From the Corner Office

Achieving career success with Junior Achievement CEO Cheryl Kunkle

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?
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Capitalizing on the promise of AI in banking with Kevin Gillen

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?
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Listen up and listen good with Rebecca Shafir

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.
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Powering up with a smile with FPL’s Dev Iglesias

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.
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Being a top-flight board member with Naomi Kent

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.
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Humor, humility and honesty with bank executive and podcast host Owen LaFave

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.
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Going strong in leadership and life with retired Tupperware CEO Rick Goings

Rick was with Tupperware for nearly 30 years, including stints as president, CEO, chairman and chairman emeritus. He was also an executive with Avon Corp., in Europe and the U.S.. He recently teamed up with leaders at Rollins College in Orlando to launch a new executive education institute: The Rick Goings Institute for Management and Executive Leadership. On this episode, Business Observer Managing Editor Mark Gordon and Rick talked about his long and varied career, having started two businesses prior to leadership roles with Avon Corp. and Tupperware. Rick also talked about how his first job — being a caddie at a country club — impacted his life and leadership approach. 
3 Takeaways:
(08:40) Real leadership is about collaboration
(15:00) Life needs to be an adventure
(17:55) “We are today the person we are, and our goal is to become the person we can become”
Timestamps:
(00:00) Introducing Rick Goings, Retired CEO, Tupperware Brands
(04:55) What is the Rick Goings Institute for Management and Executive Leadership?
(06:50) Rick’s life story, meeting the Pope, and starting in the Navy
(09:40) Starting a business and mentorship by Paul Harvey
(12:00) Why did you go to Avon?
(14:20) Rick’s career adventure
(16:00) Becoming CEO of Tupperware
(17:25) Taking feedback
(18:50) Advice from mentors
(22:00) World Youth Clubs
(25:20) Rick’s legacy
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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Authentic leadership — morning and nights — hotel exec with Jessica Cain

Jessica is the general manager of the Grand Hyatt Tampa Bay. She has more than 20 years of experience in full-service hospitality, including sales, events and hotel operations. She’s been with the Hyatt brand since 2008. On this episode, Business Observer Managing Editor Mark Gordon and Jessica talked about her start in hospitality — it includes answering a pay phone in her family’s upstate New York restaurant — and what motivates her to be a better leader. Jessica also talked about what’s influenced her leadership style, including things she aims to not do in building high-performing teams. 
3 Takeaways:
(07:40) Hospitality is about making people feel like they belong
(10:50) Good leadership is creating an environment where people are valued
(19:20) Sometimes you have to fake it until you make it, have composure
Timestamps:
(00:00) Introducing Jessica Cain, general manager, Grand Hyatt Tampa Bay   
(05:50) What motivates you, winning or not losing?
(06:55) Jessica’s hospitality career started from the beginning
(09:15) About Grand Hyatt Tampa Bay
(10:45) What is good leadership to you?
(12:30) Developing better leaders from within
(15:10) Leadership influences
(17:00) Hard to hear feedback
(18:20) Leading through uncertainty
(22:45) What is coming up in 2026 for Grand Hyatt Tampa Bay?
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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Counseling, Compassion, and Camaros with Rick Howell

Rick has been the Executive Director of Samaritan Counseling Services, based in Sarasota, since 1999. A native of Tampa, he earned a master’s in Divinity and a master’s in Theology at the Southern Baptist Theological Seminary in Louisville. He was ordained into the ministry in 1986. On this episode, Business Observer Managing Editor Mark Gordon and Rick talked about how and why he got his start in counseling — it was a personal experience of high stress — and how that’s helped him be a better leader. They also talked about why he believes passion is a No. 1 leadership attribute and how looking out for teammates and employees as a leader is never time wasted. And listen for a cool story about his first car — and a teenage trip to London.  
3 Takeaways:
(11:00) Passion sustains you through hard times
(14:30) You are not solely responsible for the success of your organization
(15:30) If you see a turtle on a fencepost, you know it didn’t get there itself
Timestamps:
(00:00) Introducing Rick Howell, executive director, Samaritan Counseling Services
(04:05) What is Samaritan Counseling Services?
(06:00) How did you get into this line of work?
(08:00) Day-to-day role
(09:30) What trends are you seeing in your clients?
(10:45) What characteristic does every leader need to have?
(13:00) Listening versus speaking as a leader
(14:10) What do you wish you knew earlier as a leader?
(15:30) Who are some of your mentors and what did you learn from them?
(17:45) Leading in uncertain times
(19:50) What is coming up for Samaritan Counseling Services? 
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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Real beer and real leadership with Matthew Rolnick

Matthew is a senior vice president of partnerships and events for The Real American Beer, based in Tampa. Prior to Real American Beer, he worked for several companies and brands, including Yaymaker, Groupon and CitySearch. On this episode, Business Observer Managing Editor Mark Gordon and Matthew talked about the value of great storytelling in leadership and what truly makes for an authentic leader. They also talked about “attention currency” and why it’s important. And listen for Matthew’s advice and tips on how to grow your career to the C-suite level.
3 Takeaways:
(10:00) Leaders need to get information from all departments
(13:15) Be cautious and you can’t win everyone over
(17:00) People don’t want to be sold to, but they want to hear a story
Timestamps:
(00:00) Introducing Matthew Rolnick, senior vice president, partnerships and events, Real American Beer
(03:00) What is Real American Beer?
(05:40) Matthew’s career trajectory
(08:00) Lessons from working at Groupon
(09:45) Leadership characteristics
(12:55) Lesson you wish you knew earlier
(15:10) Mark and Matthew’s connection
(17:00) Storytelling in leadership
(18:00) Cameo
(20:20) Advice to a young person
(22:10) 2026 with Real American Beer
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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