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The Stacking Benjamins Show

The Best Tax Prep Software of 2025 (SB1655)

The Stacking Benjamins Show

Joe Saul-Sehy | Cumulus Podcast Network

Investing, Business, Self-improvement, Education

4.2 • 1.9K Ratings

🗓️ 12 March 2025

⏱️ 71 minutes

🧾️ Download transcript

Summary

Choosing the Best Tax Software for Your Needs 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! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Transcript

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0:00.0

And now we're from our sponsors at Betterment.

0:02.6

When investing your money starts to feel like a second job,

0:06.1

Betterment steps in with a little work life balance.

0:09.1

They're an automated investing and savings app, which means they do the work.

0:13.4

While they build, manage your portfolio, you build manage weekend plans.

0:17.8

While they make it easy to invest for what matters. You just get to enjoy what matters.

0:23.3

Their automated tools, simplify the complex and put your money to work, optimizing day

0:27.8

after day and again and again.

0:30.0

So go ahead.

0:31.2

Take your time to rest and recharge because while your money doesn't need a work life balance,

0:35.9

you do.

0:37.0

Make your money hustle with Betterment.

0:38.8

Get started at Betterment.com.

0:40.6

That's B-E-T-T-E-R-M-E-N-T-com.

0:44.4

Investing involves risk, performance not guaranteed.

0:47.5

Stackers are you working on your debt plan and you're trying to lower your interest rates.

0:51.4

Navy Federal Credit Union is offering a 0% intro APR on credit card balance

0:56.5

transfers for 12 months and get $250 when you spend $2,500 in your first 90 days on a cash

1:03.6

rewards or cash rewards plus credit card. NavyFederal.org, our members are the mission.

1:10.3

Navy Federal is insured by NCUA after the intro rate expires, variable APRs are 14.9% to 18%.

1:17.6

Based on creditworthiness, rates are subject to change.

1:20.4

ATM fees for cash advances are up to $1 at non-Navy federal ATMs.

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