E16: Chris Miles: The Anti-Financial Advisor on Taking Control of Your Financial Future
Planet Wealth: Fortunes of the Brave
Release Date: 06/30/2025
Planet Wealth: Fortunes of the Brave
McKeever “Mac” Conwell, Founder and Managing Partner of Rare Breed Ventures, joins Planet Wealth CXO Mary Katherine Johnson to break down how he went from a government contractor in Maryland to launching a venture capital fund built for overlooked founders. Mac shares the unconventional path that shaped his investing lens: dropping out of school for a Northrop Grumman opportunity, building and exiting a startup through pivots and accelerators, and then entering state-backed investing where he helped design a first-of-its-kind pre-seed program for women and minorities. This episode is a...
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Dr. Felecia Froe, board-certified urological surgeon turned social impact investor, joins Mary Kathryn Johnson of Planet Wealth for a candid conversation about building wealth with purpose. As the founder behind Money with Mission and Wealth Be Hers, Dr. Froe shares how her path from medicine to real estate investing became a mission to help women gain the financial power to walk away from jobs or relationships that are not in their best interest. After reading Rich Dad Poor Dad, Dr. Froe began buying real estate and rapidly scaled to 18 properties. Then 2008 hit, and she lost everything. What...
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Joshua Kagan is a real estate and fintech builder focused on expanding access to ownership for everyday people. He is the co-founder of Bonfire and the founder of Friendly Acres, a land-focused venture designed to help people exit stranded land assets while creating affordable pathways into real asset ownership. In this episode of Fortunes of the Brave, Joshua shares how his journey from fix-and-flip investor to fintech founder reshaped his views on democratized access to real estate. Drawing on lessons from launching Bonfire during a volatile regulatory moment, he explains why land has...
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In this episode of Fortunes of the Brave, host Mary Kathryn Johnson sits down with Lisa Phillips, founder of Affordable Real Estate Investments, to unpack how she went from foreclosure to financial independence using affordable rental properties. Lisa is known for helping overlooked investors, especially Black professionals, build profitable real estate portfolios in working class and minority neighborhoods using low cost, high cash flow strategies. Lisa shares how she realized corporate America was not her long term path and reframed her engineering job as a paycheck to fund her real...
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Pamela Cytron, founder of The Founders Arena WealthTech accelerator in Arlington, Texas, has spent more than three decades at the center of fintech, wealth management and enterprise sales. In this episode of Fortunes of the Brave, Pam and host Lance Woodson dig into how wealth is really created, who gets access to it, and why the current system leaves so many founders and everyday investors on the sidelines. They unpack the broken incentives inside venture capital, the realities of raising capital in fintech, and why sales is still a contact sport even in an AI driven world. Pam explains how...
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2025 closes by revisiting the most practical lessons shared by founders, investors, and community builders across this year’s Fortunes of the Brave conversations. This recap threads together a single theme: better decisions happen when your mindset, strategy, and community support are aligned. First, we return to a mental framework for entrepreneurs and investors who feel the pressure of constant uncertainty. A five-step system called PEACE outlines how positive thinking, embracing challenge, appreciation, certainty, and empathy can reduce fear-based reactions and improve decision quality....
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For too long, retirement planning and independent fiduciary financial advice have felt reserved for the top 1 to 2 percent. In this episode of Fortunes of the Brave, Mary Kathryn Johnson sits down with Michael Scarpati, CEO and co founder of Retire.us, to unpack how technology and true fiduciary financial planning can finally open the doors for everyday Americans. Michael shares how his platform connects people with independent fiduciary financial advisors who focus on holistic retirement planning, not just selling products. They dig into the mindset barriers that keep people with 50,000 to...
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Mary Katherine Johnson sits down with Dan Egan, VP of Behavioral Finance & Investing at Betterment, to decode how our habits, narratives, and timing drive financial outcomes more than hot tips ever will. Dan explains why success comes from matching risk to time horizon, building automatic systems that spare your willpower, using tax-aware prompts (hello, long- vs short-term gains), and reframing money from a scarce enemy to a tool you can wield responsibly, and often with your community. We dig into teachable moments that stick, how to design routines that “pay yourself first,” why...
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Mary Katherine Johnson welcomes Nick Malouin, Senior Strategy Director at Electric Innovation, to unpack how innovation strategy turns ambiguity into action. From Capgemini to Electric, Nick has spent a decade taking ideas from insight to in-market—bridging hard data with human truth so teams can build products people actually want. He breaks down why the best work starts with the consumer journey, not the org chart; how to separate signal from noise with out-of-category insights; and why “possible futures” beat single-line forecasts. If you care about product development, consumer...
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Community capital, crowdfunding, and local investing take center stage in this episode of Fortunes of the Brave. Systems entrepreneur and financial innovator Janice Shade, co-founder of Milk Money Vermont and founder of Capital Innovation Lab and Fundamenta, joins host Lance Woodson to unpack how everyday people can invest in the small businesses that define their hometowns. From her early days at Seventh Generation questioning the “green premium” to designing new models for Main Street investing, Janice shows why traditional capital markets leave most founders and communities...
info_outlineThis week, Lance welcomes Chris Miles, the Cash Flow Expert and Anti-Financial Advisor. Chris shares his remarkable journey from being over $1 million in debt to achieving financial independence—twice—by the age of 39. He introduces his "work optional blueprint," a strategy centered on generating enough passive income to cover all expenses so you can work because you want to, not because you have to.
Chris critiques traditional financial advice and highlights the importance of taking personal control of your financial future. The episode explores topics like the flaws in mainstream financial planning, the benefits of infinite banking, and proven methods for creating multiple streams of passive income. Chris also explains how to leverage your business as a primary investment and how whole life insurance can function as a tax-free savings tool. With a mix of personal anecdotes and hard-won lessons, he emphasizes the power of working "right"—not just hard or smart—to achieve lasting financial freedom. This episode is packed with actionable insights for entrepreneurs and business owners ready to take their finances to the next level.
Topics Include:
- Breaking Down the “Work Optional Blueprint”
- A Critique of Mainstream Financial Advice
- Taking Control of Your Financial Future
- Understanding The Problem with 401(k)s
- Actionable Strategies for Passive Income
Connect with Chris:
Resources Mentioned in This Episode:
Beyond Rice & Beans: 7 Secrets to Free Up Cash Today
Profit First: Transform Your Business from a Cash-Eating Monster to a Money-Making Machine
Let's Get Social: Connect with Planet Wealth
Visit Us: Planet Wealth Website
Produced By: Social Chameleon