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.
Business Exit Tax Planning: How Founders Use Charitable Trusts to Reduce Taxes in 2026
In this episode of Anomaly Angle, Greg O'Brien and John Malone break down three charitable tax strategies.
Weekly Content
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Business Exit Tax Planning: How Founders Use Charitable Trusts to Reduce Taxes in 2026
June 12, 2026
In this episode of Anomaly Angle, Greg O'Brien and John Malone break down three charitable tax strategies.
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Founders Under Pressure QSBS Part III
June 12, 2026
In this Founders Under Pressure clip, John breaks down one of the biggest misconceptions around Qualified Small Business Stock (QSBS): founders hear about the potential tax-free capital gains exclusion, but many never realize certain industries are excluded entirely.
The Short-Term Rental Tax Loophole Explained
June 4, 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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