Unchained

Laura Shin
Unchained
Latest episode

1177 episodes

  • Unchained

    Why Saylor's 'Inoculate' Comment May Be a Signal He'll Sell More Bitcoin

    2026/06/09 | 1h 7 mins.
    About 80% of STRC holders are retail investors. Glenn Cameron walks through the prospectus, how Saylor's public claims differ from the reality, and why Strategy has no good options.

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    Strategy's sale of 32 Bitcoin last week came with unusual framing: Saylor said the purpose was to "inoculate the markets." Glenn Cameron, Global Head of Institutional at Onramp Bitcoin, reads that word as preparation for larger Bitcoin sales ahead.

    Glenn traces the pressure points. Strategy is trading at 84% of its Bitcoin value, making new equity issuance dilutive rather than accretive on a Bitcoin-per-share basis. Its cash reserve has been cut to roughly seven months after the company redeemed a 0%-interest convertible note. And STRC, the perpetual preferred stock Saylor has marketed as "a high yield bank account," carries a dividend the board can suspend for any reason.

    The episode's sharpest argument: 83% of STRC holders are retail investors sold a product that resembles a bank account but behaves like junior equity on a volatile Bitcoin company. No maturity, no FDIC protection, no right to redeem.

    Host:


    ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Laura Shin⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠, Host / Unchained

    Guests:


    Glenn Cameron, CFA - Global Head of Institutional at Onramp Bitcoin

    Timestamps

    📊 1:24 Risk vs uncertainty: why Glenn won't predict Bitcoin's price but will name every structural pressure point

    🔑 4:27 What 'inoculate' means: why Saylor's word choice signals a larger Bitcoin sale may be coming

    📉 6:58 Strategy below NAV: why buying Bitcoin with new stock now dilutes Bitcoin per share for existing holders

    🗣️ 12:33 Glenn's response to people who say that the criticism of Strategy is FUD: STRC has to raise the dividend if bitcoin lowers

    👥 19:57 Strrategy's section option: suspend the dividend, but 83% of holders are retail who think STRC is a bank account

    ⏰ 24:02 The 2028 cliff: $3.5B in convertibles become putable when history says a drawdown may not have recovered

    📣 29:21 Fidelity: Explore crypto careers that could change your future at https://crypto.fidelitycareers.com

    📱 30:19 Cape: Get 33% off your first six months with code unchained at https://cape.co/unchained

    🏷️ 31:02 The 'digital credits' name: why STRC's marketing label creates false expectations about legal structure and protections

    💬 36:13 Saylor's own words: three public claims that STRC is a 'high yield bank account' or money market fund

    ⚖️ 40:54 The real product: how STRC compares to actual money market funds and FDIC-insured accounts

    🔄 48:22 SATA vs STRC: same instrument, different issuer since one-third of Sata's cash reserve is in STRC

    🪣 55:42 why the staking yield of Bitmine's upcoming BMNP, an Ethereum-backed preferred at $80 par, won't cover the cost of capital
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  • Unchained

    What Two DOJ Cases Reveal About the Legal Risks of Prediction Markets: Bits + Bips

    2026/06/07 | 46 mins.
    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.

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    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.

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    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

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  • Unchained

    Is Polymarket's Oracle Problem Getting Out of Hand? - Uneasy Money

    2026/06/05 | 1h 11 mins.
    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.

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    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

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  • Unchained

    Why Mike Dudas Has Zero Exposure to ETH, but Is Bullish on Hyperliquid

    2026/06/05 | 36 mins.
    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 -

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  • Unchained

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

    2026/06/05 | 35 mins.
    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

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About Unchained
Crypto assets and blockchain technology are about to transform every trust-based interaction of our lives, from financial services to identity to the Internet of Things. In this podcast, host Laura Shin, an independent journalist covering all things crypto, talks with industry pioneers about how crypto assets and blockchains will change the way we earn, spend and invest our money. Tune in to find out how Web 3.0, the decentralized web, will revolutionize our world.
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