158. Before You Pay Your Taxes by Credit Card: Avoid These Points-Killing Mistakes
Point Me To First Class
Devon Gimbel MD
4.9 • 1.2K Ratings
🗓️ 9 March 2026
⏱️ 30 minutes
🧾️ Download transcript
Summary
If you're planning to pay taxes by credit card this year, now is the time to set up your strategy—not the week before tax day.
Every year, I see posts from people whose tax payment plans went sideways at the last minute. A declined charge, payments that didn't post, a payment that went to the wrong card—these problems are stressful on their own, but they're especially problematic when you're troubleshooting them on tax day. Listen in as I walk through the five key considerations for turning tax payments into points stress-free, plus the specific pitfalls that trip people up if they don't know to expect them.
I cover everything from creating your most powerful points-earning plan and timing your credit card applications correctly, to navigating the logistics of payment platforms and avoiding the PayPal mistakes that cost people thousands of points. I also share what you need to know about using Amex cards for tax payments, including why you should never use the virtual card number and how to access spend bonuses that make large tax bills even more lucrative for points earning.
Whether you're paying a few thousand or multiple six figures in taxes, this episode gives you the framework to maximize your points while avoiding the mistakes that derail so many people's tax payment strategies each year.
Get full show notes and transcript: https://pointmetofirstclass.com/tax-payments-points-strategy
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Transcript
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| 0:00.0 | Welcome to Point Me to First Class, the only show for employed professionals, entrepreneurs, and business owners who are looking to optimize their higher than average expenses to travel the world. |
| 0:10.7 | I'm your host, Devin Gimble, and I believe that your expenses are your greatest untapped asset, if you know how to leverage them. |
| 0:17.8 | Ready to dive into the world of credit card points and miles so you can travel |
| 0:20.9 | more, travel better, and travel often. Let's get started. Hey, everyone, welcome back to the podcast. I hope |
| 0:32.7 | your week is off to a great start. If you're listening to this episode in real time, it's early March, |
| 0:38.6 | which means that it's almost tax time for those of us based in the U.S. or required to pay taxes |
| 0:44.4 | in the U.S. And leveraging tax payments to earn points is one of my favorite ways to turn expenses, |
| 0:51.2 | especially what can be a significant expense for many of us into travel when |
| 0:55.7 | strategized correctly. I love this topic so much that it is not the first time that I've talked |
| 1:00.5 | about paying taxes by credit card on the podcast. But if you're brand new to considering |
| 1:05.1 | paying your taxes using a rewards card or cards in order to earn points, I've covered |
| 1:10.8 | the basics of what you need to know |
| 1:12.7 | to get started all the way back in episodes number six and number seven of the podcast. So you should |
| 1:18.6 | check out these episodes, especially if you haven't paid taxes by credit card yet. And you want to |
| 1:24.4 | hear about why this can be such a great points earning opportunity, |
| 1:28.2 | how to do the math so you can determine for yourself if the points earned from paying taxes |
| 1:33.1 | with a credit card or multiple credit cards justifies the processing fee you'll incur in order to do so |
| 1:39.2 | and understand how to choose the most beneficial rewards card or cards for your tax payments to |
| 1:45.4 | maximize your points earning. For a more advanced discussion and update on the payment |
| 1:50.0 | platforms available for federal tax payments and how to navigate using those to earn points |
| 1:55.8 | for tax payments, whether you're paying by personal credit card or business credit card, |
| 2:00.3 | check out last year's |
... |
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