Unchained

Strategy sold $260M of Bitcoin at a loss to fund dividends. Parker White of Apyx makes the case that it is smarter than it sounds.

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Strategy just made its largest Bitcoin sale ever, offloading 3,588 BTC for $260 million at a loss to fund preferred dividends. Days earlier it unveiled a digital capital framework: a 12-month coverage rule, a hiked STRC dividend, and a $10 billion buyback plan. Markets calmed, but the moves raise a question: has Strategy stopped being a Bitcoin company?

Parker White, CFA, founding contributor and chief investment/operating officer at Apyx, pushes back on claims that funding dollar dividends with Bitcoin sales betrays Bitcoin's ethos, framing it as smart capital management. Shin presses him on whether investors now bet on Strategy's team, not Bitcoin.

They unpack short sellers' calculus, the 2027-2029 convertible cliff Matt Walsh pegs near $6.7 billion, and Apyx's apxUSD, a tokenized yield wrapper around STRC and SATA that depegged to 72 cents in the turmoil. White defends Apyx 2.0's redemption model against 'free put option' critics and responds to critic’s contention that Strategy resembles Terra/ Luna or FTX.

Host:

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Laura Shin⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠, Host / Unchained

Guests:

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Parker White - CFA, Founding Contributor and Chief Investment/Operating Officer at Apyx

Timestamps

🏛️ 02:03 Parker on why Strategy's record Bitcoin sale to fund dividends is smart, not desperate

📋 06:24 How Strategy's new digital capital framework tries to calm the market's nerves

⚠️ 09:59 Laura and Parker spar over whether shorts or Strategy's own missteps sparked the selloff

💵 21:27 Whether prioritizing USD over Bitcoin marks a philosophical flip for Strategy

📣 26:28 Fidelity: Explore crypto careers at Fidelity today at https://crypto.fidelitycareers.com

🔐 27:10 Cape: Get 33% off your first six months with code UNCHAINED at https://cape.co/unchained

⏳ 28:09 Why Parker isn't worried about Strategy's looming $6.7 billion convert cliff

🧩 34:56 Parker on how Apyx wraps STRC and SATA into a yield bearing onchain asset

📉 36:38 What caused apxUSD's drop to as low as 72 cents and the liquidity pull

🛡️ 41:10 Parker defends Apyx 2.0's redemption rules against the free put option critics

🔄 47:53 Parker on why comparing Strategy to Terra Luna or GBTC misreads the risk
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Ari Redbord sits down with Katherine, Jessi, and Vy to talk about SEC clarity, the onshore perps boom, and DeFi's opsec problem — plus why the U.S. should hack North Korea back.

Thank you to our 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
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(use code: UNCHAINED).

The hosts of DEX in the City spend every week breaking down crypto's legal fights. This time, they're the ones answering the questions.

Ari Redbord, Global Head of Policy at TRM Labs, sits down with Katherine Kirkpatrick Bos, Jessi Brooks, and Vy Le for a wide-ranging conversation on where crypto's regulatory and security battles are actually headed.

Vy traces her path from SEC enforcement to her case for "tech-neutral" rules: regulators should regulate outcomes, not technology. Katherine explains why DCMs have become crypto's hottest acronym, as true perps and prediction markets move onshore. And Jessi makes her push to stop calling North Korea's hacks "illicit finance" and start naming them a national security threat: Pyongyang, she notes, is funding a weapons program with stolen crypto. Ari goes further — if North Korea can steal hundreds of millions from DeFi, the U.S. should steal it back. Vy pushes back on the panic over the recent hacks: most, she argues, weren't broken smart contracts at all, just sloppy operational security.

The conversation covers SEC clarity, the CFTC's moment, DeFi security, on-chain privacy, and what it really takes to keep the ecosystem safe.

Host:

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Ari Redbord - Global Head of Policy at TRM Labs and Host of TRM Talks

Hosts:

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Katherine Kirkpatrick Bos⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠, General Counsel. 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
🛡️ 02:29 OFAC's first IRGC-linked exchange sanctions on Zedcex and Zedxion

🧭 05:20 How Vy, Katherine, and Jessi went from the SEC, BigLaw, and DOJ into crypto

🎙️ 14:10 The origin story behind the DEX in the City name and its all-women cast

🏛️ 18:25 Vy on the SEC trading ambiguity for rules, and "tech-neutral" regulation

📈 22:36 Katherine on why DCMs are suddenly crypto's hottest acronym

💙 25:38 Cape: Get 33% off your first six months with code unchained at https://cape.co/unchained

🩹 26:12 Jessi on reframing illicit finance around victims, not just enforcement

🔐 30:03 Jessi and Vy on Drift, Kelp, and why the recent hacks were ops failures

🕵️ 34:52 Katherine on why privacy is necessary for on-chain markets

🔮 40:04 Lightning round: Jessi on agentic finance, Katherine on perps, Vy on vaults
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Joseph Chalom lays out why Ethereum Institutional exists, how it differs from Etherealize, and why he thinks Michael Saylor is in a pickle.

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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.


⁠⁠⁠⁠⁠⁠⁠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).

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Sharplink, BitMine, and Joe Lubin spent the past ten days launching two new organizations aimed at convincing Wall Street to build on Ethereum, backing them with commitments from more than fifty institutional supporters.

Joseph Chalom, CEO of Sharplink and a board member of the new Ethereum Institutional, joins Laura Shin to make the case that Ethereum's real competition isn't Solana or Canton. It's inertia: the reluctance of the world's largest institutions to touch financial rails they don't already trust.

Chalom walks through how Ethereum Institutional differs from Etherealize and the Enterprise Ethereum Alliance, why Robinhood building on Arbitrum still counts as a win for Ethereum, and what it would take for ETH to capture the value flowing through the network as tokenized real-world assets grow past $31 billion. He pushes back on claims that the Ethereum Foundation's culture is broken, then turns to Strategy's preferred stock drama and says plainly that Michael Saylor is in a pickle.

Host:


⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Laura Shin⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠, Host / Unchained

Guests:


⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Joseph Chalom - CEO of Sharplink

Timestamps

🚀 01:33 Why Sharplink, BitMine, and Joe Lubin launched Ethereum Institutional

🧭 05:51 How Ethereum Institutional differs from Etherealize and the EEA

🃏 10:15 Chalom says institutional inertia, not Solana, is Ethereum's real threat

💙 14:40 Cape: Get 33% off your first six months with code unchained at https://cape.co/unchained

💼 15:34 Fidelity: Explore crypto careers that could change your future at https://crypto.fidelitycareers.com

🧩 16:20 Why Chalom says Robinhood building on Arbitrum is still a win for Ethereum

⚡ 20:54 Does value actually flow back to ETH the token

🏛️ 24:33 Chalom pushes back on the idea that Ethereum's culture is broken

🤝 29:01 Why Chalom says Sharplink's shareholders and Ethereum's ecosystem are aligned

📉 32:18 Chalom says Michael Saylor is in a pickle over Strategy's preferred stock drama
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Nick Johnson's ENS vote sparked days of backlash. He and co-founder Alex Van de Sande join Uneasy Money to explain what actually happened.

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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).

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

A routine two year renewal for the ENS DAO's Security Council failed on chain this week, and Nick Johnson, founder and CEO of ENS Labs, voted against it with roughly 50% of the active supply. Some users on X have since cast him as the villain seizing a $130 million treasury.

ENS co-founders Nick Johnson and Alex Van de Sande join Kain Warwick and Taylor Monahan to untangle what the vote means, and to defend a new proposal handing day-to-day treasury and protocol decisions to a foundation instead of the DAO.

They trace how ENS's governance fight mirrors Aave's, why its treasury has trailed a savings account, why Johnson never trusted ETH-weighted voting, and why his conviction in token governance has weakened.

The conversation lands on the question hanging over every well-funded DAO: once a protocol accumulates enough money to matter, can any voting mechanism decide who controls it?

Hosts:


⁠Kain Warwick⁠ - Host of Uneasy Money and Founder of Infinex and Synthetix


⁠Taylor Monahan⁠ - Co-host of Uneasy Money and Security Expert

Guests:


Nick Johnson - Founder and CEO of ENS Labs


Alex Van de Sande - Cofounder of ENS

Timestamps

🗳️ 02:14 Kain unpacks whether Nick really controls the ENS Security Council vote

🔥 06:37 Taylor pushes back: is the pile-on on Nick actually fair?

⚔️ 11:30 Kain calls it a DAO governance proxy war, echoing Aave's Stani fight

🍯 15:00 Nick on why a DAO treasury becomes a honeypot for capital allocation

🪙 28:01 Nick on why ETH-weighted voting would have left ENS open to a takeover

⚖️ 32:47 Nick clarifies what the ENS Labs proposal actually changes at the DAO

🏛️ 40:27 Nick argues the DAO should stop trying to run ENS day-to-day

📣 52:04 Cape: Get 33% off your first six months with code unchained at https://cape.co/unchained

🍴 58:56 Could a fork let Nick walk off with ENS's treasury? Alex says no

🎤 01:13:31 Taylor asks Nick and Alex point blank: why are you still here?
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David Lawant, Head of Research at Anchorage Digital, breaks down why Bitcoin's lack of native yield puts constant pressure on treasury companies, and makes the case that Michael Saylor's playbook is evolving rather than breaking.

Host:


Steven Ehrlich, Host of Bits + Bips: The Interview and Head of Research at Sharplink

Guest:


David Lawant, Head of Research at Anchorage Digital

This clip is from a longer conversation on Strategy's Stretch rescue plan and Bitcoin's options market. Full episode here: https://youtube.com/live/VwBxQTcJeXc 

New Bits + Bips interviews are posted regularly - subscribe to catch the next one.

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 A new Citi report reveals why retail's crypto excitement has quietly collapsed

📉 00:17 Retail's bet on the Mag Seven just hit a multiyear low

😨 01:15 The unsettling reason retail fears Saylor becoming Bitcoin's buyer of last resort

🃏 01:44 Revisiting Saylor's infamous "sell your organs before your Bitcoin" line

🪙 02:34 The yield problem: why Bitcoin generates nothing, while Ethereum and Solana pay

📈 03:06 David on covered calls and the fast rise of synthetic yield strategies

🏛️ 04:39 Saylor, the OG who wrote the playbook on institutional Bitcoin accumulation

⚓ 06:28 Why David says Strategy is quietly weathering the storm better than anyone
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