Rent your personal home to your business for up to 14 days per year. The rental income is tax-free to you personally, and the business deducts the full rental expense.

Establish a formal accountable plan to reimburse employees (including owner-employees) for business expenses tax-free. The business deducts the reimbursement; the employee pays no income or payroll tax on it.

Defer and potentially eliminate capital gains taxes by investing in Qualified Opportunity Zone Funds within 180 days of a capital gain event.

Spread the recognition of capital gains from a property sale over multiple years by receiving payments in installments, keeping annual income in lower tax brackets.

A dollar-for-dollar tax credit for qualified research expenses including wages, supplies, and contract research. Startups can apply up to $500,000/year against payroll taxes.

A business owner creates their own insurance company to insure business risks. Premiums paid to the captive are deductible by the business; the captive pays tax only on investment income under §831(b).

Deduct up to $5.00 per square foot for energy-efficient improvements to commercial buildings, including HVAC, lighting, and building envelope upgrades.

A defined benefit plan allows high-income self-employed individuals and business owners to contribute $200,000–$300,000 per year based on actuarial calculations, far exceeding 401(k) limits.

Contribute after-tax dollars to a 401(k) plan (up to the ~$70,000 total 2026 limit minus pre-tax contributions) and convert them to Roth, creating tax-free growth on a much larger balance.

Transfer appreciated assets into a CRT, receive an immediate charitable deduction, avoid capital gains on the sale, and receive income payments for life or a term of years.

Founders and investors in qualified small businesses can exclude up to $10 million (or 10× their adjusted basis) in capital gains from federal income tax when selling stock held for more than 5 years.

Invest capital gains from any source into a Qualified Opportunity Fund within 180 days to defer the gain until December 31, 2026, and eliminate all taxes on appreciation after 10 years.

An ILIT owns your life insurance policy, keeping the death benefit out of your taxable estate while providing liquidity to pay estate taxes or transfer wealth to heirs tax-free.

Transfer assets into a GRAT, receive annuity payments for a term of years, and pass all appreciation above the IRS hurdle rate to heirs completely free of gift and estate tax.

Invest in qualifying film, TV, or entertainment productions to generate federal deductions under §181 and state tax credits of 20–40% of qualifying production expenditures.

Donate a conservation restriction on qualifying land to a land trust, generating a charitable deduction equal to the reduction in property value — often 2–5× the cost of the easement.

Executives and highly compensated employees can defer a portion of their compensation to future years, deferring income tax until the funds are received — typically in lower-income retirement years.

Hire your children or spouse in your business to shift income to lower tax brackets. Children under 18 working for a sole proprietorship or partnership owned by parents are exempt from FICA taxes.

Employers who provide or pay for childcare facilities for employees receive a tax credit of 25% of qualifying childcare expenditures and 10% of childcare resource and referral expenditures, up to $150,000/year.

Many states allow S-Corps and partnerships to elect to pay state income tax at the entity level, generating a federal deduction that bypasses the $10,000 SALT cap for individual owners.

Non-qualified deferred compensation plans allow highly compensated employees to defer a portion of salary or bonus to a future date, deferring income taxes until distribution.

Incentive Stock Options qualify for long-term capital gains rates if held correctly, but the spread at exercise is an AMT preference item. Strategic exercise timing minimizes total tax.

Invest capital gains into a Qualified Opportunity Fund within 180 days to defer the original gain until 2026 and eliminate all appreciation on the QOZ investment after a 10-year hold.

A Family Limited Partnership allows transfer of assets to family members at a valuation discount (typically 20–40%) due to lack of control and marketability, reducing estate and gift tax exposure.

A Charitable Lead Trust pays income to a charity for a set term, then passes the remaining assets to heirs. Creates an upfront charitable deduction and reduces estate taxes.

Private Placement Life Insurance wraps a customized investment portfolio inside a life insurance policy structure, providing tax-free growth, tax-free loans, and estate tax-free death benefits.

A self-directed IRA allows investment in alternative assets including real estate, private loans, and businesses — generating tax-deferred (Traditional) or tax-free (Roth) returns.

Qualified Small Business Stock (QSBS) under Section 1202 allows founders, employees, and investors to exclude up to $10 million (or 10x basis) in capital gains when selling stock held for more than 5 years.

Investments in oil and gas working interests allow immediate deduction of 65–80% of the investment as Intangible Drilling Costs (IDC), plus ongoing depletion allowances on production.

Investments in qualified film and television productions generate state tax credits (25–35% of production spend) plus federal deductions under IRC §181 for productions under $15M.

STR properties with average guest stays of 7 days or less are NOT subject to passive activity loss rules, allowing losses to offset active W-2 or business income.

Qualify as a Real Estate Professional to treat all rental losses as non-passive, allowing unlimited deduction against any income including W-2 wages. Requires 750+ hours per year in real estate activities.

Accelerates depreciation on commercial and residential rental property by reclassifying components into shorter recovery periods (5, 7, or 15 years) instead of 27.5 or 39 years.

Each cryptocurrency trade, swap, or exchange is a taxable event. Proper structuring — holding periods, loss harvesting, and entity selection — can dramatically reduce crypto tax liability.