Running a Business
Tax strategies, liability protections, home office rules, and legal loopholes built specifically for business owners.
Available Loopholes
Each entry below is a plain-English guide to a specific legal right, rule, or workaround — including the exact laws that back it up.
Self-Employed Health Insurance Deduction — Deduct 100% of Premiums From Your Income Taxes
Potential savings $1,500–$15,000+ per year in federal income tax depending on premium costs and tax bracket
The Augusta Rule — Rent Your Home to Your Business Tax-Free
Potential savings $2,000 - $15,000+ per year in tax deductions
Delaware Shareholder Inspection Rights (DGCL § 220)
Potential savings Varies — access to information that can prevent or support litigation
Home Office Deduction — Deduct Your Home Expenses as a Self-Employed Business Owner
Potential savings $1,000 – $10,000+ per year in federal and state tax deductions
Section 1031 Like-Kind Exchange — Defer Capital Gains on Investment Real Estate Indefinitely
Potential savings Potentially hundreds of thousands in deferred capital gains tax on appreciated investment property
Section 179 & Bonus Depreciation — Deduct Business Equipment Immediately
Potential savings Tens of thousands in deferred or eliminated taxes in year of purchase
Accountable Plan Reimbursements — Pay Yourself Back From Your Business Tax-Free
Potential savings Can shift thousands of dollars of business costs into deductible reimbursements without treating them as wages
Cost Segregation Study — Accelerate Real Estate Depreciation for Bigger Deductions
Potential savings $20,000–$200,000+ in accelerated first-year deductions depending on property value
De Minimis Safe Harbor Election — Expense Small Equipment and Tools Instead of Capitalizing Them
Potential savings Accelerates deductions for small-dollar asset purchases
QSEHRA Reimbursements — Let a Very Small Employer Reimburse Health Costs Without a Group Plan
Potential savings Can shift significant medical premium and expense costs into a tax-favored reimbursement structure
Qualified Small Business Stock Exclusion — Potentially Exclude a Huge Share of Startup Exit Gain
Potential savings Potentially excludes millions of dollars of gain in the right QSBS case
Retirement Plan Startup Tax Credit — Let the IRS Subsidize a New Small-Business 401(k), SEP, or SIMPLE
Potential savings Up to $5,000 per year for startup costs, plus additional related credits in some cases
Research Payroll Tax Credit — Use the R&D Credit Even Before Your Startup Owes Income Tax
Potential savings Up to $500,000 per year against payroll taxes for qualifying small businesses
Safe Harbor 401(k) Plan — Let Owners and Executives Max Out Contributions
Potential savings Allows highly compensated employees to defer up to $23,000–$30,500/year; saves $3,000–$10,000+ in annual taxes per HCE
Small Business Startup Cost Deduction — Deduct Up to the Immediate Limit Before Amortizing the Rest
Potential savings Accelerates deductions for pre-opening business costs
Work Opportunity Tax Credit (WOTC) — Get Up to $9,600 Per New Hire
Potential savings $2,400–$9,600 per qualifying new hire in federal tax credits
Not Sure How This
Applies to You?
Our consulting service connects you with the right guidance for your specific situation — no jargon, no hourly billing surprises.