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

Erin McLeod has worked in public relations, communications, consulting, health care, hospitality and the club industry. She’s been with the Senior Friendship Centers in Sarasota since 2004; she has been CEO of the nonprofit since 2015. On this episode, Business Observer Managing Editor Mark Gordon and Erin talked about her career origins and how she, on the spot, thought of a top-notch acronym on the spot in a job interview several years ago. She called it CPR, when asked what she would bring to the organization: Communication, professionalism and relationships. Erin and Mark also talked about the connections between being an accountable parent and an accountable leader.

3 Takeaways:

1. (12:20) This is not a sprint, it’s a marathon
2. (15:00) Dream big, get stuff done, have fun, no drama
3. (17:00) The quicker you address tough situations the better

Timestamps:

(00:00) Introducing Erin McLeod, President & CEO of Senior Friendship Centers

(04:15) What is Senior Friendship Centers?

(06:10) How did Erin get to Senior Friendship Centers?

(08:40) What does leadership mean to you?

(10:50) Who influenced your leadership style?

(12:40) Balancing your employee’s work style

(15:40) Approach to leadership you wish you knew earlier?

(16:40) Addressing conflict

(20:40) Storytelling in leadership

(22:30) Imposter syndrome

(23:40) Senior Friendship Center in 2026

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Dara Shareef is the managing partner of Benchmark International, where he oversees the transaction team in the firm’s U.S. headquarters in Tampa. Benchmark recently made a big splash in the region, in signing a naming rights deal for what’s now Benchmark International Arena, home of the Tampa Bay Lightning. On this episode, Business Observer Managing Editor Mark Gordon and Dara talked about lessons in empathy and grit he learned from his mother and high school football coach, respectively, and how to grow into being a decisive leader. They also talked about his methods of conflict resolution and helping to get people on opposing sides to reach consensus.

3 Takeaways:

1. (10:00) Leadership is about accountability
2. (15:05) Don’t place artificial limits on yourself
3. (18:30) Deal with conflict head on and in the moment

Timestamps:

(00:00) Introducing Dara Shareef, Managing Partner, Benchmark International

(04:20) What is Benchmark International?

(06:20) Winning naming rights for the Tampa Bay Lightning's arena

(07:45) How did Dara get into this field?

(10:00) What does leadership mean to you?

(11:10) Influences in leadership

(13:00) Growing up

(14:20) Lessons from playing football

(16:00) Tough decisions that shaped Dara’s career

(18:15) Handling conflict

(21:00) Leadership advice

(23:30) What legacy do you hope to leave?

(25:00) What is coming for Benchmark International?

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Sophia Shaw has had many interesting roles, from leading the Chicago Botanical Garden, to being an Adjunct Professor at the Kellogg School of Management. After all that, her work is just getting started. On this episode, Business Observer Managing Editor Mark Gordon and Sophia talk about Sophia's start up, PlanPerfect, her 'why' to get into nonprofit work, the importance of planning to plan and why initiative is a crucial leadership characteristic. They also talked about the times she’s struggled with Impostor Syndrome, and how she’s gotten over it.

3 Takeaways:

1. (07:45) Leaders need to understand what it takes to execute strategy
2. (12:15) When conflict arises, go back to the strategic plan
3. (14:00) Most people want to go to work knowing what they have to do

Timestamps:

(00:00) Introducing Sophia Shaw, co-founder, PlanPerfect

(03:30) What is PlanPerfect?

(04:30) Why did you start PlanPerfect?

(07:45) What are must-have leadership characteristics

(09:20) Knowing your “why”

(10:20) Learning from mistakes

(12:00) Working through conflict

(15:30) Sophia’s leadership influences

(17:10) Handling imposter syndrome

(19:50) What does Sophia look for in good leaders?

(21:10) Plan Perfect 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.

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