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February 2, 2021 75 min

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)

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    Episode links: 



  • Shehan Chandrasekara:
  • Dan Hannum: 


  • CoinTracker:
  • ZenLedger:


  • LIFO, HIFO, FIFO: (written by Shehan)
  • 1040 Question:
  • 1099 Misc:
  • 1099 B:

    Regulatory research:

  • 2014 IRS Tax Guidance:
  • IRS Virtual Currency page:
  • IRS gains and losses:
  • Equipment write-offs:
  • IRS sues Coinbase:
  • 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:
  • De minimis exemption:'The%20De%20Minimis'%20exemption%20means,period%20with%20a%20physical%20address.
  • FinCEN intends to apply FBAR to cryptocurrency held offshore:


  • Bitcoin Cash Fork:

    Yield farming and social tokens:

  • (written by Shehan)
  • Alex Masmej:

    Crypto tax guides

  • BlockFi:
  • Coinbase:
  • Nerd Wallet:

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