#tax-planning
Tax Planning
Strategic tax planning to minimize liability and maximize savings
The Post-Filing Tax Retrospective: A 30-Day Debrief That Makes Next April Boring
A 30-day post-filing playbook for small business owners — read last year's return line by line, log friction points while they hurt, recalculate quarterly estimates against real-time P&L, fix one workflow per pain point, and evaluate S-corp election, Solo 401(k), Section 179, and Augusta Rule moves while your CPA is still in fresh-mind mode.
Section 1374 Built-In Gains Tax: The Five-Year Window That Catches C-Corp to S-Corp Conversions
When a C corporation converts to an S corporation, Section 1374 imposes a 21% corporate-level tax on appreciated assets disposed of during a five-year recognition period. This guide walks through NUBIG, NRBIG, the 2026 rules, a worked example, and seven planning moves to avoid a six-figure surprise.
Section 45Q Carbon Capture Credit: How Industrial and Direct Air Capture Projects Monetize Sequestration
Section 45Q pays $85 per ton for industrial carbon capture and $180 per ton for direct air capture, claimable for twelve years, transferable for cash, and exposed to recapture for up to seventeen years. This guide explains thresholds, disposal pathways, OBBBA changes, and the bookkeeping discipline that protects the credit.
Section 6166 Estate Tax Deferral for Closely-Held Businesses: The 14-Year Installment Election in 2026
How executors of closely-held business estates use IRC Section 6166 to defer federal estate tax across 14 years at a 2% rate, with the 2026 inflation-adjusted $1.94M base, the 35% eligibility test, election mechanics, and the acceleration events that kill the deferral.
Section 754 Election: How Partnerships Use Inside Basis Step-Ups to Save Incoming Partners and Heirs From Phantom Gains
A Section 754 election lets a partnership adjust the inside basis of its assets when an interest transfers or property is distributed, preventing incoming partners and heirs from being taxed on appreciation that economically belonged to the seller. The election is permanent, covers both 743(b) and 734(b) adjustments, and matters most for real estate, family, and professional service partnerships.
Tax Planning During Divorce: QDROs, Post-TCJA Alimony, and Section 1041 Property Transfers
A practitioner's guide to the tax mechanics of divorce — how a QDRO splits a 401(k) penalty-free, why alimony in agreements executed after 2018 is no longer deductible, how Section 1041 carryover basis can turn a 50/50 settlement into an unequal one, and how the Section 121 home-sale exclusion survives when one spouse moves out.
401(k) Hardship Withdrawals and Plan Loans Under SECURE 2.0: When to Tap Retirement Funds Without Wrecking Your Future
A record 6% of 401(k) participants took a hardship withdrawal in 2025. This guide compares hardship withdrawals, plan loans, and SECURE 2.0 penalty-free distributions—with the actual tax math, deemed-distribution traps, and a decision framework for when to tap retirement funds.
529-to-Roth IRA Rollover: Move $35,000 of Unused College Savings Into Tax-Free Retirement
SECURE 2.0 lets the beneficiary of a 529 plan roll up to $35,000 of unused college savings into a Roth IRA tax-free and outside Roth income limits, provided the account is 15+ years old, contributions are 5+ years seasoned, and the beneficiary has earned income. This guide walks through the five federal tests, the state tax clawbacks that can erase the benefit, and a clean five-year execution plan.
The Accountable Plan: How S-Corp Owners Reimburse Themselves Tax-Free for Home Office, Mileage, and Travel
A working IRS-compliant accountable plan lets S-Corp owners reimburse home office, 72.5¢/mile mileage, internet, and travel tax-free—turning otherwise-lost expenses into deductible corporate spending. This guide covers the three §1.62-2 requirements, a worked $3,126 home office calculation, the five mistakes that get plans reclassified as wages, and the monthly bookkeeping rhythm that keeps it audit-proof.
Donor-Advised Funds and the Charitable Bunching Strategy: Beating the 2026 Tax Floor with Concentrated Giving
The OBBBA's 0.5% AGI floor and 35% deduction cap take effect in the 2026 tax year, raising the cost of small annual gifts. Concentrating four years of donations into a single donor-advised fund contribution can add roughly $39,600 in total deductions for a $200,000-AGI couple while keeping the recipient charities on their normal schedule.
ESOP Section 1042 Rollover: How C-Corp Owners Can Sell to Employees and Defer (or Eliminate) Capital Gains Tax
Section 1042 of the IRC lets a C-corporation owner selling shares to an ESOP defer federal capital gains tax indefinitely — and potentially eliminate it through step-up at death. This guide covers the five qualifying conditions, what counts as Qualified Replacement Property, the floating-rate-note diversification strategy, and the trade-offs founders should weigh against a strategic sale.
Nonqualified Deferred Compensation: Section 409A, Rabbi Trusts, and the 20% Penalty Executives Need to Avoid
Section 409A lets companies defer executive pay above 401(k) limits, but a single misstep triggers immediate taxation on every vested dollar plus a 20% federal penalty and premium interest. Here is how NQDC plans, rabbi trusts, and the six permissible distribution triggers actually work.