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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Why the Crypto Industry Is So Upset About the IRS’ Proposed New Tax Reporting Rules - Ep. 575
The IRS sparked a storm of controversy when it released proposed new rules for crypto transaction reporting earlier this year. The new rules seek to define who is considered a broker, what types of transactions need to get reported, and the kinds of digital assets that need to be included, but many in the industry consider them overly broad and ultimately unworkable.
Lawrence Zlatkin, VP of Tax at Coinbase, and Shehan Chandrasekera, Head of Tax Strategy at tax software firm CoinTracker, discuss the crypto industry’s specific objections to the proposed new rules, and what might be a better way forward. They also delve into how the regulations would apply to stablecoins and NFTs, potential blockchain-based solutions for the reporting requirements, and what the likely outlook and timeline for the proposals to come into effect are.
Listen to the episode on Apple Podcasts, Spotify, Overcast, Podcast Addict, Pocket Casts, Stitcher, Castbox, Google Podcasts, Amazon Music, or on your favorite podcast platform.
Show highlights:
What the newly proposed IRS regulations around crypto are and when they are likely to go into effect
what entities qualify as a broker and why this may pose a problem
what the implications for the industry are if these regulations were passed
the number of additional reports the IRS is expecting to receive if these regulations are adopted
how the regulations would apply to stablecoins and NFTs
what the five types of brokers are under the proposed regulations and the three types that they exclude, according to Shehan
the unprecedented amount of comments submitted
what suggestions Coinbase and CoinTracker have in mind for better tax regulation
why Lawrence thinks that DeFi exchanges should be treated the same as centralized ones
whether people should have privacy concerns about the new proposals
what some blockchain-based solutions for tax reporting are, such as attestation tokens
what the next steps for the IRS proposed regulation are
how long it will take to actually implement these regulations
Thank you to our sponsors!
LayerZero
Popcorn Network
Guests:
Shehan Chandrasekera, Head of Tax Strategy at CoinTracker
Lawrence Zlatkin, VP of Tax at Coinbase
Links
Previous coverage of Unchained on crypto taxes, with appearances from Shehan and Lawrence:
Everything You Need to Know About Filing Your 2022 Crypto Taxes
Your 2021 Crypto Taxes: How to Handle NFTs, DAOs, Airdrops and More
Everything You Need to Know About Your 2020 Crypto Taxes
Why You Shouldn’t Trust Crypto Exchange Reports for Your Taxes
The IRS Is Cracking Down on Crypto Taxes: What You Need to Know
Could the Bank Secrecy Act Harm Crypto? Coin Center Thinks So
Infrastructure Investment and Jobs Act (117th Congress)
Proposed rule:
IRS proposed rule text: Gross Proceeds and Basis Reporting by Brokers and Determination of Amount Realized and Basis for Digital Asset Transactions
U.S. Department of the Treasury, IRS Release Proposed Regulations on Sales and Exchanges of Digital Assets by Brokers
CoinDesk: How the Crypto Industry Responded to the IRS Proposed Broker Rule
Twitter thread from Ji Kim of Crypto Council for Innovation
CNBC: President Joe Biden to sign the bipartisan infrastructure bill into law—here's how crypto investors will be impacted
IRS issues guidance, seeks comments on nonfungible tokens
Coinbase first comment letter
Coinbase second comment letter
CoinTracker comment letter
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Everything You Need to Know About Filing Your 2022 Crypto Taxes - Ep. 453
Lawrence Zlatkin, VP of Tax at Coinbase, and Shehan Chandrasekera, Head of Tax Strategy at CoinTracker, give a full accounting of everything U.S. crypto traders should be aware of as we inch closer to April 18. The two tax experts discuss the latest on how the IRS is approaching crypto taxation, going deep on everything from staking rewards to NFT royalties. Just a heads up: This interview is meant for informational purposes only and should not be construed as financial or tax advice.
Show highlights:
what’s new this year when it comes to reporting crypto transactions
why staking is now firmly on the IRS’s radar
how capital gains tax works for crypto
the types of crypto transactions that are taxable as income
the five situations where a crypto user incurs a taxable event
the types of crypto activity that are not taxable
what crypto holders can do to make tax time easier
the IRS forms you need for various types of crypto transactions
typical mistakes that crypto users make when it comes to filing their taxes
why there’s not much you can do if you have assets stuck in Voyager, Celsius or other bankrupt crypto firms
why you might consider arguing a “theft loss deduction”
what to know about the Ethereum Merge as it relates to taxes
things NFT creators should be aware of during tax time
how the U.S. tax system can or cannot be applied to DeFi
what tax forms you can expect to receive if you’re a Coinbase customer
how corporations holding crypto may soon see favorable changes to current accounting rules
why $5,000 is a key threshold for crypto donations
Thank you to our sponsors!
Crypto.com
FTSE
Halborn
NYU
Links
Previous coverage of crypto taxes on Unchained:
Your 2021 Crypto Taxes: How to Handle NFTs, DAOs, Airdrops and More
Everything You Need to Know About Your 2020 Crypto Taxes
Why You Shouldn't Trust Crypto Exchange Reports for Your Taxes
The IRS Is Cracking Down on Crypto Taxes: What You Need to Know
Guests:
Shehan:
Twitter
CoinTracker
Lawrence:
Twitter
Links:
Digital Assets | Internal Revenue Service
IRS CCA 202302012 (Crypto charitable donations)
IRS CCA 202302011 (Coins which have substantially lost in value. Ex: Luna)
MiCA – Overview of the New EU Crypto-Asset Regulatory Framework (Part 1) | HUB | K&L Gates
CNBC: President Joe Biden to sign the bipartisan infrastructure bill into law—here's how crypto investors will be impacted
S&P Global: What the US infrastructure bill means for cryptocurrency brokers and owners
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Your 2021 Crypto Taxes: How to Handle NFTs, DAOs, Airdrops and More - Ep.320
Two crypto tax experts, Shehan Chandrasekera, certified public accountant and head of strategy, Tax, at Cointracker, and John Cardone, senior director of Washington National Tax at RSM US LLP, explain everything crypto traders need to understand when filing taxes for 2021. Show topics:
-the five types of transactions that constitute a taxable crypto event -how NFT taxes should be reported -why the sale of collectibles (NFTs) is taxed differently than the sale of crypto property (tokens) -what type of forms you might receive from crypto exchanges and why this information is usually incomplete -why the crypto provision in the infrastructure bill most likely won’t affect retail traders -why John wants a digital asset-specific 1099 form -how staking income will be taxed this year (and why this might change soon) -how to report taxes for… airdrops like ENS and SOS income earned via a play-to-earn game like Axie Infinity the sale of virtual land wrapping Bitcoin onto Ethereum rewards received via a crypto credit card -how to save money on taxes going forward -how Shehan and John think crypto taxes will evolve -why the IRS listed a job posting for someone who could exploit crypto wallets
Thank you to our sponsors!
Crypto.com: https://crypto.onelink.me/J9Lg/unconfirmedcardearnfeb2021
Beefy Finance: https://beefy.finance
Bosonic: https://bosonic.digital/
Alchemy Pay: https://alchemypay.org
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Episode Links
John Cardone
https://www.linkedin.com/in/john-cardone-436412b1/
Shehan Chandrasekera
https://twitter.com/TheCryptoCPA
Helpful Links
Shehan’s tax guide: https://www.forbes.com/sites/shehanchandrasekera/2022/01/24/quick-guide-to-filing-your-2021-cryptocurrency--nft-taxes/?sh=d5c00f765f9d Staking rewards case: https://twitter.com/TheCryptoCPA/status/1489268205877035016 US Gov. job posting: https://sam.gov/opp/799a1650bd5349b6af4f646842999187/view
2022 Crypto Tax Guides
CoinTracker: https://www.cointracker.io/blog/crypto-tax-guide CryptoTrader.Tax: https://cryptotrader.tax/blog/the-traders-guide-to-cryptocurrency-taxes Koinly: https://koinly.io/cryptocurrency-taxes/ ZenLedger: https://www.zenledger.io/guides/crypto-tax-us
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Everything You Need to Know About Your 2020 Crypto Taxes - Ep.210
In this episode, Shehan Chandrasekara, head of strategy at CoinTracker, and Dan Hannum COO at Zen Ledger, take a deep dive into the world of crypto taxes. Over an hour and fifteen minutes they tackle a bevy of topics ranging from why the IRS is asking about your crypto history to explaining the proper way of reporting yield farming income. Shehan and Dan give up their hard-earned tax secrets and tips learned through building their respective cutting-edge crypto tax software. Here is a list of talking points covered in the discussion:
how the IRS is handling crypto this year (1:20)
where to start with reporting crypto and what constitutes a taxable event (5:59)
bitcoin corner cases:
mining, with a description of calculating cost basis (19:48)
wages (27:01)
peer-to-peer transactions outside of exchanges (28:23)
defi and taxes:
yield farming — and how it's like Russian nesting dolls (31:45)
how the IRS taxes earned interest (36:32)
airdrops (40:15)
crypto transactions that are not taxable: purchases, withdrawals, and stablecoins (46:28)
navigating tax documents (51:24-58-10)
NFT’s and social tokens (57:14)
tax loss harvesting (1:03:09)
how having coins on platforms like Robinhood and Paypal can have an effect on your taxes (1:05:05)
proposed tax changes (1:06:50)
crypto tax software and tips for the upcoming year (1:10:29)
Thank you to our sponsor!
Crypto.com: http://crypto.com
Episode links:
Guests
Shehan Chandrasekara: https://twitter.com/TheCryptoCPA
Dan Hannum: https://twitter.com/DHannum8
Software
CoinTracker: cointracker.io
ZenLedger: zenledger.io
Accounting
LIFO, HIFO, FIFO: https://www.forbes.com/sites/shehanchandrasekera/2020/09/17/what-crypto-taxpayers-need-to-know-about-fifo-lifo-hifo-specific-id/?sh=7077f8e936aa (written by Shehan)
1040 Question: https://fortune.com/2020/09/28/the-irs-is-adding-a-cryptocurrency-question-to-form-1040-for-2020/
1099 Misc: https://www.irs.gov/pub/irs-pdf/f1099msc.pdf
1099 B: https://www.irs.gov/forms-pubs/about-form-1099-b
Regulatory research:
2014 IRS Tax Guidance: https://www.irs.gov/pub/irs-drop/n-14-21.pdf
IRS Virtual Currency page: https://www.irs.gov/businesses/small-businesses-self-employed/virtual-currencies
IRS gains and losses: https://www.irs.gov/pub/irs-pdf/p550.pdf
Equipment write-offs: https://www.section179.org/section_179_deduction/
IRS sues Coinbase: https://www.theverge.com/2017/11/29/16717416/us-coinbase-irs-records
How holding crypto at PayPal or Robinhood or any platform that does not allow you to transfer to an address off-platform could affect your taxes: https://www.forbes.com/sites/shehanchandrasekera/2021/01/28/exiting-robinhood-could-create-a-tax-nightmare-for-crypto-users/?sh=106b74a84ad6
De minimis exemption: https://www.investopedia.com/ask/answers/09/series63-050509.asp#:~:text='The%20De%20Minimis'%20exemption%20means,period%20with%20a%20physical%20address.
FinCEN intends to apply FBAR to cryptocurrency held offshore: https://www.coindesk.com/fincen-foreign-crypto-exchange-disclosure-rule
Backstory:
Bitcoin Cash Fork: https://www.coindesk.com/bitcoin-cash-has-split-into-two-new-blockchains-again
Yield farming and social tokens:
https://decrypt.co/resources/what-is-yield-farming-beginners-guide
https://www.cointracker.io/blog/defi-yield-farming-crypto-tax-guide (written by Shehan)
Alex Masmej: https://www.coindesk.com/man-who-sells-himself-now-wants-buyers-to-control-his-life
Crypto tax guides
BlockFi: https://blockfi.com/crypto-tax-laws
Coinbase: https://www.coinbase.com/learn/tips-and-tutorials/crypto-and-bitcoin-taxes-US
Nerd Wallet: https://www.nerdwallet.com/article/investing/bitcoin-taxes
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