This Week on Unchained: Crypto Taxes, DeFi Strategies, Predictions Markets & Bitcoin’s New Era

Good Sunday! Here’s what we unpacked this week on Unchained:

• 💵 Bits + Bips: The Interview

  From DeFi yield strategies to crypto ETFs and taxes, two experts explain why risk, structure, and compliance matter more than headline returns.

• 🎯 How to Trade Prediction Markets Without an Opinion
  Markus Thielen explains why Polymarket’s edge is math, not inside information — how “near-certain” trades work, why the crowd is the signal, and what could come next for prediction market tokens.

• 🔥 Uneasy Money
  The Jupiter–Kamino showdown escalates, Hyperliquid’s ADL design comes under scrutiny, and the team breaks down whether Lighter’s 0% model is brilliance… or bait.

• 🤖 DEX in the City
  How AI agents exploited smart contracts for pennies, why Citadel’s DeFi letter shook the industry, and why U.S. regulators are suddenly in a “race to the top.”

• 📉 Is Bitcoin Entering a New Phase?
  How 2025 became a year of policy wins but price pain, why some analysts say the four-year cycle is over, and whether privacy coins could ever dethrone BTC.

• 🏦 Bits + Bips on TradFi’s Crypto Scramble
  Why banks need crypto more than ever, what BlackRock’s staked-ETH ETF could mean, and how Ethereum and Solana yields are becoming Wall Street’s new obsession.

• 🪓 The Chopping Block on Web3’s Collapse
  Why Farcaster’s pivot revived the “Web3 is dead” debate, why social apps keep failing, and how L1 valuations are sparking a market-wide reset — plus the burnout wave hitting founders.

Bits + Bips: Crypto Investing Is About Managing Risk, Not Chasing Upside

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.

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

How to Trade Prediction Markets Without an Opinion on the Event

Prediction markets are all the rage, but how do you trade them without a leg up on information? Markus Thielen says it’s about math and  “the wisdom within the crowd.”

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.”

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

Uneasy Money: Is Jupiter Incompetent or Evil? And Is Hyperliquid’s ADL Flawed?

Tensions are rising in Solana’s DeFi space. Is the blockchain in its “competitive post-DeFi summer era?”

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.

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

How AI Agents Hacked Smart Contracts for $1 Apiece – DEX in the City

The DEX in the City crew dives into Citadel’s controversial DeFi regulation letter, the CFTC’s “race” to regulate crypto, and how AI agents can hack smart contracts for $1 each.

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.

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

Will Bitcoin’s New Phase Change It Forever? And Is the 4-Year Cycle Dead?

The crypto markets are disappointing, but our experts aren’t pessimistic. Here’s why one thinks 2026 will prove the four-year cycle is dead.

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.

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

Bits + Bips: Why TradFi Knows It Needs Crypto More Than Ever to Stay Relevant

TradFi needs crypto as competition heats up—and the incumbents are scrambling for “dance partners.”

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.”

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

The Chopping Block: Web3 Dies, L1 Valuations Clash & Crypto Burnout

The Chopping Block confronts a reality check as Web3 social unravels, L1 valuations ignite a market-wide reckoning, and new research exposes massive ADL failures hiding in plain sight.

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.

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

In Case You Missed It 👀

Bitcoin Briefly Pops Following Fed Rate Cut, Optimistic 2026 Outlook

The FOMC lowered the federal funds rate by 25 basis points, navigating tensions between still-elevated inflation and growing concern over employment.

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