The Personal Finance Podcast
Host: Andrew Giancola
Episode Title: 10 Tax Moves Everyone Should Review Each Year
Date: March 4, 2026

Episode Overview

Andrew Giancola breaks down 10 essential tax strategies everyone should review annually, aimed at both W2 employees and business owners. The focus: actionable ways to save money on taxes, optimize investment strategies, adjust withholdings, and maximize deductions for both immediate and long-term wealth building.

Andrew uses a friendly, empowering tone as he demystifies key tax tools, provides real-life examples, and offers practical checklists. The episode is rich with detail, memorable quotes, and step-by-step guidance suitable for listeners at various stages of their financial journey.

1. Maximize Tax-Advantaged Accounts

[08:34]

• 401(k) & Similar Accounts:

  • Contribution limit in 2026 is $24,500 for traditional 401(k)s.
  • Options also include 457 and 403(b) plans.
  • “If you are in the 30% tax bracket or above, this is a definite consideration for you because you need to reduce your overall taxable income.” — Andrew [11:08]

• Solo 401(k) for the Self-Employed:

  • Up to $72,000 total contribution (including employer portion) in 2026.
  • Requires no employees; otherwise, consider SEP or SIMPLE IRAs.

• Roth Accounts:

  • Roth 401(k) and Roth IRA allow after-tax contributions and tax-free growth.
  • 2026 Roth IRA limit: $7,500.
  • No required minimum distributions (RMDs) for Roth IRAs.
  • “The more that you can get in a Roth, it is absolutely incredible what you can do.” — Andrew [15:41]

• Strategic Order of Investing:

  1. Capture employer 401(k) match
  2. Fund HSA (if eligible)
  3. Fund Roth IRA/401(k)
  4. Max out 401(k)

2. Adjust Your Withholding

[18:36]

• Avoid Giving the Government a Free Loan:

  • A big tax refund means you overpaid taxes throughout the year.
  • “Every time you get a tax return, you actually overpaid the government and you gave them a free loan.” — Andrew [19:13]

• W-4 Form:

  • Adjust to tailor federal tax withheld from your paycheck.
  • More withheld = bigger refund; less withheld = bigger paycheck now.
  • Review W-4 after major life events (raise, marriage, child, buying a house, new side business) or annually.

• IRS Tax Withholding Estimator:

  • Free tool to estimate proper withholding.

3. Tax Loss Harvesting

[28:11]

• What It Is:

  • Selling investments at a loss in taxable accounts to offset capital gains and reduce tax bill.

• Rules and Tips:

  • Short-term losses offset short-term gains; long-term losses offset long-term gains.
  • Deduct up to $3,000 of excess losses against ordinary income; carry over remainder to future years.
  • “Let losses help you with your tax bill, not just hurt you.” — Andrew [30:12]
  • Beware the wash-sale rule: cannot repurchase the same or substantially identical security within 30 days.

• Crypto Spotlight:

  • As of now, no wash-sale rules for crypto, but this may change—consult a CPA.

4. Review Roth Conversion Opportunities

[36:46]

• What Is a Roth Conversion:

  • Moving funds from a traditional IRA/401(k) to a Roth IRA, paying tax now for tax-free growth later.

• When Does It Make Sense:

  • Years of unusually low income.
  • Before income-boosting events or RMD age.
  • If you expect to move to a higher-tax state or anticipate tax rate increases.
  • During market declines (convert at lower balances).

• When to Avoid:

  • If already in a high tax bracket, or lacking cash to pay taxes on conversion.

• Quote:

  • "Strategically a CPA is going to help you tremendously when you do this." — Andrew [41:54]

5. Check Your Capital Gains Exposure

[43:12]

• Short-Term vs. Long-Term:

  • Short-term gains (assets held <1 year): taxed as ordinary income (up to 37%).
  • Long-term gains (held >1 year): taxed at 0%, 15%, or 20% depending on your income.

• Special Watchouts:

  • Actively managed mutual funds may trigger distributions even if you don’t sell shares.
  • Real estate, business, and crypto sales should be reviewed for gains/losses.

6. Optimize Your HSA (Health Savings Account) Strategy

[45:34]

• Triple Tax Benefits:

  • Tax-deductible contributions, tax-free growth, tax-free withdrawals for qualified medical expenses.

• Best Practices:

  • Only available with high-deductible health plans.
  • Invest HSA money for long-term growth (Fidelity recommended).
  • Track receipts carefully—reimburse yourself anytime, even years later.

• Tip:

  • “IRS doesn't limit when you reimburse yourself for old medical expenses—just save your receipts!” — Andrew [48:12]

7. Review and Optimize Your Charitable Giving Strategy

[50:42]

• Standard Deduction Thresholds (2026):

  • Single: $15,300
  • Married filing jointly: $30,600

• Bunching Donations:

  • Group multiple years’ donations into one year to surpass standard deduction and itemize.

• Donor-Advised Funds (DAFs):

  • Make a large donation for a current-year deduction, distribute to charities over several years.

• Donate Appreciated Assets:

  • Avoid capital gains by giving stocks/funds directly to charities.

• Qualified Charitable Distributions (QCDs):

  • For those 70.5+, make up to $100,000/year in IRA distributions directly to charity.

• Checklist for Givers:

  1. Are you exceeding the standard deduction?
  2. Should you bunch gifts?
  3. Have appreciated stock to donate?
  4. Is this a high-income year?
  5. Are you eligible for a QCD?
  6. Consider a DAF if appropriate.

8. Review Your Business Deductions

[55:18]

• Key Deductions:

  • Business expenses: software, supplies, services, insurance, advertising, professional fees.
  • Home office deduction (simplified: $5/sq ft up to 300 sq ft).
  • Mileage for business driving—use apps to track.
  • Depreciation (Section 179) allows for immediate expensing of many purchases.

• Optimize Structure:

  • Review whether to be LLC, S Corp, or C Corp as business grows.
  • Entity choice has major tax implications.

• Pro Tip:

  • “Don’t commingle business and personal accounts. Clean records are your best friend.” — Andrew [56:42]

9. Revisit 529 Plans & Education Tax Benefits

[59:15]

• 529 Plans:

  • After-tax contributions, tax-free growth/withdrawals for education expenses.
  • Now also cover K–12 tuition (up to $10,000/year) and apprenticeships.
  • Some states offer deduction for contributions—check your state’s rules.
  • Unused balances can be rolled into a Roth IRA for the beneficiary under certain conditions.

• Education Credits:

  • American Opportunity Tax Credit (AOTC): up to $2,500/eligible student, phases out at higher incomes.
  • Lifetime Learning Credit: up to $2,000/return, includes grad school/continuing ed.

10. Run a Forward-Looking Tax Projection Each Year

[01:02:11]

• Proactive, Not Reactive:

  • Don't just do taxes after the fact—forecast your tax bill during the year!
  • Estimate your total income, marginal tax bracket, and tweak contributions or withholdings as needed.
  • Key questions:
    • Should you increase 401(k)/HSA contributions?
    • Should you realize capital losses?
    • Should you perform a Roth conversion?
    • Should you bunch business expenses or delay income into next year?

• Adjust Withholdings and Quarterly Payments:

  • Use W-4 if W2 employee; adjust quarterly estimated payments if self-employed.

• Quote:

  • “This is what real wealth builders do—they think about taxes and ways to reduce those taxes overall.” — Andrew [01:04:22]

Notable Quotes & Memorable Moments

• “Every time you get a tax return, you actually overpaid the government and you gave them a free loan.” [19:13]
• “Let losses help you with your tax bill, not just hurt you.” [30:12]
• “The more that you can get in a Roth, it is absolutely incredible what you can do.” [15:41]
• “Don’t commingle business and personal accounts. Clean records are your best friend.” [56:42]
• “This is what real wealth builders do—they think about taxes and ways to reduce those taxes overall.” [01:04:22]

Key Takeaways

• Max out tax-advantaged accounts, review and adjust withholdings, and optimize charitable giving to maximize tax savings.
• Assess unique scenarios for Roth conversions and education planning.
• Business owners should be diligent about deductions and business structure.
• Proactive, annual tax planning is essential for effective wealth building.

Resources Mentioned:

• Master Money Academy (Andrew’s financial education platform)
• IRS Tax Withholding Estimator
• HSA receipt tracking tools (spreadsheet & AI-powered options, per show notes)
• Donor-advised fund platforms like Daffy

For Listeners: “You shouldn’t be stressed about money. You should feel hope. You could be the first person in your family to build wealth—and I want to help you get there.” — Andrew [01:07:38]

End of Content Summary