Podcast Summary: The Stacking Benjamins Show

Episode: The Tax Basics You Should've Learned Years Ago (But Nobody Taught You) SB1768

Date: December 1, 2025
Main Guests: Joe Saul-Sehy (Host), OG (Co-host), Doug (Joe’s Mom’s Neighbor), Hannah Cole (Tax Expert & Author)

Overview

This episode focuses on demystifying taxes for everyday people—especially side hustlers, freelancers, and anyone intimidated by the U.S. tax system. Joe and OG are joined by tax expert Hannah Cole, who delivers a back-to-basics, approachable "taxes 101" session designed for those who feel lost when it comes to the IRS, deductions, business expenses and credits. The discussion highlights key differences between deductions and credits, setting up tax systems for side hustles, when to hire a bookkeeper, and resetting your mindset about financial skills. The episode mixes practical advice with humor and real-life stories, embodying the “fun and functional” tone the Stacking Benjamins Show is known for.

Key Discussion Points & Insights

1. Why Taxes Aren’t as Scary as They Seem (10:19–11:56)

• Hannah Cole debunks the myth that taxes are impossible for regular people to understand, especially those looking to start a side hustle or become self-employed.
  • "The tax code is really there for you. Like, there is no better place to get easy access to the benefits of being a business than the U.S. tax code." (10:49 - Hannah Cole)
• Even very small, garage-based businesses can access significant tax benefits.

2. Mindset About Money & Taxes (12:13–15:54)

• The self-defeating belief that creative people or artists MUST be bad with money is false.
  • "Artists, frankly, because they have to be, they are so resourceful... As soon as you start to believe that yourself, you can make it come true." (13:25 - Hannah Cole)
• Belief in your ability to learn new financial skills—rather than some inborn talent—makes all the difference.

3. What a Tax Return Actually Does: The “Reconciliation” (16:48–19:32)

• The U.S. uses a “pay as you go” tax system.
  • Employees have taxes withheld each paycheck; self-employed people must estimate and pay quarterly.
  • The tax return “settles up” yearly estimates with the actual year’s results.
  • "The whole point of filing a tax return is to reconcile the estimates that we were paying in throughout the current year with the actual once we can do the math once the year is over..." (18:07 - Hannah Cole)
• Not knowing your tax liability mid-year does NOT make you “bad at taxes."

4. Deductions, Credits, and How Write-Offs (Actually) Work (21:31–26:48)

• Common “write-off” misconceptions (helpfully illustrated via a "Schitt’s Creek" clip).
  • The government doesn’t “pay you back” for business purchases; instead, legitimate expenses reduce taxable income.
  • Ordinary and necessary expenses (IRS language) are deductible.
    • “If I earn $1,000 from sunlight tax, but I spend $100 on a microphone... [and more]... those are actually subtracted from my taxable income.” (23:00 - Hannah Cole)
• Difference between deduction and credit:
  • Deductions lower taxable income (lower-strength benefit).
  • Credits are dollar-for-dollar reductions of your tax bill (super-strength).
    • “Tax credits are super valuable.” (26:57 - Hannah Cole)

5. Bookkeeping Basics & Systems for Side Hustlers (27:00–34:39)

• First step: open a separate bank account (does not need to be a formal business account) and, if possible, use a separate card for expenses.
  • “The very best thing that you can do is to just open a separate bank account for your gig, for your side hustle.” (27:15 - Hannah Cole)
• Bookkeeping doesn’t have to be complex:
  • For beginners: use a spreadsheet tracking income and expenses.
  • As income grows: consider bookkeeping software (with professional setup for double-entry systems).
    • “It’s very easy to get turned around... undo[ing] the mess... is way more expensive than just shelling out for a good competent bookkeeper on the front end.” (35:06 - Hannah Cole)

6. Systems for Tax Success (36:19–40:13)

• Three core systems:
  1. Bookkeeping – categorize, tally, and summarize expenses.
  2. Receipt tracking – keep digital or physical records by year; you need these if you're audited.
  3. Tax documents – organize all tax forms for easy access.
  • “Bookkeeping is where you actually say, oh, these three expenses... were supplies... these were professional development.” (37:18 - Hannah Cole)
• Startup Expense Deductions:
  • You can deduct certain expenses before you officially launch, up until you “advertise” your business.
  • “Advertising is like saying, hello world, I'm open. That's the moment your business starts.” (39:14 - Hannah Cole)

7. Managing Quarterly Taxes & Withholding (29:46–33:50 and 31:13–32:26)

• Once your business/side hustle grows, you may be required to make quarterly estimated tax payments to avoid penalties.
  • “If quarterly taxes apply to you... you have to pay quarterly taxes or you'll be assessed a quarterly penalty and daily interest.” (30:58 - Hannah Cole)
• W-2 holders can increase withholding to cover side gig taxes by submitting a new W-4.
• Pro tip: After a windfall (e.g. speaking fee), you can manually submit payment to the IRS right away, not just quarterly.

8. Broader Investing Lessons: Handling Market Panic (49:03–64:35)

• Segment debunks financial panic and market catastrophe clickbait, e.g. “Sell everything!” TikTok.
• Long-term perspective and diversification always win over market timing or panic selling.
  • "What happens in the next six months... in 20 years, Nvidia might not even be a company. Who gives a crap?" (52:20 - OG)
  • "Every time... you were a loser if you tried to guess." (56:58 - Joe Saul-Sehy)
• Hindsight reminders: Even sharp recent corrections (“COVID crash,” 2012, etc.) felt terrifying in the moment, but “panic never wins the day.”
• Emphasizes goals-based planning, risk management, and emotional competence as investor virtues.

Notable Quotes & Memorable Moments

• On artists and money skills:
  • “We're incredible. We're real, like doers, and we make things that are invisible to people suddenly become real... And, yeah, we get kind of fed this line that we're bad at money..." (13:25 – Hannah Cole)
• On what the tax return really does:
  • “…the purpose of a tax return. It’s the reconciliation times where you settle up and make change.” (18:31 – Hannah Cole)
• On the “write-off” myth:
  • “Yeah, it’s when you buy something for your business and the government pays you back for it.” (22:02 – Schitt’s Creek clip via Joe Saul-Sehy)
  • “The government doesn’t pay for your lamp.” (22:23 – Hannah Cole)
• On bookkeeping priorities:
  • “I honestly think [a spreadsheet] is not a bad way to go when your side hustle is pretty sidey, you know, like nice and small.” (34:57 – Hannah Cole)
• On starting to track expenses before you form your business:
  • “A lot of people don’t realize that your business expenses can start before your business starts. There’s a category...called startup expenses.” (38:46 – Hannah Cole)

Timestamps for Important Segments

| Timestamp | Segment | |-----------|---------| | 10:05 | Introduction of Hannah Cole, “Taxes 101 for humans” | | 12:13 | Addressing mindset and financial skills (artist stereotype) | | 16:48 | The purpose of a tax return explained | | 21:31 | Business deductions and the truth about write-offs (plus Schitt's Creek clip) | | 25:58 | Deductions vs Credits clarified | | 27:15 | Bookkeeping basics—separate accounts/cards | | 29:46 | Managing quarterly estimated taxes | | 31:13 | Increasing W2 withholding to manage gig tax liability | | 33:12 | Making manual IRS payments after variable gig income | | 38:46 | Starting to track “startup expenses” before official business launch | | 52:06 | Market bubble talk, Nvidia/AI, why panic is never an investment plan | | 56:58 | Diversification, staying the course, and goal-based investing |

Additional Resources from the Episode

• Hannah Cole’s “Visual Guide to Business Deductions”:
  Available at sunlighttax.com/deductionsguide
• Hannah Cole’s book:
  • Taxes for Humans: Simplify Your Taxes and Change the World When You’re Self-Employed (linked in show notes)
• Mentioned podcast episodes:
  • Sunlight Tax Podcast’s episode on start-up expenses

Tone & Style

The episode maintains the casual, witty, and demystifying spirit that’s the hallmark of Stacking Benjamins. Joe, OG, and Doug blend playful banter with actionable insight, and Hannah Cole brings warmth, encouragement, and practical step-by-step advice—making taxes feel like something any regular person can conquer.

Who Should Listen & Why

• Side hustlers, freelancers, and new entrepreneurs: A rare, judgment-free walkthrough of the essentials
• Anyone scared of the IRS or “bad at taxes”: Mindset shifts and approachable explanations
• Listeners bored by financial jargon: Entertaining, lighthearted, and never condescending

Summary

This episode is a must-listen for anyone who wants a clear, confidence-boosting crash course in taxes—especially if you’re venturing into self-employment or still feel like the IRS code is a foreign language. With concrete advice, myth-busting, and encouragement from a tax expert who gets what it’s like to be “bad with numbers”—plus the ever-present SB laughs and pop-culture moments—you’ll walk away understanding how tax returns work, what actually counts as a “write-off,” why credits matter more than most realize, and how to keep the IRS from ruining your side hustle dreams.

"You don't have to memorize the Internal Revenue Code. Nobody does."
— Hannah Cole (15:54)

"Every time you tried to guess, you were a loser."
— Joe Saul-Sehy (56:58)