The Clinton Donnelly Show

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

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 matters How some taxpayers may have been charged penalties during the affected period Why Form 843 may be used to request a refund or abatement Why certified mail and proof of delivery matter Why relief may not happen automatically Why timing matters before the July 10, 2026 deadline This 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

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.

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 is Why missing 1099s trigger it Why the IRS calculations are often wrong How it differs from a full audit What to do if you receive one This 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.

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 6174 Why receiving one means you are on the IRS radar How the IRS identifies crypto activity through wallets and exchanges The limits on amending past tax returns Why responding immediately may not always be the right move How early monitoring can help identify potential audit risk If 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.

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.

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 targeting Why many past audits resulted in no change How Palantir’s SNAP platform narrows down audit candidates Why crypto investors are a growing focus for enforcement How Form 1099-DA will increase IRS visibility What IRS Letters 6173 and 6174 mean What to do if you receive an IRS crypto notice Why contacting the IRS directly may not be the best first step Learn 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.

Can tools like OpenClaw be used to report crypto traders to the IRS and earn a reward? In this episode, Clinton Donnelly breaks down a viral post on X claiming that someone built an OpenClaw system to scan Reddit and social media for people not paying crypto taxes, then report them to the IRS for a payout. At first glance, it sounds serious. But the reality is very different. Clinton explains how the IRS whistleblower program actually works, including: Why rewards can reach up to 30% The requirement for cases involving over $200,000 in unpaid taxes Why information from public sources, like social media, does not qualify He also shares a real example from his own experience that highlights something many people underestimate: The IRS has been paying attention to public behavior for years. If you’re posting about not paying taxes or engaging with that kind of content, you may be creating visibility you don’t fully understand. This episode separates the viral claim from reality and explains what actually matters when it comes to IRS enforcement and crypto tax compliance. ⚠️ 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. For personalized guidance, visit: https://www.cryptotaxaudit.com/crypto-tax-consultation

What is IRS Form 4564, and why is it showing up in crypto audits? In this episode, Clinton Donnelly explains how IRS audits begin, what Form 4564 is asking for, and how it connects to 1099-DA reporting and Form 8949. More importantly, he breaks down why crypto tax reporting feels so confusing right now. It’s not just taxpayers struggling. Tax preparers are trying to interpret incomplete data, and even IRS auditors are working through how these forms apply in practice. If your numbers don’t match or your reporting feels unclear, this episode explains why.

Can you use your crypto to help buy a house without selling it? In this episode, Clinton Donnelly explains how crypto-backed loans work and why they can create a highly leveraged position. You’ll hear: • How borrowing against crypto changes your risk • Why having two loans increases exposure • What happens when the market drops • How liquidation can trigger a tax event • Why paying these loans off quickly matters This is not about avoiding crypto loans. It’s about understanding how they work so you can make better decisions.

If you file a tax extension, you still need to pay your taxes by April 15. In this episode, Clinton Donnelly explains how IRS tax extensions work, the difference between filing late and paying late, and what happens if you underpay. He breaks down failure-to-file penalties, failure-to-pay penalties, interest, and why estimating your taxes correctly matters. You’ll learn: • What a tax extension actually does • Why an extension does not extend your payment deadline • How IRS interest and penalties can build up • Why paying an estimate by April 15 matters For personalized help, visit: https://www.cryptotaxaudit.com/crypto-tax-consultation

If your 1099-DA shows numbers that seem way higher than your actual crypto profits, you’re not alone. This is one of the most common points of confusion for crypto investors. Many exchanges report total proceeds instead of cost basis, which can make your gains look far bigger than they really are. In this episode, Clinton Donnelly explains why this happens, how cost basis actually works, and what the IRS expects you to report. You’ll also learn why moving between wallets and exchanges can break tracking, and what kind of records you need to keep in case you’re ever audited. If you’ve looked at your crypto tax forms and thought, “this can’t be right,” this will make it clear.

Cashing out crypto isn’t as simple as moving funds to your bank. Many transactions are delayed, flagged, or even rejected due to compliance and anti-money laundering (AML) rules. In this episode, Clinton Donnelly, founder of CryptoTaxAudit, is joined by Hugo Leijtens, Chief Strategy Officer at Cense, to explain why banks struggle with crypto transactions and what individuals need to do to avoid issues. They discuss real-world scenarios, including large transfers being rejected, account closures, and how documentation and source-of-funds reporting play a critical role in successful cash-outs. In this episode: Why banks reject crypto transfers How AML rules affect crypto cash-outs What “source of funds” means in practice Common mistakes that trigger compliance flags How to prepare for large crypto withdrawals The role of tax reporting, including 1099-DA Guest: Hugo Leijtens is Chief Strategy Officer at Cense. His background spans Microsoft, international startups, blockchain innovation, and AI-driven financial intelligence. He has contributed to digital banking systems and compliance-focused blockchain solutions. Learn more: 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 regulations can change, and individual circumstances vary. You should consult a qualified professional before making financial decisions.

If you received a 1099-DA from a crypto exchange, you may be wondering what it means for your tax return. In this video, crypto tax expert Clinton Donnelly explains how 1099-DA reporting works and why the information reported by exchanges may not reflect your true gain or loss. You will learn: • What the 1099-DA form is • Why exchange reporting may be incomplete or incorrect • How IRS Form 8949 is used to report the correct numbers • What crypto traders should watch for when filing their tax return If your crypto tax forms look confusing or incorrect, you can speak with a crypto tax expert here: https://www.cryptotaxaudit.com/crypto-tax-consultation Official website: https://www.cryptotaxaudit.com Disclaimer This video 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. Watching this video does not create a client relationship with Clinton Donnelly or CryptoTaxAudit. For personalized guidance, visit https://www.cryptotaxaudit.com/crypto-tax-consultation

Gary Cardone explains why the “global reset” is really a trust reset: incentives shift, institutions crack, and Bitcoin demand matters more than narratives. Clinton Donnelly connects the macro view to real-world tax and compliance consequences for U.S. crypto holders. What you’ll learn: • Why trust is breaking and why authenticity starts paying again • How taxes + incentives move people, businesses, and capital • How Gary thinks about Bitcoin demand, price levels, and regulation 📞 Book a consultation with Clinton’s team: https://www.cryptotaxaudit.com/crypto-tax-consultation Quick answers: Q: What’s the big theme of this conversation? A: Trust is breaking, incentives are shifting, and consumers have more power than they think. Q: What’s Gary’s Bitcoin lens? A: Demand beats narratives. He treats BTC like a long-term optionality asset. Q: What’s the practical takeaway? A: Build real services, avoid leverage traps, and plan for tax + regulatory uncertainty. 👤 About the host: Clinton Donnelly is the founder of CryptoTaxAudit and is known as the “Crypto Tax Fixer,” focusing on IRS representation, crypto tax compliance, and audit defense. 🔗 Follow Gary Cardone: X (Twitter): https://x.com/GaryCardone YouTube: https://www.youtube.com/@garycardone Website: https://garycardone.me/ 💬 Drop your questions in the comments: What do you think is the biggest risk to Bitcoin right now: regulation, trust, or liquidity? #Bitcoin #Crypto #TaxPolicy #FederalReserve #BitcoinPrice #CryptoTax #GaryCardone #ClintonDonnelly #CryptoTaxAudit #macroeconomics 📌 Disclaimer This video 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. Watching this video does not create a client relationship with Clinton Donnelly or CryptoTaxAudit. For personalized guidance, visit 👉 https://www.cryptotaxaudit.com/crypto-tax-consultation

IRS Form 1099-DA is reported by exchanges under Internal Revenue Code Section 6045(g), but taxpayers must report cryptocurrency gains under Treasury Regulation 1.1012-1(j). If you copy the 1099-DA directly onto IRS Form 8949 without adjustment, your capital gains may be reported incorrectly.In this video, Clinton Donnelly, founder of CryptoTaxAudit, explains:• Why exchange reporting and taxpayer reporting follow different rules• How transferred crypto creates lot-order mismatches• Why 1099-DA proceeds may not reflect your actual cost basis• How to subtract exchange-reported proceeds on Form 8949• How to enter your correct crypto gain summary• How to reconcile reporting without triggering IRS correspondenceThis applies to traders using Coinbase and other exchanges that issue 1099-DA forms.If you traded across wallets and exchanges, this matters.📞 Book a professional crypto tax review:https://www.cryptotaxaudit.com/crypto-tax-consultation Disclaimer: This video 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.Watching this video does not create a client relationship with Clinton Donnelly or CryptoTaxAudit.For personalized guidance, visit👉 https://www.cryptotaxaudit.com

When crypto assets are divided in a divorce, the cost basis transfers with them. That means future capital gains tax liability may follow the asset, and incorrect reporting can trigger IRS audits affecting both partners. 👨‍⚖️ Clinton Donnelly, founder of CryptoTaxAudit and known as the “Crypto Tax Fixer,” explains how forensic wallet tracing, joint tax returns, and cost basis allocation can create unexpected legal and tax exposure during and after divorce. What You’ll Learn: • How forensic crypto audits work in divorce proceedings • What happens to cost basis when assets are split • Why selling transferred crypto can create unexpected capital gains • How IRS audits can extend to both former spouses • When filing separately may limit exposure • Why accurate gain calculation matters during asset division This video is especially relevant if you: • Hold Bitcoin, Ethereum, or other digital assets • Are married and file jointly • Are going through divorce or separation • Have significant unrealized crypto gains • Are concerned about IRS audit exposure 💼 Need an accurate crypto gain calculation during divorce or asset division? Schedule a consultation: 👉 https://www.cryptotaxaudit.com/crypto-tax-consultation For more on capital gains and reporting requirements: Official IRS page on capital gains: https://www.irs.gov/taxtopics/tc409 Disclaimer: This video 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. Watching this video does not create a client relationship with Clinton Donnelly or CryptoTaxAudit. For personalized guidance, visit 👉 https://www.cryptotaxaudit.com/crypto-tax-consultation

Crypto taxes changed in a big way for 2026.In this video, Clinton Donnelly explains how the new 1099-DA works, how the IRS now separates cryptocurrency from other property, and why reporting mistakes are more likely to trigger audits than ever before.👨‍⚖️ Clinton Donnelly is the founder of CryptoTaxAudit, known as the Crypto Tax Fixer, and a leading expert in IRS crypto audits, tax compliance, and gain calculations.Meet the hosts:Clinton Donnelly → https://www.cryptotaxaudit.com/clinton-donnellyBen Weber (Director of Crypto Analytics) → https://www.cryptotaxaudit.com/ben-crypto-tax-expertWhat this video covers:- What the new 1099-DA reports (and what it doesn’t)- How crypto is now separately identified on IRS capital gains forms- Why total proceeds must match (or exceed) IRS records- FIFO vs specific identification, what actually works in real life- Cost basis issues across wallets, exchanges, and hardware wallets- Why Safe Harbor does not change ongoing reporting rules- The most common mistakes that lead to IRS noticesIf you’re trading crypto, moving assets between wallets, or filing taxes in 2026, this is required viewing.📞 Book a private crypto tax consultation👉 https://www.cryptotaxaudit.com/crypto-tax-consultationDisclaimer: This video 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.Watching this video does not create a client relationship with Clinton Donnelly or CryptoTaxAudit.

This video explains how U.S. crypto tax rules apply to common crypto activity.It covers trading, transfers, fees, losses, and retirement accounts.It reflects current IRS guidance, including Form 1099-DA.Clinton Donnelly, founder of CryptoTaxAudit, and Ben, Director of Crypto Analytics, answer practical questions about crypto tax reporting.They focus on how transactions are reviewed when proceeds, cost basis, or records are incomplete or misunderstood.Topics covered include:• Crypto tax reporting basics and where to start• How Form 1099-DA reports proceeds• Why cost basis reconciliation is required• Whether exchange to wallet transfers can be misclassified• How missing or incorrect data affects tax reporting• Tax treatment of wrapped tokens and staking receipt tokens• How to transfer crypto into an S Corporation correctly• How Celsius bankruptcy losses are typically reviewed• Whether Bitcoin network fees are taxable events• How losses for worthless crypto assets are evaluated• Rules for crypto held in Roth IRAs• Risks of intermingling retirement assets• How retirement withdrawals affect tax bracketsDisclaimer: This video is for educational and informational purposes only.It does not constitute legal, tax, or financial advice.Tax laws and IRS procedures can change.Every situation is different.Consult a qualified tax professional before taking action.Watching this video does not create a client relationship with Clinton Donnelly or CryptoTaxAudit.For personalized guidance, visithttps://www.cryptotaxaudit.com/crypto-tax-consultation

Most people are told that IRAs and 401(k)s are the foundation of retirement planning.But decades into these strategies, many Americans still reach retirement age without enough savings to live comfortably.In this video, Clinton Donnelly, founder of CryptoTaxAudit, explains:• Why traditional retirement accounts often fall short• How inflation and fund fees affect long-term outcomes• What Social Security realistically provides in retirement• Why contribution limits and withdrawal penalties matter• How some investors think differently about long-term growthThis is not about hype or predictions, it’s about understanding the structure behind common retirement strategies and asking better questions about long-term financial planning.👇 What do you think? Let us know in the comments.📞 Need help with crypto tax planning or reporting?👉 https://www.cryptotaxaudit.com/crypto-tax-consultation ⚠️ Disclaimer: This video 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.Watching this video does not create a client relationship with Clinton Donnelly or CryptoTaxAudit.For personalized guidance, visit:👉 https://www.cryptotaxaudit.com/crypto-tax-consultation