Russ Hayles made a career change over a decade ago to become a full-time investor and real estate salesman. JD and Russ break down his decisions to go from an economics professor and high school teacher to real estate guru. Russ openly discusses his strategies, tips and advice on how others can make a similar transition. Flips, long-term holds and sales are all on the table for this conversation. Russ shares how his background in economics shaped his approach to decision-making (including the sunk cost mindset that every investor must master), the hard lessons from his first flip gone wrong, and how he built a scalable partnership model to grow a portfolio of over 25 rental properties—without chasing hype or speculation.Topics Covered with Timestamps00:01:14 | Introducing Guest: Who is Russ Hales?

00:01:26 | Transitioning from Teaching & Coaching to Real Estate

00:03:55 | The First Flip: Buying on Whitesburg & Everything That Went Wrong

00:05:00 | Foundation Failures, Redos & Learning the Hard Lessons

00:08:51 | Understanding Sunk Cost Fallacy in Real Estate

00:10:54 | Making Decisions Based on Current Facts — Not Past Spend

00:13:31 | Advice to Sellers: Why Repairs Don’t Always Add Sale Value

00:15:19 | Pricing Strategy: Quick Sale vs. Waiting for the Right Buyer

00:16:24 | Deciding Flip vs. Buy-and-Hold: How Russ Evaluates Each Property

00:18:01 | Portfolio Snapshot: 26 Rentals & The Cash Flow Reality

00:21:51 | The Short-Term Rental Pivot: When Huntsville Changed the Rules

00:23:20 | The Truth About Airbnb Restrictions in Huntsville

00:26:31 | Long-Term Plan: Paying Off Rentals for Retirement Cash Flow

00:29:13 | Partnership Structure: Dividing Labor & Avoiding Conflict

00:32:15 | Life Balance & Humor: Still Playing Basketball at Age 43