The Clinton Donnelly Show

Clinton raises the possibility that recent regulatory actions against the crypto industry could be part of a larger plan to regulate or even kill off crypto investing in America. He discusses the IRS treating cryptocurrencies as securities under tax law, which would be consistent with the SEC's current enforcement of securities law on cryptocurrencies. Clinton also presents several potential i...

Clinton discusses the two private letter memorandums issued by the IRS’ chief counsel office in January 2023 regarding the treatment of cryptocurrencies for taxation purposes. He explores the definition of the term "security," which is a term of art and has a specific meaning in the tax code, and he notes that the definition of "security" is not applicable to cryptocurrencies....

Clinton explores the topic of whether the current tax break limit for capital losses should be changed. He proposes that Congress increase the capital loss limitation in code section 1211 to $15,000 starting this year (versus the current $3,000 limit), retroactively and inflation adjusted thereafter. He explains how capital gains and losses are taxed, and the annual limit on the amount of capital...

Clinton discusses how cryptocurrency theft losses (thefts, rug pulls, and scams) can be claimed to reduce tax bills. By claiming theft losses, investors can itemize deductions and save money on their taxes, even if they lost money due to closures of exchanges. However, claiming theft losses can be difficult as investors must prove the asset was taken with criminal intent, which can be challenging...

Clinton discusses the issue of tax non-compliance among US crypto investors. Despite the IRS Commissioner's announcement that the IRS could bring in another $1 trillion if given additional funding, there are many crypto investors who haven't paid taxes on their crypto income, leading to a $46 billion increase in funding for digital asset enforcement. This problem is most prevalent among ta...

Clinton compares the accuracy of various crypto tax calculation services, including Accointing, Bitcoin.tax, CoinTracking, CoinTracker, CoinLedger, CoinPanda, CryptoTaxCalculator, Node40, Ledgible, TaxBit, TokenTax, and ZenLedger. His team benchmarked these services using centralized and decentralized exchange data and discovered significant differences in their calculations. He also presents his...

This live-streamed AMA video aired on March 14, 2023. Hosted by Meta Mona, Clinton Donnelly answers the top questions this tax season, including how to account for crypto theft losses (such as FTX, Celsius, and BlockFi), how to handle NFT and Play2Earn tax calculations, and US expatriation options to reduce or eliminate your crypto taxes. #TaxesAreSexy 💎 Guest: Meta Mona For daily insights into t...

Clinton discusses the IRS enforcement methods used for crypto investors, who are seen as wealthier taxpayers. The IRS received $46 billion in funding from Congress to enforce tax compliance laws for digital asset owners, with a potential to harvest an additional $1 trillion in revenue. The 22 million non-compliant taxpayers are divided into three categories: puny investors, hiders, and deniers. Ar...