#24 Terry Roberts

In this episode, Stafford sits down with Terry Roberts, a man who spent decades navigating the corporate world with companies like IBM, Procter & Gamble, Kimberly-Clark, Boston Scientific, and Medtronic only to walk away and bet on himself.

After realizing in his mid-50s that corporate advancement had a ceiling, Terry made a hard pivot. No safety net, no guarantees. Just a decision to learn real estate from scratch. Over the next several years, he built a portfolio strong enough to replace his income and step away from corporate life on his own terms.

Now semi-retired, Terry shares what that transition really looked like; the uncertainty, the discipline, and the long game most people aren’t willing to play. This is a conversation about reinvention, knowing when to pivot, and building something that actually gives you freedom.

Outside of business, Terry is a family man first. He’s been married to his college sweetheart Gina for over 40 years, with three daughters, a growing crew of grandkids, and a life centered around family, faith, and Mississippi State athletics. You’ll usually find him at a game, at the lake house on the Tombigbee, or in the shop working with his hands.

He also co-hosts the Cardiovascular Matters podcast alongside Dr. Craig Walker, where they dig into heart health and real-world medical insights.

This one’s about what happens when you stop waiting for permission and start building your own path.