Tax planning is everything that happens before April. This is the playbook.
Most owners and high-earners overpay tax because nobody's running the year-ahead playbook. The moves that actually lower your tax bill happen between January and October — not in April. Every article in this category covers one specific move, with the dollar math, the documentation, and the timing.
Tax planning is the discipline of making the right decisions before they're irreversible. The S-corp election in March is different from the S-corp election in October. The Cash Balance plan opened by year-end shelters $80K more than the one opened in February. The cost seg study run in Q2 changes the entire year's tax picture. Every article in this category is a concrete move — explained mechanically, dollarized, and tied to the situation it fits.
5 clusters. Articles grouped by what you're actually trying to solve.
Each cluster covers one operational area in depth. Articles within a cluster reinforce each other; clusters cross-link between categories where the topics overlap.
S-Corp Mechanics
4/7 liveElection timing · reasonable comp · accountable plan · payroll · distributions · late-election remedies
Entity Structure
1/5 liveLLC vs. S-corp vs. C-corp · multi-entity · holdco / opco · disregarded entities · series LLCs
Retirement Vehicle Stacking
4/5 liveSolo 401(k) · SEP · Cash Balance · mega-backdoor Roth · HSA · NQDC · sequencing across vehicles
Equity Comp + Exit
2/5 liveRSU sell plans · ISO/NSO · 83(b) · QSBS Section 1202 · AMT · founder stock
Year-Ahead Tactics
1/4 liveQuarterly estimates · year-end moves · safe-harbor rules · tax projection · planning calendar
34 articles in Tax Planning
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Late S-Corp Election Relief: Rev. Proc. 2013-30 Step-by-Step
Rev. Proc. 2013-30 is the silent workhorse of small-business tax planning. It lets owners go back 3 years and 75 days to claim S-corp treatment they should have had all along. Here's the exact playbook we use.
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How to Elect S-Corp Status: A Step-by-Step Form 2553 Walkthrough
Form 2553 is one page that controls tens of thousands of dollars in annual tax savings. Here's every line, every signature, every common mistake, and what happens after the IRS receives it.
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Trump Accounts Are Here: Should Your Family Open One?
A new account for kids. Born 2025-2028? A free $1,000 seed, $5K/yr limit, S&P 500 only, locked to age 18, then it becomes an IRA. Tax-deferred, not tax-free. Here is the plain-English guide.
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LLC vs. S-Corp: The Tax Math by Income Level (with Worked Examples)
Most break-even articles handwave the math. This one runs it line by line across six income levels, with the actual self-employment tax, federal income tax, payroll cost, and net annual savings for each.
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S-Corp + Solo 401(k): How to Stack Retirement Contributions When You're the Only Employee
The S-corp + Solo 401(k) combination is the most powerful retirement vehicle available to solo business owners — when you set it up right. Here's how to stack $72K+ in tax-deferred contributions, and how to layer a cash balance plan on top for $200K+ totals.
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C-Corp to S-Corp Conversion: The 5-Year Built-In Gains Tax Window You Must Plan Around
C-corp to S-corp conversions look simple on paper. Then you sell an appreciated asset two years in, the BIG tax shows up at 21%, and the whole strategy unravels. Here's how the recognition window actually works and how to plan around it.
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S-Corp Health Insurance for >2% Shareholders: The W-2 Add-Back Rule Nobody Explains Right
The S-corp health insurance rule is a tax win disguised as paperwork. Done right, it converts personal premiums into an above-the-line deduction. Done wrong, it's the most common S-corp compliance failure in our cleanup work.
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S-Corp Shareholder Basis: Why It Matters, How to Track It, and What Breaks When You Don't
Shareholder basis is the most-mishandled number on S-corp returns. Get it wrong and your 'tax-free' distribution becomes a surprise capital gain — sometimes 10 years after the fact. Here's how basis actually works and how to track it right.
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Why Form an LLC? Protection, Tax Treatment, and When the Sole-Prop-to-LLC Move Pays Off
If you sell at vendor markets, run a side business, or have an EIN and a DBA but no LLC, you're a sole proprietor — whether you registered or not. Here's what an LLC actually adds, what it doesn't, and when the move pays off.
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When to Elect S-Corp: The Income Thresholds, Business Types, and Lifecycle Moments
Everyone wants to know one thing about the S-corp election: at what income does it start making money? Here's the honest break-even, plus the business types and lifecycle moments that change the answer.
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S-Corp Distributions, Draws, and Salary: The Three-Bucket Framework Every Owner Needs
Most S-corp owners use 'draw,' 'distribution,' and 'salary' interchangeably. They're not interchangeable. Each has its own tax treatment, paperwork, and audit profile — and the terminology shapes the strategy.
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QSBS Section 1202 in 2026 (After OBBBA): The Founder Tax-Free Exit Rule
OBBBA reworked QSBS in mid-2025. Pre-OBBBA stock kept the old 5-year-all-or-nothing rule. Post-OBBBA stock unlocks partial exclusions at 3 and 4 years + up to $15M per issuer. Here's what founders + early employees need to know.
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OBBBA Auto Loan Interest Deduction: Up to $10,000 Per Year
OBBBA brought back auto loan interest as a personal deduction — up to $10K/yr through 2028. Here's the qualification rules and what counts.
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OBBBA Made the QBI Deduction Permanent: What's New in Section 199A
QBI was the planning headache of 2024-2025 because it was scheduled to disappear at end of 2025. OBBBA solved it — permanent, with higher phase-out thresholds and a new minimum-deduction floor.
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OBBBA's New Tip Income Deduction: Up to $25,000 for Tipped Workers
Workers in tipped occupations can deduct up to $25,000 of qualified tip income annually under OBBBA. The deduction effectively makes that portion of tip income federal-tax-free.
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OBBBA Permanently Raised the Estate Tax Exemption to $15M Per Individual
The estate tax exemption was set to drop to ~$7M at end of 2025 (post-TCJA-sunset). OBBBA permanently raised it to $15M per individual. The estate-planning landscape for ETS-client households materially changed.
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OBBBA Restored Permanent 100% Bonus Depreciation: What It Means
The bonus depreciation phase-down that was set to hit 0% by 2027 is dead. OBBBA restored 100% permanently for property acquired after Jan 19, 2025. The single biggest provision affecting real estate investors and equipment-heavy businesses.
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OBBBA: The One Big Beautiful Bill Act — What Actually Changed
OBBBA is the biggest tax legislation since the TCJA in 2017. Here's every provision that matters to ETS clients — what changed, when it took effect, and what to do about it.
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OBBBA Changed Charitable Giving Rules: What's New for 2026
Three OBBBA changes hit charitable giving in 2026: a new $1K/$2K above-the-line deduction for non-itemizers, a 0.5% AGI floor for itemizers, and a 35% cap on itemized charitable benefit at top brackets. 2025 became a critical bunching year.
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OBBBA Expanded the Child Tax Credit to $2,200 Per Child
OBBBA made the TCJA $2,000 child tax credit permanent and bumped it to $2,200 in 2025. The bigger change: BOTH parent and child now need valid SSNs. Operationally meaningful for some filers.
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OBBBA Overtime Pay Deduction: Up to $12,500 for Workers
Workers earning overtime pay can deduct up to $12,500 ($25K joint) of qualified overtime compensation through 2028 under OBBBA. The deduction phases out above $150K/$300K MAGI.
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OBBBA SALT Cap Changes: $40,000 Through 2029
The SALT cap that was $10K under TCJA is now $40K through 2029 — with a phase-down above $500K AGI and a hard reversion in 2030. For high-property-tax filers, this is real annual money.
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OBBBA Senior Deduction: An Extra $6,000 for Age 65+
OBBBA added a new $6,000 deduction for taxpayers age 65+ on top of the existing senior standard deduction add-on. Layered with retirement-account distributions, it materially reduces taxable income for seniors.
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Late S-Corp Election: Going Retroactive Under Section 1362(b)(5)
Most S-corp election deadlines aren't actually deadlines. Section 1362(b)(5) lets you file retroactively up to 3 years and 75 days after your intended effective date. Here's the mechanics.
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RSU Sell Plan Fundamentals: Tax-Efficient Equity Comp Management
RSU shares are taxed as ordinary income at vest — whether you sell or hold. The question isn't whether to pay tax. The question is whether to hold concentrated single-stock risk after the tax event.
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Quarterly Estimates Done Right (Without the IRS Safe-Harbor Trap)
Most self-employed taxpayers use the IRS safe-harbor for quarterly estimates and get surprised by huge balances due. The safe-harbor is anti-protection for growing income. Here's the right calculation.
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HSA as Stealth Retirement: The Triple Tax Advantage Most People Underuse
HSAs have a triple tax advantage no other account offers. Max it. Invest it. Don't spend it on current medical bills. Treat it as supplemental retirement savings. Here's the strategy.
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S-Corp Accountable Plan: The Tax-Free Reimbursement Move
Accountable plans are the second-most-overlooked S-corp move (right after the election itself). $5K-$15K per year of tax-free reimbursement for owners. Here's the IRS-compliant setup.
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Mega-Backdoor Roth: The $47,500-a-Year After-Tax Strategy for 2026
Mega-backdoor Roth is the highest-leverage retirement move available to high-W-2 workers with the right 401(k) plan. $47,500/yr of after-tax space converts to Roth, tax-free at withdrawal in retirement.
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Cash Balance Plan: When the Math Works for High-Earners
Cash balance plans are the highest-contribution-capacity retirement vehicle in the IRS code — but they only fit a narrow profile. Stable $200K+ business income, age 45+, and a long planning horizon. Here's the mechanics.
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How the S-Corp Election Actually Works (and When It's Worth It)
The S-corp election is the highest-ROI tax move available to most owner-operators clearing $80K+ net. Here's the mechanical playbook — when it works, when it doesn't, and the operational pieces that have to come with it.
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LLC vs. S-Corp vs. C-Corp: Which One Fits Your Business?
Most owners pick a structure based on what a friend recommended or what was easy on LegalZoom. Here's the structural decision honestly framed — when each entity type makes sense, and what each one actually costs to operate.
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Solo 401(k) vs. SEP-IRA: Which One Fits?
Self-employed owners have two main retirement vehicles. Solo 401(k) usually wins for contribution capacity + flexibility; SEP-IRA wins for simplicity. Here's the side-by-side comparison.
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S-Corp Reasonable Compensation: How to Set It Right
Reasonable comp is the most-audited number on an S-corp return. Too low triggers the IRS. Too high overpays self-employment tax. Here's how to set it right and document the rationale.
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