431: Net Worth Of $3.9M - From Pizza Delivery to Wrangler Jeans & Louis Vuitton Shoes — The CFP Living Tax-Free in Puerto Rico

431: Net Worth Of $3.9M - From Pizza Delivery to Wrangler Jeans & Louis Vuitton Shoes — The CFP Living Tax-Free in Puerto Rico

November 3, 2025 · 41 min

About this episode

Mike Milligan shares his journey from pizza delivery to building a $3.9 million net worth through strategic financial planning and tax optimization.

🎙️ SHOW NOTES 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. 💡 KEY…

People in this episode

Host: Jace Mattinson

Guest: Mike Milligan

Topics covered

Keywords

Mentioned in this episode

Organizations: One Oak Financial, CNBC, Fox Business

Products: Louis Vuitton, Wrangler

Places: Puerto Rico, Norfolk, Virginia

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