Crypto Investors Low on Funds Might Have To Cash Out To Pay 2021 Tax Bill

Accountants focused on digital assets are bracing for clients with hefty crypto tax bills, payments made more difficult by the recent crypto sell-off

article-image

Source: Shutterstock

share

key takeaways

  • Investors may not have earmarked enough cash to meet crypto tax bills
  • For many retail traders, it’s difficult to first discern how much they owe

As tax season ramps up, cryptocurrency accountant eyes are on looming tax bills that investors may not have earmarked enough cash for.

“If people are liquidating coins to come up with the cash for taxes for 2021, that also creates a taxable event for 2022,” said Shehan Chandrasekera, head of tax at Coin Tracker. “It’s going to get messy.” 

As retail investors report 2021 cryptocurrency trading activity, they might be surprised by their tax bill — particularly newcomers, Ledgible CEO Kell Canty said.

“Come April 15, a lot of investors are going to see that they had a taxable event where they either sold crypto for crypto or sold crypto for USD, and they didn’t allocate any portion of that to satisfying the capital gains,” Canty said.

It can be complicated to track and report gains, Canty said, especially in cases where investors shifted profits from one token to another. The recent selloff has compounded those concerns, leading to the possibility that underwater, cash-starved investors won’t be able to satisfy their tax obligations.

“It’s unfortunate,” Canty said. “That’s why people need to be more thoughtful about planning that and using tools to track all of their crypto across all different exchanges and wallets and custodians and DeFi protocols to get a sense for the realized and unrealized gains that they have.”

Aside from figuring out how to pay taxes, retail investors may have a hard time pinning down how much they owe, according to Chandrasekera.

“Reporting is a huge problem right now, because exchanges are doing different things,” Chandraseker said. “If you take a look at centralized exchanges, they issue, I would say, four different types of tax forms, depending on how they interpret the existing tax codes, given the gray area, so people are very confused.”

Investors using decentralized exchanges or more than one exchange may have a particularly difficult time.

“Exchanges only have visibility into what’s happening inside that exchange,” Chandrasekera said. “But to figure out your taxes correctly, you need to connect all your wallets and exchanges and figure out that actual capital gain or loss.”

There is precedent for retail investors liquidating holdings for the tax man, said Jordan Bass, owner of Taxing Cryptocurrency.

“In 2018, there was a big top in crypto markets, then the price retraced in February, we had a little bit of a pump into March and then in April, when we were leading into tax planning, we saw a significant retracement,” Bass said. “I think maybe there was some correlation.”


Get the news in your inbox. Explore Blockworks newsletters:

  • Blockworks Daily: The newsletter that helps thousands of investors understand crypto and the markets, by Byron Gilliam.
  • Empire: Start your day with top crypto insights from David Canellis and Katherine Ross.
  • Forward Guidance: Explore the growing intersection between crypto, macroeconomics, policy and finance with Ben Strack, Casey Wagner and Felix Jauvin.
  • 0xResearch: Get alpha directly in your inbox — market highlights, charts, degen trade ideas, governance updates, and more.
  • Lightspeed: All things Solana, in your inbox, every day from Jack Kubinec and Jeff Albus.
  • The Drop: The newsletter for crypto collectors and traders, covering games, tokens, apps, memes and more.
Tags

Upcoming Events

Javits Center North | 445 11th Ave

Tues - Thurs, March 18 - 20, 2025

Blockworks’ Digital Asset Summit (DAS) will feature conversations between the builders, allocators, and legislators who will shape the trajectory of the digital asset ecosystem in the US and abroad.

Industry City | Brooklyn, NY

TUES - THURS, JUNE 24 - 26, 2025

Permissionless IV serves as the definitive gathering for crypto’s technical founders, developers, and builders to come together and create the future.If you’re ready to shape the future of crypto, Permissionless IV is where it happens.

Old Billingsgate

Mon - Wed, October 13 - 15, 2025

Blockworks’ Digital Asset Summit (DAS) will feature conversations between the builders, allocators, and legislators who will shape the trajectory of the digital asset ecosystem in the US and abroad.

recent research

monad ecosystem report graphic.png

Research

Monad's testnet launch has shown promise with 57 geographically distributed validators and over 20 live applications on day one. However, the ecosystem's true test will come with mainnet as it transitions from testing to real economic activity alongside the launch of the native gas token.

article-image

Moonrock Capital’s Simon Dedic thinks that we have to treat infra and consumer apps like the internet: build them side by side

article-image

Seismic, an encrypted blockchain, plans to release its developer testnet in a month

article-image

On the news that SOL would be part of Trump’s upcoming strategic reserve, SOL quickly surged before seeing an equally swift retracement

article-image

Senate Majority Leader John Thune said the IRS rule “puts at risk the privacy and security” of millions of Americans trading digital assets

article-image

Commerce Secretary Howard Lutnick reportedly said a bitcoin strategic reserve could be “executed on Friday”

article-image

If there’s an amount of S&P 500 pain Trump is willing to endure, we don’t know it