The Deductibles // November 2025

⚠️ Upcoming Deadlines to Know

📆 December 31, 2025 — Deadline to:

• Take required minimum distributions if you’re 73 or older to avoid penalties

• Lock in 2025 charitable contributions if you want the deduction this year

• Harvest investment gains or losses for 2025 to manage your capital gains bill

• For many cash-basis businesses, decide whether to accelerate expenses or defer income into 2026

📆 January 15, 2026 — Q4 2025 estimated tax payment due. Make this payment to stay ahead of underpayment penalties.

📆 January 31, 2026 — W-2s and most 1099-NECs due to employees and contractors. Time to make sure your books and vendor info are clean.

🎧 Tax Talk Unfiltered: Health Insurance - What Can Your Business Actually Deduct?

We’ve kicked off season 2 of TTU with a healthy boost to your deductions:

• How business owners and the self-employed can get coverage without an employer plan

• The S corp health insurance mistake that can quietly cost you your deduction

• Who should actually pay the premiums (you vs. the business) based on LLC, S corp, or C corp

• When more advanced setups like C corps with HRAs make sense

• How to use an HSA as an “ultimate retirement account” with a triple tax benefit

👉 Watch the episode ▶
To learn more, visit joingelt.com and follow @gelt-tax on YouTube for all episodes.

📺 Bootstrapper Live: Year-End Tax Moves for Business Owners

Our team chatted with Chris Sacchinelli about why Q4 is prime time for tax strategy—using your near-final 2025 numbers to decide which moves still make sense.

• How a heavy vehicle purchase and smart prepaying (software, services, even rent) can pull deductions into this year instead of next

• The real difference between home office and the Augusta rule, and how founders working from home can turn their living space into a tax asset

• When an S corp election actually saves meaningful money (and when it’s just extra admin), plus how you can sometimes elect it after you’ve seen how the year went

• How to turn “failed” bets and bad investments into tax savings with smarter loss harvesting at year-end

👉 Watch the full episode ▶ Or read the recap here.

You can always check out our content library for other useful resources

🗺️ Tax Roadmap: See Your Whole Year in One Place

When you work with Gelt, you don’t just get a CPA. You get a Tax Roadmap that shows you exactly what is happening with your taxes all year long.

👉 See how the Tax Roadmap works ▶

• Get a clear, year-round view of what Gelt is working on for you and what is coming next

• See estimated payments, tax strategy sessions, and compliance deadlines (including state-specific filings) laid out across the year

• Know which returns we will file for you and when, so you are never guessing about deadlines or next steps

• Your roadmap is custom-built each year based on your entities, states, and prior returns, and it updates in real time as items are completed

• Built to replace the typical “black box CPA” experience, the roadmap keeps you and Gelt fully aligned on priorities and timing

Questions? Visit joingelt.com or schedule a call with our team about how you can get started.

📄 Case Studies

Wondering what “good tax planning” actually does? Meet three business owners now saving $25K–$60K+ a year.

Private Dental Practice Owner — $40K+ annual savings

• Turned a new 12-op building into a tax asset with calibrated practice-to-LLC rent and cost segregation readiness.

• Layered Augusta rule, better charitable documentation, and rebuilt estimates to cut penalties and smooth cash flow.

California Dual-Business Owner — $25K annual savings

• Consolidated two ventures into one S-corp and used California PTET to restore deductibility of state taxes.

• Optimized compensation, Solo 401(k), and bookkeeping so more income stays in the business, not in filings and fees.

NJ/NY Services Founder — $60K+ annual savings

• Coordinated cross-state planning and startup loss timing to offset high W-2 and RSU income in early years.

• Set up future S-corp structure, home-office and family payroll planning so growing profits are taxed on their terms.

Read all our success stories here

📰 Gelt in the News

• ValiantCEO
  Tal shares how Gelt’s AI-native tax platform helps top earners move from reactive filing to proactive, year-round planning.
  👉 Read: Exploring Business Insights with Tal Binder of Gelt (ValiantCEO)

• MedCity News
  MedCity highlights how Gelt helps doctors and practice owners use smarter structures, retirement planning, and expense tracking to cut their 2026 tax bill.
  👉 Read: 5 High-Impact Tax Strategies Every Physician Should Use in 2026 (MedCity News)

• Product Led Growth Leaders
  Tal joins host Thomas Watkins to break down why the U.S. tax code is both complicated and full of opportunity, how Gelt pairs senior CPAs with custom tech for high-earning founders, and the key tax moves startup leaders should know, including QSBS and 83(b) elections.
  👉 Listen: Tax Time Terrors: Turning Complexity into Opportunity with Gelt’s Tal Binder (Product Led Growth Leaders)

Is Gelt a Fit for You Now?

Tax Season is upon us! As a reminder - We work with founders, investors, and business owners who are ready to go beyond basic tax prep. If you want to:

✔️ Keep more of what you earn
✔️ Plan with intention, not just react at tax time
✔️ Partner with a team that understands your goals

We’d love to help you take the next step. Schedule a call to learn more