The Stacking Benjamins Show - Episode: "The Best Tax Prep Software of 2025 (SB1655)"
Release Date: March 12, 2025
Hosts: Joe Saul-Sehy, OG
Guest: Eric Rosenberg from The College Investor
Podcast Network: Cumulus Podcast Network
Introduction
In this episode of The Stacking Benjamins Show, hosts Joe Saul-Sehy and OG delve into the realm of tax preparation software, aiming to guide listeners through the myriad of options available in 2025. Joined by Eric Rosenberg from The College Investor, the trio provides expert insights to help listeners choose the best tax software tailored to their individual financial situations.
Tax Preparation Software: Navigating the Options
Guest Introduction: Eric Rosenberg
Eric Rosenberg, a seasoned analyst from The College Investor, spearheads the discussion on tax software. With extensive experience in financial research, Eric brings a nuanced perspective to the table.
Choosing Between Software and Professionals
Eric begins by addressing a fundamental question: "Who should use tax software versus who should employ a professional accountant?" [12:17]
Eric Rosenberg: "If you're comfortable using a computer, navigating online banking, and handling emails, most modern tax software can work for you. However, if you're not tech-savvy or have highly complex financial situations, consulting an in-person accountant might be the better route."
Best Overall Tax Software: FreeTax USA
Challenging the long-standing dominance of TurboTax, Eric introduces FreeTax USA as the top choice for 2025. This software stands out for its affordability and transparency.
Eric Rosenberg: "We picked FreeTax USA as our top overall. While it's not entirely free for everyone, it's significantly cheaper than TurboTax and offers excellent value for those with straightforward tax situations."
TurboTax: Still a Top Contender but with Caveats
Despite the introduction of new competitors, TurboTax remains a prominent player. However, Eric points out issues related to pricing transparency.
Eric Rosenberg: "TurboTax offers a slick, user-friendly experience with features like automatic imports from banks and investment firms. However, their pricing can be unclear, often leading to unexpected fees at the end of the filing process."
Runner-Up: H&R Block
H&R Block secures the second spot, praised for its balance between ease of use and cost-effectiveness. It also offers unique features like PDF imports, enhancing its functionality.
Eric Rosenberg: "H&R Block is nearly as easy to use as TurboTax but typically costs a bit less. They also allow users to drag and drop PDFs from investment companies, which many competitors don't offer."
Special Mention: TaxSlayer and CashApp Taxes
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TaxSlayer is highlighted for specific user groups like landlords, offering reasonable pricing and robust features tailored to real estate investors.
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CashApp Taxes emerges as a favorite for side hustlers due to its affordability and essential features without the premium price tag.
Eric Rosenberg: "For landlords, TaxSlayer provides optimized tools to handle property-related deductions effectively. Meanwhile, CashApp Taxes is ideal for side hustlers who need to manage multiple income streams without incurring high costs."
Crypto and Complex Tax Situations
For crypto enthusiasts and active traders, traditional tax software might fall short. Eric recommends specialized crypto tax software like Koinly and CoinTracker to handle the intricacies of cryptocurrency transactions.
Eric Rosenberg: "If you're deep into crypto trading with numerous transactions, using intermediaries like Koinly can simplify the process. These tools generate the necessary tax forms that can then be imported into your main tax software."
Notable Quotes:
- Joe Saul-Sehy [08:38]: "If you’re a stacking Benjamin’s listener, you’re probably in tune with your money more than the average person. So you’re probably best suited to go with an online option."
- Eric Rosenberg [15:09]: "FreeTax USA is a great choice if you have relatively straightforward taxes and want to do it the cheapest way possible while still paying for a more premium service."
Headlines: The US Stock Market's Big Problem
Transitioning from tax software, the hosts discuss a concerning headline from the Wall Street Journal by Spencer Jacob, titled "Stocks have a big expensive problem."
Key Points:
- The US stock market, representing a mere 25% of the global economy and 4% of the world’s population, dominates two-thirds of the global stock market value.
- Historically, there has been a high correlation (0.83) between the S&P 500 and the MSCI EAFE index of non-US developed stocks. However, this correlation has plummeted to 0.54 over the past 100 trading days.
- This breakdown in correlation may signal an impending investment upheaval, potentially leading to poor returns for large US stocks in the coming years.
Discussion Insights:
- OG [50:10]: "Over the past three whole months, your long-term decision making should be based on the last 100 trading days."
- Joe Saul-Sehy [52:05]: "We’ve seen stock market declines and increased volatility. The hard part is trying to guess when the overperformance ends and when the next rotation begins."
Investment Strategies:
- Diversification remains crucial. Relying solely on large US tech stocks, despite their recent success, may not be sustainable.
- Sector rotation is inevitable, where underperforming sectors catch up, emphasizing the importance of a balanced portfolio.
OG [54:32]: "The best course of action is to be diversified, rebalance on your birthday once a year, and don’t pay attention to it. Life will go on, and you’ll be all right."
Notable Quotes:
- Joe Saul-Sehy [55:19]: "The predicted annual return for US large growth stocks is 1.8%, which would be negative after inflation. Non-US developed markets are expected to return 10%, and emerging markets value at 10.5%."
Other Segments
Trivia with Doug
Doug adds a light-hearted trivia segment, engaging listeners with interesting facts and humorous interactions:
Doug [38:43]: "What book was released on today's date way back in 1957? And until I get back, you're going to sit, sit, sit, sit."
TikTok Minute: Crypto Rug Pulls
The hosts showcase a TikTok-style segment highlighting the dangers of crypto rug pulls—schemes where creators scam investors by creating trendy meme coins and abruptly selling their holdings for profit.
TikTok Video Segment [56:21]: Explains how rug pullers use trending news and memes to pump up meme coins, attracting unsuspecting investors who then face significant losses.
Joe Saul-Sehy [57:53]: "It's really sad. People are losing tons of cash because there's professionals behind these scams."
Listener Stories and Community Engagement
Listener Story: Manoj’s Dryer Purchase
Joe shares a heartwarming story from listener Manoj, a retired dental hygienist who found a used dryer through Nextdoor and discovered it was owned by a fellow Stacking Benjamins meetup attendee, Sterling Cog. This incident underscores the community-driven spirit of the podcast.
Doug [59:22]: "We are getting people together at our meetups. People Helping People, making the friendships blossom, and stackers saving stackers money."
Conclusion
The episode wraps up with key takeaways and actionable advice:
- Choose Tax Software Based on Your Situation: Evaluate your financial complexity and tech-savviness before selecting a tax preparation tool.
- Beware of Crypto Scams: Stay informed about the tactics used in crypto rug pulls to protect your investments.
- Diversify Your Investment Portfolio: Avoid over-reliance on any single market or sector to mitigate potential risks.
Doug [62:17]: "Choose tax software based on your situation, not based on commercials or on which one you think might be best. And be cautious of crypto rug pulls—they’re making millions at your expense."
Final Words:
Joe encourages listeners to visit StackingBenjamins.com for detailed show notes and resources, including Eric Rosenberg’s tax guide.
Joe Saul-Sehy [63:49]: "Before making any financial decisions, speak with a real financial advisor. This show is for entertainment purposes only."
Notable Quotes with Timestamps:
- Eric Rosenberg [12:17]: "If you're comfortable using a computer, most modern tax software can work for you."
- Eric Rosenberg [15:09]: "FreeTax USA is a great choice if you have relatively straightforward taxes."
- OG [50:10]: "Over the past three whole months, your long-term decision making should be based on the last 100 trading days."
- Joe Saul-Sehy [52:05]: "The hard part is trying to guess when the overperformance ends and when the next rotation begins."
- Joe Saul-Sehy [55:19]: "The predicted annual return for US large growth stocks is 1.8%."
- Eric Rosenberg [17:52]: "Free Tax USA feels easier to remember and is a good choice if you have relatively straightforward taxes."
- OG [57:25]: "Rug Pull is a powerful but simple way scams are executed in crypto."
For more insights and detailed discussions from this episode, visit StackingBenjamins.com and explore their comprehensive tax guide tailored to help you navigate tax season with ease.