Fleming’s Prime Steakhouse and Wine Bar President Sheilina Henry wears her leadership style — authentically focused, mission-driven and people-centric — on her sleeve. And with a sense of humility. (The first entry on her LinkedIn profile says Girl Mom.) On this episode Sheilina talks about her restaurant career start (old-school Pizza Hut in Chicago) and how she found her way and climbed the career ladder at Tampa-based restaurant giant Bloomin’ Brands. She also talks about her mentors, what motivates her to lead people and overcoming mistakes and setbacks.

3 Takeaways:

1. (03:10) Without a customer, you have nothing, treat them well
2. (09:35) I am looking for leaders who make it through adversity
3. (17:30) Keep fighting

Timestamps:

(00:00) This episode is sponsored by Kerkering Barberio!

(01:15) Introducing Sheilina Henry, president Fleming’s Prime Steakhouse and Wine Bar

(03:10) What grew your passion in the restaurant industry?

(05:10) What led you to Bloomin Brands?

(07:45) What do you look for in leaders?

(10:35) Overcoming setbacks

(13:45) Mentors

(17:45) Developing relationships within Bloomin Brands

(20:50) Fleming’s in 2025

This week, we speak with Megan Rose, president and CEO of Better Together. Better Together, based in Fort Myers, has served more than 10,000 children across Florida, keeping families intact and out of the state system. And it’s helped nearly 40,000 people, many in ‘second-chance’ life situations, find employment across 24 states. On the episode, Better Together CEO Megan Rose talks about the importance of failing fast and failing forward, while not losing your innovative edge in nonprofit work. Megan also talks about her childhood, and how others in her community helped her family overcome some difficult circumstances.

3 Takeaways:

(14:40) There is no fear of failure, but you must learn from it

(15:05) Focus on 3 things at a time

(20:00) Self-discipline is a must-have

Timestamps:

(00:00) This episode is sponsored by Kerkering Barberio!

(01:00) Introducing Megan Rose and rapid fire questions

(02:35) Tell us about Better Together

(05:10) How Better Together helps people find employment

(08:40) What led you to this career path?

(13:40) Leadership advice

(17:20) What do you look for in leaders?

(21:25) Examples of failure you learned from

(27:15) What can we look forward to in 2025?

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.

Freddy Williams was named CEO of the Boys & Girls Clubs of Lake and Sumter County in 2012, when he was 28-years-old. Four years later he was CEO of the youth-focused nonprofit in Pinellas County. And now he’s at the helm of a Boys & Girls Club operation that stretches through Pinellas, Pasco and Hillsborough counties. On this episode Freddie chats with Business Observer Managing Editor Mark Gordon about his first summer at a Boys & Girls Club — it wasn’t necessarily voluntary; his five pillars of intentional leadership; and why Denzel Washington is the one person, dead or alive, he’d love to have dinner with.

3 Takeaways:

(14:45) A strong moral compass and a spirit of continuous improvement are key leadership characteristics

(16:50) A board is powerful if you can tap into their expertise

(17:30) Never ask someone to do something you aren’t willing to do yourself

Timestamps:

(00:00) This episode is sponsored by Kerkering Barberio!

(00:25) Introducing Freddy Williams, CEO of Boy & Girls Clubs of The Suncoast and Tampa Bay

(01:30) Rapid Fire Questions

(05:05) How did you discover the Boys & Girls Clubs?

(07:40) Kids hold on to your every word

(08:40) Freddy’s leadership style

(10:05) What does Boys & Girls Clubs do?

(11:20) Strategic Merger

(14:45) What do you look for in leaders?

(16:10) Becoming a CEO at 27

(17:20) Leadership advice

(19:25) How do you manage leading as a CEO and being involved in the programs

(21:25) What is coming up in 2025?

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.

Chris founded Aginto, a digital and marketing firm, in 2011. Clients include small and midsize companies in health care, law, industrial sectors and home services. Chris’ amazing never-quit backstory, before Aginto, includes a major life turnaround: He was unemployed, living alone, first in his car, then in a run-down motel in Sarasota with sticky floors. Desperate, he started his business while working an overnight shift at a Goodwill donation center in Sarasota. Business Observer Managing Editor Mark Gordon and Chris talked about how he was able to get through that time — which includes having an infant daughter. One key, says Chris, is he was grateful for what he had, no matter how little that was, while also never being content.

3 Takeaways:

1. (11:40) Don’t misconstrue gratefulness with content
2. (14:50) Leadership is about serving those who you are leading
3. (15:50) The 1 on 1 is a powerful leadership tool

Timestamps:

(00:00) This episode is sponsored by Kerkering Barberio!

(00:30) Introducing Chris Williams, Managing Director of Aginto

(01:30) Rapid fire questions

(04:15) What is Aginto?

(07:00) Starting a business from 0

(11:30) Keeping a positive mindset

(14:25) Characteristics of a good leader

(16:30) Leadership advice

(19:30) Involvement with Salvation Army

(21:20) What is happening in 2025 for Aginto?

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.

LaShawn has been the market leader in Tampa for JLL since 2019. Her territory covers Tampa Bay and Central Florida and she oversees more than 40 brokers. A passionate alum of the University of Kansas, LaShawn has been in the Tampa market for some 20 years and the commercial real estate business for 25 years. She’s executed over 350 assignments totaling $5 billion for institutional clients with both industrial and office portfolios. Business Observer Managing Editor Mark Gordon and LaShawn talked about JLL’s recent significant expansion in Tampa — and why the firm did it. (She’s obviously a fan of working in the office, not WFH.) They also talked about what she looks for in leaders (resilience is a big one, character, too), what she has learned from her mentors and more.

3 Takeaways:

(03:20) Relationships, relationships, relationships

(18:20) Perform and execute what is in front of you

(19:40) Be where your feet are

Timestamps:

(00:00) This episode is sponsored by Kerkering Barberio

(00:26) Introducing Lashawn Bates and rapid fire questions

(01:50) How did you get into commercial real estate and succeed?

(03:40) Building relationships

(05:40) Working for JLL and becoming a leader

(07:50) From broker to leader

(08:55) JLL’s growth in the market

(13:10) Leadership characteristics

(18:10) Leadership advice

(20:40) The importance of practicing

(22:45) Overcoming rejection

(26:20) JLL in 2025

Mark Gordon is the Managing Editor of the Business Observer. He has been with the Business Observer since 2005, where he’s written about companies, development, entrepreneurs and how government intersects with business, among other topics. He currently oversees the paper’s coverage from Tampa to Naples, in print and online, overseeing a staff of reporters and photographers, in addition to writing stories. He has written a biweekly leadership column, Leadership Matters, since 2021 in the Business Observer. And in 2023 he began hosting From the Corner Office, a weekly podcast.

In a twist, for this week’s episode From the Corner Office producer Read Corley turns the tables — and interviews host Mark Gordon. Read and Mark talked about Mark’s career in journalism, his lessons learned about leadership from interviewing hundreds of executives and entrepreneurs and his mentors. Listen for how Mark answers a question about what he would like the headline to be for his last story.

3 Takeaways:

1. (06:40) Be pragmatic
2. (07:45) Never assume, over communicate, and be clear
3. (23:10) Never be sure, double check

Timestamps:

(00:00) This episode is sponsored by Kerkering Barberio!

(00:30) Introducing Mark Gordon, Managing Editor of Business Observer

(03:35) Becoming Managing Editor and responsibilities

(06:10) Learning curve of managing people

(08:48) Favorite story Mark has written for the Business Observer

(10:30) Ideal audience member of Business Observer

(11:45) Characteristics of the best hires

(13:40) Setbacks and learning experiences

(17:00) There is no “edit” button in journalism

(20:40) Mark’s mentors

(25:20) Rapid fire questions

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.

Patrick has worked in sales, marketing, training and product development for more than 30 years. He has also been a leader in building teams and creating a sustainable positive corporate culture at both family businesses and large corporations. Brands he's worked for include Procter & Gamble and Stryker Corp. He’s been with Shepherd Insurance, and its predecessor brand in Sarasota, Al Purmot Insurance, since 2007.

Business Observer Managing Editor Mark Gordon and Patrick talked about how he and his team navigated the season of storms in the fall, working for clients while also living in the ravaged area. One key, he says, for leaders during stressful times like that is “calm is contagious.” They also talked about the must-dos in building a strong company culture and how being a youth basketball coach for his kids helped shape his leadership style. And listen for a pair of personal nuggets: the impact Patrick’s late father had on his life and what his word of the year was for 2024.

3 Takeaways:

1. (05:40) Culture is created by the team
2. (09:15) Everyone wants to feel significant
3. (16:30) If you’re looking for one aspect of a leader, is it a skill or attitude?

Timestamps:

(00:00) This episode is sponsored by Kerkering Barberio!

(00:50) Introducing Patrick Del Medico, Partner and COO of the Florida and Arizona region, Shepherd Insurance

(05:00) Creating company culture

(08:00) Lessons from basketball coaching

(11:55) Holding people accountable

(16:10) Characteristics of leadership

(18:45) Leadership lessons

(22:15) Shepherd Insurance in 2025

(24:40) Rapid fire questions

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.

Kim oversees the entrepreneurship center at the State College of Florida, where she works with and guides entrepreneurs, mentors, investors, founders, and aspiring founders. Prior to that Kim worked in branding and marketing for several iconic American brands, including Sears, Kraft Foods and FAO Schwarz, where she had profit and loss responsibility for up to $2 billion. In 2006 she founded her own marketing, branding and digital strategy firm, richmondmarketing+communications.

Business Observer Managing Editor Mark Gordon and Kim talked about how Kim navigated the early parts of career, in Corporate America, with an emphasis on taking risks, resiliency and curiosity. They also talked about how and why Kim changed gears in her career four years ago, to mentor startup business owners. And listen for the fun stories about when she worked for iconic toy brand FAO Schwarz.

3 Takeaways:

1. (04:45) Leaders have to articulate and inspire towards a vision
2. (06:00) It’s not enough to just maintain the business
3. (14:50) Integrity, honesty, and curiosity are non-negotiable

Timestamps:

(00:00) This episode is sponsored by Kerkering Barberio!

(00:50) Introducing Kim Richmond and 26 West

(02:20) Kim’s career and growing into leadership

(05:10) Learning from leaders

(07:40) FAO Schwarz and selling to a hedge fund

(11:00) Hiring actors as retail workers and marketing magic

(14:32) What do you look for in leaders?

(16:55) Guaranteeing success

(21:00) What is coming for 26 West

(23:55) Rapid fire questions

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.