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.
The $30,000 ADA Cardano Staking Tax Mistake
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 Cardano and argued that his staking rewards should be taxed when sold for dollars, not when received. The auditor disagreed, and the case went to U.S. Tax Court.
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1099-DA Is Broken: CP2000 Notices Are Coming This Fall
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 explains why confusion around the 1099-DA could lead to a high error rate, mismatched IRS records, and a wave of CP2000 notices for crypto investors this fall.
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1099-DA Disaster: Why Crypto Taxpayers Still Don’t Know What to Report
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 cost basis, crypto-to-crypto taxable trades, and confusing 1099-DA formats could create problems for taxpayers who are trying to file correctly.
He also explains why simply receiving more data does...
What I Learned at the IRS Conference About Crypto Reporting
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 face. In prior years, crypto gain calculation companies and other reporting firms were involved in these conversations. In 2026, they were no longer present.
In this episode, Clinton explains why the 1099-DA rollout created confusion for crypto taxpayers, why some...
Should the IRS Offer Crypto Tax Amnesty? Crypto Traders Need to Speak Up
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 has kept people from reporting all their crypto income, what makes crypto tax reporting difficult, and what the IRS could do beyond Form 1099-DA to help taxpayers come in from the...
Kalshi & Polymarket Taxes: Can You Lose Money and Still Owe Tax?
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 have taxable income because gambling losses may be limited and treated differently from capital losses.
Clinton covers:
• Wh...
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...
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.
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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...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...
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.
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 amen...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 i...
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 cryp...OpenClaw, IRS Whistleblowers, and the Truth About Reporting Crypto Traders
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...IRS Form 4564 and Crypto Taxes: Why Reporting Feels So Confusing Right Now
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 epis...
Can You Use Crypto for a House Deposit? What Actually Happens
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...
Tax Extension Rules: Do You Still Have to Pay by April 15?
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 personaliz...
Why Your 1099-DA Shows Millions in Crypto Proceeds (And What It Really Means)
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...
How to Cash Out Crypto Safely: Bank Compliance, AML Rules, and Tax Risks
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.
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1099-DA Crypto Taxes Explained: How to Fix Exchange Errors Using IRS Form 8949 Private Video (Scheduled)
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 form...
Bitcoin, Taxes, and the Fed in 2026 | Gary Cardone on the Global Reset
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.co...
How Do You Report Short Term 1099-DA Crypto Gains on Form 8949 (Step-by-Step Fix)
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 t...
What Happens to Crypto in a Divorce? Cost Basis, IRS Audits, and Hidden Tax Risks
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 ass...
1099-DA + Form 8949: The IRS Match That Triggers Crypto Tax Audits (2026)
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 Taxes Explained: 1099-DA, Wallet Transfers, IRAs, Losses & IRS Rules (2026 Guide)
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...
Why IRAs and 401(k)s Are Failing Crypto Investors | Retirement, Inflation & Bitcoin
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 fi...
IRS Uses Palantir for Crypto Tracking: CARF, DAC8, and What Traders Must Report
🚨 LIVE CRYPTO TAX AMA THIS FRIDAY: LIMITED SPOTSIf you trade crypto, this is information you do not want to miss.👉 Register now (free, live):https://streamyard.com/watch/YKQVzjJtqaS8This week’s AMA breaks down how the IRS actually tracks crypto today, including:• Palantir and blockchain analysis• CARF & DAC8 cross-border reporting• What foreign exchanges may report• Why “just using DeFi” doesn’t eliminate tax exposureSeats are limited and this AMA.
The IRS has used Palantir for nearly a decade to normalize and analyze large datasets, including tax data. With tools like Palantir Foundry, government agencies can now analy...
Why Did the IRS Threaten Property Seizure After a $271,000 Tax Payment?
This situation, shared publicly by Stefan Georgi, highlights how IRS enforcement systems work, why interest penalties matter, and why relying on surface-level tax software or assumptions can create serious risk.🔗 Original public post referenced in this discussion:https://x.com/StefanGeorgi/status/2005279901050413341?s=20What this video covers:•Why IRS interest does not stop automatically after payment•How levy and seizure notices are triggered•Why “tax strikes” and non-filing backfire legally•What actually happens when penalties compound•How to respond without increasing audit or enforcement riskIf you’re trading crypto, filing late, or dealing with large corrections, understanding how the IRS enforces balanc...
IRS Criminal Indictments Explained: What Happens When You Don’t Report Crypto
The IRS is about to get full visibility into your crypto activity. Starting January 2026, the 1099-DA will report every sale, exchange, and transfer you make on US exchanges.
And in 2027, the Crypto Asset Reporting Framework (CARF) brings 90+ countries into the same system.
This means:- Every transaction reported, no minimum amount- Your wallet addresses exposed through transfer data- Foreign exchanges like Binance will collect KYC and report to the IRS- DeFi won't save you
The bigger shift: the IRS is moving away from audits and toward criminal indictments. Look at the Roger Ver...
CARF Is Coming: The IRS Will See Your Wallet Activity (2027–2028 Explained)
The IRS is about to receive foreign crypto exchange data, including wallet activity, under the upcoming Crypto Asset Reporting Framework (CARF). U.S. taxpayers now have a very limited window to get compliant.In this video, Clinton Donnelly breaks down what the U.S. Treasury just proposed: participation in the Crypto Asset Reporting Framework (CARF) a global reporting system already signed by nearly 90 countries. CARF is expected to begin data collection in 2027, and foreign countries could start sending reports to the IRS in 2028.CARF goes far beyond a 1099-DA. It could include:- wallet addresses- transfers- exchanges- disposal events...
Why OG Whales Are Dumping Bitcoin for Zcash
Protect yourself from IRS crypto audits with TaxShield:👉 https://www.cryptotaxaudit.com/taxshieldOG Bitcoin whales are dumping BTC for Zcash, not because of market cycles, but because of fear.Following the Roger Ver plea deal and the newly demonstrated IRS wallet-tracing capabilities, early Bitcoin holders are panicking over old, unreported gains, potential indictment exposure, and the upcoming 1099-DA reporting rules. In this video, Clinton Donnelly breaks down the tax panic driving BTC’s decline and Zcash’s sudden 10x surge.⏱️ TIMESTAMPS00:00 Why Bitcoin has been falling for two months00:20 Zcash up 10x the rollover trade explained00:37 Fear of criminal indictment...
How Crypto Scams Really Work in 2025: Forensics Expert Reveals What Victims Don’t Know
⚠️ WARNING: The biggest threat after a crypto scam is getting robbed a second time.In 2025, crypto scams are more organized, technical, and psychologically targeted than ever before. But here’s what most victims don’t know:Scammers often install malware, steal your ID/KYC, and may continue targeting you long after the initial theft. This means your identity, your devices, and even your bank accounts may still be at risk.In this critical interview, crypto tax attorney Clinton Donnelly speaks with Joseph Albiñana, a senior blockchain investigator at CoinStructive, to expose how pig-butchering scams, romance scams, investment frauds, and “reco...
Thinking of Renouncing Your Citizenship? WATCH THIS First (Exit Tax Warning)
Renouncing your U.S. citizenship does not guarantee tax freedom, and for many people, it can create bigger tax problems than it solves.
In this video, Clinton Donnelly breaks down the real rules, including why the IRS can still pursue you for 10 years after renunciation, how Form 8854 works, and what the Exit Tax actually is.
🇺🇸 What You’ll Learn in This Video• Why U.S. citizens are taxed on worldwide income• Why moving to Dubai or Portugal doesn’t remove your IRS obligations• The one legitimate tax haven for Americans (Puerto Rico Act 60)• How the Exit Tax works whe...
Crypto’s Turning Point: Lark Davis on Trump, Regulation & the Next Bitcoin Cycle
In this exclusive interview, Clinton Donnelly sits down with crypto expert Lark Davis to unpack Trump’s proposed $2,000 stimulus, the new wave of pro-crypto regulation, and what it all means for your crypto portfolio and taxes.👨⚖️ Clinton Donnelly is the founder of CryptoTaxAudit, a leading authority in IRS representation, crypto tax compliance, and audit defense.🎙️ Lark Davis, one of the world’s most recognized crypto analysts, shares his personal tax journey, his thoughts on tokenization, and how investors can prepare for a volatile but opportunity-filled 2025.💡 What You’ll Learn:• Why Trump’s $2,000 stimulus and “run it hot” policy could reignite the crypto bull market...
Crypto Tax Losses: Avoid These 3 IRS Red Flags
When it comes to reporting crypto losses, one wrong form or bad YouTube “hack” can put you straight on the IRS’s radar.👨⚖️ Clinton Donnelly explains the three biggest mistakes crypto traders make when reporting losses and how to avoid triggering a Letter 3176C for a “frivolous” return.
💼 What you’ll learn:• How the IRS actually views theft, Ponzi, and scam-related losses• Why “obscure loopholes” can lead to frivolous-return flags• The difference between a valid theft loss and a disallowed claim• How to document proof properly under Form 4684• When it’s smart to file with CryptoTaxAudit to prevent audits
📞 Get help:👉 Book a...
Puerto Rican Act 60 Explained: How to Pay 0% Capital Gains Tax (Legally)
Can you really pay 0% capital gains tax by moving to Puerto Rico?In this video, Clinton Donnelly breaks down Puerto Rican Act 60, the IRS residency tests, and the exact mistakes that can trigger an audit if you get this wrong.💼 What you’ll learn:• How Act 60 creates a legal 0% capital gains tax incentive for U.S. citizens• The 5 residency rules you must meet to qualify• What the IRS watches for in audits (including your passport days)• Real example: Pantera Capital CEO under Senate investigation• The truth about the “Closer Connection Test” and how to avoid losing status👉 For professional help setting up your P...
IRS Weaponization Exposed: Hunter Biden, Roger Ver & Why Capital Gains Must DIE
The IRS has been weaponized by both political parties for decades. Clinton Donnelly, who defends traders in IRS audits every day, breaks down the real cases you haven't heard about and reveals why eliminating capital gains tax on digital assets is the only realistic solution.
Clinton Donnelly is the founder of CryptoTaxAudit and one of the leading crypto tax defense attorneys in the United States. He's represented hundreds of crypto traders facing IRS audits and investigations, giving him unique insight into how the system really works.
Facing an IRS Audit or Investigation?📞 Book a consultation wit...
So You’re a Bitcoin HODLer… Here’s What the IRS Thinks of That 😬
Even if you never sell your Bitcoin, you’re not immune from taxes.Borrowing against your crypto can create hidden liabilities if you’re liquidated and when you finally sell, your long-term capital gains can reach 20–30% including federal, NIIT, and state taxes.Crypto tax expert Clinton Donnelly, known as the Crypto Tax Fixer and founder of CryptoTaxAudit, breaks down the real IRS implications for Bitcoin HODLers. He explains when borrowing can make sense, when it becomes risky, and why liquidation events can surprise even seasoned investors.What you’ll learn:- How long-term capital gains on Bitcoin are actually taxed- T...
Crypto Theft: 7 Rules to Protect Keys, Wallets & Life
Crypto theft prevention starts with OPSEC, which you can actually do today. Learn the distance rule, wallet splits, and how to claim losses.If you hold digital assets, crypto theft prevention isn’t optional, it’s survival. This video breaks down practical OPSEC moves that lower real-world risk, from going quiet about holdings to creating genuine distance between you and your keys. We cover home invasion crypto scenarios and why “a few hours away” isn’t enough; your recovery stash should be a plane-trip away to prevent forced access.You’ll learn cold wallet security tactics: multiple wallets, separated locations, n...
