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. 9H AGO

    Your 1099-DA Could Make It Look Like You Made $1 Million

    Your 1099-DA may make it look like you made far more money from crypto than you actually did. In this episode, Clinton Donnelly explains why Form 1099-DA can report gross proceeds without showing your true cost basis, and why that can create serious confusion for crypto taxpayers. The key issue is simple: proceeds are not profit. A crypto trader could have millions of dollars in reported proceeds, but much lower actual taxable gain once cost basis is properly calculated. If the IRS receives a 1099-DA and your return does not account for it, that mismatch may lead to an IRS notice. Clinton breaks down: • Why 1099-DA proceeds can look much higher than real profit • Why missing cost basis creates crypto tax reporting problems • Why Coinbase-style 1099-DA forms may be hard to read • Why some accountants may struggle with complex crypto returns • How wallet transfers can distort holding periods • Why long-term crypto may appear short-term on the form • Why ignoring a 1099-DA could create IRS problems If you received a 1099-DA, traded crypto through Coinbase or another exchange, or moved crypto between wallets before selling, this episode explains what you need to understand before filing. Need help with crypto tax reporting or IRS crypto notices? Book a consultation with CryptoTaxAudit: https://www.cryptotaxaudit.com/crypto-tax-consultation Learn more: https://www.cryptotaxaudit.com

    4 min

  2. MAY 12

    Why Is My 1099-DA So High? Crypto Tax Strategy for Traders

    High-frequency crypto traders may receive 1099-DA forms with large reported numbers. The real issue is whether their tax return clearly explains those numbers. In this episode, Clinton Donnelly explains the two main strategies crypto traders may consider as 1099-DA reporting becomes more important. One option is to trade on one centralized platform so that one exchange may be able to report cost basis, sales price, and gain or loss on one 1099 form. Clinton compares this to how traditional brokerages like Merrill Lynch and Fidelity report stock activity. The other option is to keep assets in private wallets and decentralized platforms, then only use centralized exchanges when cashing out. But even then, centralized exchange activity may still be reported on a 1099-DA. Clinton also explains why a 1099-DA mismatch can create IRS audit risk. If the IRS sees numbers that do not line up with a tax return, they may ask for transaction history, exchange records, wallet activity, and DeFi activity. In this episode: • Why high-frequency crypto traders may receive large 1099-DA numbers • Why one exchange can simplify crypto tax reporting • Why private wallets can create more reporting complexity • Why cash-out activity may still be reported • How a 1099-DA mismatch can lead to IRS questions • Why professional crypto gain calculation matters • How CryptoTaxAudit helps traders prepare defensively Clinton Donnelly is the founder of CryptoTaxAudit, known as the Crypto Tax Fixer, and a leading expert in IRS representation, crypto tax compliance, and audit defense. Need help with 1099-DA reporting, crypto gain calculation, or IRS crypto audit risk? Book a crypto tax consultation: https://www.cryptotaxaudit.com/crypto-tax-consultation Learn about Tax Shield: https://www.cryptotaxaudit.com/taxshield Crypto gain calculation support: https://www.cryptotaxaudit.com/crypto-gain-calculation

    3 min

  3. MAY 7

    COVID Penalty Refunds? Why Taxpayers May Need to Act by July 10

    Some taxpayers may need to act before July 10, 2026, to preserve refund or abatement claims for certain COVID-era IRS penalties and interest. In this episode, Clinton Donnelly explains why the Kwong ruling may matter for taxpayers who were assessed IRS penalties, fees, or interest during the COVID-era deadline period. Clinton breaks down: Why COVID-era IRS deadline relief mattersHow some taxpayers may have been charged penalties during the affected periodWhy Form 843 may be used to request a refund or abatementWhy certified mail and proof of delivery matterWhy relief may not happen automaticallyWhy timing matters before the July 10, 2026 deadlineThis episode is especially relevant for taxpayers, tax professionals, business owners, crypto investors, and anyone who may have faced IRS penalties or interest during the COVID period. ✅ Book a Kwong ruling review:https://calendly.com/crypto-tax-audit/kwong-ruling?month=2026-05 📖 Read the full CryptoTaxAudit breakdown:https://www.cryptotaxaudit.com/blog/kwong-penalty-interest-abatement-covid-tax-deadlines 💼 CryptoTaxAudit consultation:https://www.cryptotaxaudit.com/crypto-tax-consultation 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. LinksDisclaimer

    6 min

  4. MAY 5

    The IRS Commissioner Problem: Anthony Parent on Tax Court, 1099-DA Chaos, and AI

    Is the IRS operating without a real Commissioner, and could that create problems for Tax Court cases, IRS appeals, and crypto tax enforcement? In this episode, Clinton Donnelly speaks with Anthony Parent of IRSMedic about the IRS Commissioner problem, Tax Court authority, IRS delegation orders, and what may happen when enforcement continues without clear leadership at the top. Anthony explains why he filed a motion to vacate in U.S. Tax Court, why he believes the absence of a Commissioner of Internal Revenue may create structural problems, and how this could affect certain IRS collection and Tax Court matters. The conversation also covers Form 1099-DA and the crypto tax reporting problems expected in 2026. Clinton and Anthony explain why 1099-DA may confuse taxpayers, why gross proceeds do not equal taxable income, and why missing cost basis could trigger IRS mismatch issues or CP2000-style notices. They also discuss AI in tax law, why tools like TaxGPT can produce confident but wrong answers, and why tax professionals who use AI lazily may create serious problems for their clients. Anthony Parent is the founder of IRSMedic and helps taxpayers with complex IRS, offshore disclosure, international tax, and tax controversy matters. Follow Anthony Parent and IRSMedic: Website: https://irsmedic.com/ YouTube: https://www.youtube.com/@irsmedic X / Twitter: https://x.com/IRS_MEDIC Need help with crypto tax reporting, Form 1099-DA, IRS letters, or audit risk? Book a crypto tax consultation: https://www.cryptotaxaudit.com/crypto-tax-consultation Get 1099-DA and crypto tax help: https://www.cryptotaxaudit.com/tax-crypto-pricing Learn more about TaxShield IRS monitoring: https://www.cryptotaxaudit.com/taxshield 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, Anthony Parent, IRSMedic, or CryptoTaxAudit.

    34 min

  5. APR 30

    Missed a 1099? Why the IRS Sends a CP2000 Notice

    Miss a 1099 and the IRS may assume you underreported income. A CP2000 notice is triggered when the IRS compares the 1099s they received with what was included on your tax return and finds a mismatch. They calculate additional tax and send you a notice to review or challenge. Clinton Donnelly explains: What a CP2000 notice isWhy missing 1099s trigger itWhy the IRS calculations are often wrongHow it differs from a full auditWhat to do if you receive oneThis is not an audit, but it does require a response. Review your situation before it escalates:https://www.cryptotaxaudit.com/crypto-tax-consultation Disclaimer This content 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.Listening does not create a client relationship with Clinton Donnelly or CryptoTaxAudit.

    4 min

  6. APR 28

    What Should You Do If You Get IRS Letter 6174 for Crypto?

    If you’ve received IRS Letter 6174 or 6173 related to crypto, it’s important to understand what it actually means before taking any action. In this episode, Clinton Donnelly explains why the IRS is sending these letters to crypto traders, what information they may already have, and how these notices fit into broader IRS enforcement around digital assets. He also breaks down: The difference between IRS Letter 6173 and 6174Why receiving one means you are on the IRS radarHow the IRS identifies crypto activity through wallets and exchangesThe limits on amending past tax returnsWhy responding immediately may not always be the right moveHow early monitoring can help identify potential audit riskIf you’ve traded crypto and received one of these letters, understanding your position before responding is critical. Clinton Donnelly is the founder of CryptoTaxAudit, known as the “Crypto Tax Fixer,” and a leading expert in IRS representation, crypto tax compliance, and audit defense. This content 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. For more information or to review your situation, visit:https://www.cryptotaxaudit.com/crypto-tax-consultation ⚠️ DISCLAIMER This content 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.

    6 min

  7. APR 23

    CP2000 Notices and Crypto Tax Mistakes Explained

    If you’ve received a CP2000 notice from the IRS related to crypto, you’re not alone. A CP2000 letter is issued when the IRS believes income was not reported correctly, often based on forms like the new 1099-DA for digital assets. In many cases, crypto investors did report their income, but errors in how it was reported can trigger these notices. This is a high-volume, low-cost way for the IRS to review returns and request additional payment. You typically have 60 days to respond. The real issue is not missing income. It is incorrect reporting. Many people respond incorrectly by sending incomplete information or reacting emotionally instead of presenting clear, structured data the IRS expects. Handled properly, these notices can often be resolved and in some cases corrected. Clinton Donnelly, founder of CryptoTaxAudit, explains how CP2000 notices work and what crypto investors should do next.

    2 min

  8. APR 21

    IRS AI and Crypto Audits: How Investors Are Being Identified

    The IRS is changing how it identifies crypto investors who may have underreported their income. In this episode, Clinton Donnelly, founder of CryptoTaxAudit, explains how artificial intelligence and tools like Palantir’s SNAP platform are helping the IRS move beyond outdated audit systems and focus on higher-probability audit targets. If you have traded crypto and your reporting is not fully accurate, this shift matters. In this episode: How the IRS is using AI to improve audit targetingWhy many past audits resulted in no changeHow Palantir’s SNAP platform narrows down audit candidatesWhy crypto investors are a growing focus for enforcementHow Form 1099-DA will increase IRS visibilityWhat IRS Letters 6173 and 6174 meanWhat to do if you receive an IRS crypto noticeWhy contacting the IRS directly may not be the best first stepLearn more or get help:https://www.cryptotaxaudit.com/crypto-tax-consultation ⚖️ 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.

    5 min
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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
    199
  • Rating
    Clean
  • Copyright
    © Clinton Donnelly
  • Show Website
    The Clinton Donnelly Show

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