Skip to main content
Unchained

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

70 min episode · 2 min read
·
Shihan Chandrasekara

Episode

70 min

Read time

2 min

Topics

Investing, Leadership, Sales & Revenue

AI-Generated Summary

Key Takeaways

  • Tax Loss Harvesting: Sell crypto assets below cost basis before year-end to realize losses that offset capital gains with no dollar limit, or claim up to three thousand dollars against ordinary income if no gains exist, with excess losses carrying forward to future tax years.
  • Crypto Wash Sale Loophole: Unlike stocks requiring thirty-day waiting periods, crypto wash sales remain legal under current IRS rules since digital assets classify as property not securities, though transactions must demonstrate economic substance beyond tax avoidance to withstand potential audits.
  • Exchange Tax Reporting Changes: Starting 2025 tax year, centralized exchanges issue Form 1099-DA showing only proceeds without cost basis, requiring investors to maintain separate records. Full cost basis reporting begins 2026 but only covers transactions occurring entirely within single exchanges.
  • DeFi Risk Management Philosophy: Steakhouse Financial prioritizes institutional-grade vaults with lower risk profiles, arguing one percent additional annual yield proves worthless with ten percent probability of total capital loss. Prime vaults track Treasury bill rates plus or minus fifty to one hundred basis points.
  • Tokenized Credit Complexity: Private credit products like Fazanara MF1 accrue interest daily but mark down losses only when fund administrators require provisions, creating price charts that appear stable until sudden drops occur, unlike liquid high-yield ETFs with continuous price fluctuations.

What It Covers

Shihan Chandrasekara from CoinTracker and Sebastian Derevo from Steakhouse Financial discuss year-end crypto tax strategies, wash sale rules, DeFi risk management, and the evolving landscape of tokenized credit and stablecoin lending protocols.

Key Questions Answered

  • Tax Loss Harvesting: Sell crypto assets below cost basis before year-end to realize losses that offset capital gains with no dollar limit, or claim up to three thousand dollars against ordinary income if no gains exist, with excess losses carrying forward to future tax years.
  • Crypto Wash Sale Loophole: Unlike stocks requiring thirty-day waiting periods, crypto wash sales remain legal under current IRS rules since digital assets classify as property not securities, though transactions must demonstrate economic substance beyond tax avoidance to withstand potential audits.
  • Exchange Tax Reporting Changes: Starting 2025 tax year, centralized exchanges issue Form 1099-DA showing only proceeds without cost basis, requiring investors to maintain separate records. Full cost basis reporting begins 2026 but only covers transactions occurring entirely within single exchanges.
  • DeFi Risk Management Philosophy: Steakhouse Financial prioritizes institutional-grade vaults with lower risk profiles, arguing one percent additional annual yield proves worthless with ten percent probability of total capital loss. Prime vaults track Treasury bill rates plus or minus fifty to one hundred basis points.
  • Tokenized Credit Complexity: Private credit products like Fazanara MF1 accrue interest daily but mark down losses only when fund administrators require provisions, creating price charts that appear stable until sudden drops occur, unlike liquid high-yield ETFs with continuous price fluctuations.

Notable Moment

When Stream Finance lost eighty million dollars, some DeFi lending vaults experienced rapid exodus from two hundred fifty million to sixty million dollars within days, despite prime vaults having no direct exposure, demonstrating how contagion fears drive institutional capital flight regardless of actual risk isolation.

Know someone who'd find this useful?

Episode Transcript

If you traded, like, ETPs, if you have ETFs, there's there's a second step that you need to do in addition to relying on the ten nine nine b that you're getting from the broker. Wow. That does sound quite complicated. Hi, everyone. Welcome to Bits and Bips, the interview. I'm your host, Steve Ehrlich, executive editor at Unchained, and we've got a terrific lineup for you today. First, I'm gonna be joined by Shihan Chandrasekara, head of strategy at CoinTracker, And then we're gonna follow-up with Sebastian Derevo, a cofounder at the DeFi platform Steakhouse Financial. We have a lot to talk about today. Sheehan's gonna join us to discuss, year end tax strategies, things that everybody should be considering when, wrapping up the year. We're gonna cover tax loss harvesting, wash trading, and what's coming down the pike in 2026. So, so let's get started. Welcome, Shian. Yeah. Thanks, Steve. Thanks. Just one very quick disclaimer. Nothing that, either, I or my guest say here is tax or financial advice. For more information and disclosures, please check out, unchained.com/bitsandbips. So, Shian, let's yeah. Let's let's get right into it. 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 current tax law? Yeah. Sure. So cryptocurrencies, like, you know, Bitcoin or even NFTs, they are treated as property according to IRS rules. 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, those are considered taxable event. I guess, like, one easy way for you to kinda think about crypto taxes is is kinda thinking about how stocks are taxes taxed. So crypto taxes are very similar to stock. How how top how stocks are taxed, with some exceptions. Okay. Yeah. And, since this is kind of a a year end sort of tax wrap up, I would imagine we might have you back in, the the spring to talk about when it comes to filing. But, what are some of the things that people should be thinking about, when it comes to sort of finishing out the year, especially in a year where, I mean, a few assets are up, but but a lot are down. Right. I would say, like, number one thing, you should consider doing, like, especially in December is what we call taxes harvesting. So, basically, I would look at all the wallets and exchanges you have and go asset by asset and see which assets are below the cost basis. Cost basis means how much you paid for it. If the value is below the cost basis, you could consider selling them and realize the loss. And if you want, you can buy it back, in this year or next year, depending on, like, you know, how you wanna maintain the question …

Get the full transcript (11,646 words) + summary by email — free

One-time email with the complete transcript and AI summary of this episode. No account needed.

One email, no spam. We’ll also show you what SignalCast does.

Browse all Unchained transcripts →

You just read a 3-minute summary of a 67-minute episode.

Get Unchained summarized like this every Monday — plus up to 2 more podcasts, free.

Pick Your Podcasts — Free

Keep Reading

Books, tools, and gear mentioned in this episode

SignalCast may earn commission on purchases via these links. As an Amazon Associate, SignalCast earns from qualifying purchases.

Products

  • Private credit products like Fazanara MF1 accrue interest daily but mark down losses only when fund administrators require provisions, creating price charts that appear stable until sudden drops occur, unlike liquid high-yield ETFs with continuous price fluctuations.

company

  • Shihan Chandrasekara from CoinTracker and Sebastian Derevo from Steakhouse Financial discuss year-end crypto tax strategies, wash sale rules, DeFi risk management, and the evolving landscape of tokenized credit and stablecoin lending protocols.
  • Shihan Chandrasekara from CoinTracker and Sebastian Derevo from Steakhouse Financial discuss year-end crypto tax strategies, wash sale rules, DeFi risk management, and the evolving landscape of tokenized credit and stablecoin lending protocols.
  • When Stream Finance lost eighty million dollars, some DeFi lending vaults experienced rapid exodus from two hundred fifty million to sixty million dollars within days, despite prime vaults having no direct exposure, demonstrating how contagion fears drive institutional capital flight regardless of actual risk isolation.

More from Unchained

We summarize every new episode. Want them in your inbox?

Similar Episodes

Related episodes from other podcasts

Explore Related Topics

This podcast is featured in Best Crypto Podcasts (2026) — ranked and reviewed with AI summaries.

Read this week's Investing & Markets Podcast Insights — cross-podcast analysis updated weekly.

You're clearly into Unchained.

Every Monday, we deliver AI summaries of the latest episodes from Unchained and 192+ other podcasts. Free for one show.

Start My Monday Digest

No credit card · Unsubscribe anytime