Eleni founded Gates Hospitality Group, which handles brand building, corporate communications, public relations and more for restaurants and other businesses, earlier this year. She was previously head of investor relations and corporate communications for East Manatee County-based First Watch Restaurant Group. On this episode Business Observer Managing Editor Mark Gordon and Eleni talked about what she’s learned from some important hospitality mentors on company culture, motivating teams and more. They also talked about her big step in working for corporate brands to going out on her own and going back to school for her MBA.

3 Takeaways:

1. (05:50) Be intentional about how you communicate with specific audiences
2. (16:00) A leader is never above any work in the organization
3. (17:00) Be a human, not the boss

Timestamps:

(00:00) Introducing Eleni Gates, Founder and Principal, Gates Hospitality Group

(04:00) What is Gates Hospitality Group?

(06:15) Starting at First Watch

(08:20) Working for Chris Tomasso

(09:30) IPO-ing with First Watch

(13:00) Dealing with imposter syndrome

(14:30) Learning from Ken Pendery

(17:25) What is good leadership?

(19:00) Leadership advice

(20:30) Learning from her parents

(23:00) Storytelling in leadership

(24:20) Gates Hospitality Group in 2025

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AG Lafley is the former CEO of consumer products giant Procter & Gamble, where he ran the company for 15 years over two different tenures. Since retiring and moving to Sarasota, he has worked with small businesses and nonprofits, and also led the development and operations at the Bay Sarasota. On this episode Business Observer Managing Editor Mark Gordon and AG talked about how he overcame difficulties and challenges at P&G, and why leading with a customer-first mindset, even in such a large organization, was a priority. They also talked about why it was important for him to be a “say do” leader.

Key Takeaways:

(05:30) Crisis is opportunity

(05:45) Leadership is not genetically determined, it can be built

(12:35) Great leaders take accountability and create accountability

(17:30) Leadership is a navigation job

(19:40) Know yourself, be yourself, and play to your strengths

(20:40) Understand the art of going slow to go fast

(21:20) Leadership is thinking, decision making, and doing

Timestamps:

(00:00) Introducing AG Lafley, retired CEO, Procter & Gamble; founding CEO, The Bay Park Conservancy

(05:00) Keys to being a great leader

(06:30) Seizing leadership opportunities early in life

(09:00) Becoming CEO of Procter & Gamble

(12:00) Decisions made in the first 100 days of being CEO

(17:15) What is leadership?

(19:25) Leadership advice

(22:00) Learning to ‘go slow to go fast’ from the Japanese

(27:45) AG’s leadership legacy

(31:30) What is coming up at Bay Park Conservancy?

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Darla has more than 20 years of experience in everything from corporate sales and operations to leadership development. She currently runs Darla Bonk Consulting, and, with her husband, Architectural Metal Flashings. Two more biographical nuggets: She’s a Fort Myers city councilwoman and she hosts a weekly podcast, “On Your Way.” On this episode, Business Observer Managing Editor Mark Gordon and Darla talked about her diverse and winding career, what she learned from her parents about leadership — who have been married for 70 years — and how the power of being intentional in all her communications has helped be a better leader.

3 Takeaways:

1. (08:15) Listen for cues to get consensus
2. (14:00) Leaders need the ability to pivot
3. (15:30) Communication is everything

Timestamps:

(00:00) Introducing Darla Bonk, CEO and founder, Darla Bonk Consulting

(07:45) What did you learn about leadership being on the City Council?

(10:15) Learning from leaders in Darla Bonk Consulting

(11:30) Growing up as Darla Bonk

(13:50) What do you look for in leaders?

(15:25) Leadership advice

(16:00) Storytelling in leadership

(17:00) Balance short term wins and long term planning

(18:10) Imposter syndrome

(19:00) Lessons from her parents

(20:45) Darla’s leadership legacy

(21:30) Darla Bonk in 2026

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Jennifer Grondahl has been with the Baltimore Orioles since 2018, splitting her time between Maryland and the team’s spring training home in Sarasota. Prior to the Orioles, she was president of the YMCA Foundation of Sarasota; founded and ran a marketing and events company in Sarasota; and was the executive director of the American Cancer Society. On this episode, Business Observer Managing Editor Mark Gordon and Jennifer talked about her passion for cooking, mistakes she’s learned the most from, overcoming Imposter Syndrome leading with love, her mentors — and notably, her passion for cooking.

3 Takeaways:

1. (13:45) Every leader needs humility
2. (14:45) Take feedback
3. (17:40) Communication is the key to everything

Timestamps:

(00:00) Jennifer Grondahl, Senior Vice President of Communications, Baltimore Orioles

(06:00) What have you learned from David Rubenstein?

(08:35) Jennifer growing up

(09:50) Jennifer’s career trajectory

(11:05) Learning from mistakes

(13:30) What does every leader need?

(17:40) How do you handle conflict?

(18:50) Handling imposter syndrome

(21:50) Leadership advice

(23:00) What is coming in 2026?

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Andrew Wright is the founder of three companies: Franklin Street, a full-service commercial real estate firm with more than $7 billion in transaction volume over 20 years; private equity firm Ally Capital Group; and Next Level Brands, a hospitality/dining company. On this episode, Business Observer Managing Editor Mark Gordon and Andrew talked about his humble and blue-collar origin story, which led him to put a premium on work ethic and hustle. They also talked about what he looks for in leaders and his biggest investment regrets.

3 Takeaways

1. (10:44) Anchor in your vision, but not at the expense of personal integrity
2. (13:04) Leaders need to be the guarantor of culture
3. (17:04) Profit and growth are often on opposite ends of the spectrum

Timestamps:

(00:00) Introducing Andrew Wright, founder and chairman, Franklin Street

(06:44) What are you primarily working on right now?

(08:44) What does leadership mean to you?

(10:44) Holding people accountable

(13:19) Leadership advice

(16:44) Decisions that shaped Franklin Street

(18:24) Being patient

(22:14) Storytelling in leadership

(23:19) Anything you would want a mulligan on?

(25:49) What are you looking forward to in 2026?

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Tim is a go-to thought leader in investing in startups, entrepreneurship and related topics in both Southwest Florida and the entire Sunshine State. In addition to being a partner at Fifth Avenue Family Office in Naples, which works with a select group of high net-worth families, Tim is also chair of the Tamiami Angel Funds. Tim has been named to Florida Trend magazine’s list of Florida’s 500 Most Influential Business Leaders six times and was named a 2025 Business Hall of Fame Laureate by Junior Achievement of Southwest Florida. On this episode, Business Observer Managing Editor Mark Gordon and Tim talked about what being fired taught him about the leader he wants to be. They also talked about the do's and don’ts of making good investor presentations and how a startup entrepreneur can know when he or she is getting to yes.

3 Takeaways:

1. (14:10) Leaders are successful because of the teams they build
2. (18:45) Failure happens when you are trying to do great things, you need resilience
3. (22:30) Storytelling is art and science

Timestamps:

(00:00) Introducing Tim Cartwright, Partner and Co-Founder, Fifth Avenue Family Office

(06:20) What is Fifth Avenue Family Office and Tamiami Angel Funds?

(08:35) What have you learned from working with leaders of these organizations?

(13:55) What defines good leadership?

(16:25) Who influenced your leadership style?

(18:00) Resilience and overcoming setbacks

(21:00) What role does storytelling play in leadership?

(24:15) What is the biggest “not to do” in pitching a business

(26:00) What is on the horizon for your entities?

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Global business brokerage Transworld Business Advisors is based in South Florida, with a heavy presence on the west coast of the state. Andy Cagnetta, after owning and running a pasta shop in Connecticut, joined Transworld in 1995. In 1997, driven, his bio says, “by his entrepreneurial spirit and belief in the industry’s potential, he purchased the company.” Transworld now has multiple Florida offices, including one in Tampa, and a global presence, from the Middle East to Mexico. On this episode, Business Observer Managing Editor Mark Gordon and Andy talked about what he wants his leadership legacy to be (it’s short and sweet) and how he leads high-performing teams. They also talked about some of his charitable work, which includes cooking a lot of pasta.

3 Takeaways:

(07:40) Successful business owners are not afraid to do the gritty work

(08:30) Have a high tolerance for pain with people

(17:00) In a negotiation, not everything is about money

Timestamps:

(00:00) Introducing Andy Cagnetta, CEO, Transworld Business Advisors

(04:30) What is Transworld Business Advisors?

(05:40) How did you get into this line of work?

(07:00) What have you learned from other leaders?

(09:05) Balancing employee pain points

(10:50) Who are your influences?

(13:30) Storytelling in leadership

(14:30) Something you wish you knew earlier?

(15:30) What do you look for in leaders?

(16:45) Negotiating tips

(19:45) What legacy do you want to leave?

(21:15) Transworld Business Advisors in 2026

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John Burpee has been in the Florida commercial real estate market for more than 30 years. He consults with national investment firms, financial institutions and private investors, and has brokered more than $2.1 billion in commercial investment real estate deals. He’s also president of the Florida Gulfcoast Commercial Association of Realtors, and has worked as a court-appointed receiver. On this episode, Business Observer Managing Editor Mark Gordon and John talked about his mentors, what he has learned from working for some high-achieving executives and how he approaches difficult conversations.

3 Takeaways:

(10:20) If the deal is right, buyers come from all over

(11:30) Put the buyer and seller in the room together

(14:25) You stay even with your competition Monday through Friday, 9-5. You get ahead of them every minute before and after that.

Timestamps:

(00:00) Introducing John Burpee, President & CEO, John Burpee & Associates

(04:45) What is John Burpee & Associates?

(06:15) Leadership insights

(09:20) Managing the operations and leadership

(10:50) Learning lessons

(12:35) Dealing with conflict

(14:00) Lessons from Grandfather

(15:25) What legacy do you want to leave?

(17:15) The market in 2026