Winning in leadership and life with Chuck Wolfe

March 19, 2026

Chuck Wolfe has been CEO of the Chiles Group since 2018. The company oversees several assets, including the organic Gamble Creek Farms in Manatee County. The company previously owned and operated three waterfront restaurants in Manatee. Prior to hospitality, Chuck was in politics and strategic planning, including a 12-year stint as CEO for the Victory Fund, a national advocacy group supporting LGBTQ candidates. Chuck was also a senior aide to the late Florida Gov. Lawton Chiles for seven years. On this episode, Business Observer Managing Editor Mark Gordon and Chuck talked about leadership — and life lessons — he learned from everything from the boy scouts to political campaigns. They also talked about his process for making key decisions and how he overcomes setbacks.

3 Takeaways

(15:10) Listen more than you speak
(16:45) Direction is more important than certainty
(23:50) Hiring is the most important thing you can do

Timestamps

(00:00) Introducing Chuck Wolfe, CEO, Chiles Group
(07:30) What is the Chiles Group?
(10:00) Working with Lawton Chiles
(13:30) What did you learn from Governor Chiles?
(15:55) Leading with certainty when so much is uncertain
(20:05) Who influenced your leadership?
(23:10) What leadership characteristics do you look for?
(27:45) What is coming up in 2026 for the Chiles Group?

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