Ep130: Mike Milligan on The Tax Strategies That Could Get You in Trouble

Mike Milligan, author, adjunct professor, and financial services veteran, joins Eunicia Peret for a candid and eye-opening conversation about the tax strategies being marketed to high-income earners, and the real risks behind them. Drawing from his personal story of growing up in a financially constrained environment to becoming deeply immersed in tax code and financial strategy, Mike shares his mission to protect individuals from costly mistakes. Together, they break down several widely promoted “too good to be true” strategies, from Roth conversion loopholes to real estate tax plays and software depreciation schemes, and explain why many of them leave clients exposed. This episode is a must-listen for anyone who wants to understand the difference between tax planning and tax selling, and how to protect both your wealth and your future.Key Takeaways:Not all tax strategies are created equal: Just because something is marketed heavily doesn’t mean it’s compliant or sustainable If you can’t explain it, don’t do it: Complexity without clarity is often a red flag Roth conversion “loopholes” can be dangerous: Many strategies lack IRS backing and may be challenged later Sales-driven advice creates exposure: Advisors selling products often highlight benefits while ignoring risks Real estate isn’t always a tax solution: Poorly structured deals can create ongoing losses despite promised tax benefits Cost segregation and depreciation have limits: They don’t apply universally and can be misused Software and AI investment schemes require scrutiny: Real money is at risk, often for minimal real return Tax planning must happen proactively: Waiting until tax season is too late to create meaningful change Your network determines your outcomes: Having the right professionals protects you from costly mistakes Taxes are your biggest expense: Strategic planning can legally reduce and optimize what you payTimeline Summary:[00:00:00] Introduction to Mike Milligan and his background [00:02:00] Early exposure to entrepreneurship and financial literacy [00:05:00] Why Mike focuses on protecting individuals from bad strategies [00:07:00] The problem with “fiduciary” messaging in financial services [00:09:00] Roth conversion strategies and hidden risks [00:12:00] Why lack of IRS backing should raise concerns [00:14:00] “Tax-free” Roth conversion claims explained [00:17:00] The reality behind annuity-based tax strategies [00:19:00] Real estate tax strategies and where they fail [00:22:00] Cost segregation misconceptions and financial losses [00:23:00] Software depreciation and AI investment schemes [00:26:00] The risks of blockchain and node-based investments [00:28:00] What real tax strategies look like when done correctly [00:30:00] The importance of having the right advisory team [00:31:00] Tax planning vs. tax preparation [00:33:00] Final thoughts on protecting wealth and making informed decisions