The Clinton Donnelly Show

Hosted by Clinton Donnelly

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Episodes

223

Latest episode

Oct 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

October 27, 20264 min

How does the IRS identify crypto investors?

How do exchange records connect crypto investors with the IRS? Clinton Donnelly of CryptoTaxAudit discusses IRS Letters 6173, 6174 and 6174-A, exchange information, and crypto tax reporting. He also shares his analysis of AI, Palantir, IRS case selection, notices concerning 2024 tax returns, and staffing and collections. The episode closes with bringing prior-year crypto reporting up to date. Received an IRS letter? Request a letter review to understand what the IRS is asking and your next steps: https://www.cryptotaxaudit.com/audit-letter-review Scan every page and upload them together as one clear PDF. Uploading your letter does not count as responding to the IRS or extend its deadline. Sources and background U.S. Treasury: IT modernization and Palantir partnership, September 22, 2025: https://home.treasury.gov/news/press-releases/sb0260 IRS: Letters to cryptocurrency owners, July 26, 2019. Historical background: https://www.irs.gov/newsroom/irs-has-begun-sending-letters-to-virtual-currency-owners-advising-them-to-pay-back-taxes-file-amended-returns-part-of-agencys-larger-efforts Learn more about CryptoTaxAudit: https://www.cryptotaxaudit.com/ Disclaimer This content is for educational and informational purposes only and does not constitute tax, legal, or financial advice. Individual circumstances vary. Consult a qualified professional about your situation. Views expressed are the speaker’s analysis and should not be treated as a prediction or guarantee.

October 20, 20262 min

Crypto wallets and mixers: What just changed?

FinCEN has withdrawn two proposals involving unhosted wallets and crypto mixing. Clinton Donnelly of CryptoTaxAudit discusses the proposed reporting requirements for banks and financial institutions and why he sees the withdrawals as a shift in regulatory direction. The discussion covers KYC information, suspicious activity reports (SARs), Tornado Cash, and Clinton’s comparison with the SEC and CFTC. He also shares his interpretation of the Trump administration’s approach to reducing regulation. FinCEN’s official announcement: https://www.fincen.gov/news/news-releases/fincen-announces-withdrawals-proposed-digital-asset-related-rules Learn how CryptoTaxAudit can help: https://www.cryptotaxaudit.com/ Crypto tax preparation and services: https://www.cryptotaxaudit.com/tax-crypto-pricing This content is for educational and informational purposes only and does not constitute tax, legal, or financial advice. Tax rules depend on individual facts and circumstances. Consult a qualified professional about your situation.

October 13, 20262 min

Can You Replace a Tax Return You Already Filed? | Superseding Returns

Can you replace a tax return you've already filed with the IRS instead of submitting an amended return? In this episode of The Clinton Donnelly Show, Clinton Donnelly explains how superseding tax returns work and why filing an extension may provide taxpayers with more flexibility when their tax calculations are not yet finalised. Clinton discusses a recommendation from National Taxpayer Advocate Erin Collins, shared at a meeting he attended in Washington, DC. The discussion covers: What a superseding tax return is. How superseding returns differ from amended returns. How an IRS filing extension can affect the deadline for submitting a replacement return. Why this approach may be useful for crypto investors waiting on more accurate capital gains calculations. How CryptoTaxAudit uses superseding returns when working with clients. For taxpayers dealing with complicated cryptocurrency transactions, having additional time to finalise gain calculations may make this filing strategy worth considering. About CryptoTaxAudit CryptoTaxAudit specialises in cryptocurrency tax calculations, tax reporting and IRS audit defense. Website: https://www.cryptotaxaudit.com/ Speak with a crypto tax expert: https://www.cryptotaxaudit.com/contact Disclaimer: This episode is for educational and informational purposes only. It does not constitute legal or tax advice. An extension to file does not extend the deadline to pay taxes. Individual circumstances and IRS requirements may vary.

October 6, 20264 min

Crypto Tax Software Said $140K. The Real Gain Was $89K

Crypto tax software can produce questionable results when transaction history or cost basis is incomplete. In this episode, Clinton Donnelly shares two real client examples involving missing crypto records. In one case, records from an old exchange were unavailable. Trade confirmation emails and Coinbase records helped support that incoming Bitcoin represented a transfer of the client’s own assets rather than taxable income. Working In another case, crypto tax software calculated approximately $140,000 in gains . The client believed the figure was closer to $90,000 . After a professional gain calculation, the result was $89,000 , with Clinton estimating roughly a $20,000 tax difference based on the tax rate discussed in the example. Working Learn more about CryptoTaxAudit: https://www.cryptotaxaudit.com/ Crypto tax pricing: https://www.cryptotaxaudit.com/tax-crypto-pricing This episode is for educational and informational purposes only and does not constitute tax, legal or financial advice.

September 29, 20269 min

$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.

September 22, 20264 min

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.

September 15, 20264 min

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 experiences 00:23 IRS reporting and taxpayer clarity 00:43 Document length, cost basis and form formats 01:43 Reporting estimates and IRS implementation 03:24 Data summaries and closing views

September 8, 20266 min

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 CryptoTaxAudit Get help with an IRS letter Contact the team Follow the podcast for more discussions about crypto taxes, IRS notices, and audit preparation.

September 1, 20266 min

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/

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.

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