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PODCAST

The Clinton Donnelly Show

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.

business investing

All Episodes

00:08:34

Puerto Rican Act 60 Explained: How to Pay 0% Capital...

The Clinton Donnelly Show ·

2025/11/04

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•

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00:06:04

IRS Weaponization Exposed: Hunter Biden, Roger Ver &...

The Clinton Donnelly Show ·

2025/10/28

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

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00:02:46

So You’re a Bitcoin HODLer… Here’s What the IRS...

The Clinton Donnelly Show ·

2025/10/21

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

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00:06:20

Crypto Theft: 7 Rules to Protect Keys, Wallets & Life

The Clinton Donnelly Show ·

2025/10/14

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

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00:08:48

Your Accountant Is NOT Ready For 1099-DA Crypto Tax Form

The Clinton Donnelly Show ·

2025/10/07

The 2025 tax season is bringing the biggest change to crypto tax reporting in years. Centralized exchanges will now send the IRS a Form 1099-DA, detailing every single one of your crypto sales, exchanges, and even transfers. For active traders, this could be a document that is dozens of pages long.Is your current accountant prepared to handle this?In this episode of the Clinton Donnelly Show, we break down exactly what the 1099-DA means for you as a US crypto investor. He'll cover why standard

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00:04:30

Trump OKs Bitcoin in 401(k)s: The Ownership Illusion...

The Clinton Donnelly Show ·

2025/09/30

Trump just opened the door for Bitcoin in 401(k)s, but here’s the catch: you may never actually own it.Clinton Donnelly explains what this executive order really means, where the IRS tax traps are hidden, and why your “Bitcoin in retirement” may be an illusion.👨‍⚖️ What you’ll learn:• What Trump’s order allows and what it doesn’t• Why Bitcoin withdrawals from 401(k)s always convert to fiat• Why you can’t ever take Bitcoin “in kind” from a retirement plan• Hidden rules: 5-year lock-ins, 10% early

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00:06:52

Top 5 Crypto Tax Questions Answered: Wallets,...

The Clinton Donnelly Show ·

2025/09/23

Are you confused about how crypto taxes actually work? 🤔These are your questions, answered. Clinton Donnelly, founder of CryptoTaxAudit, tackles the Top 5 crypto tax questions our viewers ask most.What you’ll learn in this video:• Do you pay taxes on stablecoin transactions?• What is “cost basis” and why does it matter for crypto?• Is moving crypto between wallets taxable?• How do you report crypto trades and exchanges to the IRS?• Can you use losses to reduce your crypto tax bill?Clinton explains

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00:03:37

Why Crypto Taxes Need an Expert (Not AI or Reddit...

The Clinton Donnelly Show ·

2025/09/19

Are you thinking about trusting AI or Reddit for crypto tax tips? The IRS just fined taxpayers $162M in penalties for following bad advice.🔗 IRS press release: https://www.irs.gov/newsroom/irs-assesses-162-million-in-penalties-over-false-tax-credit-claims-tied-to-social-media?utm_source=chatgpt.comIf you want to avoid costly mistakes, you need a real crypto tax expert on your side.AI and Reddit can recycle information, but cannot provide judgment, foresight, or accountability. That’s where an

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00:02:59

Is 0% Long-Term Capital Gains Tax Possible Under...

The Clinton Donnelly Show ·

2025/09/16

There’s a growing debate over whether America should eliminate the capital gains tax. President Trump and Secretary Lutnick have suggested that tariff revenue, possibly as high as $750 billion, could be used to offset taxes, even reducing them for households under $150,000.Clinton Donnelly, founder of CryptoTaxAudit, breaks down why capital gains tax reform is being discussed, what it could mean for crypto investors, and whether 0% long-term capital gains is realistic.💼 What you’ll learn in this

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00:07:08

IRS Installment Agreement Explained: Maximum Time,...

The Clinton Donnelly Show ·

2025/09/09

Are you struggling to pay your tax bill? The IRS payment plan might be your lifeline, but not everyone qualifies. In this video, Clinton Donnelly, founder of CryptoTaxAudit and known as the “Crypto Tax Fixer,” breaks down how installment agreements really work, who gets approved, and the red flags that lead to denial.What you’ll learn:- The IRS payment plan rules and time limits- Who qualifies and who gets denied - Options if you owe back taxes and can’t pay in full- Key strategies to avoid

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00:02:19

IRS 1099-DA in Under 3 Minutes: What Crypto Exchanges...

The Clinton Donnelly Show ·

2025/09/05

What is IRS Form 1099-DA?It’s the brand-new IRS form for digital assets, arriving in 2026. U.S. crypto exchanges like Coinbase, Robinhood, Kraken, Gemini, and Fidelity will now be required to report your crypto sales, swaps, and even wallet transfers — including the wallet addresses involved.Clinton Donnelly, founder of CryptoTaxAudit and known as the “Crypto Tax Fixer,” breaks down what this means for traders:- Which exchanges will issue Form 1099-DA- What’s being reported (sales, swaps, transfers,

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00:04:46

Crypto Inheritance Taxes Explained: Step-Up Basis,...

The Clinton Donnelly Show ·

2025/09/02

What happens to your crypto when you die? The IRS has strict rules on inheritance, estate taxes, and the powerful step-up basis that can save heirs from massive capital gains.Clinton Donnelly, founder of CryptoTaxAudit and known as the “Crypto Tax Fixer,” breaks down how the $15 million lifetime exemption, the 40% estate tax rate, and the step-up basis apply to crypto holders in 2025.💼 What you’ll learn in this video:• How the new $15M estate tax exemption (Genius Act 2025) works• Why estates over

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00:02:26

What Is the IRS FIFO Rule for Crypto Taxes in the...

The Clinton Donnelly Show ·

2025/08/28

What is FIFO in crypto taxes, and why does the IRS say it matters in 2025?FIFO means “First In, First Out.” When you sell crypto without specifically identifying which units you’re selling, the IRS assumes the first coins you bought are the first ones you sold.Starting with the 2025 tax year (filed in 2026), the IRS requires cost‑basis methods to be applied on a by‑account (wallet‑by‑wallet) basis. If you don’t (or can’t) provide a specific identification, then FIFO becomes the default inside that

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00:05:17

Is All Crypto Income Taxable? IRS Rules, Capital...

The Clinton Donnelly Show ·

2025/08/26

Is all crypto income taxable? The IRS doesn’t treat every crypto move the same. Selling, trading, mining, staking rewards, and airdrops are taxable. Wallet transfers, collateral staking, and borrowing against crypto are not. But here’s the catch: if a lender liquidates your collateral, the IRS counts it as a taxable sale.Clinton Donnelly, founder of CryptoTaxAudit and known as the “Crypto Tax Fixer,” explains the difference between taxable and non-taxable crypto activity, what really needs to be

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00:03:16

What Does Cynthia Lummis’ Crypto Tax Bill Really Mean...

The Clinton Donnelly Show ·

2025/08/21

Quick answer: It delays taxes until you sell your coins, but in many cases, you could end up paying more to the IRS, not less.👨‍⚖️ Clinton Donnelly, founder of CryptoTaxAudit and known as the “Crypto Tax Fixer,” explains why this bill matters and how it compares to current IRS rules for mining and staking. Using a $10K mining example, he shows the surprising difference between taxing coins at the moment you earn them versus when you eventually sell.💼 In this video, you’ll learn:- How the IRS

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00:04:48

Could Trump’s Tariff Plan Replace the IRS Income Tax? 🤔

The Clinton Donnelly Show ·

2025/08/19

Trump proposed that tariffs — collected through a Department of External Revenue — could reduce or even replace the IRS’s reliance on income taxes. In this video, Clinton Donnelly explains how tariffs might bring in $1 trillion per year, why the IRS still collects over $2.5 trillion from income taxes, and whether tariffs alone could realistically fund the U.S. government. Clinton Donnelly, founder of CryptoTaxAudit and known as the Crypto Tax Fixer, breaks down:• How tariffs compare to IRS income

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00:04:08

💵 $5M Citibank Account Closed After $1M Coinbase...

The Clinton Donnelly Show ·

2025/08/15

When Citibank closed a client’s $5 million account after a single Coinbase transfer, it showed the brutal reality of debanking. Donald Trump’s new executive order claims to protect political targets, but does it actually stop banks from shutting down crypto users?In this video, Clinton Donnelly explains:• What debanking is and how it happens• Why Trump’s order doesn’t fix FinCEN’s “high-risk” crypto rules• How global FATF guidance drives anti-crypto banking policies• Why cash laundering is still a

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00:04:13

1099-DA, MiCA & 2025: How New Rules Will Track Every...

The Clinton Donnelly Show ·

2025/08/12

2025 is a turning point for crypto taxation — and the reporting net is tightening. Under the EU MiCA rules and U.S. broker-dealer regulations, exchanges will start sending detailed transaction data, including wallet transfers, to tax authorities. By 2026, the IRS will receive 1099-DA forms for U.S. taxpayers, making it harder than ever to stay under the radar.In this video, Clinton Donnelly breaks down:- What new IRS & EU reporting rules mean for crypto traders- How blockchain graphing analysis

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00:08:14

Crypto Framework 2026 — Bo Hines, IRS, and the Fight...

The Clinton Donnelly Show ·

2025/08/05

Is this the Golden Age of Crypto?Executive Director of Digital Assets Bo Hines shares his policy recommendations to usher in a new era for digital assets — but what’s actually in the framework, and what does it mean for your taxes?In this video, Clinton Donnelly breaks down the newly released Crypto Framework 2026 and how it could reshape IRS oversight, wallet tracking, and staking rules by 2026.What you’ll learn:• Why the wash sale rule is “a tax on stupid” (Clinton’s words)• How staking, mining,

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00:37:23

Are Crypto Gains Tax-Free in Portugal for U.S....

The Clinton Donnelly Show ·

2025/07/29

Are crypto gains tax-free in Portugal for U.S. citizens? Not exactly. 🇺🇸🇵🇹In this video, international tax expert Clinton Donnelly explains how U.S. citizens are taxed on their cryptocurrency—even if they live in Portugal under the NHR regime.✅ Learn:- Whether Portugal taxes crypto gains under NHR- Why U.S. citizens still owe tax on global crypto income- How the IRS treats long-term vs. short-term crypto gains- Real examples of how to report crypto sales from Portugal- The truth behind

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170 results

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