The Stacking Benjamins Show

Episode: Stop Leaving Money on the Table at Tax Time (SB1798)

Date: February 2, 2026
Hosts: Joe Saul-Sehy, OG, Doug

Episode Overview

This lighthearted but informative episode of The Stacking Benjamins Show dives into the essential tax changes for 2026 that could mean more money back for listeners at tax time. Joe, OG, and Doug discuss seven new tax rules (primarily highlighted in a recent Wall Street Journal article), offer practical tax planning tips, and keep the conversation entertaining with trivia, personal stories, and their signature banter—all aimed at helping listeners "stack more Benjamins."
Tone: Friendly, playful, jargon-light, educational.

Key Discussion Points and Insights

1. Tax Season Philosophy & Prep Mindset

• Start Early: OG stresses being ahead on tax prep to reduce stress and avoid last minute filings, noting the limited availability of CPAs come March and April.
  • Quote: "You still have to pay in April... For the vast majority of people, extending just kicks the can down the road. Now you just ruined your summer." (04:13–04:35)
• Professional Advantage: Early filers get priority attention from their tax advisors.
  • Quote: "If you're one of the first people there, you get your tax person when they're fresh, when they're excited." — Joe (05:01)

2. The 7 Big Tax Changes for 2026

Sourced from Wall Street Journal (Ashley Ebling and Richard Rubin)

1. Increased Standard Deduction

• Single: Up $750 to $15,750
• Married Filing Jointly: $31,500
• 65+ Additional Deduction: $2,000; New Senior Deduction: $6,000 (for next three years)
• Quote: "There's a few dollars. This one's going to be easy... your tax software is going to do this one for you." — Joe (09:54)
• Note: Most filers will find tax prep simpler; fewer need to itemize.

2. Expanded SALT (State and Local Tax) Deduction

• Raised Limit: Up to $40,000 (phased out for higher incomes: phases down starting at $500K AGI; at $600K+, the deduction cap reverts to $10,000).
• Quote: "They changed it, and now you can go up to 40k, but it’s still limited by income... if you're in that sweet spot... you get a little bit of a benefit there." — OG (11:38–12:47)

3. New Tips Income Deduction

• Up to $25,000 for qualifying service industry workers.
• Important Criteria: Income must be legitimately classified as tip income (not mandatory service charges or unqualified reclassifications).
• Quote: "If you don't work in a tip business, don't try to make part of your income, tip income. And if you do, get some pro help." — OG (15:04–15:50)
• Online Creators/Patreon angle: Potential for creators to use this, but must tread carefully.

4. Overtime Pay Deduction

• Up to $12,500 for eligible workers.
• Requires precise classification; not all overtime will count.

5. Auto Loan Interest Deduction

• Deduct up to $10,000 in new car loan interest.
• Quote: "Have you looked at the price of a new car recently? ...All those things now." — OG (16:34)

6. Increased Child Tax Credit

• Maximum increased by $200 per child.

7. Charitable Giving Adjustments (previewed, expanded later)

• New Floor (2026): Deductions only count once charitable contributions exceed 0.5% of AGI.
• Cap: Itemized deductions (for high income) capped at 35% of AGI.

3. Additional Tax Planning Strategies & Smart Moves [Second Segment]

Based on an Ally Text article, the hosts discuss:

1. Retirement Account Maximization

• Prioritize employer match; increase contributions with raises.

2. Tax-Loss Harvesting

• Not as important for younger/smaller investors except with crypto (no wash sale rules yet), but can offset gains or up to $3K of ordinary income.

3. Health Savings Accounts (HSAs)

• Triple tax advantage: deduct contributions, grow tax-free, tax-free distributions for healthcare.
• Use for now or later (“don’t let perfect be the enemy of good”).
• Quote: "If you're somebody who just has an HSA and you're using it tax free to pay for your stuff... Still beautiful." — Joe (35:09)

4. Strategic Tax Bracket Management

• Diversify buckets (pre-tax, Roth, brokerage) for flexibility in retirement.
• Don't get caught up in “all Roth vs. all pre-tax” arguments; unknowns make flexibility king.
• Quote: “We don’t know where tax brackets are going to go... Give yourself the flexibility.” — Joe (38:34)

5. Charitable Giving Strategies (detailed)

• New limits/floors make timing and batching gifts more important.
• Standard deduction minimizers: consider giving larger amounts less often to maximize deductions.

6. 529 Plan Optimization

• Use for state tax deduction and tax-free growth/withdrawals.

7. Income Timing & Deferral

• Recognize and manage income (and deductions) in optimal years.

8. Asset Location Optimization

• Place tax-inefficient investments in sheltered accounts; tax-efficient funds in taxable accounts.

4. Notable Quotes & Memorable Moments

• On tax procrastination:
  "Now you just ruined your summer. Because it can be like—kids start going back to school and you're going, ‘Oh crap, I still do my tax!’" — OG (04:13)

• On the new purpose-driven auto loan deduction:
  "Which to OG to your point, could be one tenth of the interest that you paid on that high-interest loan." — Joe (18:24)

• On hotel rooms and personal boundaries:
  "I would rather sit in a hotel lobby and drink coffee all night than share a room with another human being—not even my kids. I'll sleep in the car." — OG (28:31)

• On the never-ending Roth vs. pre-tax debate:
  "This is an idiotic argument because we don't know where tax brackets are going to go... Give yourself flexibility." — Joe (38:15)

Timestamps for Key Segments

| Segment | Timestamp | |---------------------------------------------------- |-----------| | Opening banter and tax preparation mindset | 00:00–06:01 | | Seven Big Tax Changes for 2026 | 09:18–20:57 | | Tips Income and Overtime Deductions | 13:54–16:34 | | Auto Loan Deduction and Car Talk | 16:34–20:57 | | Tax Planning Smart Moves (Retirement, HSA, etc.) | 31:03–42:14 | | Debating Roth vs. Pre-tax and Flexibility | 37:38–39:35 | | Charitable Deduction Changes | 39:35–40:50 | | Personal finance trivia and TikTok minute | 26:10–31:01 | | Seattle vs. Boston Super Bowl meetup plug | 45:31–49:13 | | Three big to-dos and closing jokes | 49:13–51:50 |

Fun & Notable Moments

• Willie Nelson IRS Story:
  Story about Willie Nelson settling $16.7M in back taxes. Quips about tax shelters:
  “Where do homeless accountants live? In tax shelters, right?” — Doug (50:01)

• Movie Theater Sticker Shock:
  A humorous bit about someone spending nearly $290 at the movies—including 28 hot dogs—as a tongue-in-cheek take on inflation and lifestyle creep. (42:14–44:54)

• Hotel Room Banter:
  Running joke about OG absolutely refusing to share a hotel room, even with friends or family, leading to a lively TikTok discussion segment. (28:31–30:50)

Actionable Takeaways (Doug’s “Big Three”)

1. Review Tax Changes:
   Tax rules and your life change every year—review both and grab opportunities for bigger refunds.

2. Be Strategic with Flexibility:
   Don't obsess over precision (e.g., all Roth vs. all pre-tax). Build flexibility and adaptability into your financial plan.

3. Check the Updated Tax Guide:
   Stacking Benjamins’ monthly-updated tax guide is available at stackingbenjamins.com/guides.

Resources Mentioned

• Show Notes & Tax Guide
• Wall Street Journal Tax Article (if you subscribe)
• [Ally Text Tax Optimization Article]
• OG and Anna’s Financial Planning Team

Closing Thoughts

Combining solid, practical tax tips with humor and banter, Joe, OG, and Doug help make tax season less intimidating—and maybe even a little fun. Listeners are reminded to stay adaptable, maximize their deductions, and always check with qualified professionals when it comes to nuanced or complex tax situations.

Final Joke:
"There are three types of accountants: those who can count and those who can’t." — Doug (50:22)

—Summary prepared for listeners who want to keep more money in their pocket this tax season and enjoy the ride doing it!