The Clinton Donnelly Show

Illinois passed SB 3019, introducing a 0.2% tax on digital asset transactions by Illinois residents. At first glance, 0.2% may seem insignificant. Clinton Donnelly argues that the real issue is not the size of the tax. It is the precedent it creates. In this episode, Clinton explains: What the Illinois Digital Asset Tax Act does Why it is being described as a “privilege tax” Which exchanges and br...

The IRS is moving toward stricter crypto tax reporting through expanded 1099-DA requirements and potential application of wash sale rules to digital assets. In this episode, we break down what is actually changing, how it affects crypto investors, and why this represents a major shift in how digital assets are tracked and taxed. We cover: • How wash sale rules may apply to crypto transactions • Wh...

A new AI wealth fund proposal would give the public a 50% stake in major AI companies. In this episode, Clinton Donnelly breaks down the American AI Sovereign Wealth Fund Act and explains why this proposal may be more political talking point than future tax law. Clinton looks at the risks of forced public ownership in AI companies, including government control, shareholder influence, corruption ri...

ADA Cardano staking rewards may be taxable when received if the taxpayer has dominion and control, but Paschall v. Commissioner also raises important questions about constructive receipt and Cardano validator mechanics. In this episode, Clinton Donnelly, founder of CryptoTaxAudit and known as the Crypto Tax Fixer, breaks down Paschall v. Commissioner, T.C. Memo. 2026-46. Paschall was staking Carda...

The IRS rolled out Form 1099-DA, and Clinton Donnelly says the first version is already creating serious problems for crypto investors and tax preparers. In this episode, Clinton explains why the 1099-DA collects the data the IRS wants, but fails to help taxpayers file correctly. The information may be there, but it is hidden, buried, and difficult to enter properly on a tax return. He also explai...

The IRS says tax season was a success, but crypto taxpayers may be facing a very different reality. In this episode, Clinton Donnelly explains why the new IRS Form 1099-DA may give the IRS more crypto transaction data while still leaving taxpayers and tax preparers unsure what numbers actually belong on the tax return. Clinton breaks down how IRS automation, CP2000 under-reporting letters, missing...

Clinton Donnelly recently attended the CERCA IRS conference, where IRS electronic tax reporting, taxpayer communication, automation, and modernization were discussed with IRS leadership. One major takeaway stood out: CryptoTaxAudit was the only crypto-related firm attending the conference. That matters because the 1099-DA is becoming one of the most important reporting forms crypto taxpayers will...

Should the IRS offer a crypto tax amnesty program for traders who want to become compliant? In this episode, Clinton Donnelly asks crypto traders, investors, tax professionals, and anyone affected by crypto reporting problems to share constructive feedback. CryptoTaxAudit is preparing a proposal or recommendation for cryptocurrency tax amnesty. The goal is to gather real-world comments about what...

Are you trading on Kalshi, Polymarket, or other prediction markets? In this episode, Clinton Donnelly explains why prediction market taxes can be confusing, especially when activity may be treated differently depending on whether it looks like gambling or capital asset activity. One of the biggest issues discussed is the 90% loss rule. In some cases, a trader could lose money overall and still hav...

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,...

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 b...

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 taxpaye...

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...

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...

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...

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 r...

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 accur...

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...

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...

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...

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 act...

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...

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 is...

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...

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, businesse...