In this episode of Radical Wealth Plan, I’m sitting down with my good friend and longtime business partner, David Bailey. We’ve known each other for over 20 years, and in that time, I’ve watched David build an incredible real estate portfolio from the ground up.
David’s journey is a fascinating one—he started in the corporate world, working alongside some of the biggest names in real estate, including his legendary mentor, Sam Freshman. But instead of staying in the comfort of a high-paying job, he made the bold move to strike out on his own. In this episode, we talk about what it really takes to leave a steady paycheck and start building wealth through real estate.
We get into the lessons he learned from his family, the first properties he bought, and the tough decisions he had to make during market downturns. David also shares some of the biggest mistakes he made—like being too conservative—and what he would do differently if he could go back. And if you’re looking to get into real estate investing yourself, you’ll love hearing his strategies for finding the best deals, negotiating smart, and playing the long game.
This conversation is packed with wisdom, personal stories, and real, actionable insights from someone who’s been in the trenches for decades. Whether you’re a seasoned investor or just getting started, you won’t want to miss this one!
Timestamps
00:00:00 Introduction
00:03:30 Early Influences & Family Lessons in Business
00:06:50 Finding the Right Mentor & Early Career in Real Estate
00:12:00 Transitioning from Corporate to Independent Real Estate Investing
00:17:30 The First Big Real Estate Deal
00:23:00 Surviving Economic Downturns & Learning from Market Cycles
00:28:00 Key Investment Strategies & Mistakes
00:35:00 How to Find and Acquire Profitable Real Estate Deals
00:42:30 Real Estate vs. Other Investments
00:49:00 The Future of Los Angeles Real Estate & Market Trends
00:55:00 Mindset, Success, and Wealth-Building Lessons
01:17:00 Lightning Round
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