In this episode of The Deal Scout, host Susan Reilly sits down with Chris Miles, also known as the Anti-Financial Advisor, to uncover his unconventional path to financial freedom and the hard lessons learned along the way.

Once a traditional financial advisor, Chris realized that the advice he was giving—401(k)s, paying off mortgages early, saving aggressively—wasn’t working, not even for his own father. His wake-up call came when he saw firsthand that the “American Dream” retirement strategy wasn’t delivering results. This epiphany launched him into the world of entrepreneurship, real estate investing, and ultimately, financial independence at the age of 28.

But Chris’s story isn’t just a highlight reel. He also shares the devastating financial setback that cost him over a million dollars, and how it taught him critical lessons about liquidity, diversification, and business integrity. From that failure, he rebuilt his wealth with a new philosophy—focusing on cash flow over accumulation and creating passive income streams that allow entrepreneurs to become work-optional.

In this candid conversation, Chris also opens up about the emotional toll of financial and personal failures, including two divorces, and how leaning into relationships—not retreating from them—became a game-changer for his business and personal growth. His advice for entrepreneurs? Don’t grind yourself into the ground. Build freedom into your life now through smarter investments and meaningful relationships.

Whether you’re a business owner, investor, or aspiring dealmaker, this episode offers a blueprint for breaking free from the traditional financial mold—and building lasting wealth on your own terms.

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Susan Reilly is a licensed real estate broker, but this podcast is not a substitute for professional advice. We strongly recommend that you consult with a qualified financial advisor, legal counsel, and tax professional before making any financial decisions or taking any actions based on the information provided in this podcast.

From Financial Advisor to Financial Freedom: Chris Miles' Journey Beyond Wall Street

The Deal Scout