Unchained

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

  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 Learn more about your ad choices. Visit megaphone.fm/adchoices

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• How to Trade Prediction Markets Without an Opinion on the Event - Ep. 979

  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: Paradigm Claims Polymarket Trading Figures Are Double Counted Polymarket Opens US App to Waitlisted Users Intercontinental Exchange to Invest $2 Billion in Polymarket Crypto.com and Kalshi Lead Prediction Market Coalition Setup Kalshi Hits $11B Valuation After $1B Raise: Report 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 Learn more about your ad choices. Visit megaphone.fm/adchoices

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• Uneasy Money: Is Jupiter Incompetent or Evil? And Is Hyperliquid's ADL Flawed? - Ep. 976

  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: Jupiter COO Says Vault’s ‘Zero Contagion’ Claim Was Not Fully Accurate Uneasy Money: Did Solana Dapp Kamino Break the Golden Rule of DeFi? Uneasy Money: Hyperliquid’s Dilemma After 10/10: Protect Itself or Its Users? Linda Xie on How Mini-Apps Are Helping Farcaster Take on Web2 Social Media 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 Learn more about your ad choices. Visit megaphone.fm/adchoices

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• How AI Agents Hacked Smart Contracts for $1 Apiece - DEX in the City - Ep. 975

  Sponsor: UniswapCitadel 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: Kraken Valued at $20 Billion After $200 Million Raise From Citadel Securities CFTC Approves Spot Crypto Trading on U.S. Exchanges CFTC’s New Pilot Allows BTC, ETH and USDC as Derivatives Collateral Samourai Wallet Founders Could Serve 5 Years for $237 Million Laundering 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 Learn more about your ad choices. Visit megaphone.fm/adchoices

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

  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 Learn more about your ad choices. Visit megaphone.fm/adchoices

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