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:

1. (15:10) Listen more than you speak
2. (16:45) Direction is more important than certainty
3. (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?

Join us every week as we interview business leaders to learn what makes them great, what they look for in growing leaders, and much more.

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Toni founded her fractional CEO firm, The C Society, in June 2025. One of her goals is to bring high-level leadership to restaurant and hospitality companies with the overhead. She was previously president of restaurant brand Perkins and managing director for Little Ceaser’s Pizza, Canada. On this episode, Business Observer Managing Editor Mark Gordon and Toni talked about her career, both with large brands and now, leading a consulting firm. They talked about how she builds high-performing teams and how leadership is more than a position, it’s a seat at the table that shapes the entire organization.

3 Takeaways:

1. (09:30) Great brands and great leaders do not grow on their own
2. (13:15) Root your strategy in data
3. (20:40) Feedback is a gift, but consider the source

Timestamps:

(00:00) Introducing Toni Ronayne, founder and fractional CEO, the C Society

(07:00) What The C Society?

(10:05) Toni’s role at Perkins

(12:35) Handling the visioning of a legacy brand

(15:50) Leadership mentors

(19:30) Imposter Phenomenon

(20:30) Valuable feedback

(26:32) What is coming up in 2026 with The C Society?

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Jon Kaupla was appointed to run the Center for Executive and Leadership Education at the USF Muma College of Business last July. The center is designed to deliver practical, high-impact learning experiences for current and emerging leaders. Prior to USF, Jon spent nearly a decade leading the Center for Professional & Executive Development at the Wisconsin School of Business. On this episode, Business Observer Managing Editor Mark Gordon and Jon talked about the power of being vulnerable and admitting mistakes as a leader, and he’s personally taken that approach to advance his career.

3 Takeaways:

1. (07:15) Peer relationships are key in management
2. (13:30) The power of the pause
3. (16:00) Reprioritization is key throughout your career

Timestamps:

(00:00) Introducing Jon Kaupla, Executive Director, Center for Executive and Leadership Education

(05:00) What is the Center for Executive and Leadership Education?

(06:50) What makes good leaders?

(10:00) Adapting to feedback

(11:30) Mentors

(13:20) Handling conflict as a leader

(15:15) Tough decisions

(17:20) What is coming in 2026?

Join us every week as we interview business leaders to learn what makes them great, what they look for in growing leaders, and much more.

Visit businessobserverfl.com for more.