Greg Schaefer on Building Mental Grit, Betting on Yourself, and the Entrepreneur’s Endurance Mindset

This week, Jessica sat down with Greg Schaefer, founder of Schaefer Enterprises and a committed endurance athlete, to talk about what it really takes to push beyond limits—on the trail and in business. In this conversation, Greg shares how the discipline and mindset forged through endurance sports have shaped his entrepreneurial path. From leaving corporate life to bet on himself, to building a company that reflects his values, Greg opens up about the highs and lows of founder life—and the mental frameworks that help him keep moving forward. He also explores the emotional journey of leadership, how he’s learning to enjoy the climb, and what long-distance racing taught him about business pacing, resilience, and letting go of ego. From start lines to strategy calls, Greg’s story is one of inner drive, calculated risk, and the belief that you can go further than you think. About Greg Schaefer Greg Schaefer has built a life where business, athletics, family, and resilience converge. As founder and president of Schaefer Enterprises, Inc., he grew a boutique Manhattan insurance agency into a nationally respected firm serving industries from healthcare to construction. In 2019, he sold the company to private equity, a milestone reflecting his vision, leadership, and client-first values. As a husband to Dr. Maryann Mikhail and father to sons James and Jax—both elite athletes in soccer and tennis—Greg’s deepest drive comes from setting an example of discipline and heart for his family, whom he calls his “why.” Outside the boardroom, Greg has tested his limits as a 18-time Ironman competitor, including six full-distance races and two coveted starts at the Ironman World Championships in Kona. A former Division I basketball player, he carries lessons of endurance and mental toughness from the court to the marathon finish line, racing not just for himself but to inspire his boys and honor his wife’s unwavering support. Each race reinforces his belief that grit—not circumstance—defines success. In 2023, Greg faced his toughest challenge: a diagnosis of Young-Onset Parkinson’s Disease. Instead of retreating, he leaned into his “dog in the fight” mentality, bolstered by his family’s love—Maryann’s relentless pursuit of the best care and his sons’ reassuring hugs. Today, as a motivational speaker, he shares raw, optimistic stories of resilience, family, and facing adversity head-on. Whether in business, sport, or health, Greg’s message is clear: the race never ends, and we are stronger when we run it together. LinkedIn: https://www.linkedin.com/in/gregory-schaefer-cic-cpia-aci-4892027/ Website: https://gregoryschaefer.com/    Host: Jessica Kriegel Website: jessicakriegel.com LinkedIn: linkedin.com/in/jessicakriegel Instagram: @jess_kriegel Culture Partners Website: culturepartners.com LinkedIn: linkedin.com/company/culturepartners