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 #9: Small Business Tax Credits You Might Be Missing
This week’s content focuses on the latest Anomaly Angle, breaking down practical tax strategies and opportunities business owners may be overlooking. The episode reinforces Anomaly’s proactive approach to tax planning — going beyond compliance to identify opportunities, maximize available tax benefits, and make smarter financial decisions throughout the year.
Weekly Content

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S Corp Debt Explained: The Basis Trap Business Owners Miss
September 21, 2026
In this episode of Founders Under Pressure, Greg O’Brien explains why S Corp debt generally doesn’t increase shareholder basis, how that can prevent business owners from deducting certain losses, and why converting a business with significant debt to an S Corporation may create additional tax consequences.

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Why You Should NOT Be an S Corporation
September 21, 2026
Greg O’Brien and John Malone break down why an S Corporation isn’t always the right move for business owners, covering when an S Corp election makes sense, the $85K–$90K profit benchmark, debt and basis limitations, multiple shareholders, raising capital, selling a business, and why appreciating real estate generally shouldn’t be held in an S Corp.

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Business Losses Don't Always Mean You're Losing Money
September 21, 2026
Can your business show a loss and still be financially healthy? In this short video, Greg explains why a reported business loss doesn't always reflect the true financial picture and how owner compensation can impact your bottom line. Learn why understanding the numbers behind your tax return is essential for making better business decisions.
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