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TAX SZN🤑

Our top Tax Strategy episodes 🎙

Think You Might Owe the IRS in April? 3 (Easy!) Ways to Lower Your Tax Bill

There are a few accounts in the tax-advantaged investing world that allow contributions right up until the tax deadline, making them incredible options for last-minute savings. Listen now.

“High Earner, Not Rich Yet”: Must-Have Hacks for HENRYs and HENRIETTAs

The math is a little bit different for our high earners—here are our favorite tax tips and hacks to keep more money in your pocket for the long term. Listen now.

Deep Dive: Set Yourself Up to Pay No Penalties or Taxes in Early Retirement

We’re covering how much you’d need to save and invest to retire early, and then breaking down how to strategically access those funds for the most optimal tax-free outcomes. Listen to or watch the episode.

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Our Tax System’s Unproductive Love Affair with Capital Gains

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3 Ways to Lower Your Tax Bill in 2025 (and How to Navigate Those Weird Rollover IRA Forms)

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How to Contribute Thousands of Extra Roth Dollars Each Year: The Mega Backdoor Roth IRA [2025]

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In These Tax Brackets? The HSA + High-Deductible Plan Might be Cheaper for You [2025]

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Does the Child Tax Credit Change the Traditional vs. Roth Calculus in 2025?

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Tax-Optimized Investing Strategies for Full-Time Workers with Side Hustles

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How I Organize My Money for a Stress-Free Tax Season

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Is FICA Tax the Key to Solving the Traditional vs. Roth 401(k) Debate Once and for All?

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Over-Contribute to a 401(k)? Here’s What I Did

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Will You be in a Higher Tax Bracket in Retirement? Maybe, But It’s Unlikely

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Accidentally Contributed to a Roth IRA? Don’t Make My Mistake: A Case Study of Errors [2025]

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I Finally Met with a CPA. Here’s What I Learned.

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Should You Convert Your Rollover IRA to Roth?

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Side Hustle Taxes: The (Free) Way I’m Keeping Track of my 1099 and W2 Income Tax

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Why the Taxable Brokerage Account (Almost) Beats the Roth IRA in 2025

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The Ultimate Traditional 401(k) vs. Roth 401(k) Debate: Traditional Wins

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Why the Traditional 401(k) is Almost Definitely the Better Option if You’re Single

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Focus on What You Can Control: Preparing for When Markets Go Down

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How Rich People Legally Avoid Taxes, and You Can, Too [2025]

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How to Optimize Your Taxes for Early Retirement and Save Thousands

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Learn the ins and outs of tax-smart investing

One of the biggest expenses of your life? Taxes.

As you earn more money, investing in a tax-advantaged way becomes a game-changing strategy—our Tax-Smart Investing Masterclass teaches you everything you need to know and includes tools that help you implement your strategy and know exactly how it’s going to impact your tax bill now, and in the future.

Check it out