Unchained

Was Michael Saylor wrong to sell Bitcoin? Matt Cole breaks from his fellow critics on Strategy, S&P's junk rating on MSTR, and whether the model is breaking.

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Strive's Matt Cole had just lived through what he called the most difficult day in the history of digital credit when he sat down to defend it. STRC had touched $82.50, SATA had slipped into the low nineties, and the Bitcoin treasury trade was suddenly the most argued-over corner of crypto.

Cole came from a pension background and built Strive into one of the largest Bitcoin treasury companies around a single conviction: that structured credit can solve an income problem fiat can't. The critics, he argues, can't even agree with each other on what is actually wrong.

Was last week a leverage liquidation or a crack in the model? Did Michael Saylor quietly change his story? And is wrapping Bitcoin in preferred stock a betrayal of its ethos or the bridge most people actually need? Laura Shin pressed on all of it.

Host:


⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Laura Shin⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠, Host / Unchained

Guests:


⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Matt Cole - Chairman and CEO of Strive

Timestamps

🎙️ 02:07 What Strive is, and why Matt calls SATA the company's main product

🏦 10:16 Could Strive cut SATA's 13% yield without breaking par?

👥 15:45 Who is actually buying SATA, and the one buyer Matt says he's never met

📣 25:15 Fidelity: Explore crypto careers and make the decision that could change your future at https://crypto.fidelitycareers.com

🔒 25:58 Cape: Use code unchained for 33% off at https://cape.co/unchained

💧 27:28 What Matt thinks really drove last week's STRC drop, and why SATA didn't follow

🏛️ 31:28 Why Matt won't fault Saylor for selling, and the S&P rating he calls a joke

⚖️ 50:53 Is buying SATA un-Bitcoin? Matt answers the Mallers vs Saylor critique
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Kalshi just brought crypto perps to the US, targeting a $90 trillion offshore market. Its Head of Crypto, John Wang, explains the bet, the risks, and who Kalshi is actually competing with.

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Thank you to our sponsor!


⁠⁠⁠Fidelity⁠⁠⁠: Fidelity has been building in crypto and DeFi since 2014 — now they're hiring. Explore career opportunities at one of the most forward-thinking names in finance here: ⁠⁠⁠crypto.fidelitycareers.com⁠⁠⁠.


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The $90 trillion offshore market for crypto perpetual futures just got its first US-regulated entrant. Kalshi — the prediction market exchange that raised $1 billion at a $22 billion valuation — launched the first CFTC-approved crypto perps, becoming the only domestic exchange approved on launch day.

John Wang, Kalshi's Head of Crypto, joins Laura Shin to map how perpetual futures work, why Kalshi's guarantee fund and segregated accounts differ from what offshore venues provide, and how the exchange plans to compete with Hyperliquid, Coinbase, and Kraken.

Wang pushes back on CME Group CEO Terry Duffy's claim that crypto perps are "a disaster waiting to happen," noting CME's own futures carry higher leverage than Kalshi's platform. He covers the ARCA and Galaxy block trades on Kalshi's prediction markets, insider trading protections built around athlete and congressional staff lists, and the regulatory filings separating Kalshi from perps on equities. Wang estimates only 0.2% of the US has adopted perpetual futures — the real growth has barely started.

Host:


⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Laura Shin⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠, Host / Unchained

Guests:


⁠⁠⁠⁠⁠⁠⁠⁠⁠John Wang - Head of Crypto at Kalshi

Timestamps

🎯 02:51 Why Kalshi chose crypto perps as its first product outside prediction markets

🔧 05:15 What a perpetual future is and why traders prefer it over options and standard futures

🤓 11:14 The metric that reveals real demand: Kalshi's ratio of trading volume to open interest

🛡️ 14:19 How Kalshi plans to onboard Americans, and how its risk model differs from Hyperliquid's auto-deleveraging

🏛️ 21:05 Wang on Terry Duffy's claim that crypto perps are 'a disaster waiting to happen'

🎓 23:17 Fidelity: Explore crypto careers that could change your future at https://crypto.fidelitycareers.com

📱 24:00 Cape: Get 33% off your first six months at https://cape.co/unchained

🤝 25:32 How institutions are pitching its perps to institutions — and which ones have so far done trades

🌐 33:09 How Kalshi plans to compete with Hyperliquid, Coinbase, Kraken, and Robinhood

🔍 41:14 How Kalshi attempts to prevent insider trading — and what John thinks about its rivalry with Polymarket

💰 46:16 Kalshi's roadmap after its $1 billion raise at a $22 billion valuation
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The government export-controlled Anthropic's best model. Kain, Luca, and Taylor debate whether Dario talked his way into it and what the shutdown means for every AI lab.

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⁠⁠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.

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A reported jailbreak of Anthropic's most powerful model, Fable, triggered US government export controls, and the Uneasy Money hosts argue Dario Amodei's response on the call with the administration made it inevitable. Kain, Taylor, and Luca dig into what Dario got wrong, why a company about to go public had no one in Washington who could speak the government's language, and what it means that the shutdown drew no public backlash.

Porter Stowell, CEO of W3.io and a Coinbase alum, joins for the first half with his read on the exchange's big announcement day: agentic payments on Base, tokenized stocks, and a ground-up trading rebuild. Midway through, Luca drops something unannounced: Igloo has built a financial instrument to list crypto tokens directly on the NYSE as securities, with protocol revenue flowing back to holders.

The episode closes on Strategy, and why Kain thinks selling 32 Bitcoin, then buying back 1,587 two weeks later, exposes the structural risk of a belief-based asset with one dominant buyer.

Hosts:


⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Kain Warwick⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠, Founder of Infinex and Synthetix


⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Taylor Monahan⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠, Security Expert


⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Luca Netz⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠, CEO of Pudgy Penguins

Guest:


⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Porter Stowell - CEO of W3.io

Timestamps
🏦 03:16 Porter Stowell on why Coinbase's announcement day signals a real shift in how the exchange competes

💬 06:26 Luca on why Coinbase's core trading product still lags: charts that won't load and page refreshes to buy Bitcoin

🤖 17:40 Porter on why agentic payments on Base is the real sleeper from Coinbase's announcement day

📋 25:10 What "real" means in Coinbase's tokenized stocks launch and whether the custody approach actually differentiates it

💡 34:15 Luca reveals Igloo's instrument to list crypto tokens directly on the NYSE as securities

📣 41:12 Multichain Advisors: Navigate TGEs, go-to-market, and capital markets advisory at https://multichainadv.com

🧠 41:54 What Fable was, why it scared security researchers, and how a reported jailbreak report ended it

⚠️ 48:36 Taylor on why Anthropic's communications with the government made the Fable export control inevitable

🏛️ 57:09 Kain on why the Fable shutdown is the 'first fracture' in AI, and what the lack of pushback means

🌍 01:00:18 Binance's EU license bid in doubt, and Kain's contrarian case that losing Europe is bullish

📉 01:07:32 Strategy sold 32 Bitcoin on June 1 then bought back 1,587: what the panic reaction revealed about Bitcoin's concentration risk
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Zach Pandl, Head of Research at Grayscale Investments, argues that speculative retail flows, not geopolitical fundamentals, drove the recent gold and Bitcoin selloffs. His read: momentum chasing built gold from $4,000 to well above $5,000, then rotated out to chips and pre-IPO trades. The underlying deficit-and-debt case for both assets hasn't changed, and he's calling the dip a buy for longer-horizon investors.

He closes with Grayscale's H2 DeFi revenue thesis. Hyperliquid is the clearest proof of concept: a protocol with a clear use case, real revenue, and value returned to token holders. Grayscale applied a discounted cash flow model to Aave and published a price target on the token.

Host:


Steven Ehrlich, Host of Bits + Bips: The Interview and Head of Research at Sharplink - https://x.com/Steven_Ehrlich

Guest:


Zach Pandl - Head of Research at Grayscale Investments - https://x.com/LowBeta

This clip is from a longer conversation on the Fed's hawkish pivot, the SpaceX IPO, crypto winter, and Strategy's preferred equity. Full episode here: https://www.youtube.com/live/WIlLtRQidQg?si=ONIIkcPElZFgpa8l 

We go live every Thursday at 12:00pm ET - subscribe to catch it live.

Sponsors


Cape: Your biggest crypto vulnerability isn't your wallet, it's your phone number. Cape is America's privacy-first mobile carrier that rotates your SIM identity daily and blocks SIM swaps before they happen. Get 33% off your first six months at https://cape.co/unchained (use code: UNCHAINED).

Chapters

🔍 00:00 Steve on gold and Bitcoin's worst quarter - what happened during the Iran war

📊 00:57 Why Pandl argues speculation, not fundamentals, drove both the run-up and the selloff

🥇 02:42 The buy case - Pandl on what to do when speculative excess washes out

💡 03:25 Steve asks about second-half assets and Standard Chartered's Uniswap call

💰 03:50 Why Hyperliquid and Aave anchor Grayscale's H2 DeFi revenue thesis
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The federal government pulled Anthropic's Fable 5 offline with no public process — and Jessi Brooks makes the case it's a crypto chokepoint story, not just an AI one.

Thanks to our sponsor!


👉 Fidelity: Fidelity has been building in crypto and DeFi since 2014 — now they're hiring. Explore career opportunities at one of the most forward-thinking names in finance here: https://crypto.fidelitycareers.com.


👉 Cape: Your biggest crypto vulnerability isn't your wallet, it's your phone number. Cape is America's privacy-first mobile carrier that rotates your SIM identity daily and blocks SIM swaps before they happen. Get 33% off your first six months at https://cape.co/unchained (use code: UNCHAINED).

The federal government forced Anthropic to take Fable 5 offline last week, and the justification is still murky. Jessi Brooks makes the case that what began as a cybersecurity story is really a chokepoint story, one crypto has seen before. With no transparent process, no technical experts cited, and no clear legal authority, she argues the administration has effectively invented KYC for AI, raising questions far beyond Anthropic.

Katherine Kirkpatrick Bos, Jessi Brooks, and Vy Le work through two regulatory moves with real market-structure stakes. The CFTC released a near-300-page proposed rule on prediction markets, amending Rule 40.11 and clearing political event contracts. The SEC moved to repeal Reg NMS Rules 611 and 610E, two-decade-old market pillars.

Vy Le argues the repeal is crypto's real opening: stop forcing AMMs to fit the old rules and start building the replacement, where solver auctions and cryptographic attestations let investors and regulators verify execution in real time. The throughline across the week is the same: when Washington moves this fast and quietly, is crypto the cautionary tale or the fix?

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


⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Vy Le - Co-host of DEX in the City and General Counsel of Veda

Timestamps
🤖 03:04 Why the Fable 5 shutdown is a chokepoint story, not just a security one

🔑 09:36 Jessi on why inventing KYC for AI with no process echoes the Gensler era

☢️ 18:48 Why Vy Le puts AI on the threat level of the nuclear bomb

🏛️ 22:36 What the CFTC's near-300-page prediction-markets rule changes in Rule 40.11

📣 34:21 Fidelity: Explore crypto careers that could change your future at https://crypto.fidelitycareers.com

📈 36:32 Why the SEC's Reg NMS repeal could clear the way for onchain markets

⚙️ 41:18 Why Vy Le says crypto already built the tools for better best execution

📑 46:42 Why Citi's 'tokenized shares' aren't shares, plus Coinbase's onchain dividends

🦕 51:26 Crypto good news: Jurassic Finance tokenizes dinosaur bones
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