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

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

1 hour 10 minutes Posted Dec 13, 2025 at 6:30 pm.

Intro

How crypto fits into existing tax law

What investors should be thinking about before year-end—and how tax loss harvesting works

The wash sale rule: Is it safe to use in crypto?

How upcoming legislation could change crypto taxes

Stablecoins and taxes: Are there any special rules?

The hidden tax complexity of trading crypto ETPs and ETFs

What the new 1099-DA form is—and what it will (and won’t) tell the IRS

The key things Shehan says crypto investors should watch closely

Intro

Understanding Steakhouse Financial and its growth rate

What “risk curation” actually means and why Steakhouse focuses on institutions

How Steakhouse vaults generate stablecoin yields

What risk curators can—and can’t—control in a decentralized environment

What recent volatility revealed about DeFi vaults and the collapse of Stream Finance

Whether “safe” high yield is even possible

The liquidity problem with tokenized credit funds onchain

How Steakhouse is positioning for the stablecoin boom

How stablechains like Tempo and Plasma could change the game

Why Steakhouse plans to integrate tokenized deposits

Steakhouse’s 2026 bet on non-USD stablecoins

0:00

1:10:27

Download MP3

Share at current time

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:

🎬

🧾

📅

🔁

⚖️

💵