The Clinton Donnelly Show

Clinton Donnelly
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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.

  1. 2d ago

    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 programmeWhat IRS Letters 6173, 6174 and 6174-A already explainWhy eligibility rules may not be the main compliance problemWhat crypto gain calculation software can and cannot reconstructWhy missing or misaligned transaction records remain difficult to automateHow complex trading activity increases gain-calculation costsWhy simplifying your exchanges, wallets and trading activity can reduce future tax problemsThe 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.

  2. Jul 21

    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.

  3. Jul 14

    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.

  4. Jul 10

    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 doesWhy it is being described as a “privilege tax”Which exchanges and brokers may be affectedWhy small taxes can grow over timeThe Boston Tea Party comparisonWhy Illinois could push crypto investors and businesses elsewhereWhy Clinton sees the policy as anti-growth and pro-corruptionThe 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.

  5. Jul 7

    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.

  6. Jul 2

    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 proposalThe proposed 50% public stake in major AI companiesWhy costs could be passed down to consumersThe risk of government becoming a major shareholderThe BlackRock and ESG comparisonWhy AI companies may push back or leaveWhy election-season proposals often become political talking pointsDisclaimer: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/

  7. Jun 23

    The $30,000 ADA Cardano Staking Tax Mistake

    ADA Cardano staking rewards may be taxable when received if the taxpayer has dominion and control, but Paschall v. Commissioner also raises important questions about constructive receipt and Cardano validator mechanics. In this episode, Clinton Donnelly, founder of CryptoTaxAudit and known as the Crypto Tax Fixer, breaks down Paschall v. Commissioner, T.C. Memo. 2026-46. Paschall was staking Cardano and argued that his staking rewards should be taxed when sold for dollars, not when received. The auditor disagreed, and the case went to U.S. Tax Court. Clinton explains why the taxpayer lost, why this was a non-binding memorandum decision, and why the case still matters for crypto investors who earn staking rewards. Topics covered: • What happened in Paschall v. Commissioner • Why the taxpayer argued staking rewards should be taxed when sold • Why the auditor disagreed • Why the taxpayer represented himself against five IRS lawyers • Why this decision is not binding on every future Tax Court case • How IRS Revenue Ruling 2023-14 relates to staking rewards • What “dominion and control” means for staking income • Why Clinton believes the taxpayer may have made a strategic error • How constructive receipt could matter in future staking tax arguments • Why Cardano’s epoch system and validator mechanics may create important tax questions • The difference between self-created assets and validator-received rewards The key issue is timing. Are ADA staking rewards taxable when they are generated, when they are credited, when the taxpayer has dominion and control, or when they are actually received? This case does not answer every future staking tax question, but it is an important development for Cardano staking, crypto tax reporting, and IRS treatment of proof-of-stake rewards. Official IRS Revenue Ruling 2023-14: https://www.irs.gov/pub/irs-drop/rr-23-14.pdf Book a crypto tax consultation: https://www.cryptotaxaudit.com/crypto-tax-consultation Shield yourself from IRS crypto audits: https://www.cryptotaxaudit.com/taxshield Get your crypto gains calculated: https://www.cryptotaxaudit.com/crypto Learn more about CryptoTaxAudit: https://www.cryptotaxaudit.com/ Disclaimer This episode is for educational and informational purposes only and does not constitute legal, tax, or financial advice. Tax laws and IRS procedures can change, and every situation is unique. You should consult with a qualified tax professional before taking any action based on this content. Listening to this episode does not create a client relationship with Clinton Donnelly or CryptoTaxAudit. For personalized guidance, visit: https://www.cryptotaxaudit.com/crypto-tax-consultation

  8. Jun 16

    1099-DA Is Broken: CP2000 Notices Are Coming This Fall

    The IRS rolled out Form 1099-DA, and Clinton Donnelly says the first version is already creating serious problems for crypto investors and tax preparers. In this episode, Clinton explains why the 1099-DA collects the data the IRS wants, but fails to help taxpayers file correctly. The information may be there, but it is hidden, buried, and difficult to enter properly on a tax return. He also explains why confusion around the 1099-DA could lead to a high error rate, mismatched IRS records, and a wave of CP2000 notices for crypto investors this fall. In this episode: Why the 1099-DA is harder to use than a normal 1099 Why some tax preparers may refuse crypto returns Why Clinton expects a roughly 75 percent error rate How a missed or mismatched 1099 can turn into a CP2000 notice Why CP2000 notices may be based on wrong IRS assumptions Why taxpayers should respond and push back on numbers they do not believe Resources: TaxShield audit defense:https://www.cryptotaxaudit.com/taxshield?afmc=spotify Crypto gain calculation:https://www.cryptotaxaudit.com/crypto-gain-calculation?afmc=spotify Book a consultation:https://www.cryptotaxaudit.com/crypto-tax-consultation?afmc=spotify About Clinton Donnelly:Clinton Donnelly is an Enrolled Agent and founder of CryptoTaxAudit, known as the Crypto Tax Fixer. He helps crypto investors understand IRS notices, crypto tax reporting problems, and audit defense. Disclaimer:This episode is for educational and informational purposes only and does not constitute legal, tax, or financial advice. Tax laws and IRS procedures can change, and every situation is unique. Consult a qualified tax professional before taking action.

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About

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.

Information

  • Creator
    Clinton Donnelly
  • Years Active
    2023 - 2026
  • Episodes
    211
  • Rating
    Clean
  • Copyright
    © Clinton Donnelly
  • Show Website
    The Clinton Donnelly Show