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Tax Cafe — Autarky Tax and Accounting
Autarky Tax & Accounting
Tax Cafe
Practical guides, tax planning strategies, and accounting insights from our CPAs and Enrolled Agents
NIL & Student-Athlete Tax
Individual Tax · Jun 24, 2026
NIL Earners & Student-Athletes: Your Complete Tax Guide
International Tax · Jul 23, 2026
International Student-Athletes, NIL Income, U.S. Tax Residency, and FIRPTA
International Tax · Jul 24, 2026
O-1A and P-1A Athletes: The Only NIL Solutions for International Collegiate Athletes
Individual Tax · Jul 25, 2026
The Jock Tax and NIL: How State Income Taxes Follow Student-Athletes Across State Lines
NIL & Student-Athlete Tax · Jul 27, 2026
The Arizona Sports Agency Landscape: Who Protects Your Wealth?
NIL & Student-Athlete Tax · Jul 27, 2026
NIL Isn't Free: What Every Student-Athlete Should Know Before Signing
110 posts
Self-Directed IRAs: The Tax Rules, the Prohibited Transaction Traps, and What the IRS Watches
A self-directed IRA allows you to invest retirement funds in real estate, private equity, precious metals, and other alternative assets. The tax benefits are real. So are the prohibited transaction rules — and violating them can disqualify the entire IRA and trigger immediate tax on the full balance.
Tax-Loss Harvesting: The Strategy That Works — and the Wash-Sale Rule That Kills It
Tax-loss harvesting is one of the few tax planning strategies available to investors in real time. Done correctly, it converts paper losses into real tax savings. Done carelessly, the wash-sale rule eliminates the benefit entirely. Here is how to do it right.
Charitable Remainder Trusts: How to Sell Appreciated Assets, Defer Tax, and Generate Lifetime Income
A charitable remainder trust lets you contribute appreciated assets, take an immediate charitable deduction, avoid capital gains tax on the sale, and receive income for life or a term of years. It is one of the most powerful tools in estate and tax planning — and one of the most underused.
The Section 199A QBI Deduction: How Pass-Through Business Owners Can Deduct 20% of Income
The qualified business income deduction under Section 199A allows eligible pass-through business owners to deduct up to 20% of their qualified business income. The rules are complex, the limitations are significant, and most owners are not optimizing it. Here is how it actually works.
SECURE 2.0 Act: The Retirement Rule Changes That Actually Matter for Your Tax Plan
SECURE 2.0 made over 90 changes to retirement account rules. Most are minor. A handful are genuinely significant — and several create planning opportunities that most taxpayers are not yet using. Here is what you need to know.
What It Means When Your Accounting Firm Fires You — And What to Do Next
Getting dropped by your CPA or accounting firm is more common than most people realize — and it is rarely about the money. Understanding why it happens, what your rights are, and how to find the right replacement can save you from a much bigger problem down the road.
Qualified Opportunity Zones: The Tax Deferral Strategy Most Investors Are Underusing
Qualified Opportunity Zones offer three distinct tax benefits — deferral, reduction, and permanent exclusion of capital gains. Most investors know the name but not the mechanics. Here is how the strategy actually works, and where it goes wrong.
Passive Activity Loss Rules: What Real Estate Investors Get Wrong Every Year
The passive activity loss rules under IRC Section 469 are among the most misunderstood provisions in the tax code. Most real estate investors believe their rental losses are freely deductible. They are not — and the exceptions are narrower than most advisors explain.
The Backdoor Roth IRA: Why High Earners Often Pay More Tax Than They Should
The backdoor Roth IRA is widely promoted as a tax-free retirement strategy for high earners. But done wrong, it triggers the pro-rata rule and a surprise tax bill. Here is what your advisor may not be telling you.