Cheryl Kunkle was named CEO of youth financial literacy nonprofit Junior Achievement in Fort Myers in January. Prior to this role, she held leadership positions for health care and medical nonprofits, including the ALS Association and the Muscular Dystrophy Association. And prior to getting into nonprofit work, Cheryl was a teacher. On this episode of From the Corner Office, Cheryl and Business Observer Managing Editor Mark Gordon talked about how and why she got into nonprofits; a piece of feedback she received as a young leader that has proved invaluable as she has grown into her career; and a few big goals she and the team at Junior Achievement have for 2026 and beyond.

3 Takeaways:

1. (07:00) Every organization needs to evolve
2. (11:00) Every individual has different priorities but you have to unite them under a common goal
3. (12:30) You don’t have to carry the weight of the organization on your shoulders

Timestamps:

(00:00) Introducing Cheryl Kunkle, president and CEO, Junior Achievement of Southwest Florida

(04:45) What is Junior Achievement of Southwest Florida?

(06:25) What is Junior Achievement most known for?

(08:00) Cheryl’s career arch

(10:30) Lessons from mentors

(12:00) Hard to hear feedback

(13:45) Trusting your team

(15:35) What do you look for in new hires?

(16:40) What are you looking forward to in 2026 with Junior Achievement?

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Forbes Riley, author of Pitch Secrets A to Z: How to Increase Your Influence, Impact, and Income, lays out the keys to making a great pitch: It’s not about the sale. And it’s not really about the product, either. She joins Business Observer Managing Editor Mark Gordon for a rollicking conversation about all things pitch.

3 Takeaways:

1. (08:00) Get to ‘yes’
2. (15:50) There’s no such thing as a perfect pitch
3. (23:45) Buy your competition

Timestamps:

(00:00) Introducing Forbes Riley, president, Forbes Riley Media

(04:15) Name association

(10:10) Forbes Riley’s background

(15:00) Get people to say ‘yes’

(18:40) Letter F of the book, Pitch Secrets A to Z

(23:00) R is for research

(27:10) Pitching provides a solution to someone’s problem

(27:50) What is coming up the rest of the year?

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Fintech CEO Tad Phelps, even at the helm of a 400-employee financial technology company, is something of a man of the people. He holds CEO sessions open only to non-management employees. He has a CEO Council of future leaders. And he loves to quote University of Georgia football coach Kirby Smart. Hear his leadership strategies in this conversation with Business Observer Managing Editor Mark Gordon.

3 Takeaways:

1. (05:20) Be visible for your employees, answer questions
2. (08:00) Create ways for your employees to grow
3. (14:00) Integrity and emotional intelligence are must have leadership characteristics

Timestamps:

(00:00) Introducing Tad Phelps, CEO, Fintech

(02:30) What is Fintech?

(05:00) What is a CEO session?

(07:40) What is the CEO council?

(10:45) Making a large organization feel small

(12:25) How did you get into this business?

(13:45) Must have leadership characteristics

(15:00) Leadership influences

(16:40) Hard to hear feedback

(17:50) Leadership legacy

(18:45) What is coming up for Fintech?

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Jennie was named the first-ever firmwide managing partner for Shumaker last year. A Sarasota native and well-known civic leader in town, Jennie leads the strategy and direction for Shumaker, a top 200 law firm in the country. On this fast-paced episode, Jennie and Business Observer Managing Editor Mark Gordon talked about her career, striving for big goals and how she handles the pressure of her high-impact work.

3 Takeaways:

1. (07:25) Always be learning
2. (08:22) Recommended reading: Extreme Ownership, Leading Through Change, and Leaders Eat Last
3. (09:10) Don’t be afraid to believe in innovative leadership

Timestamps:

(00:00) Introducing Jennie Compton, Managing Partner, Shumaker

(04:45) What is your role as National Managing Partner?

(07:25) How did you grow into this role?

(09:00) What stands out that you learned from Harvard?

(10:30) How is Shumaker handling AI?

(15:15) Why did you become an attorney?

(16:10) What characteristic does every leader need?

(17:00) What lesson do you know now that you wish you knew earlier?

(17:50) How do you handle uncertain times?

(19:00) Hard to hear feedback

(20:10) How do you handle setbacks?

(22:00) What are you looking forward to?

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Kelly and his father, Roland Caldwell, founded Caldwell Trust Co. in 1993, and Kelly became CEO in 2007. Today the company manages more than $2 billion in assets, has more than 50 employees and offices in Sarasota, Venice and Vero Beach. On this episode, Kelly tells Business Observer Managing Editor Mark Gordon about what he looks for in aspiring leaders, how he has refined his leadership style over the years and his future growth plans for the company.

3 Takeaways:

1. (07:50) You need to be recruiting all the time
2. (15:15) Stay calm, don't overreact, grow
3. (20:10) Build the emotional bank account with your clients

Timestamps:

(00:00) Introducing Kelly Caldwell, President and CEO, Caldwell Trust Co.

(03:20) What is Caldwell Trust Company?

(04:20) How did you get into this business?

(07:10) Spending a third of your time recruiting

(08:40) How have you evolved as a leader?

(11:00) Tell us about your father, the founder of Caldwell Trust Co.

(15:00) One leadership principle everyone should have

(16:15) What behaviors do you celebrate even when they are not moving the bottom line?

(19:35) How do you create accountability without creating fear?

(21:20) What is coming up in 2026?

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Kourtney Sanchez was named CEO of United Way Suncoast in June, after a national search for a new leader. Prior to the United Way CEO role, Kourtney was the chief impact officer for the Tampa Bay Buccaneers, where she was also executive director of the Glazer Family Foundation and the Glazer Vision Foundation. Kourtney and Business Observer Managing Editor Mark Gordon, on this episode, talk about her first five weeks as leader of one the region’s most prominent nonprofits — and dealing with the challenge of taking on that role after a well-respected and accomplished CEO held it.

3 Takeaways:

1. (15:00) Listen first
2. (16:00) Celebrate curiosity
3. (17:30) Emotional intelligence is a super power

Timestamps:

(00:00) Introducing Kourtney Sanchez, CEO, United Way Suncoast

(03:55) One word for your first 5 weeks at United Way Suncoast

(05:20) What is United Way Suncoast?

(08:40) How do you follow a great leader?

(10:00) Kourtney’s role at the Tampa Bay Buccaneers

(11:10) Cool experience working for an NFL team

(13:30) Kourtney’s lessons from her grandfather

(14:50) One leadership principle everyone needs

(15:40) Leadership behaviors you want to celebrate

(17:00) Hard to hear feedback but helped you grow as a leader

(19:10) How did you develop your EQ?

(20:45) Learning from mentors

(23:20) What is coming up for you?

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An engineer by training and education, Karen has held multiple leadership roles at The Mosaic Co. since joining the business in 2004 as a director of operations strategy. On this episode, Karen and Business Observer Managing Editor Mark Gordon talked about leading with purpose and clarity during challenging times and some of the steps she took to rise in her career with one of the largest publicly-traded companies in Florida.

3 Takeaways:

1. (10:15) Energy is a must have leadership characteristic
2. (13:00) Give candid feedback with the purpose of helping others
3. (18:40) Finding the answer yourself does not teach anyone anything?

Timestamps:

(00:00) Introducing Karen Swager, Executive Vice President, Operations, The Mosaic Co.

(04:10) What is The Mosaic Company?

(05:40) Why join The Mosaic Company?

(09:25) What advice would you give to young professionals to rise?

(10:15) Must-have leadership characteristic

(11:10) How do you keep your energy up?

(12:25) Leadership influences

(14:10) Hard to hear feedback

(16:25) Dealing with imposter syndrome

(19:10) What is the future of The Mosaic Company?

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Brian Henriquez has been in the electrical and power generation industry for more than two decades and now runs Suncoast Power Solutions which delivers top-tier generator installation, maintenance and repair services across the Tampa Bay region. On this episode, Business Observer Managing Editor Mark Gordon and Brian talked about how he helps grow and train leaders, what a strong company culture means to him, his biggest challenges as a leader and more.

3 Takeaways:

1. (14:00) Patience is key as a leader
2. (15:30) Be honest with your employees
3. (24:00) Get your generator BEFORE the storm comes

Timestamps:

(00:00) Introducing Brian Henriquez, founder, Suncoast Power Solutions

(08:00) What is Suncoast Power Solutions?

(11:50) Growing the business

(13:50) Growing as a leader

(15:30) Creating accountability without fear

(19:00) Business mentors

(21:50) What motivates you as a business owner?

(24:00) What are you looking to the last 6 months of the year?

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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