 OpenZeppelin co-founder Manuel Araoz declares all of DeFi unsafe and advises friends and family to exit Aave, MakerDAO, and Compound 🔹 ThorChain remains offline two weeks after $10.8M hack – claims they disclosed the same vulnerability 17 days before the exploit 🔹 Zama's cUSDC contract frozen by Circle via court order in Overnight Finance dispute, highlighting privacy protocol limitations on freezable stablecoins 🔹 Hyperliquid hits $75 and flips Solana in FDV as CFTC approves Kalshi's BTCPERP – the first regulated US perpetual futures product Hosts ⭐️Haseeb Qureshi, Managing Partner at Dragonfly  ⭐️Tarun Chitra, Managing Partner at Robot Ventures ⭐️Tom Schmidt, General Partner at Dragonfly  Guest⭐️Joe Lubin, Co-Founder of Ethereum, Founder & CEO of ConsenSys Timestamps 00:00 Intro 01:06 Saylor Sells BTC & Market Panic                                        05:07 STRC Death Spiral & DAT Risks 07:07 Ethereum Foundation Exodus & CROPS 13:04 The "Not Second Foundation" Debate 17:58 Quantum Q-Day: 50% by 2032 23:47 Is All of DeFi Unsafe? 31:11 ZK Composability & Bridge-Free Architecture 34:19 Security Deployment Lag & AI Arms Race 40:18 Anti-Fragility & Formal Verification 47:36 Zama USDC Freeze & Privacy vs Courts 50:33 CFTC Perps Approval & Hyperliquid at $75 55:53 Hyperliquid's Distribution Flywheel 01:00:46 Joe Lubin's Ethereum Bull Case Disclosures Learn more about your ad choices. Visit megaphone.fm/adchoices

The CFTC reclassified perps as futures. Katherine and Jessi parse what the ruling actually permits and what it means for Hyperliquid. Plus: if your AI agent gets scammed, who pays? Thanks to our sponsor! Explore crypto careers that could change your future at https://crypto.fidelitycareers.com The CFTC approved a perpetual Bitcoin futures contract for KalshiEX, and crypto Twitter immediately got it wrong. Katherine Kirkpatrick Bos untangles what actually changed, why the switch from swap to futures classification matters for retail access, and what the ruling leaves wide open on leverage and decentralized exchanges. Jessi Brooks and Katherine explore the fact that AI agents can now place orders, not just give advice. They revisit their paper "The Agents at the Gate" and make clear why Robinhood's move to let agents charge your Gold Card raises liability questions that existing consumer protection law was never built to answer. In the strangest segment, they also dug into a New York lawsuit where an anonymous plaintiff is claiming legal ownership of nearly 40,000 dormant crypto wallets. Jessi explains why the lost-property theory will probably fail — and why even a partial win could force centralized exchanges into an impossible spot. Hosts: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Katherine Kirkpatrick Bos⁠⁠⁠⁠⁠⁠, General Counsel at StarkWare. Previously held senior legal roles across DeFi and centralized exchanges. ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Jessi Brooks⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠, General Counsel at Ribbit Capital⁠⁠⁠⁠⁠⁠⁠⁠⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices

Strategy sold BTC. Can its preferred dividend stack survive without Bitcoin growing at least 11.5% year? Plus, they cover Jamie Dimon calling Brian Armstrong “full of shit.” --- Heads up! If you haven’t yet, be sure to subscribe to Bits + Bips, since the show will migrate there in a few weeks. Follow us on ⁠⁠⁠⁠⁠⁠⁠⁠Apple Podcasts⁠⁠⁠⁠⁠⁠⁠⁠, ⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠, ⁠⁠⁠⁠⁠⁠⁠⁠Spotify⁠⁠⁠⁠⁠⁠⁠⁠, ⁠⁠⁠⁠⁠⁠⁠⁠X⁠⁠⁠⁠⁠⁠⁠⁠, ⁠⁠⁠⁠⁠⁠⁠⁠Unchained⁠⁠⁠⁠⁠⁠⁠⁠ and wherever you get your podcasts. ---- Strategy sold Bitcoin for the first time since 2022 — 32 BTC to cover preferred stock dividends. Ram, Austin, and Chris discuss whether that small sale signals a deeper structural tension between equity holders, preferred holders, and Bitcoin itself. They also covered the news that Anthropic filed for an IPO at a valuation approaching $1 trillion. The hosts lay out the bull and bear cases  and ask whether retail investors can realistically get a 10x out of a company already priced like a finished product. Unpacking a spicier moment, they also discussed the moment when JPMorgan’s Jamie Dimon called Coinbase’s Brian Armstrong “full of shit” on live TV over the Clarity Act. Ram says crypto's window of peak political power is closing fast, while Austin gives crypto lobbyists a great idea for how to turn the banks’ stablecoin yield crusade against them. Hosts: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Austin Campbell — Founder, Zero Knowledge Consulting; Adjunct Professor, NYU Stern ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Ram Ahluwalia⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠, Co-Host, CEO of Lumida ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Chris Perkins⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠, Co-Host, CEO of 250 Digital Asset Management Learn more about your ad choices. Visit megaphone.fm/adchoices

Steve Sosnick on the ratchet effect in equities, the AI bandwidth parallel, Kevin Warsh’s impossible first week, and why crypto is the unsexy trade right now. --- Thank you to our sponsor! Coinbase: Get 20% off the first year of your Coinbase One annual plan at coinbase.com/unchained. Heads up! If you haven’t yet, be sure to subscribe to Bits + Bips, since the show will migrate there in a few weeks. Follow us on ⁠⁠⁠⁠⁠⁠⁠Apple Podcasts⁠⁠⁠⁠⁠⁠⁠, ⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠, ⁠⁠⁠⁠⁠⁠⁠Spotify⁠⁠⁠⁠⁠⁠⁠, ⁠⁠⁠⁠⁠⁠⁠X⁠⁠⁠⁠⁠⁠⁠, ⁠⁠⁠⁠⁠⁠⁠Unchained⁠⁠⁠⁠⁠⁠⁠ and wherever you get your podcasts. ---- Equities are near all-time highs, the Fed’s preferred inflation gauge just hit a multi-year peak, Iran ceasefire talks are producing a familiar ratchet effect in markets, and Bitcoin is quietly underperforming tech stocks on a nine-month volatility low. Steve Sosnick, chief strategist at Interactive Brokers, joins Steve Ehrlich to map what’s actually driving these unique market dynamics. They cover the two vulnerabilities that could change things, the uncomfortable parallel between today’s AI capex and the 1999 bandwidth buildout, what $120 billion in money market inflows says about where retail cash is actually sitting, the challenge Kevin Warsh faces walking into an already-skeptical FOMC, and why crypto is currently losing the competition for momentum-chasing money to AI stocks, upcoming IPOs, and even a memory chip ETF. Host: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Steve Ehrlich, Head of Research at SharpLink and Host of Bits + Bips: The Interview - https://x.com/Steven_Ehrlich Guest: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Steve Sosnick — Chief Strategist at Interactive Brokers Learn more about your ad choices. Visit megaphone.fm/adchoices

A co-founder of OpenZeppelin said he’s urging friends to exit blue chip DeFi. Isaac Patka and Mike Silagadze explain what he got right, what he got wrong, and what needs to change. ======================================================== Thank you to our sponsor! ⁠⁠⁠⁠⁠Coinbase One⁠⁠⁠⁠⁠: Get 20% off the first year of your Coinbase One annual plan at ⁠⁠⁠⁠⁠coinbase.com/unchained⁠⁠⁠⁠⁠. ======================================================== A co-founder of OpenZeppelin set off a firestorm on Crypto Twitter this week by declaring that he now considers all of DeFi unsafe, citing superhuman AI coding agents and the asymmetry between attackers and defenders.  Isaac Patka, certifications lead at Security Alliance, and Mike Silagadze, CEO of Ether.Fi, join Laura Shin to push back on that framing — and to make the case that the real problem isn’t AI finding sophisticated zero-days, it’s that 90% of hacks are still embarrassing opsec failures.  They cover the full threat taxonomy: opsec and parameter mistakes, contagion from bridge failures, AI-enabled social engineering, and the decentralization theater that leaves protocols unable to protect their own users.  Mike makes a pointed argument for why every serious DeFi protocol needs a hard pause button and a blacklist mechanism, while Isaac explains the three-multisig architecture that should be the minimum standard. Plus, both lay out the practical question every user should ask before putting money into any protocol. Host: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Laura Shin⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠, Host / Unchained Guests: ⁠⁠⁠⁠Isaac Patka (@isaacpatka) — Certifications Lead at Security Alliance & Co-founder of Shield3 ⁠⁠⁠⁠Mike Silagadze (@MikeSilagadze) — CEO of Ether.Fi Learn more about your ad choices. Visit megaphone.fm/adchoices

Illia Polosukhin, founder of NEAR and co-author of 'Attention Is All You Need,' on why confidentiality will let crypto become daily commerce — plus, some Near lore. ======================================================== Thank you to our sponsors! ⁠⁠Multichain Advisors⁠⁠: Get help navigating TGEs, go‑to‑market, BD and partnerships, capital markets advisory, PR, media placements, KOL activations and more at ⁠⁠multichainadv.com⁠⁠. ⁠⁠⁠⁠⁠Coinbase One⁠⁠⁠⁠⁠: Get 20% off the first year of your Coinbase One annual plan at ⁠⁠⁠⁠⁠coinbase.com/unchained⁠⁠⁠⁠⁠. ======================================================== Before co-founding NEAR Protocol, Illia Polosukhin was on the eight-person Google Brain team that wrote the transformer paper — the architecture behind every large language model running today. He never mentioned it. When Kain Warwick found out two weeks ago, via a crypto AI chatbot, his reaction was: you have to be kidding me. That backstory sets the tone for a conversation that moves from how transformers actually came together, to why confidentiality is what unlocks on-chain commerce for real businesses, and what NEAR is doing to keep criminals off its network without becoming a surveillance layer. The hosts also get into the Ethereum Foundation's identity crisis, why Illia thinks decentralization is a tool and not a goal, and what the economy looks like when AI handles execution and blockchain handles coordination. Host: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Kain Warwick⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠, Founder of Infinex and Synthetix ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Taylor Monahan⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠, Security Expert ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Luca Netz⁠⁠⁠⁠⁠⁠⁠, CEO of Pudgy Penguins Guest: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Illia Polosukhin — Co-Founder, NEAR Protocol - https://x.com/ilblackdragon Learn more about your ad choices. Visit megaphone.fm/adchoices