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

Unchained

Laura Shin

News, Tech News, Business News

4.6 • 1.3K Ratings

🗓️ 13 December 2025

⏱️ 70 minutes

🔗️ Recording | iTunes | RSS

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Summary

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

Transcript

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0:00.0	If you traded like ETPs, if you have ETS, this is the second step that you need to do in addition to relying on the 1099B that you are getting from the broker.
0:09.0	Wow, that does sound quite complicated.
0:12.6	Hi, everyone. Welcome to Bits and Bips, The Interview.
0:16.4	I'm your host, Steve Ehrlich, executive editor at Unchained, and we've got a terrific lineup for you today.
0:22.6	First, I'm going to be joined by Sheehan Chandrasakara, head of strategy at CoinTracker.
0:28.6	And then we're going to follow up with Sebastian Daravow, a co-founder at the DFI platform, Stakehouse Financial.
0:35.6	We have a lot to talk about today. Sheehan's going to join us to
0:39.0	discuss a year-in tax strategies, things that everybody should be considering when wrapping up the year.
0:45.4	We're going to cover tax loss harvesting, wash trading, and what's coming down the pike in
0:49.8	2026. So let's get started. Welcome Sheehan. Yeah, thanks, Steve.
0:55.0	Thanks. Just one very quick disclaimer. Nothing that either I or my guest say here is tax or financial advice.
1:04.0	For more information and disclosures, please check out Unchained.com backslash bits and bibs.
1:10.0	So Sheehan, let's, yeah, let's get right into it. A lot of people check out Unchained.com backslash bits and bibs.
1:13.5	So Sheehan, let's get right into it.
1:18.5	A lot of people listening have probably been paying taxes on their crypto for years, but for anyone that is kind of new, can you just briefly explain how crypto falls in line with
1:27.0	current tax law?
1:28.3	Yeah, sure. So crypto currencies like Bitcoin or even NFTs, they're treated as property according to IRS rules.
1:36.3	So that means whenever you cash out or go from one crypto to another or when you earn crypto through staking or any type of rewards,
1:46.5	those are considered taxable event.
1:48.8	I guess like one easy way for you to kind of think about crypto taxes is kind of thinking about how stocks are taxes, taxed.
1:56.6	So crypto taxes are very similar to how stocks are taxed with some exceptions.
2:03.6	Okay. Yeah. And since this is kind of a year-end sort of tax wrap-up, I would imagine we might have you back in the spring to talk about when it comes to filing.
	...

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