“An Operator At Heart” with Stephen Shannon

In this episode, I flew to Dallas to sit down with Stephen Shannon—entrepreneur, investor, and family office operator—to discuss his journey across private equity, real estate, and capital management. We explore the principles behind his investment strategy, the challenges of building credibility, and the hard lessons he’s learned about leadership, trust, and execution.

Episode Highlights

• From Memphis to Texas: Navigating different markets, building networks, and embracing Texas’ economic advantages.
• A Career in Capital: Starting on Wall Street, managing family office investments, and launching his own company.
• Principles of Smart Investing: Prioritizing execution, avoiding over-engineered deals, and learning from failures.
• A Costly Business Lesson: Overcoming a failed business deal early on, a dishonest operator, and what it taught him about due diligence.
• The Secret to Strong Teams: Hiring based on strengths, trusting your team, and building a business culture from the ground up.
• How to Find Work-Life Balance: Staying grounded in faith, prioritizing family, and redefining long-term success.