Keeping our community on the cutting edge of tax, business and more
We produce weekly content for both the general public as well as more exclusive content for our client community. Our focus is on fresh tax strategies, relevant law changes and business opportunities.
Anomaly Angle #5: Hire Your Kids? Trump Accounts & Family Tax Strategies
Discover how to legally hire your children, maximize tax savings, and build generational wealth with Roth IRAs and the new Section 530A Trump Accounts.
Weekly Content

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The Short-Term Rental Tax Loophole Explained
June 16, 2026
In this video, John breaks down: • How STR tax strategy works • Why material participation matters • How cost segregation creates paper losses • Common mistakes investors make • Why proactive tax planning matters before buying If you’re a founder, investor, or high-income earner looking into real estate tax strategy, this is one of the most important concepts to understand.

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Former IRS Commissioner Explains How the IRS Really Works
April 17, 2026
What does the IRS really focus on when auditing taxpayers and small businesses? Former IRS Commissioner Chuck Rettig joins Anomaly CPA for an unprecedented discussion on what drives IRS enforcement, common audit red flags, and the most underused tax benefits available to small business owners and real estate investors.

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Cost Segregation Explained: How Real Estate Owners Reduce Taxes (US Guide)
April 15, 2026
Cost segregation allows real estate investors to accelerate depreciation and unlock larger upfront tax deductions. Instead of treating a property as a single asset, it breaks it into components with different depreciation timelines—impacting cash flow and long-term tax strategy. This is one of the most overlooked ways to reduce tax liability in real estate.

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How to Reduce Capital Gains Tax on Real Estate (Cut an $80K Tax Bill)
April 17, 2026
A client was expecting an ~$80K tax bill after selling a rental property. What changed? We looked beyond the transaction and found an opportunity within their existing portfolio to reduce it. In this episode, we break down how timing, structure, and the right strategy can significantly impact capital gains. If you’re dealing with real estate or a major taxable event, this is worth watching.
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