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

Nov 3, 2025

Mike Milligan, CFP® and founder of One Oak Financial, built a $3.9M net worth through savvy financial planning, real estate, and private placements. He shares insights on how his Puerto Rico residency helps optimize tax strategies, and why he believes Roth accounts are essential for long-term wealth. Mike discusses balancing luxury and simplicity in life, from traveling the globe to choosing quality over quantity in spending, like his $1,300 Louis Vuitton sneakers paired with $30 Wrangler jeans.

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INSIGHT

Net Worth Built Around Business And Experiences

Mike Milligan's net worth is $3.9M with over one-third in real estate and significant business value.
He prioritizes spending on life experiences rather than chasing arbitrary higher net worth targets.

ADVICE

Convert IRAs To Roth In Low Brackets

Convert pre-tax IRA dollars to Roth while in lower tax brackets to lock in tax-free future growth.
Pay taxes now at a lower rate so your investments compound tax-free for decades.

ADVICE

Use Backdoor Roths And Avoid Pro-Rata Rules

Use backdoor Roth contributions or 401(k) Roth options to get money into a Roth despite income limits.
Move traditional IRAs into an employer 401(k) to avoid pro-rata complications when backdooring.

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🎙️ 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 TAKEAWAYS

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

🔊 SOUND BITES

"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."