Personal Spending: Shoes, Meals, and Trips

In this episode, we sit down with Mike Milligan, CFP®, author, and founder of One Oak Financial — a nationwide planning firm based out of Norfolk, Virginia. Mike shares how he built his $3.9 million net worth through a combination of real estate, private placement deals, his financial planning firm, and strategic Roth IRA conversion planning — all while now living part-time as a Puerto Rico resident to optimize his tax strategy.

Mike goes deep into the misunderstood world of Roths, explains how to think about taxes over your entire lifetime (not just this year), and reveals why so many wealthy people quietly invest outside the public markets. He also shares his perspective on life design — from traveling to 60+ countries, to eating Michelin-star meals, to buying $1,300 Louis Vuitton sneakers while still rocking $30 Wrangler jeans.

Before becoming a CFP… Mike delivered pizzas at Little Caesars in college. Now he's appearing on CNBC and Fox Business — and helping people build one-of-a-kind financial plans for one-of-a-kind lives.

This episode blends tactical tax strategy, lifestyle design, and a philosophy for actually using your money while you're alive.

• Mike's net worth is $3.9 million, with more than one-third in real estate

• He believes the Roth is the most flexible, durable tax tool available

• He uses Puerto Rico residency to convert at lower tax brackets

• Wealth is built fastest via business and private deals, not just public markets

• He automates investments and keeps cash to buy assets "on sale"

• Money is a tool to create experiences, not the end goal

• Travel is one of his core pillars — he's visited 63+ countries

• He values independence + creativity over corporate systems

• Childhood lesson: count every penny

• Best career hack: learn from people already living the life you want

• "I delivered pizzas."

• "I wear Wrangler jeans and Louis Vuitton shoes."

• "A Roth is just a tax strategy — the investments are unlimited."

• "We want to spend our money, not just accumulate it."

• "Most CPAs plan taxes for this year — not your lifetime."