Unchained

Latest Episodes:

DEX in the City: How Privacy in Crypto Makes Everyone's Finances More Secure - Ep. 982 Dec 18, 2025

Show notes

The SEC this week held a roundtable on financial surveillance and privacy in another sign of the major shift in the regulator's approach to crypto.

In this DEX in the City episode, Espresso co-founder Jill Gunter joins hosts Jessi Brooks and Katherine Kirkpatrick Bos to unpack the major talking points and takeaways from the roundtable. And more importantly, what it signals about the SEC’s approach to crypto and privacy.

With legacy financial institutions coming onchain, like JPMorgan and DTTC, they discuss how crypto can actually help prevent data breaches and have a better product for users and companies alike.

Interestingly, Jill recounts how she lost $30,000 in an exploit involving crypto mixer Railgun and why she didn’t even try to hide it from regulators at the roundtable.

Plus, was Do Kwon's sentence excessive? Well, according to Jessi, it’s a complicated question, but she unpacks what people misunderstood about the judge’s decision.

Hosts:

Jessi Brooks, General Counsel at Ribbit Capital
Katherine Kirkpatrick Bos, General Counsel at StarkWare

Guest:

Jill Gunter, Co-founder and Chief Strategy Officer at Espresso Systems

Links:

Unchained:

Jessi's and Katherine's paper on programmable risk management

Timestamps:

🚀 00:00 Introduction

⚡️ 3:23 How SEC privacy roundtable marks a sea change in the regulatory approach to crypto

💡 12:39 Why privacy is also important for legacy institutions moving onchain

📍 17:31 How projects and institutions can be compliant while collecting less data

🤧 24:57 Jill recounts being the victim of a hack and seeing the hackers use a privacy protocol

❕️ 30:36 Why Jill says the hack did not change her perspective on crypto privacy

😎 33:30 How far the crypto industry has come since Tornado Cash

⚔️ 35:54 The debate over proof of innocence

⚖️ 42:09 What everyone misunderstood about Do Kwon's sentence

💫 52:24 Shoutout to Save the Children for their innovative Bitcoin initiative

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The Chopping Block: Hyperliquid vs. Tarun, ADL Transparency & The Coming Perps Arms Race - Ep. 981 Dec 17, 2025

Show notes

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 episode features special guest Vladimir Novakovski, Founder of Lighter, joining the crew to unpack the fallout from October 10’s historic perpetuals liquidation event and the ADL research that sparked a public clash with Hyperliquid. The panel digs into how auto-deleveraging really works, why these failures were long hidden inside centralized exchanges, and what decentralized perps must fix to truly outperform TradFi.

The conversation then turns to the intensifying perp wars. With Lighter’s zero-fee trading model, premium tiers for pros, and a looming token launch, the hosts debate whether crypto is headed for a Robinhood-style fee reset, why TVL may matter more than volume, and how RWAs, FX perps, and cross-margining are reshaping market structure. Finally, they tackle the growing divide between tokens and equity as devcos get acquired and tokenholders are left behind.

Perps are evolving, incentives are breaking — let’s get into it.

Show Highlights

🔹 ADL research ignites a firestorm — Tarun’s paper on auto-deleveraging sparks a public clash with Hyperliquid and Paradigm, exposing how opaque ADL systems really are.

🔹 October 10 liquidation shock — Repeated ADLs during crypto’s largest liquidation day reveal structural fragility long hidden inside both CEXs and DEXs.

🔹 Fairness vs predictability in perps — Why traders care less about perfect algorithms and more about knowing when and how ADLs will hit.

🔹 Lighter’s design tradeoffs — Vladimir Novakovski explains Lighter’s less-aggressive ADL approach, insurance fund buffers, and trader-friendly risk parameters.

🔹 Zero-fee perps debate — Lighter’s free retail tier + paid pro tier raises the question: is crypto headed for a Robinhood-style fee reset?

🔹 TVL beats volume — The panel argues TVL is the most honest signal of trust in perp exchanges, especially during market stress.

🔹 RWAs and FX perps surprise — Euro and index perps outperform expectations, challenging assumptions about which real-world assets actually trade onchain.

🔹 Tokens vs equity explode — Devco acquihires (Axelar, Tensor) leave tokenholders behind, reigniting debates over incentive alignment and crypto M&A.

Hosts:

⭐️Haseeb Qureshi, Managing Partner at Dragonfly ⭐️Tarun Chitra, Managing Partner at Robot Ventures

Guest

⭐️Vladimir Novakovski, Founder & CEO. Lighter.

Links:

Tarun Chitra’s Autodeleveraging: $653 million lost to a greedy heuristic?

🔗 https://x.com/kenchangh/status/1994854381267947640

⁠Disclosures⁠

Timestamps

00:00 Intro

01:38 Tarun’s ADL Paper Sparks Backlash

05:24 Research vs Bag Defense

06:27 How ADLs Actually Work

12:27 Fairness vs Predictability

24:14 Tarun’s Inspiration

28:17 Zero-Fee Perps Explained

34:12 Perp Wars Heat Up

38:15 RWAs Trade Onchain

41:49 Token Launch Reality

47:19 Tokens vs Equity Clash

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Bits + Bips: What Could Spark the Next Crypto Bull Cycle? - Ep. 980 Dec 16, 2025

Show notes

Thank you to our sponsors, Mantle!
On this episode of Bits + Bips, hosts Ram Ahluwalia, Austin Campbell, and Chris Perkins are joined by Elisabeth Kirby, Head of Market Structure at Tradeweb, for a wide-ranging conversation about the future of crypto markets — and who will control them.

They unpack why US market structure legislation stalled, how the SEC’s enforcement-first approach shaped the last cycle, and what it signals that JPMorgan, BlackRock, and others are moving forward with tokenization.

The group debates whether Ethereum’s institutional edge is durable, whether Canton can scale beyond early adopters, and why Solana’s “decentralized Nasdaq” vision still faces hard questions.

The episode closes with a sober look at macro conditions, risk appetite, and why crypto may be stuck waiting, even as the long-term institutional thesis quietly strengthens.

Hosts:

Ram Ahluwalia, CFA, CEO and Founder of Lumida
Austin Campbell, NYU Stern professor and founder and managing partner of Zero Knowledge Consulting
Christopher Perkins, Managing Partner and President of CoinFund

Guest: Elisabeth Kirby, Head of Market Structure at Tradeweb

Links:

The S.E.C. Was Tough on Crypto. It Pulled Back After Trump Returned to Office.

Timestamps:

🎬 0:00 Intro

🗳️ 1:56 Impact of crypto market structure legislation getting pushed into 2026

📰 12:55 Howthe New York Times articleof the SEC’s regulation of crypto missed crucial context

🏦 22:12 How JPMorgan’s tokenized money market fund on Ethereum changes the tone for TradFi onchain

🏛️ 32:18 Whether Canton can become the real institutional chain and what could derail it

🧑‍💻 45:10 What Solana’s “decentralized Nasdaq” pitch gets right and where it still looks shaky

🌍 49:58 How macro, Fed expectations, and a rotation into “boring” assets are squeezing crypto risk-taking

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Bits + Bips: Crypto Investing Is About Managing Risk, Not Chasing Upside - Ep. 978 Dec 13, 2025

Show notes

Subscribe to Bits + Bips: https://bitsandbips.beehiiv.com/subscribe

On this bundled episode of Bits + Bips, Unchained executive editor Steve Ehrlich digs into the less obvious risks shaping crypto returns, from DeFi yield to tax reporting.

First, Sebastien Derivaux, co-founder of Steakhouse Financial, explains why chasing high yield can be dangerous, how institutional risk curation works onchain, and why the future of stablecoins won’t be limited to the US dollar.

Then, Shehan Chandrasekera, CPA and Head of Tax Strategy at CoinTracker, breaks down what crypto investors need to know heading into 2026, including tax loss harvesting, the wash sale gray zone, hidden tax obligations in crypto ETFs, and why the new 1099-DA form won’t tell the full story.

Host:

Steve Ehrlich, Executive Editor at Unchained

Guests:

Shehan Chandrasekera, CPA, Head of Tax Strategy at CoinTracker
Sebastien Derivaux, Co-Founder & Partner at Steakhouse Financial

Timestamps:

🎬 0:00 Intro
🧾 1:10 How crypto fits into existing tax law
📅 2:14 What investors should be thinking about before year-end—and how tax loss harvesting works
🔁 4:54 The wash sale rule: Is it safe to use in crypto?
⚖️ 9:27 How upcoming legislation could change crypto taxes
💵 11:22 Stablecoins and taxes: Are there any special rules?
📊 13:47 The hidden tax complexity of trading crypto ETPs and ETFs
📄 16:39 What the new 1099-DA form is—and what it will (and won’t) tell the IRS
👀 22:31 The key things Shehan says crypto investors should watch closely
22:32 Intro
22:59 Understanding Steakhouse Financial and its growth rate
24:59 What “risk curation” actually means and why Steakhouse focuses on institutions
27:52 How Steakhouse vaults generate stablecoin yields
30:39 What risk curators can—and can’t—control in a decentralized environment
35:28 What recent volatility revealed about DeFi vaults and the collapse of Stream Finance
39:33 Whether “safe” high yield is even possible
41:33 The liquidity problem with tokenized credit funds onchain
49:48 How Steakhouse is positioning for the stablecoin boom
51:24 How stablechains like Tempo and Plasma could change the game
52:47 Why Steakhouse plans to integrate tokenized deposits
54:55 Steakhouse’s 2026 bet on non-USD stablecoins

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How to Trade Prediction Markets Without an Opinion on the Event - Ep. 979 Dec 13, 2025

Show notes

Visit our website for breaking news, analysis, op-eds, articles to learn about crypto, and much more: unchainedcrypto.com

Thank you to our sponsor!

Walrus

The prediction market meta is piping hot and everyone wants a piece of the pie.

In this episode of Unchained, 10x Research founder Markus breaks down what the competition boils down to. Plus, will other platforms follow Polymarket's lead and launch a token?

He also walks through a “near certain” trade nestled in Polymarket and shares 10 strategies that can be used to trade prediction markets without an opinion.

One key nugget: “It's the wisdom within the crowd.”

Guest:

Markus Thielen, CEO of 10x Research

Previous appearance on Unchained:

How to Invest in This Bitcoin Downtrend: Bits + Bips

Links

Unchained:

Timestamps:

🚀 00:00 Introduction

💡 3:07 Why Markus says prediction market adoption is still in its infancy

👀 6:23 Are speculators abandoning bitcoin for prediction markets?

🧏 8:10 How trading prediction markets differ from crypto markets

⚖️ 11:48 How Polymarket and Kalshi compare in strengths and weaknesses

⚡️ 15:12 Why Markus thinks Polymarket and Kalshi are likely to remain the dominant players

📝 19:15 What traders should consider when choosing a prediction market platform

💥 23:05 How the POLY Airdrop could give Polymarket an edge

⁉️ 26:39 Will other prediction markets launch a token?

💡 33:19 How risks in trading prediction markets differ from crypto markets

🧠 36:31 Markus walks through a “near certain” Bitcoin trade paying 63% annualized

🤯 39:58 Strategies to trade prediction markets without having an opinion

❕️ 51:48 Why Markus avoids “moon shot” trades

⚠️ 54:11 How to trade by finding “wisdom within the crowd”

🤺 1:00:17 How prediction markets enable hedging against real world outcomes

📃 1:02:34 Final thoughts on how traders should approach prediction markets

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Uneasy Money: Is Jupiter Incompetent or Evil? And Is Hyperliquid's ADL Flawed? - Ep. 976 Dec 12, 2025

Show notes

Thank you to our sponsor, MultiChain Advisors!The beef between Solana dapps Jupiter and Kamino has taken a new dimension as Kamino has accused Jupiter of lying about contagion risks.

In this episode of Uneasy Money, hosts Kain Warwick, Luca Netz and Taylor Monahan dive into whether Jupiter misled users and raise questions about Kamino's response.

Plus, after Tarun Chitra’s paper on Hyperliquid’s ADL, they dig deep into the exchange’s design: did they cause unnecessary liquidations on Oct. 10?

At the same time, they break down Lighter's 0% fees model. Does it resemble Robinhood? And how smart is it actually?

Plus, what Farcaster's big pivot means for the future of Web3 social, and what Taylor says it would take to crack it.

Hosts:

Luca Netz, CEO of Pudgy Penguins
Kain Warwick, Founder of Infinex and Synthetix
Taylor Monahan, Security at MetaMask

Links:

Unchained:

Timestamps:

🚀 00:00 Introduction

😬 1:18 Did Jupiter mislead users?

🤔 9:19 Did Kamino really block Jupiter over contagion risks?

💡 11:15 Why Kain says Solana is in its “post-DeFi summer growth” era

🧐 12:38 Should Jupiter even care about its lending business line?

👀 18:06 Whether Hyperliquid's algorithm screwed users during the Oct. 10 crash

🎯 21:29 Luca reveals why his Oct. 10 losses on Hyperliquid weren’t so bad

🫨 24:54 Why Taylor says DPRK traders got saved by Oct. 10

💥 30:38 Why Kain is optimistic a rival HL model would emerge

⁉️ 32:02 Are Lighter users the product?

🧠 33:26 Why Kain thinks Lighter's model is genius

⚖️ 39:10 Whether Lighter resembles Robinhood

💁‍♂️ 44:47 Farcaster’s pivot: Is Web3 social DOA?

💡 50:53 What drives VC investment in crypto and why decentralization is not enough

💥 56:46 Kudos to Dan Romero for not launching a token, and whether more founders would be better off abstaining

👀 1:04:46 Whether having too much money is bearish for projects

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How AI Agents Hacked Smart Contracts for $1 Apiece - DEX in the City - Ep. 975 Dec 11, 2025

Show notes

Sponsor: Uniswap
Citadel has sparked uproar with a letter calling on the SEC to regulate DeFi protocols as exchanges. But the company's requests may not be totally unreasonable.

In this episode of DEX in the City, hosts Jessi Brooks, Katherine Kirkpatrick Bos, and Vy Le dig into Citadel's controversial letter and how it is a reminder that “crypto is a bubble.”

They also discuss how the CFTC and SEC are in a “race to the top,” plus Jessi explains how AI agents can exploit smart contracts they haven’t been trained on for just $1 apiece.

Plus, Vy calls on the crypto community to support Samourai developers.

Hosts:

Jessi Brooks, General Counsel at Ribbit Capital
Katherine Kirkpatrick Bos, General Counsel at StarkWare
TuongVy Le, General Counsel at Veda

Links:

Unchained:

Samourai pardon petition

Timestamps:

🚀 00:00 Introduction

💡 3:05 What Citadel's SEC letter on tokenized securities and DeFi says about how TradFi views crypto

👀 6:50 Why Vy says Citadel's suggestions are not unreasonable

🤔 9:31 Is Citadel shooting itself in the foot?

❌️ 11:13 What Jessi says Citadel got wrong

📍 13:42 How crypto is a bubble (or a cult?), but Citadel’s position is more mainstream

🧠 19:39 Why the CFTC greenlighting spot crypto trading on regulated exchanges matters

💡 22:57 Katherine explains Bitnomial’s advantage

💥 26:53 Why Jessi says the CFTC and SEC are in a race to regulate crypto

🧏‍♀️ 31:30 Why KK loves the CFTC’s tokenized collateral pilot

🧠 33:47 Why Anthropic's study on smart contract security is so scary for crypto

⚠️ 36:31 How AI agents could exploit 1,000 smart contracts for $1 apiece

📝 41:42 How community members can support Samourai wallet developers

💫 44:00 Crypto good news shoutout for the week

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The Chopping Block: Web3 Dies, L1 Valuations Clash & Crypto Burnout - Ep. 977 Dec 11, 2025

Show notes

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 episode starts with Farcaster’s pivot and Tarun’s claim that “Web3 is dead,” at least the A16z-style ownership economy. With Web3 social struggling, the crew digs into why spam, airdrops, and weak network effects keep sinking these apps — and why prediction markets may be crypto’s accidental social network.

We then jump to the L1 valuation fight. Haseeb recaps his debate with Santiago over whether chains are wildly overpriced or simply early, sparking a broader discussion on PE ratios, L1 “premiums,” and how many chains the world can realistically sustain.

Next up: Ken Chan’s viral “I wasted 8 years in crypto.” The team unpacks burnout, sugar-water loops, and why nihilism tends to hit founders right as the market turns. And finally, Tarun walks through his ADL research and how October 10’s cascading liquidations exposed major flaws in current systems.

Markets evolving, narratives collapsing — let’s get into it.

Show highlights

🔹 Farcaster pivots; Tarun calls A16z-style “ownership economy” Web3 (NFTs, own-your-posts) officially dead.

🔹 Web3 social stalls — Twitter clones drowned in spam, airdrop farming, and weak network effects; prediction markets emerge as the real crypto social layer.

🔹 Users’ revealed prefs — People claim to want decentralization/privacy but consistently choose convenience and incumbents.

🔹 RIP “Web3” — Term traced from Gavin Wood to A16z marketing; panel agrees it no longer reflects where crypto is actually succeeding.

🔹 L1 valuation battle — Santi’s PE-ratio critique vs Haseeb’s long-horizon “onchain finance will be huge” thesis; debate centers on how to value chains post-ICO/NFT era.

🔹 How many L1s survive? — Tarun expects activity to concentrate in a small set due to issuance, liquidity, and coordination costs; L1 “premium” still props up dino chains.

🔹 Burnout + disillusionment — Ken Chan’s “I wasted 8 years” resonates but feels mistimed amid strong fundamentals; panel contrasts sugar-water casino loops with real infra building.

🔹 ADL failures exposed — Tarun’s research shows October 10’s cascading liquidations revealed outdated ADL assumptions; better algorithms could’ve saved hundreds of millions.

Hosts⁠

⭐️Haseeb Qureshi, Managing Partner at Dragonfly

⭐️Robert Leshner, CEO & Co-founder of Superstate

⭐️Tarun Chitra, Managing Partner at Robot Ventures

⭐️Tom Schmidt, General Partner at Dragonfly

Links

Ken Chan’s “I Wasted 8 Years of My Life in Crypto”

🔗 https://x.com/kenchangh/status/1994854381267947640

Tarun Chitra’s Autodeleveraging: $653 million lost to a greedy heuristic?

🔗 https://x.com/kenchangh/status/1994854381267947640

Disclosures

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Will Bitcoin's New Phase Change It Forever? And Is the 4-Year Cycle Dead? - Ep. 974 Dec 10, 2025

Show notes

The crypto sector has celebrated a lot of policy wins in 2025, but price wise, it has arguably been a year to forget.

In this episode of Unchained, Bitwise Head of Research Ryan Rasmussen and Arca Portfolio Manager David Nage join host Laura Shin to discuss the disappointing crypto markets and why their outlook on 2026 is more positive.

They also explained why Vanguard's crypto pivot is a huge deal, questioned whether Bitcoin could ever be unseated by privacy coins, and discussed why they don’t see the bubble in the DAT market hurting crypto.

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Guests:

Ryan Rasmussen, Head of Research at Bitwise
David Nage, Portfolio Manager at Arca

Previous appearance on Unchained:

The LayerZero-Wormhole Contest Shows How to Value a Crypto Business

Links:

Unchained:

Other relevant links:

Timestamps:

🚀 00:00 Introduction

🤔 01:42 Is the four-year cycle dead?

💡 3:50 Why David says Bitcoin is having its “Facebook moment”

⚡️ 11:42 Why Ryan does not believe Bitcoin OGs are disillusioned

💥 14:43 Why David thinks liquidity may be returning to the market

❕️ 17:21 What is driving Vanguard and Bank of America's adoption of crypto

🚨 24:34 The importance of Bitwise 10 Crypto Index Fund's ETF transition

💡 28:30 Why BITW excludes memecoins, stablecoins and, wrapped tokens, etc.

🔮 31:15 What tokenization means for the future of finance

👀 35:56 What the future holds for digital asset treasuries

⚠️ 39:45 How unwinding of DATs could affect Bitcoin

🧏 41:11 What Stripe's 1.5% fees suggest about the future of stablecoin competition

📈 46:43 Why David says stablecoin adoption is similar to email

🤔 48:55 Could Bitcoin be toppled as the privacy meta rises?

🔮 56:45 Ryan and David share their 2026 crypto outlook

✴️ 1:02:01 Ryan’s 2026 Bitcoin price target

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Bits + Bips: Why TradFi Knows It Needs Crypto More Than Ever to Stay Relevant - Ep. 973 Dec 09, 2025

Show notes

Thank you to our sponsors!

Hosts Ram Ahluwalia, Austin Campbell, and Chris Perkins dig into why interest rates may not fall as quickly as markets hope, why oil demand could surprise to the upside, and how retail keeps buying every dip—even while consumer confidence hits new lows.

The trio also breaks down the growing collision between TradFi and crypto: whether banks can compete with blockchain-native distribution, how BlackRock’s staked ETH ETF filing could reshape the market, and how yields on Ethereum and Solana represent a brand-new financial primitive.

Plus, they examine Ripple’s controversial raise, Citadel’s push to regulate DeFi, and why major incumbents are now in a frantic race to choose their crypto “dance partners.”

Hosts:

Ram Ahluwalia, CFA, CEO and Founder of Lumida
Austin Campbell, NYU Stern professor and founder and managing partner of Zero Knowledge Consulting
Christopher Perkins, Managing Partner and President of CoinFund

Links:

Unchained:

BlackRock Files S-1 for Staked ETH ETF

Timestamps:

👏 0:00 Intro
📉 2:06 Whether there’s any real path to lower rates
🛢️ 5:07 Why Ram is bullish on oil demand
🤖 6:12 The biggest constraint on AI adoption
🇯🇵 7:02 Is Japan raising rates still a “nothing burger”?
🛍️ 9:57 How retail keeps buying every dip
🏦 12:21 Can crypto beat banks’ entrenched distribution?
📉 18:00 Why Ram thinks you should “sell the Bitcoin rallies”
📼 20:13 Are we reliving the 1970s?
⛓️ 24:47 How BlackRock’s staked ETH ETF filing could reshape the market
⚖️ 30:28 How staking yields will trade against Fed short rates
💼 38:59 Ripple’s controversial “raise” — and the unusual protections granted to Citadel and Fortress
🛡️ 47:52 How Citadel is fighting DeFi to defend its moat

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