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

    $100,000 IRS Tax Bill: What Actually Happens Next?

    In this focused excerpt from a longer Q&A, Clinton Donnelly speaks with Michael Raanan of Landmark Tax Group about what happens after a substantial IRS tax bill arrives. Michael explains why the first step is to open the notice, check the deadline, and determine whether the amount is actually correct. They then discuss how the IRS evaluates a taxpayer’s ability to pay and when options such as payment plans, penalty abatements, offers in compromise, or hardship status may apply. They also discuss why promises to settle IRS debt for “pennies on the dollar” can be misleading, and Clinton shares a crypto example involving Bitcoin used as collateral that resulted in a significant tax bill. This episode is a focused excerpt from a longer conversation with Michael Raanan. Related article:https://www.cryptotaxaudit.com/blog/resolve-100000-irs-tax-bill Full original discussion:https://youtu.be/ELBgtO67oYw CryptoTaxAudit:https://www.cryptotaxaudit.com/ Landmark Tax Group:https://landmarktaxgroup.com/ Disclaimer: This episode is for educational purposes only and does not constitute tax or legal advice. Tax outcomes depend on each taxpayer’s individual facts and circumstances. Consult a qualified professional about your situation.

  2. Sep 22

    What happens when a cryptocurrency exchange faces sanctions?

    Clinton Donnelly of CryptoTaxAudit discusses the BitBank sanctions story, access to the U.S. dollar system, and the risks associated with holding crypto on an exchange. The discussion covers correspondent banking, potential effects on customer deposits and withdrawals, and the distinction between exchange solvency risk and sanctions exposure. Clinton also references FTX before turning to the wider role of the U.S. dollar in international payments. He also shares his views on BRICS, alternatives to the U.S. dollar, and Bitcoin’s possible role in international trade. These potential future developments are discussed as analysis rather than established outcomes. Book a private crypto tax consultation:https://www.cryptotaxaudit.com/crypto-tax-consultation U.S. Treasury source:https://home.treasury.gov/news/press-releases/sb0632 Visit CryptoTaxAudit:https://www.cryptotaxaudit.com/ Disclaimer: This episode is for educational and informational purposes only and does not constitute legal, tax, or financial advice.

  3. Sep 15

    Is Form 1099-DA Helping Crypto Taxpayers?

    Form 1099-DA provides transaction information to the IRS. How useful is it for taxpayers and their preparers? Clinton Donnelly of CryptoTaxAudit discusses customer experiences with the forms for the 2025 tax year, including document length, first-year cost-basis reporting, different exchange formats and Form 8949 boxes. He also considers crypto income reporting estimates, questions around study methodology and a hypothetical scenario involving filing errors and audits. He closes with his views on clearer data summaries for taxpayers and preparers. Crypto tax preparation support:https://www.cryptotaxaudit.com/ In this episode:00:00 Taxpayer and preparer experiences00:23 IRS reporting and taxpayer clarity00:43 Document length, cost basis and form formats01:43 Reporting estimates and IRS implementation03:24 Data summaries and closing views

  4. Sep 8

    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.

  5. 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/

  6. 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.

  7. 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.

  8. 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.

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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
    220
  • Rating
    Clean
  • Copyright
    © Clinton Donnelly
  • Show Website
    The Clinton Donnelly Show

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