How To Stop Overpaying On Taxes With Michael Uadiale

In this episode of the On The Rise Podcast, host Jeremy Dyer sits down with Michael Uadiale, a CPA who helps entrepreneurs and families build lasting financial freedom that can be passed on for generations. Michael shares his own painful introduction to the US tax system after immigrating from Nigeria — and how that experience shaped his conviction that too many business owners are giving away money the government never asked for. He breaks down why taxes are not a punishment but a set of government incentives, what red and green flags to look for in a tax advisor, why meeting with your CPA once a year is a losing strategy, and what it means to turn 13 to 18 years of your productive work life over to the IRS through simple inaction. A practical and eye-opening episode for any entrepreneur who wants to stop being reactive and start building real tax strategy.   00:00 Introduction 00:52 Michael Uadiale's Background and Immigration Story 02:15 The $80,000 Tax Bill That Started a Mission 03:48 Too Many Business Owners Are Overpaying Taxes 05:56 Why Jeremy's Early CPA Said "You Make a Lot, You Pay a Lot" 07:49 Taxes Are a Roadmap — Not a Punishment 09:30 How COVID Proved the Government Uses Tax Law to Shape Behavior 11:00 Why Real Estate Has Such Strong Tax Benefits 13:17 How to Find the Right Tax Advisor for You 14:00 Red Flag — All You Hear Is No 16:30 Specialist vs. Generalist — Why It Matters 18:55 The Customer Avatar — Finding Your Tax Advisor Match 20:44 Why Meeting Once a Year Is a Losing Strategy 23:25 Looking Through the Windshield, Not the Rearview Mirror 24:58 The 13 to 18 Year Tax Jail Explained 26:27 The First Step to Getting Right With Your Taxes in 2026 27:01 How to Connect With Michael Uadiale