Tax strategies
44 plays in this category. Each one covers the mechanics, who it fits, and the estimated impact — then generates a deep dive against your own numbers.
- Tax
Cost Segregation Study
Front-load depreciation on real estate to slash current-year taxes.
$15K–$150K+ per property in year 1 - Tax
REPS + Short-Term Rental Loophole
Turn W-2 income into tax-free passive rental losses.
$30K–$200K+ W-2 tax offset - Tax
1031 Like-Kind Exchange
Defer capital gains indefinitely by rolling into bigger real estate.
20–37% of gain deferred - Tax
Qualified Opportunity Zones
Defer + eliminate capital gains via OZ funds.
Full elimination of QOF gains after 10 yrs - Tax
Augusta Rule (§280A(g))
Rent your home to your business up to 14 days/year — tax-free.
$5K–$25K/yr tax-free income - Tax
QBI Deduction §199A
Deduct 20% of pass-through business income.
Up to 20% off taxable business income - Tax
S-Corp Election + Reasonable Salary
Slash self-employment tax on profits above ~$50K.
$5K–$25K+/yr SE tax savings - Tax
Bonus Depreciation + §179
Expense equipment, vehicles, and property in year one.
Full cost × marginal rate in year 1 - Tax
Installment Sale §453
Spread capital gains over years to stay in lower brackets.
5–15% effective rate reduction - Tax
Cost Seg + STR Loophole Stack
Combine bonus depreciation with STR material participation to erase W-2 tax.
$50K–$250K+ W-2 offset in year 1 - Tax
W-2 → 1099 → S-Corp Conversion
Same work, 15–25% more take-home via S-Corp structure.
$15,000–$40,000/year additional take-home on $150k+ income - Tax
§1202 QSBS Basis Packing
Pack basis into C-Corp pre-clock; exclude $10M or 10× basis.
$2M–$20M+ federal tax elimination on exit - Tax
§1045 QSBS Rollover
Sell QSBS before 5 years — roll gain into new QSBS.
Defer 20–37% cap gains + preserve §1202 exclusion - Tax
§1244 Ordinary Loss Stock
Small business stock losses = ordinary (not capital) up to $50k/$100k.
$18–37k tax benefit per failed investment vs capital loss treatment - Tax
§1341 Claim of Right
Recover taxes paid on income you had to return later.
Full recovery of prior-year tax paid at higher bracket - Tax
§199A Rental Safe Harbor (Rev. Proc. 2019-38)
250 hours of rental services = QBI 20% deduction on rental income.
20% deduction on net rental income (up to bracket cap) - Tax
ERC Recapture Defense
IRS is clawing back Employee Retention Credits. Defend yours.
Avoid 100% clawback + 20% penalty + interest - Tax
S-Corp Reasonable Comp Optimization
Lower your W-2, raise your distribution; save on FICA.
$5K–$25K/yr FICA savings - Tax
§199A QBI Deduction Optimization
20% off qualified business income — if you structure right.
20% of QBI = $10K–$100K+/yr - Tax
FinCEN BOI Reporting
Report beneficial ownership or face $500/day fines.
Avoid $500/day + criminal penalties - Tax
§691(c) IRD Deduction
Heirs recover estate tax paid on IRAs and deferred comp.
Recover 15–40% double-taxation on IRD assets - Tax
§1035 Tax-Free Insurance/Annuity Exchange
Swap old annuity/life policy for better one — zero tax.
Escape 1–3% fee drag; preserve tax deferral - Tax
§1256 60/40 Treatment
Futures & broad-based options — 60% long-term regardless of holding.
~10% rate reduction vs equity short-term trading - Tax
§475(f) Trader Mark-to-Market Election
Qualify as a trader — deduct unlimited losses against ordinary income.
Unlimited loss deduction; ~$20K+ expense deductions - Tax
No-Tax State Residency Migration
Establish domicile in FL / TX / TN / NV / WY / SD / WA / AK.
5–13.3% of income annually - Tax
§83(b) Election Playbook
Elect within 30 days on restricted equity — convert future ordinary income to LTCG.
Convert 37% ordinary income to 0–20% LTCG on entire appreciation - Tax
§831(b) Micro-Captive Insurance Company
Insure your own business risks — deduct up to $2.8M/yr of premiums, receive tax-free.
$300K–$1M+ annual tax deferral/arbitrage - Tax
HSA Max-Fund & Invest (Triple Tax-Free)
The only triple-tax-free account — deduct in, grow tax-free, withdraw tax-free for medical.
$1.5K–$3.5K/yr immediate + $500K+ tax-free at retirement - Tax
§179 + Bonus Depreciation on 6,000+ lb Vehicle
Write off up to 100% of a business SUV/truck in Year 1.
$15K–$60K Year-1 deduction = $5K–$25K refund - Tax
Annual Property Tax Assessment Appeal
Appeal your county assessment every year — 60% success rate, 8–15% tax cut.
$400–$5,000/yr per property, recurring - Tax
§1202 QSBS Stacking Across Multiple Trusts
Multiply the $10M QSBS gain exclusion by gifting QSBS shares into non-grantor trusts — each gets its own $10M cap.
$2.3M+ federal tax saved per additional $10M exclusion stacked - Tax
§1045 QSBS Rollover (Reset the 5-Year Clock)
Sell QSBS before 5 years and roll gain into new QSBS within 60 days — preserve deferral and restart clock.
Full capital gains deferral until eventual §1202 qualification - Tax
§1244 Small Business Stock Ordinary-Loss Election
Convert up to $100K ($50K single) of stock losses from capital to ordinary — huge tax savings if the startup fails.
$25K–$37K/yr additional refund if the venture fails - Tax
§1400Z Qualified Opportunity Zones (Active Through 2026)
Defer + reduce + eliminate capital gains by rolling into a QOF invested in designated Opportunity Zones.
0% federal tax on 10+ year QOF appreciation - Tax
§127 Employer Student Loan Repayment ($5,250 Tax-Free)
Owner-employee's own company pays $5,250/yr toward the owner's student loans — tax-free to employee, deductible to business.
$1,900–$2,400/yr in FIT+FICA per participant - Tax
§139 Qualified Disaster Relief Payments (Tax-Free to Employees)
During federally-declared disasters, employer pays employees tax-free reimbursements — no W-2, fully deductible.
$5K–$25K tax-free per affected employee annually - Tax
S-Corp Accountable Plan — Tax-Free Owner Reimbursements
S-corp reimburses owner for home office, mileage, cell, internet — fully deductible to corp, tax-free to owner.
$3K–$15K/yr in FIT + SE-equivalent savings - Tax
§162(l) — >2% S-Corp Shareholder Health Insurance Deduction
S-corp pays your health premiums, adds to W-2 (no FICA), you deduct above-the-line — net: pre-tax health.
$2K–$5K/yr in FIT + full FICA savings on premiums - Tax
Late S-Election Relief (Rev. Proc. 2013-30)
Missed the 2.5-month S-election deadline? File Form 2553 up to 3 years 75 days late with reasonable cause — no PLR fee.
$10K+ in PLR fees + full retroactive S-corp benefits - Tax
S-Corp Reasonable Compensation Study — Defensible SE-Tax Savings
Document 'reasonable' owner salary with a formal study — safely take more as distributions, saving 15.3% SE tax.
$5K–$15K/yr in SE-equivalent tax savings + audit defense - Tax
C-Corp Retained Earnings at 21% Flat — Compound Below Personal Rates
C-corp reinvests profits at 21% flat vs pass-through 37% top rate — 16-point rate arb per dollar retained.
16-point rate arbitrage per dollar retained - Tax
§41 R&D Credit + §174 Capitalization Optimization
R&D credit worth 6–10% of qualifying wages — payroll-tax offset for startups <5 yrs old.
$30K–$500K/yr credit + payroll-tax offset - Tax
S-Corp Shareholder Debt Basis via Direct Loan
Loan personal cash directly to S-corp (not via bank) — creates debt basis, unlocks previously-suspended loss deductions.
$20K–$150K in unlocked deductions × 37% = $7K–$55K tax value - Tax
§199A Aggregation Election — Combine Entities for Bigger QBI Deduction
Aggregate related pass-throughs into one §199A calculation — clear wage/UBIA limits, unlock full 20% QBI.
$5K–$50K/yr in QBI deduction restored