The Stacking Benjamins Show
Episode: Best Tax Software for 2026 (And Handling Market Drops) SB1805
Date: February 18, 2026
Guests: Robert Farrington (The College Investor)
Hosts: Joe Saul-Sehy, OG
Tone: Fun, approachable, conversational
Episode Overview
This episode dives deep into two hot personal finance topics for early 2026:
- Choosing the Best Tax Software for 2025 Returns – Featuring expert insights from Robert Farrington of The College Investor, who annually tests and rates all major filing platforms.
- Market Drops in Precious Metals & Crypto – Joe and OG dissect recent volatility in gold, silver, and crypto, discussing the nature of speculation, risk, and misinformation in the investment world.
The playful banter and lighthearted segments typical of Stacking Benjamins are preserved, but the core of the episode is a practical, expert-backed breakdown on tax prep solutions and some valuable reality checks for investors.
Key Discussion Points & Insights
1. How The College Investor Tests Tax Software
- [05:22] Joe welcomes Robert Farrington back to the show to discuss what goes into their detailed annual tax software comparison.
- Robert and his team run multiple mock tax returns through over a dozen tax software platforms, much like a financial "Consumer Reports."
"You mean you don't like filing mock tax returns across a dozen software programs? Like, come on, that's the best thing to do in November and December." – Robert [05:44]
- They consider common and complex tax situations: simple filings, investors, side hustlers, landlords, and student loan borrowers.
2. Best Overall Tax Software Picks
[06:48]
"Is FreeTax USA your overall champion in 2026?" – Joe
"Yeah, FreeTax USA is where it's at. It's our overall pick for the best tax software. Covers the most robust circumstances. It's a good just all-around pick." – Robert [06:48]
Why FreeTax USA?
- Free for federal filings; lower cost for states ($15.99).
- Handles a broad range of scenarios (employment income, investments, side hustles) with user-friendly data entry.
Important Caveat
- FreeTax USA might not be best for every situation (e.g., frequent traders, those requiring multiple state filings, or highly specialized needs).
"While FreeTax USA is the good all-around pick, you might not be an all-around situation." – Robert [08:09]
3. The Competition: Runners-Up
[08:41-10:12]
- TurboTax
- Still a leader—especially for investors and people who value access to in-person help (new this year: physical TurboTax offices in select cities).
- Integrates online, virtual, and in-person support, but at a higher price point.
-
"You can start online...call...get virtual support, or...go into the store and get a real person to talk to." – Robert [09:13]
- Increasing transparency in pricing, but customers’ lack of tax knowledge can still trigger unexpected upcharges.
- H&R Block
- Similar multifunnel experience as TurboTax, with robust human support. Their pricing clarity has improved.
- The confusion often lies with users not knowing what tax forms they need, leading to surprise upsells.
4. Best Truly Free Tax Filing Options
[12:13]
-
Cash App Taxes
- Best for "free file" category, offering both federal and state for $0 (if you qualify).
- Well-suited to simple situations (like single W2), but not for multi-state filers or those with K-1s or other complications.
- [13:22] Audit Defense is available as an add-on.
- Revenue model: Getting users into Cash App banking products—though not required.
"They're trying to get you into their banking products...of course they are highly encouraging for you to use it." – Robert [14:18]
-
Chime – New runner-up; also robust and user-friendly, but with limitations like Cash App (no multi-state support, limited credits).
"Chime came out of the gate with a really great product and not very many issues at all that I saw." – Robert [15:34]
5. Best Software by Specific Use Case
[16:14–18:39]
- Student Loan Borrowers:
- TaxSlayer (classic tier): Most features at lowest price, simple to use. "[TaxSlayer] consistently improved year after year."
- Cash App Taxes can work for very simple cases.
- Investors & Crypto Traders:
- TurboTax: Top for active traders due to seamless brokerage and crypto exchange integrations (can import many transactions, Form 8949 uploads, Coinbase, etc.).
- H&R Block is a reliable backup but TurboTax has the edge on integrations.
- Important new development: The new Form 1099-DA (Digital Asset) means the IRS is now more aggressively tracking crypto, so meticulous reporting is extra important.
"Every stacker...this is the first year that we're getting the new 1099 DA...make sure you're reporting that stuff accurately." – Robert [22:05]
- Landlords:
- TaxSlayer: Handles depreciation and Schedule E, best value for rental property owners.
- Side Hustles (non-real estate):
- For simple gig work: Cash App Taxes
- For heavier/complex needs: TaxSlayer (classic tier); fees are much less than TurboTax/H&R Block’s self-employed levels.
- Tracking advice: Use apps like Everlance to monitor mileage and expenses as you go, not at tax time.
"If you’re driving...Everlance is a cool tool...tracks all your mileage." – Robert [25:51]
6. When to Get Professional Help?
[27:25]
- FreeTax USA offers affordable pro support ($45), and TaxSlayer’s premium tiers offer on-demand assistance for growing businesses.
- [28:09] For truly complex or multi-state tax situations, or businesses generating significant revenue, consider working with a local CPA for personalized planning—not just data entry.
"Filing your taxes is basically data entry...But there is tax planning, and this is where you can meet with an accountant or CPA..." – Robert [28:09]
7. Handling Precious Metals and Crypto Market Drops
[34:06] Headline Segment
Joe and OG recount a recent historic drop in precious metals and crypto:
- Silver fell over 25%, gold saw its largest daily drop since the 1980s, and crypto tumbled.
- Joe links the drop to Federal Reserve news and broader market volatility; OG emphasizes the inherent volatility of assets that produce no earnings, with value driven by speculation.
"Prices of things that don't produce any value are going to be much more volatile..." – OG [35:31]
Lessons for Investors:
- FOMO and recency bias drive many to chase asset classes after the gains are gone.
"The reason you're attracted to something is because all of a sudden it looks cool. All of a sudden it's up a whole bunch." – OG [37:27]
- Concentrating in single sectors or assets increases the range (and risk) of outcomes.
- Long-term, gold and crypto are highly volatile; don't confuse short-term spikes as reliable emergency fund material.
"You don't want...if somebody had gold as their emergency fund...and then my gold dropped through the floor." – Joe [42:18]
8. Misinformation in Financial Media: AI Deepfake Warnings
[43:51ff]
- Joe highlights a widely-circulated (phony) TikTok video featuring an AI-generated Peter Lynch "explaining" silver market manipulation (e.g., JP Morgan, CME data).
- The voice and persona are fake, yet the delivery and production are highly convincing.
- OG and Joe stress the danger of such content:
"Watch out for AI people. It's ugly." – Joe [47:16]
"We will never ask you to invest in a venture that we're doing together. That's not a thing that we will do or have done." – OG [49:18]
Notable Quotes & Memorable Moments
- [06:48] "FreeTax USA is where it's at. It's our overall pick for the best tax software." – Robert
- [10:40] "Americans still aren't transparent on what tax forms they need when they start the process." – Robert
- [13:22] "If you get a letter from the IRS and you need assistance...that’s what [Audit Defense] is for." – Robert
- [22:05] "This is the first year that we're getting the new 1099 DA, a digital asset 1099...make sure you're reporting that stuff accurately." – Robert
- [37:27] "The reason you're attracted to something is because all of a sudden it looks cool..." – OG
- [47:16] "Watch out for AI people. It's ugly." – Joe
Timestamps for Key Segments
- [05:22] Start of Tax Software Deep Dive (Robert Farrington joins)
- [06:48] FreeTax USA crowned best overall
- [08:41] TurboTax and H&R Block as runners-up
- [12:13] Best Free File: Cash App Taxes explained
- [16:14] Best for Student Loan borrowers (TaxSlayer)
- [18:39] Best for Investors and Crypto (TurboTax, H&R Block)
- [22:05] New developments: Form 1099-DA for crypto
- [23:41] Best for Landlords and Side Hustlers
- [27:25] When to pay for professional help
- [34:06] Headline: Precious metals and crypto market volatility
- [43:51] AI-generated Peter Lynch and misinformation warning
Actionable Takeaways
- Don’t default to last year’s tax software; match your needs (investments, rental property, student loans, state returns) to the best fit.
- Truly free options are best for uncomplicated filings; more complex returns require more robust—and sometimes pricier—platforms.
- For heavy investing or crypto activity, integration/import features of TurboTax (or H&R Block) are worth the premium.
- Track deductible expenses all year if you have a side hustle.
- Use caution when researching market events online—deepfakes and AI-powered misinformation abound.
- Diversification still matters—don’t chase “hot” asset classes after the run-up.
Resources and Further Reading
- Full tax software deep dive: TheCollegeInvestor.com
- Episode show notes and links: StackingBenjamins.com
- Report AI-generated financial deepfakes to social media platforms.
For more lighthearted financial wisdom, tax guidance, and a break from financial doomscrolling, catch the next episode in Joe’s mom’s basement!