Unchained

Vinny Lingham warned 18 months ago that Michael Saylor would harm Bitcoin more than FTX. Now he maps how the Strategy empire breaks and the one move that could slow the bleed.

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Strategy's stock has fallen over 80% from its November 2024 high, its STRC preferred trades well below par, and a fresh $335 million raise has done nothing to restore confidence.

Vinny Lingham, co-founder of Praxos Capital, tweeted in October 2024 that Michael Saylor would do more damage to Bitcoin than FTX. On Unchained, he argues the collapse was always predictable, and that this is not a Ponzi but what he calls a 'Saylor scheme.'

Lingham maps how the empire breaks once MSTR trades at a discount to mNAV, why the 32-Bitcoin sale and the $1.5 billion buyback of 2029 converts blew Saylor's runway, and why $6.7 billion in convertible notes raises default risk by 2028. He also weighs a Soros-style attack theory and the switch to bimonthly dividends.

His fix is the one thing Saylor won't do: stop buying, stop diluting, wait it out. The question is who removes the biggest buyer of Bitcoin, him or the market.

Host:


⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Laura Shin⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠, Host / Unchained

Guests:


⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Vinny Lingham - Co-founder of Praxos Capital

Timestamps

📉 01:11 Strategy in free fall: why Vinny says the collapse was always coming

🪤 06:24 Why buying back 2029 debt blew Saylor's runway

₿ 07:36 The '32 years of dividends' claim and what a deeper bear market does to it

🏚️ 10:23 How the MSTR empire actually breaks: the discount-to-mNAV trap

🎯 13:35 Why is Strategy faltering? Is it leverage or a Soros-style attack on MSTR?

💙 16:38 Cape: Get 33% off your first six months with code unchained at https://cape.co/unchained

💚 17:32 Fidelity: Explore crypto careers that could change your future at https://crypto.fidelitycareers.com

📆 18:15 Why switching to bimonthly dividends makes the problem worse

⏳ 19:29 The $6.7B convertible-note overhang and the 2028 default risk

🛟 22:07 Can MSTR be saved, and the most likely outcome from here
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An anti-MEV activist spent weeks building 66 fake contracts to trap the sandwich bot jaredfromsubway.eth. Then jared's operators did the one thing nobody expected.

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Thank you to our 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).

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A new R&D lab called Ethlabs has split from the Ethereum Foundation, backed by Bitmine and Joe Lubin. Its first stated goal is solving a '15 minute finality problem' that none of the hosts can quite explain the point of.

Kain Warwick, Taylor Monahan, and Luca Netz ask whether a breakaway staffed largely by ex-EF people can really escape the EF's habits, or just rebuild a smaller version of them. 

Then the conversation turns to fomo's $75M raise from non-crypto VCs, and why a trading app that never calls itself a wallet may have cracked the onboarding flow the rest of crypto keeps getting wrong.

The hosts also trace a CryptoPunks judge ordering a self-represented plaintiff to handwrite filings to stop the AI slop, the anti-MEV activist who trapped sandwich bot jaredfromsubway.eth with 66 fake contracts, and the WSJ's claim that Polymarket paid creators to stage fake winning bets.

Hosts:


⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Kain Warwick⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠, Founder of Infinex and Synthetix


⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Taylor Monahan⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠, Security Expert


⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Luca Netz⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠, CEO of Pudgy Penguins

Timestamps

🧪 02:06 Ethlabs breaks from the EF: what the new R&D lab is actually for

🤔 03:57 Why the 'fifteen minute finality' framing baffles the hosts

📈 15:40 fomo's $75M raise and why a no-token trading app pulled it off

🧱 21:45 The wallet lesson: why building for trading beats building for custody

💙 30:48 Cape: Get 33% off your first six months at https://cape.co/unchained

⚖️ 31:44 The CryptoPunks lawsuit where a judge ordered AI-slop filings handwritten

🥪 41:04 What a sandwich bot is and why jaredfromsubway.eth became infamous

🪤 45:34 How an anti-MEV activist trapped Jared with 66 fake token contracts

🏛️ 50:46 Why Jared running to the courts under the CFAA makes no sense

😤 56:36 Kain on the exploiter who cries foul when someone finally steals from him

📺 59:20 The WSJ claim that Polymarket paid creators to stage fake winning bets
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The crew debates whether Saylor's STRC preferred shares are "Luna for suits," unpacks the ETH Labs spin-out and Ethereum Foundation layoffs, breaks down the CME's lawsuit against the CFTC to kill domestic perps, and weighs whether Meta's leaked prediction market Arena is a real threat to Polymarket.

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, Saylor's STRC preferred shares, which have broken below their $100 target. Laura argues it's a confidence crisis, Tarun calls it "Luna for suits," and Haseeb pushes back — there's no death spiral, Saylor can just defer dividends and "burn the boat." Then the Ethereum Foundation shakeup: ETH Labs spinning out with seven senior EF members while the EF lays off 20% of its headcount.

The back half covers the CME suing the CFTC to block domestic perps — which Haseeb frames as "suing for the right to not compete" — and Meta's leaked prediction market Arena, where Tom reveals this is Meta's third or fourth attempt at prediction markets. Let's get into it.

Listen to the episode on Apple Podcasts, Spotify, Pods, Fountain, Podcast Addict, Pocket Casts, Amazon Music, or on your favorite podcast platform.

Show highlights

🔹 Saylor's STRC preferred shares break below $100 target — Tarun calls it "Luna for suits"

🔹 Haseeb pushes back: no death spiral, no margin calls — Saylor can defer dividends and "burn the boat"

🔹 Tom reveals Strategy execs are cold-calling crypto funds to sell them STRC — "very Luna"

🔹 ETH Labs spins out with 7 senior EF members as the Foundation lays off ~20% of headcount

🔹 CME sues CFTC to block domestic perps — Haseeb: "suing for the right to not compete"

🔹 Haseeb proposes 100-year futures as a workaround to route around the lawsuit

🔹 Meta leaks prediction market Arena — Tom reveals this is Meta's third or fourth attempt at prediction markets

🔹 Tarun argues prediction markets will be viewed as information social networks within five years

Hosts

⭐️Haseeb Qureshi, Managing Partner at Dragonfly 

⭐️Tom Schmidt, General Partner at Dragonfly 

⭐️Tarun Chitra, Managing Partner at Robot Ventures

Guest

⭐️Laura Shin, Journalist, Author of ‘The Cryptopians,’ Founder and CEO of Unchained

Timestamps

00:00 Intro

01:10 STRC & Strategy: Saylor "Luna for suits"

12:33 No death spiral — burn the boat

17:06 Strategy execs cold-calling crypto funds

20:06 Ethereum Foundation shakeup & ETH Labs spin-out

27:33 ETH Labs is the ghost of Tomasz

35:20 CME sues CFTC to block domestic perps

44:44 100-year futures as a workaround

50:29 Meta's prediction market "Arena"

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Three years ago, Chris Perkins sat across from Terry Duffy in Congress and made the case for perpetuals. Duffy pushed back — hard. Now Duffy's CME is suing the very regulator that finally allowed them.

The CME argues Bitcoin perpetual futures are really swaps and should carry far more collateral. Chris traces the Dodd-Frank history that created the swap-versus-future divide, and Austin Campbell lays out why picking this fight in a post-Chevron court could backfire on the incumbent. Is a perpetual a swap or a future, and who gets to decide?

Hosts:


Austin Campbell - Host of Bits + Bips, Founder of Zero Knowledge Group, and Adjunct Professor at NYU Stern


Ram Ahluwalia - Co-host of Bits + Bips and CEO of Lumida


Chris Perkins - Co-host of Bits + Bips and Head of Franklin Crypto

This clip is from a longer conversation on tokenization, the AI trade, and the CME's lawsuit against the CFTC. Full episode here: https://youtube.com/live/oSiOeWq_pKE 

We go live every Monday at 4:30pm ET - subscribe to catch it live. 

Sponsor


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 The incumbent sues its own regulator: what the CME is actually claiming

📜 01:22 Chris on Terry Duffy, and the testimony fight that set this up

🏛️ 02:12 The Dodd-Frank origin story, traced back to the 2009 G20

⏱️ 03:12 Why a 'swap' costs five days of margin and a future costs two

🌊 04:42 Constrain leverage onshore and watch it flee offshore

⚠️ 05:15 Austin: why the CME should be careful what it wishes for

🧨 06:26 The Dodd-Frank footnote where Congress admits it punted

🤝 08:20 ICE, OKX, and Kraken: where the dance partners line up

🎯 09:12 What the market really needs out of all this
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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.

========================================================

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.


⁠⁠⁠⁠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 cape.co/unchained (use code: UNCHAINED).

========================================================

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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