The Clinton Donnelly Show

Hosted by Clinton Donnelly

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214

Latest episode

Aug 2026

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About the show

Welcome to The Clinton Donnelly Show, where Clinton shares real world strategies, time tested tactics, and expert discussions with influencers about cryptos, taxes, audits, and the regulatory framework that’s evolving around cryptos.

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60 recent

August 18, 20263 min

Missing Crypto Records? How to Prove Your Cost Basis to the IRS

Missing crypto transaction records can make it difficult to calculate and support your cost basis accurately. When exchange data is incomplete or no longer available, crypto tax software may calculate gains using incomplete information. In this episode, Clinton Donnelly explains ways missing crypto records may be reconstructed using supporting evidence such as trade confirmation emails. He also shares a client case involving Bitcoin transferred from a closed exchange to Coinbase. Although the original exchange transaction history was unavailable, email confirmations were used alongside Coinbase records to support that the incoming Bitcoin represented a transfer of the taxpayer’s own assets rather than taxable income. Clinton also discusses reasonable good-faith estimates, the Cohan rule, and the use of reasonable estimates when complete documentation is unavailable. Need help with missing crypto records, gain calculations, or an IRS crypto issue? CryptoTaxAudit specializes in complex crypto tax reporting, gain calculations, and IRS audit defense. https://www.cryptotaxaudit.com/ Disclaimer This episode is for educational and informational purposes only and does not constitute tax, legal, or financial advice. Every taxpayer’s circumstances are different. Consult a qualified tax professional regarding your specific situation.

August 11, 20269 min

California’s Billionaire Tax, Wealth Flight, and the Residency Trap

California’s proposed billionaire wealth tax could impose a one-time tax of up to 5% on covered wealth above $1 billion. In this episode, Clinton Donnelly breaks down what that could mean in practice, including the potential need to liquidate investments, the additional tax consequences that can follow, and why some wealthy residents may decide to leave California altogether. Clinton also looks at the longer-term impact of wealth leaving the state, how California determines tax residency, and why simply moving or changing your mailing address may not be enough. The episode covers: California’s proposed 5% billionaire wealth tax The liquidity problem created by a large wealth-tax bill Capital gains triggered by selling assets Why wealthy residents may leave California The potential effect on future state tax revenue California residency audits The Bragg residency factors What it actually takes to establish that you have left California A real client example involving California residency issues while living abroad Disclaimer: This episode is for general educational and informational purposes only and does not constitute legal, tax, investment, or financial advice.

August 4, 20262 min

The 1099-DA Mismatch That Could Trigger an IRS Audit

Crypto exchanges may report a transaction as short-term or long-term based on when the asset was transferred onto the exchange. That can create a reporting mismatch when crypto was bought elsewhere, moved through private wallets, and held for more than a year before being sold. In this episode, Clinton Donnelly explains: Why exchanges may not know your true cost basis How wallet transfers can affect 1099-DA reporting Why a long-term holding may appear as short-term How the IRS compares exchange-reported proceeds with your tax return What can trigger IRS correspondence or an audit Learn more: https://www.cryptotaxaudit.com/ Disclaimer: This episode is for educational purposes only and does not constitute tax, legal, investment, or financial advice. Consult a qualified tax professional about your individual situation.

August 4, 20261 min

Used BitMEX, BitMart or AscendEX? Download Your Records Now

If you have traded on BitMEX, BitMart, AscendEX, or another cryptocurrency exchange that is closing operations, download your transaction history before you lose access. Without those records, it may become much harder to prove your crypto cost basis for tax purposes. Missing transaction data can also cause crypto tax software to use older or lower cost basis figures, potentially overstating your gains and showing more tax due than is correct. In this episode, Clinton Donnelly, EA, explains why taxpayers are responsible for maintaining their records under Internal Revenue Code Section 6001 and why affected traders should act as soon as possible. Download and securely store any available: Trade history Transaction history Deposit and withdrawal records CSV exports Account statements This content is for general educational purposes and is not individualized tax advice. Learn more: https://www.cryptotaxaudit.com/

July 28, 20264 min

4 Crypto Tax Fixes Proposed to the IRS: Will They Actually Help?

The National Taxpayer Advocate has proposed four changes intended to help cryptocurrency investors correct reporting mistakes, understand the tax rules and reconstruct missing transaction records. But do these recommendations address the real problems crypto taxpayers face? Clinton Donnelly, EA, examines each proposal and explains why crypto tax compliance is more complicated than issuing additional guidance or recommending better software. This episode covers: Why the IRS has resisted creating a crypto tax corrective programme What IRS Letters 6173, 6174 and 6174-A already explain Why eligibility rules may not be the main compliance problem What crypto gain calculation software can and cannot reconstruct Why missing or misaligned transaction records remain difficult to automate How complex trading activity increases gain-calculation costs Why simplifying your exchanges, wallets and trading activity can reduce future tax problems The proposals identify a genuine need for better taxpayer support. However, they may underestimate the difficulty of reconstructing activity across multiple exchanges, wallets, blockchains and trading platforms. For active crypto investors, accurate gain calculation should be treated as part of the annual cost of trading, rather than an unexpected expense discovered during tax season. Learn more: https://www.cryptotaxaudit.com/ Disclaimer This episode is for educational and informational purposes only and does not constitute tax, legal, accounting or financial advice. Tax laws and IRS procedures may change, and their application depends on your specific facts and circumstances. Consult a qualified tax professional regarding your individual situation.

July 21, 202610 min

The “0% Crypto Tax” CRAT Strategy the IRS Just Targeted

The IRS has officially classified certain abusive Charitable Remainder Annuity Trust arrangements as listed transactions. CRAT strategies have been promoted to crypto investors and other owners of highly appreciated assets as a way to claim a charitable deduction, receive annuity payments, and potentially pay 0% tax. But these arrangements can involve strict disclosure requirements, substantial penalties, high setup costs, and the risk of the IRS challenging the entire structure. In this episode, Clinton Donnelly, EA, explains: • How a Charitable Remainder Annuity Trust works • How CRATs are used with appreciated crypto and other assets • Why certain abusive CRAT arrangements are now listed transactions • How the charitable deduction and annuity payments are calculated • When Form 8886 disclosure may be required • The penalties associated with failing to disclose • Why the promised tax savings may not justify the cost and risk If you already participate in a CRAT arrangement, have it independently reviewed to determine whether it falls within the new IRS listed-transaction rules. Learn more: https://cryptotaxaudit.com/ Official IRS announcement: https://www.irs.gov/newsroom/treasury-irs-issue-final-regulations-naming-certain-charitable-remainder-annuity-trust-transactions-as-listed-transactions Disclaimer: This episode is for educational purposes only and does not constitute tax, legal, or financial advice. Every taxpayer’s circumstances are different. Consult a qualified professional before making decisions involving a charitable trust or listed transaction.

July 14, 20264 min

Is Crypto Bridging Taxable? Wrapped Assets vs. Mint & Burn

The answer depends on what actually happens to the asset during the bridge. In this episode, crypto tax expert Clinton Donnelly explains why different bridging methods can produce different tax outcomes. A wrapped asset may not create an immediate taxable event if the original asset remains locked and ownership does not change. A mint-and-burn or swap-based bridge may be treated differently if the original asset is sold, exchanged, or otherwise disposed of. 🔹 How wrapped assets work 🔹 Why ownership transfer matters 🔹 When bridging may create a taxable sale or exchange 🔹 How cost basis may carry over or reset 🔹 What records the IRS is likely to examine 🔹 Why DeFi bridge transactions can be difficult to document 🔹 How centralized reporting may differ from self-custody and DeFi The key question is not simply whether you used a bridge. ⚖️ The key question is whether the original asset remained yours or whether it was sold, exchanged, or disposed of. Understanding the mechanics of the bridge is essential before deciding whether the transaction created a capital gain or loss. 🔗 Read the complete crypto bridging tax guide: https://www.cryptotaxaudit.com/blog/crypto-asset-bridging-taxation-explained 📊 Need help reviewing your crypto transactions or calculating your gains? https://www.cryptotaxaudit.com/ Disclaimer: This episode is provided for general educational and informational purposes only. It does not constitute tax, legal, accounting, investment, or financial advice. Digital asset tax treatment depends on the specific facts, transaction mechanics, ownership structure, jurisdiction, and applicable law. Consult a qualified tax professional regarding your individual circumstances.

July 10, 20264 min

Illinois’ 0.2% Crypto Tax: Small Rate, Dangerous Precedent

Illinois passed SB 3019, introducing a 0.2% tax on digital asset transactions by Illinois residents. At first glance, 0.2% may seem insignificant. Clinton Donnelly argues that the real issue is not the size of the tax. It is the precedent it creates. In this episode, Clinton explains: What the Illinois Digital Asset Tax Act does Why it is being described as a “privilege tax” Which exchanges and brokers may be affected Why small taxes can grow over time The Boston Tea Party comparison Why Illinois could push crypto investors and businesses elsewhere Why Clinton sees the policy as anti-growth and pro-corruption The central question is simple: Once a tax exists, how confident are you that it stays at 0.2%? For practical crypto tax guidance and audit support: https://www.cryptotaxaudit.com/ Disclaimer This episode is for educational purposes only and does not constitute tax, legal, investment, or financial advice. Digital asset tax rules vary by jurisdiction and individual circumstances. Consult a qualified professional before making decisions based on your personal situation.

July 7, 20266 min

Crypto Taxes Are Changing: IRS Wash Sale Rules & 1099-DA Breakdown

The IRS is moving toward stricter crypto tax reporting through expanded 1099-DA requirements and potential application of wash sale rules to digital assets. In this episode, we break down what is actually changing, how it affects crypto investors, and why this represents a major shift in how digital assets are tracked and taxed. We cover: • How wash sale rules may apply to crypto transactions • What 1099-DA reporting means for exchanges and investors • How IRS visibility into wallet activity is increasing • Why compliance risk is rising even for retail traders • What to expect for 2025–2026 tax filing cycles • The broader direction of crypto tax enforcement in the United States This episode is an educational breakdown based on current regulatory developments and is not financial or legal advice.

July 2, 20264 min

50% Stake in AI Companies? Why This AI Wealth Fund May Never Become Law

A new AI wealth fund proposal would give the public a 50% stake in major AI companies. In this episode, Clinton Donnelly breaks down the American AI Sovereign Wealth Fund Act and explains why this proposal may be more political talking point than future tax law. Clinton looks at the risks of forced public ownership in AI companies, including government control, shareholder influence, corruption risk, company relocation, and higher costs being passed down to ordinary consumers. This is not current tax law. It is a proposed bill, and most proposed bills never become law. Topics covered: Bernie Sanders’ AI wealth fund proposal The proposed 50% public stake in major AI companies Why costs could be passed down to consumers The risk of government becoming a major shareholder The BlackRock and ESG comparison Why AI companies may push back or leave Why election-season proposals often become political talking points Disclaimer: This episode is for educational and informational purposes only. It is not legal, tax, investment, or financial advice. Proposed legislation is not the same as current law. Always consult a qualified tax or legal professional about your specific situation. Crypto Tax Audit: https://www.cryptotaxaudit.com/