From the Corner Office

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:
(07:50) You need to be recruiting all the time
(15:15) Stay calm, don't overreact, grow
(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?
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.

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:
(07:25) Always be learning
(08:22) Recommended reading: Extreme Ownership, Leading Through Change, and Leaders Eat Last
(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?
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.

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:
(05:20) Be visible for your employees, answer questions
(08:00) Create ways for your employees to grow
(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?
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.

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:
(08:00) Get to ‘yes’
(15:50) There’s no such thing as a perfect pitch
(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?
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.

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:
(07:00) Every organization needs to evolve
(11:00) Every individual has different priorities but you have to unite them under a common goal
(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?
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.

Kevin Gillen has been in the banking industry for some 40 years, and a Tampa Bay and Sarasota executive for Synovus Bank since 2020. On this episode of From the Corner Office, Kevin and Business Observer Managing Editor Mark Gordon talked about the power — and perils — of AI in banking and other sectors, and some of the trendlines Kevin sees in the region’s economy the rest of 2026. They also talked about Synovus Bank’s transition to Pinnacle in the merger between the two institutions and why hiring is so important to maintain a strong culture. 
3 Takeaways:
(12:20) Be ultra selective with who you hire
(14:00) People first mentality
(19:20) Change is a breeder for opportunity
Timestamps:
(00:00) Introducing Kevin Gillen, Regional President, Gulf Coast, Synovus Bank/Pinnacle Financial Partners
(02:15) Rapid fire questions - Book recommendations, dream dinner meeting, tv shows, and emojis
(09:00) Synovus and Pinnacle merger
(14:35) Kevin’s top level thoughts on AI
(19:50) Expectations for Sarasota-Bradenton market
(23:45) 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.

Rebecca is an ADHD and executive function coach, and founder of Mindful Communication. Based in Sarasota, Rebecca is a speech language pathologist and author of the book, “The Zen of Listening: Mindful Communication in the Age of Distraction.” She has been studying listening behaviors and activities for more than 25 years. On this episode of From the Corner Office, Rebecca and Business Observer Managing Editor Mark Gordon talked about what mindful listening can do for executives and leaders as opposed to actively listening, and why that’s even more crucial in the AI, high-distraction era. She also talked about key steps any leader can take to be more mindful when they listen to others. 
3 Takeaways:
(14:45) Get comfortable with silence
(17:30) If we listen with curiosity, the speaker really feels like we care
(23:50) “Get into the movie of the speaker”
Timestamps:
(00:00) Introducing Rebecca Shafir, founder, Mindful Communication 
(04:40) What is Mindful Communication?
(06:15) What is mindful listening?
(09:30) How do you work with leaders that have ADHD?
(12:00) Working with physicians to become better listeners
(14:10) How do you help your clients be better listeners
(17:10) Curiosity and clarity
(18:55) Why should we be better listeners in the AI era?
(20:55) Example of how better listening could have been used to implement an AI tool
(23:30) Practical ways for busy leaders to be better listeners
(26:50) What is coming up for you 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.

Dev Iglesias has been with FPL for nearly a decade, working her way up from a marketing and communications role. Well-known in the Sarasota-Bradenton community for being one of the faces of FPL’s storm and outage response teams, Dev got into this field after initially chasing a career in sports communications and marketing. On this episode of From the Corner Office, Dev and Business Observer Managing Editor Mark Gordon talked about how she got into the customer service side of the power and energy business, her leadership mentors and how she keeps a positive outlook and attitude among what could be chaotic and confusing situations. 
3 Takeaways:
(11:20) When you speak 1:1, it lowers defenses
(15:35) Empathy is the most important leadership skill
(22:00) You can be uncertain, just be honest
Timestamps:
(00:00) Introducing Dev Iglesias, Director of external affairs for Southwest Florida region, Florida Power & Light  
(07:15) Gut instinct or data? Winning or not losing?
(09:00) Dev’s role at FPL
(10:40) Dealing with negativity?
(12:50) Growing up in a large, tight-knit family
(15:20) Must-have leadership characteristic
(16:15) Mentors
(18:20) Hard to hear feedback
(21:10) Leading in uncertain times
(24:40) Preparing for an emergency
(27:45) What is coming up?
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.

Naomi Kent has been working helping senior executives and leaders find the right company boards to sit on, and then be engaged and productive board members while there. She’s worked overseas and in New York and Chicago, and is now based in Naples. On this episode of From the Corner Office, Naomi and Business Observer Managing Editor Mark Gordon talked about the themes and patterns she has seen in working with top executives and leaders, and how leaders can position themselves to get on boards. 
3 Takeaways:
(07:20) Boards like board members from other industries
(10:40) Most people join a board before they retire
(18:25) Great leaders hire great people
Timestamps:
(00:00) Introducing Naomi Kent, Founder and CEO, The Boardroom Co.   
(03:17) Leadership habits you refuse to comprise on
(05:10) What is The Boardroom Co.?
(07:00) Joining boards outside of your industry
(11:00) How did you get involved with boards?
(13:00) Do’s and don’ts of being a board member
(15:10) Curiosity and clarity
(18:00) What makes a successful CEO?
(20:10) How do you become a board member?
(24:30) What are you looking forward to for the rest 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.
Visit businessobserverfl.com for more.

Owen LaFave has been with The Bank of Tampa for 13 years and in the banking industry for more than 20 years. He also hosts The Bank of Tampa’s The Money Market Podcast. On this episode, Business Observer Managing Editor Mark Gordon and Owen talked about how he got into banking, his key leadership lessons — they revolve around the three Hs: humor, humility and honesty — and why being a dependable leader matters to him, a lot. And listen for how Owen became known as the “banker with sign” guy. 
3 Takeaways:
(08:50) Employees come first
(15:10) Leaders need humility, honesty, and humor
(15:45) You don’t always need to have the answer
Timestamps:
(00:00) Introducing Owen LaFave, Pinellas County Market President, The Bank of Tampa
(05:30) What did you learn about leadership from team sports?
(06:10) Owen’s career path
(08:50) The Bank’s leadership philosophy
(10:25) Creation of “Banker with Sign”
(13:15) The success of The Money Market Podcast
(15:10) Leadership characteristics
(15:45) Leadership lessons you wish you knew
(16:30) How do you help employees make a decision?
(18:15) How do you lead with certainty?
(19:45) Best leadership advice
(22:30) Bank of Tampa 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.