What if the secret to extraordinary wealth isn’t about betting on the next big thing, but buying something tried-and-true—like a plumbing business, a car wash, or a cleaning company? What if the future of entrepreneurship isn’t on Wall Street or in Silicon Valley, but on Main Street—if only we knew how to seize it?

My guest today is Codie Sanchez, founder and CEO of Contrarian Thinking, a digital education platform and media company with over 6 million followers

In her new book, Main Street Millionaire: How to Make Extraordinary Wealth Buying Ordinary Businesses, Codie lays out her bold argument: that buying profitable, established, cash-flowing businesses is the most underrated path to building wealth—and that now is the time to act. Why? Because America is facing a generational handoff. Over 40 million Americans are hitting retirement age, and baby boomers—who currently own nearly two-thirds of small businesses with employees—are poised to sell. Codie calls it a “silver tsunami,” and for those who know how to navigate it, it could mean once-in-a-generation opportunity.

In our conversation, Codie opens up about her own unlikely journey from journalism to Wall Street to Main Street. We talk about how she made the leap, the psychological hurdles to entrepreneurship, and how she thinks about power, relationships, and the future of work in an AI-driven world.

This episode aired originally March 26, 2025

Learn more about Farnoosh's upcoming literary workshop Book to Brand. Early bird registration is now open!

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We're exploring two topics that are at each end of the life spectrum - child savings accounts and Medicaid. First, what is a Trump account? Farnoosh began contributing to her kids' accounts over the weekends. She has pros, cons and even a great hack for making the most of these accounts. Plus, is 20% a good amount for a home downpayment? And how to increase your chances of qualifying for Medicaid?

Learn more about Farnoosh's upcoming literary workshop Book to Brand. Early bird registration is now open!

Hosted on Acast. See acast.com/privacy for more information.

My guest today is someone I've known and admired for a long time — Bobbi Rebell, CFP®, founder of Financial Wellness Strategies and author of Launching Financial Grownups: Live Your Richest Life by Helping Your (Almost) Adult Kids Become Everyday Money Smart, as well as How to be a Financial Grownup. Bobbi was previously a global business news anchor and personal finance columnist at Thomson Reuters, and held positions at CNBC, CNN and PBS, so she's spent decades translating money into plain English for millions of people.

But today we're talking about a new chapter: Bobbi just became a Certified Financial Therapist — a credential that sits at the intersection of money and mindset, and one she worked hard for, the long way, no shortcuts. We're going to dig into why she pursued it, what financial therapy actually is, and how understanding our money psychology — from childhood money memories to the algorithms shaping our spending — can change how we feel about our financial choices, even the ones we didn't fully choose.

Follow Bobbi on Substack.

Learn more about Farnoosh's upcoming literary workshop Book to Brand. Early bird registration is now open!

Hosted on Acast. See acast.com/privacy for more information.