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

8 snips

Dec 13, 2025

Guest

Sebastien Derivaux

Guest

Shehan Chandrasekera

Shehan Chandrasekera, CPA and Head of Tax Strategy at CoinTracker, delves into the complexities of crypto tax reporting, emphasizing the significance of tax-loss harvesting and the implications of the new 1099-DA form. Sebastien Derivaux, Co-founder of Steakhouse Financial, highlights the risks of high-yield chasing in DeFi, the future of stablecoins beyond the US dollar, and the importance of institutional-grade risk curation. Together, they discuss crucial tax strategies and emerging trends shaping the crypto landscape.

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ADVICE

Harvest Losses Before Year-End

Do tax-loss harvesting before year-end by selling assets below cost basis to realize losses.
Use realized losses to offset crypto or stock gains and carry remaining losses forward.

ADVICE

Don't Flip Sales For Just Tax Losses

Avoid immediate buybacks purely for tax reasons because transactions lacking economic substance can trigger IRS scrutiny.
Wait a reasonable period and keep a plausible non-tax rationale if you re-enter a position.

INSIGHT

Wash-Sale Loophole May Be Temporary

Wash-sale protection currently applies to stocks and securities but not to crypto, creating a temporary mismatch.
Legislative proposals may close this loophole, so the current advantage may not last.

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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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