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.

Visit businessobserverfl.com for more.

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?

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.

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.

Ronde is one of the most recognized professional athletes in Tampa Bay, having played 16 seasons for the Buccaneers in a Hall of Fame career that included a Super Bowl win. Ronde has remained active in the region’s sports and philanthropic communities since his 2012 retirement, and is general chairman of Copperhead Charities, which puts on the Valspar Championship PGA Tour event every March. On this episode, Business Observer Managing Editor Mark Gordon and Ronde talked about how being doubted and overlooked fueled his career — even as he reached the pinnacle of his sport. They also talked about the coaches he learned the most from, including Mike Tomlin and Tony Dungy.

3 Takeaways:

1. (09:10) You’re either getting worse or better, staying the same is impossible
2. (24:00) Leadership does not always come from the top
3. (24:30) Being in a position of power does not make you powerful, empowering others does

Timestamps:

(00:00) Introducing Ronde Barber, Pro Football Hall of Famer

(04:45) What is the Valspar Championship?

(07:40) Making the Valspar Championship bigger

(10:10) Learning from his mother

(15:40) Being doubted and overlooked

(20:50) Learning from legendary coaches

(22:55) Being coached by Jeff Hafley

(25:17) Updates to the experience of the Valspar Championship

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.

Craig Albernaz was named manager of the Baltimore Orioles — who host spring training in Sarasota — last October. Craig played college baseball at Eckerd College in St. Petersburg and then in the minor leagues for eight seasons, including seven with the Tampa Bay Rays. On this episode, Business Observer Managing Editor Mark Gordon and Craig talked about his rise in baseball, from working in the minor leagues in the Tampa Bay Rays organization to being a coach with the San Francisco Giants and the Cleveland Guardians. A key lesson in all those stops, says Craig: constant communication, on things good and bad, is essential.

Takeaways:

1. (06:10) Cultivate an environment where people can thrive
2. (07:00) Have the conversation before the conversation
3. (09:40) Know the purpose of your role
4. (12:10) “No second class citizens”
5. (17:30) You spend too much time with coworkers to not hire great people

Timestamps:

(00:00) Introducing Craig Albernaz, Manager, Baltimore Orioles

(04:00) Being named Manager of the Baltimore Orioles

(05:40) Learning from Stephen Vogt an elite communicator and Cleveland Guardians Manager

(09:15) Midwest League Coach of the Year

(11:20) Learning from the Rays organization

(13:30) Lessons from parents

(15:05) Top priorities when going to Spring Training

(17:10) What do you look for when hiring a staff?

(19:00) Pete Alonzo joining the Orioles

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.

Lee Wetherington founded Lee Wetherington Homes in Sarasota in 1981. He has since moved the company, one of the largest-builders in the Sarasota-Manatee region, to Lakewood Ranch. On this episode, Business Observer Managing Editor Mark Gordon and Lee talked about the ups and downs of being in the homebuilding business in Florida for more than 40 years, and the key decisions he had to make — in both good and bad times. They also talked about what he learned about leading from his time serving in combat in the Vietnam War.

3 Takeaways:

1. (12:00) Be patient, give clear and concise commands
2. (13:30) Build trust with transparency and truth
3. (20:00) Always know your numbers

Timestamps:

(00:00) Introducing Lee Wetherington, founder, Lee Wetherington Homes

(03:05) What is Lee Wetherington Homes?

(05:00) Starting Lee Wetherington Homes when interest rates were 18%

(06:40) Restructuring the company in 2010

(10:40) Lessons from the recession

(11:45) Lessons from the Marines in Vietnam

(13:30) How do you build trust in teams?

(16:20) Leading with certainty

(18:30) Mentors

(20:00) Advice to young entrepreneurs

(21:00) Being involved in philanthropy

(25:30) What are you looking forward to 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.

Debbie LaPinska has been chief people office of CabinetWorks Group, based in Michigan, since November 2024. Prior to CabinetWorks, she worked at Venice-based window and door manufacturer PGT Innovations for 31 years, rising to chief human resources officer, and after that, chief customer officer. She joined several other former PGT executives at CabinetWorks Group. On this episode, Business Observer Managing Editor Mark Gordon and Debbie talked about the shifts in her career and she dealt with what she thought, at the time, was a major setback. They also talked about how she won over a group of 50 truck drivers in one leadership role, partially by meeting them as their day started at 3:30 a.m.

3 Takeaways:

1. (08:15) Sometimes you have to make unpopular decisions as the leader
2. (11:20) Being honest and transparent is key in hard decisions
3. (15:50) If you are good with people, you can lead any function

Timestamps:

(00:00) Introducing Debbie LaPinska, Chief People Officer, CabinetWorks Group

(03:45) What is CabinetWorks Group?

(06:30) What did you learn from Jeff Jackson?

(08:45) How did you work through letting people go in the recession?

(10:10) Building trust with teams and communicating challenging messages

(13:30) Defining leadership

(16:30) Don’t have to know everything, just need to know enough to be dangerous

(19:20) Valuable feedback

(22:40) 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.

Nicci Bucher was named CEO of the YMCA of Greater St. Petersburg in late 2025. Prior to this role, Nicci spent 20 years in the YMCA network, most recently as COO of the YMCA of Central Florida, where she oversaw a $51.6 million operational budget. On this episode, Business Observer Managing Editor Mark Gordon and Nicci talked about her leadership styles and principles and how she creates a strong workplace culture through trust and transparency. They also talked about how she has overcome feelings of impostor syndrome, especially in the current stage of her career.

3 Takeaways:

1. (08:45) Be authentic as a leader
2. (12:00) Buy into your team, you are not above doing something in the business
3. (17:30) Good workplace culture is trust and transparency

Timestamps:

(00:00) Introducing Nicci Bucher, President and CEO, YMCA of Greater St. Petersburg

(05:45) What is the YMCA of Greater St. Petersburg?

(06:20) Starting her career at Department of Children and Families, and what did you learn from that time?

(08:30) Leadership style

(09:30) Leadership characteristic every leader should have

(10:15) Leadership influences

(12:50) Giving others autonomy

(13:50) Leadership lessons Nicci wishes she knew early

(15:40) Nicci’s transition to CEO role

(17:20) What is good workplace culture?

(18:30) Great leadership advice

(19:34) Dealing with imposter syndrome

(22:00) Growing in the role of CEO

(23:40) Looking forward to 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.