Unchained

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

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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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        UnchainedBy Laura Shin