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?

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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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?

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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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?

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.