Crypto advisors are honing in on digital asset tax preparation, as highlighted by Bryan Courchesne of DAIM and Saim Akif of Akif CPA. With the current date of June 20, 2025, we find ourselves roughly six months away from the next tax season. Advisors are urging crypto investors to be tax-ready, underscoring the multifaceted challenges posed by the asset class. The conversation isn’t just about taxes; it’s about staying ahead in a rapidly evolving financial landscape.
Navigating the Tax Labyrinth
Cryptocurrency tax planning is not a task for the faint-hearted. Courchesne emphasizes the unique tax scenarios that digital assets present. Unlike traditional equities and bonds, cryptos are not shackled by wash-sale rules, allowing for more strategic tax-loss harvesting. This means investors can convert holdings like Bitcoin (BTC) directly into Ethereum (ETH) or Solana (SOL) without cashing out, a flexibility not afforded by conventional assets. This flexibility is also opening new avenues, as seen in Bitcoin-backed loans opening the real estate market to crypto-rich, tax-free.
Yet, the real challenge lies in the web of platforms investors use. Picture this: a trader active on multiple centralized exchanges (CEXs) like Coinbase or Binance, and decentralized platforms (DEXs) such as Uniswap. Every transaction—be it a trade, airdrop, or staking reward—can trigger a taxable event. And here’s the kicker: tracking these isn’t just a year-end task; it’s a year-round marathon.
Centralized vs. Decentralized: A Tax Reporting Dilemma
The centralized exchange experience is fraught with its own set of hurdles. Unlike transferring Amazon stock between brokerage accounts, moving crypto from Kraken to Coinbase doesn’t seamlessly carry over your cost basis. This often leaves investors manually tracking each transaction—a daunting task that can culminate in a tax-time headache.
Decentralized exchanges, however, take complexity to a new level. Platforms like Uniswap don’t issue cost-basis reports, leaving traders to meticulously log every swap. Miss one transaction, and you could face inaccurate tax reporting—potentially triggering IRS scrutiny or missing valuable deductions. As Akif highlights, new IRS regulations starting in 2025 will require wallet-level cost basis reporting, further complicating matters for those who self-custody their assets.
Preparing for Tax Season: Strategies and Tools
So, how can crypto investors ready themselves for tax season? Courchesne suggests leveraging crypto tax software from the outset. But don’t trust it blindly—double-check the reported activity to ensure its accuracy. For those feeling overwhelmed, hiring a crypto tax specialist or advisor can provide peace of mind.
Additionally, downloading all transaction logs for your CPA to analyze is crucial. As Akif notes, with institutional crypto inflows soaring to $35 billion, the demand for specialized tax advisory services has never been higher. The introduction of IRS Form 1099-DA in 2026 will further shift the landscape, making compliance non-negotiable. This shift is part of a broader trend of institutional adoption, as evidenced by JPMorgan’s filing for a trademark for a digital asset platform.
The Road Ahead
As crypto adoption continues to rise, tax reporting will undoubtedly evolve. However, investors must remain vigilant in tracking their trade activity to avoid costly mistakes. The stakes are high, and as the tax landscape shifts, so must the strategies of those navigating it.
The conversation surrounding crypto tax preparation is far from over. Will investors adapt to the new regulations and embrace the tools at their disposal, or will they find themselves entangled in the complexities of this nascent financial frontier? As the next tax season looms, these questions remain at the forefront of the crypto advisory world.
Source
This article is based on: Crypto for Advisors: Digital Asset Tax Preparation
Further Reading
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Steve Gregory is a lawyer in the United States who specializes in licensing for cryptocurrency companies and products. Steve began his career as an attorney in 2015 but made the switch to working in cryptocurrency full time shortly after joining the original team at Gemini Trust Company, an early cryptocurrency exchange based in New York City. Steve then joined CEX.io and was able to launch their regulated US-based cryptocurrency. Steve then went on to become the CEO at currency.com when he ran for four years and was able to lead currency.com to being fully acquired in 2025.
