Is Michael Saylor’s Empire Cracking?

Good Sunday!

Michael Saylor's Bitcoin strategy made him one of crypto's biggest winners. Now some believe it could become one of its biggest risks.

Investor Vinny Lingham explains why he thinks the Strategy empire is starting to crack, what could trigger the next phase of the unwind, and the one move he believes could stop it.

Meanwhile, a crypto exchange asked Carmen Li to make a market in her own index.

The unusual request exposes a conflict of interest that's long been accepted in crypto, just as a multi-trillion-dollar market for AI compute begins to emerge.

Here’s more on what we unpacked this week on Unchained:

⚖️ Why CME Is Suing the CFTC Over Bitcoin Perp
CME is taking the extraordinary step of suing its own regulator after the CFTC approved the first onshore Bitcoin perpetual futures. The crew unpacks the legal battle, what it means for prediction markets, and why public opinion on AI could matter more than crypto realizes.

 🧪 Ethereum’s Exodus, MEV Wars & Crypto’s Next Big Bet
Former Ethereum Foundation researchers launch a new lab, raising questions about Ethereum’s future direction. The panel also dives into anti-MEV traps, CryptoPunks’ AI courtroom drama, Polymarket controversy, and why one crypto app may have finally solved onboarding.

💰 Is Strategy’s Bitcoin Playbook Actually Breaking?
As Strategy’s preferred shares come under pressure, Strive’s Matt Cole defends the digital credit model. He explains why Bitcoin-backed credit isn’t broken, whether Saylor made the right call by selling BTC, and why critics may be asking the wrong questions.

 🌉 Why You No Longer Have to Choose Between TradFi and Crypto
Tokenized stocks, yield-bearing money funds, and Coinbase’s latest push are blurring the line between traditional finance and crypto. The panel explores what makes a token "real," whether money market funds threaten stablecoins, and why Wall Street and crypto are beginning to merge rather than compete.

All these episodes are available on Apple Podcasts, Spotify, Fountain, Podcast Addict, Pocket Casts, Amazon Music, or on your favorite podcast platform.

In Case You Missed It 👀

Is Strategy’s Problem Bitcoin, or That One Man Decides Everything?

On Monday, the question was whether STRC’s dip below par meant trouble. Now the entire capital stack is underwater, the common stock is at a two-year low, and a securities probe may be in the works. Here’s where Strategy stands.

Strategy’s STRC Drawdown Continues Despite $300 Million Cash Boost. What Gives?

It’s been an ugly few weeks for Strategy’s STRC. Here’s why it’s trading so far below par and what the company can do to get it back to $100.

Wall Street Loves Ethereum, So Why Doesn’t the Market Love ETH?

The biggest names in finance are building on Ethereum, but ETH itself is bleeding value against bitcoin. Here’s where the money is really going.

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