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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