Rob Massey, a crypto tax advisor at Deloitte since 2012, highlights that the current self-assessment tax system remains in place despite evolving rules for Bitcoin. He emphasizes that taxpayers must report all transactions, regardless of size, as no de minimis exemption has been enacted by the IRS.
Massey notes that 1099 forms from brokers are insufficient for a complete tax picture. He warns that the IRS monitors on-chain activity, meaning even small payments, such as paying a service provider, are considered taxable events. This requires rigorous tracking of cost basis, especially after multiple wallet transfers.
Business leaders are increasingly inquiring about the tax implications of ETFs, leverage, and Bitcoin lending. Massey advises that for historical unreported transactions, such as the 2015 pizza purchase, taxpayers should work with legal and accounting professionals to prepare a full narrative and rectify their filings.
Regarding international operations, Massey points out the lack of tax treaties for Bitcoin, which complicates cross-border transactions. He suggests that Bitcoiners should advocate for clearer regulatory guidance from the Treasury, specifically concerning lending, asset characterization, and cost basis calculations.
