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The Clinton Donnelly Show: Daily Summaries Delivered
by Clinton Donnelly
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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- 1 weeks ago3 min
Crypto Tax Extensions 2027: April 15 Deadlines & Superseding Returns
Crypto taxes not ready by April 15, 2027? Filing an IRS tax extension gives you more time to prepare your return, but it does not extend the deadline to pay taxes owed.In this episode, Clinton Donnelly of CryptoTaxAudit explains the difference between filing and payment deadlines, why cryptocurrency gain calculations and K-1 forms can delay tax preparation, and why overpaying taxes does not earn favorable IRS treatment.Clinton also discusses superseding tax returns, how they differ from amended returns, and how they may help taxpayers correct previously filed information within the applicable filing deadline.Crypto tax services and pricing:https://www.cryptotaxaudit.com/tax-crypto-pricingDisclaimer: This episode is for educational purposes only and does not constitute legal, tax, or financial advice. Tax laws can change. Consult a qualified tax professional. Listening does not establish a client relationship with CryptoTaxAudit.
- 2 weeks ago4 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-reviewScan 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 backgroundU.S. Treasury: IT modernization and Palantir partnership, September 22, 2025:https://home.treasury.gov/news/press-releases/sb0260IRS: 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-effortsLearn more about CryptoTaxAudit:https://www.cryptotaxaudit.com/DisclaimerThis 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.
- 3 weeks ago2 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-rulesLearn how CryptoTaxAudit can help:https://www.cryptotaxaudit.com/Crypto tax preparation and services:https://www.cryptotaxaudit.com/tax-crypto-pricingThis 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.
- 4 weeks ago2 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 CryptoTaxAuditCryptoTaxAudit 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/contactDisclaimer: 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.
- Oct 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. WorkingIn 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. WorkingLearn more about CryptoTaxAudit:https://www.cryptotaxaudit.com/Crypto tax pricing:https://www.cryptotaxaudit.com/tax-crypto-pricingThis episode is for educational and informational purposes only and does not constitute tax, legal or financial advice.
- Sep 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-billFull original discussion:https://youtu.be/ELBgtO67oYwCryptoTaxAudit: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.
- Sep 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-consultationU.S. Treasury source:https://home.treasury.gov/news/press-releases/sb0632Visit CryptoTaxAudit:https://www.cryptotaxaudit.com/Disclaimer: This episode is for educational and informational purposes only and does not constitute legal, tax, or financial advice.
- Sep 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 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
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About The Clinton Donnelly 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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