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.

A sixth-generation Floridian, Kevin founded Tampa-based Golden Road Advisors, a registered investment advisor firm, in 2021. Prior to Golden Road, Kevin was a financial advisor for wealth management companies in the area, including Morgan Keegan and a decade with Raymond James. A proud University of Florida alum, Kevin also helped launch the school’s wealth management studies program and teaches a class on finance at the school.

Business Observer Managing Editor Mark Gordon and Kevin spoke about his mindset on helping mentor and guide the next generation of financial industry leaders — a key, he says, is to avoid making broad judgements and generalizations about Gen Z and millennials. Kevin also talked about the values he believes every leader should have. And stay tuned for some rapid fire questions with a distinct Gator theme.

3 Takeaways:

1. (08:25) You can’t hire someone unless you are willing to take responsibility for their family
2. (13:45) Build the job you wish you had in the industry
3. (14:10) Start with the end in mind and work backward

Timestamps:

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

(01:20) What is Golden Road Advisors?

(02:00) Going out on his own, it’s about starting

(04:45) Teaching at UF and hiring Gen Z

(09:10) Building an apprenticeship program

(11:40) Kevin’s experience working with Gen Z

(13:20) Advice for other businesses hiring Gen Z

(16:15) What have you learned as an entrepreneur through this apprenticeship program?

(19:50) Where will you be in 3-5 years?

(21:15) 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.