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. 4d ago

    Fewer IRS Staff. Does That Mean Fewer Crypto Audits?

    Could fewer IRS employees mean fewer crypto audits? Clinton Donnelly, founder and CEO of CryptoTaxAudit, discusses IRS staffing changes, automation, and what they could mean for cryptocurrency investors. This episode covers workforce reductions, planned customer service hiring, AI-assisted systems, and audit selection. Clinton also discusses CP2000 and CP2501 notices and shares CryptoTaxAudit’s approach to tax return preparation and its reported client audit outcomes. Client results and comparisons discussed are figures reported by CryptoTaxAudit. Have questions about your crypto taxes or an IRS letter? Visit CryptoTaxAuditGet help with an IRS letterContact the team Follow the podcast for more discussions about crypto taxes, IRS notices, and audit preparation.

  2. Sep 1

    14,000 IRS Employees Retained Access to Sensitive Systems

    TIGTA found that more than 14,000 IRS employees on administrative leave retained access to one or more sensitive systems. Clinton Donnelly explains what this potential security risk could mean for crypto holders, including what 1099-DA and exchange data may reveal, why private-wallet balances are not automatically visible to the IRS, and how a virtual mailbox may help protect your home address. The report did not establish that a material breach occurred or that the retained access was misused. Read the full article:https://www.cryptotaxaudit.com/blog/can-tax-authorities-be-trusted-with-crypto-data Learn more:https://www.cryptotaxaudit.com/

  3. Aug 18

    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/ DisclaimerThis 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.

  4. Aug 11

    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 taxThe liquidity problem created by a large wealth-tax billCapital gains triggered by selling assetsWhy wealthy residents may leave CaliforniaThe potential effect on future state tax revenueCalifornia residency auditsThe Bragg residency factorsWhat it actually takes to establish that you have left CaliforniaA real client example involving California residency issues while living abroadDisclaimer: This episode is for general educational and informational purposes only and does not constitute legal, tax, investment, or financial advice.

  5. Aug 4

    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 basisHow wallet transfers can affect 1099-DA reportingWhy a long-term holding may appear as short-termHow the IRS compares exchange-reported proceeds with your tax returnWhat can trigger IRS correspondence or an auditLearn 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.

  6. Aug 4

    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 historyTransaction historyDeposit and withdrawal recordsCSV exportsAccount statementsThis content is for general educational purposes and is not individualized tax advice. Learn more:https://www.cryptotaxaudit.com/

  7. Jul 28

    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.

  8. 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.

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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
    217
  • Rating
    Clean
  • Copyright
    © Clinton Donnelly
  • Show Website
    The Clinton Donnelly Show

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