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Retirement and benefit plans

SEP, SIMPLE, solo 401(k), and defined benefit plans compared, plus health coverage options for owners and the credits for starting a plan.

22 guides, each written by a CPA licensed in the US and Canada.

Tax Planning

Captive Insurance for Small Businesses: How 831(b) Micro-Captives Work and the IRS Risks

A captive insurance company is a wholly owned subsidiary formed to insure the risks of its parent company. 831(b) micro-captive basics.

Sep 5, 2026
Tax Planning

Early Withdrawal from Retirement Accounts: Penalties, Exceptions, and SEPP Plans for Business Owners

Withdrawals from 401(k) and IRA accounts before age 59.5 trigger a 10% early withdrawal penalty plus ordinary income tax.

Sep 5, 2026
Tax Planning

Health Insurance Deduction Options for Small Business Owners

Self-employed business owners can deduct health insurance premiums as an above-the-line deduction. Health insurance is one of the largest personal.

Sep 5, 2026
Tax Planning

Health Insurance Options for Self-Employed Business Owners: Marketplace, SHOP, ICHRA, and QSEHRA

Self-employed business owners can deduct health insurance premiums as an above-the-line deduction on Form 1040 (not on Schedule C).

Sep 5, 2026
Tax Planning

Health Savings Account (HSA) Strategy for Small Business Owners

HSAs provide a triple tax benefit: tax-deductible contributions ($4,300 individual, $8,550 family in 2025), tax-free growth.

Sep 5, 2026
Tax Planning

Health Savings Accounts (HSAs) for Small Business Owners: Triple Tax Advantage

HSAs offer a triple tax benefit: tax-deductible contributions, tax-free growth, and tax-free withdrawals for medical expenses.

Sep 5, 2026
Tax Planning

HSA for Business Owners: Triple Tax Advantage, Contribution Limits, and Investment Strategy

Health Savings Accounts (HSAs) offer a triple tax benefit: contributions are deductible, growth is tax-free, and qualified withdrawals are tax-free.

Sep 5, 2026
Tax Planning

HSA Strategy for Small Business Owners: Triple Tax Advantage (2025)

An HSA paired with a high-deductible health plan offers triple tax savings: contributions are pre-tax, growth is tax-free.

Sep 5, 2026
Tax Planning

Involuntary Conversions: Deferring Gain on Insurance Proceeds Under IRC 1033

When business property is destroyed, stolen, or condemned, IRC 1033 lets you defer the gain if you replace the property within the statutory period.

Sep 5, 2026
Tax Planning

IRC 1035 Tax-Free Exchange: How to Swap Life Insurance and Annuity Policies Without Triggering Tax

IRC 1035 allows taxpayers to exchange one life insurance policy, endowment contract. Permitted IRC 1035 exchanges. Covers deductibility rules, policy.

Sep 5, 2026
Tax Planning

QSEHRA: How Small Employers Can Reimburse Health Insurance Tax-Free

A Qualified Small Employer Health Reimbursement Arrangement (QSEHRA) under IRC 9831(d) allows employers with fewer than 50 full-time employees.

Sep 5, 2026
Tax Planning

Retirement Plan Comparison for Business Owners: Solo 401(k) vs. SEP-IRA vs. SIMPLE IRA vs. Defined Benefit

Choosing the right retirement plan is one of the highest-impact tax decisions a business owner can make. 2025 retirement plan contribution limits: | Plan.

Sep 5, 2026
Tax Planning

Retirement Plan Comparison for Self-Employed: SEP IRA vs. Solo 401(k) vs. SIMPLE IRA

The Solo 401(k) allows the highest contributions for most self-employed business owners ($23,500 employee + 25% employer = up to $70,000 total in 2025).

Sep 5, 2026
Tax Planning

Retirement Plan Comparison for Small Business Owners: Solo 401(k), SEP-IRA, SIMPLE IRA, and Defined Benefit

Solo 401(k) allows $23,500 employee deferral plus up to $46,500 employer contribution ($70,000 total for 2025). SEP-IRA allows 25% of compensation.

Sep 5, 2026
Tax Planning

Retirement Plan Startup Tax Credit: Up to $15,000 for New 401(k) or SIMPLE Plans (SECURE 2.0)

Small businesses with up to 50 employees can claim a tax credit of up to $5,000/year for 3 years for starting a retirement plan.

Sep 5, 2026
Tax Planning

Retirement Plans for Small Businesses with Employees: SIMPLE IRA, SEP, and 401(k)

Small businesses with employees have different retirement plan considerations than solo operators. Retirement plans for businesses with employees.

Sep 5, 2026
Tax Planning

Self-Employed Health Insurance Deduction: How Business Owners Deduct Premiums Above the Line

Self-employed business owners can deduct health, dental, and vision insurance premiums for themselves and their families as an above-the-line deduction.

Sep 5, 2026
Tax Planning

Self-Employed Health Insurance Deduction: Rules for Sole Proprietors and S-Corp Owners

Self-employed individuals can deduct 100% of health insurance premiums (medical, dental, vision) for themselves, their spouse, and dependents.

Sep 5, 2026
Tax Planning

SEP IRA vs. Solo 401(k) vs. SIMPLE IRA: Retirement Plan Comparison for Small Business

Solo 401(k) allows the highest contribution ($23,500 employee + 25% employer, up to $70,000 combined for 2025). Compare SEP-IRA, solo 401(k), and SIMPLE.

Sep 5, 2026
Tax Planning

Small Business Retirement Plans: Solo 401(k) vs. SEP IRA vs. SIMPLE IRA (2025)

The Solo 401(k) allows the highest contributions ($70,000 in 2025 for those under 50, $73,500 for 50+, $81,250 for ages 60-63).

Sep 5, 2026
Tax Planning

Solo 401(k) vs. SEP IRA vs. SIMPLE IRA: Which Retirement Plan Is Best for Your Business?

A side-by-side comparison of the three main retirement plans for small business owners: contribution limits, employee obligations, deadlines.

Sep 5, 2026
Tax Planning

Tax Treatment of Insurance Claims and Proceeds for Small Businesses

Insurance proceeds received by a business are generally not taxable if they reimburse a deductible loss (replacing destroyed equipment.

Sep 5, 2026

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