The Best Tax Prep Software of 2025 (SB1655)
The Stacking Benjamins Show
Joe Saul-Sehy and Josh ‘OG’ Bannerman, CFP
4.4 • 2K Ratings
🗓️ 12 March 2025
⏱️ 64 minutes
🧾️ Download transcript
Summary
Tax season is here—so which software should you trust with your hard-earned Benjamins? Eric Rosenberg from The College Investor joins us to break down the best options, whether you're a side hustler, crypto investor, or just looking for a free filing solution.
- Will TurboTax take the crown again, or is there a surprise champ? You might be shocked by which software stands out this year.
- H&R Block’s virtual tax prep – If you want real humans to double-check your numbers, this might be your go-to.
- Which tax software works best for unique situations – Side gigs, stock trading, crypto investments… different situations call for different solutions.
- Navigating Tax Day without the stress – Tips to avoid last-minute panic and make sure you’re not leaving money on the table.
- Crypto scams and meme coins – Because tax season isn’t stressful enough without adding that mess into the mix.
Meanwhile, Doug serves up world-famous trivia with a nod to classic children’s books, beloved authors, and sing-song rhymes. Plus, we take a detour into sector betting, market trends, and—of course—movie recommendations.
If tax season feels overwhelming, this episode breaks it down, keeps it light, and helps you pick the right software to file with confidence.
Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201
Enjoy!
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Transcript
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| 0:00.0 | At some point far in the future, historians will probably ask, what was daily life like in the early 21st century? |
| 0:09.7 | Well, one thing we know for sure. |
| 0:13.1 | Nobody will ever point to these two clowns and say, this was how you should have been stacking Benjamins. |
| 0:24.1 | Live! This was how you should have been Stacking Benjamin's. Live from Joe's mom's basement, it's the Stacking Benjamin's show. |
| 0:43.7 | I'm Joe's Mom's Neighbor, and we have a phrase here, riffing off Game of Thrones. |
| 0:45.4 | Tax Day is coming. |
| 0:48.1 | But don't you worry one little bit. |
| 0:49.3 | I think I nailed that, didn't I? |
| 0:52.0 | But don't you worry one little bit. I love the guy that stops the open part way through to pat himself on the back. |
| 0:55.9 | Man, I got that. |
| 0:57.4 | I mean, I rehearsed and I rehearsed and I rehearsed. |
| 1:00.1 | Like, yes, you're so good. |
| 1:01.9 | You're so good. |
| 1:03.1 | Don't you worry, listener. |
| 1:05.1 | Because today we're going to dive into all the good, bad, and ugly when it comes to software programs with a man from |
| 1:12.3 | the team that did the research so you don't have to from the college investor, Eric Rosenberg. |
| 1:18.6 | In our headlines, Wall Street Journal writer Spencer Jacob says that stocks have a big expensive |
| 1:24.6 | problem. Do we agree? We'll share and help you navigate your portfolio. |
| 1:30.2 | And of course I'll swoop in with some incredible trivia. |
| 1:33.6 | There I am pat myself in the back again. |
| 1:35.6 | That's sure to amaze your friends. |
| 1:38.2 | And now here are two guys who believe the only thing better than a good laugh is a better bank account. |
... |
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