Which 8 Year-End Tax Planning Checkpoints Should a 30-Year-Old Entrepreneur Review?
Stop tipping the IRS. These 8 founder-friendly year-end moves turn December into your biggest tax win of the year.
Summary of What This Blog Covers
- 8 smartest year-end moves for 30-something founders
- Contributions, Roth conversions, harvesting, estimates, bunching
- Exact steps you can run this week
1. Max the Right Contributions
Solo 401(k), SEP, HSA — traditional vs Roth based on this year’s bracket vs future you.
2. Model a Roth Conversion
Low-income year? Convert pre-tax dollars to Roth and pay tax now at a discount.
3. Harvest Gains & Losses
Sell losers to offset winners. Up to $3k ordinary income offset + carryforward.
4. True-Up Estimated Payments
Hit safe harbor (100%/110%) or annualize — avoid the penalty sting.
5. Bunch Charitable Giving with a DAF
Front-load years of giving → itemize big this year, take standard deduction later.
6. Time Expenses & Income
Prepay 2026 expenses, delay invoices if it drops a bracket.
7. Clean Books & Categorize
Reconcile, tag everything — turns March chaos into a boring filing.
8. Sketch Your 2026 Bracket Plan
Look two years ahead — seed next year’s moves now.
Year-End Founder Checklist (copy-paste)
☐ Contributions funded (Solo 401(k)/SEP/HSA)
☐ Roth conversion modeled & executed
☐ Gains/losses harvested
☐ Safe harbor or annualized payments met
☐ DAF funded & grants scheduled
☐ Expenses prepaid / income delayed
☐ Books clean & categorized
☐ 2026 bracket plan drafted
Book Your Year-End Founder Review
Insogna runs the numbers live: contribution limits, Roth modeling, harvesting plan, estimate true-up, DAF setup, and a two-year bracket sketch. Whether you searched “tax preparer near me for entrepreneurs,” “CPA in Austin for founders,” or “year-end tax planning,” we make April feel boring in the best way.
Frequently Asked Questions
1) Solo 401(k) or SEP — which is better?
Solo 401(k) usually wins (higher limits + Roth option). SEP is simpler if you missed the 12/31 deadline.
2) When does a Roth conversion actually make sense?
Low-income years, big future tax risk, or when you can fill a bracket cheaply.
3) How much can I put in a DAF this year?
Cash = 60% AGI limit, appreciated stock = 30% AGI. No required distribution — bunch big.
4) What expenses can I safely prepay?
Insurance, subscriptions, software — anything that qualifies under the 12-month rule.
5) Kiosk or planning-forward CPA?
Pick the one who models two years ahead and gives you a checklist before 12/31.
