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.

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Jennifer has been at the helm of the foundation, which supports and enhances the Sarasota School District’s public education system, since 2015. Prior to joining the foundation Jennifer worked in banking, real estate, fundraising and more.

Business Observer Managing Editor Mark Gordon and Jennifer talked about the mission of the foundation, including its why: ensuring success for students and teachers. They also talked about her winding career and how she found a way to lead and help others advance in their careers — and life. And they talked about what she looks for in good leaders, with integrity and curiosity at the top of the list.

3 Takeaways:

1. (03:55) Relationships are everything
2. (11:10) Leadership is the values you uphold
3. (14:25) Aim for excellence, not perfection

Timestamps:

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

(00:50) Introducing Jennifer Vigne, CEO of Education Foundation of Sarasota County

(03:55) How did you get to the Education Foundation?

(05:05) What is the mission of the Education Foundation?

(06:30) How did you know you wanted to be a leader?

(10:45) Characteristics of good leadership?

(14:00) Developing as a leader

(17:00) What is a failure you learned from?

(18:50) What is on the horizon in 2025?

(22:10) Rapid fire questions

John is a Philly guy who has taken to loving his new adopted hometown in Manatee County. He worked in accounting and finance for the Philadelphia Phillies baseball team for 15 years, starting as an intern in the ticketing office and working his way up to director of finance. He and his family relocated to the area in 2020, where he took a position heading up finance and accounting for the University Park Country Club. He was named COO and GM in 2021.

Business Observer Managing Editor Mark Gordon and John spoke about the challenges in having multiple boards and people in charge with the homeowner associations at UPCC, and how he navigates that. They also talked about his keys to advancing in an organization, which is wrapped around hustle, integrity and paying attention to details. And, of course, John and Mark talked about his passion for all things Philly sports (and cheesesteaks) and the resiliency and character he developed in having grown up there.

3 Takeaways:

1. (08:40) The power of networking is undeniable
2. (14:30) Lead with empathy
3. (16:20) You have 2 ears and 1 mouth for a reason

Timestamps:

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

(00:30) Introducing John Fetsick, COO and General Manager of University Park Country Club

(02:00) How John makes decisions for 2500+ constituents

(06:20) Growing up in Philadelphia and working for the Phillies

(10:22) Lessons from working with the Phillies

(12:30) Putting yourself in position to become Director of Finance

(14:15) What do you look for in leaders?

(16:15) Leadership advice

(18:00) Working in the Moneyball Era

(19:30) Overcoming setbacks

(21:45) Moving from Philadelphia to Sarasota

(24:15) UPCC in 2025

(25:45) 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.

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John started an IT consulting business (now managed service provider, MSP) while a junior at the University of Florida in 2007. He sold that company to CRS in 2015. The Cape Coral-based company works with a host of companies in Southwest Florida on technology and related issues.

Business Observer Managing Editor Mark Gordon and John talked about CRS’ core values — passion, respect, collaboration and innovation — and the role they play in the company’s culture, and its success. They also talked about how and why CRS downsized its client roster, and became a more efficient and profitable business. And listen for the rapid-fire questions, where John, an admitted tech-geek, readily names what he says is the best Star Wars movie.

3 Takeaways:

1. (06:55) The transition from clients to partners was essential
2. (09:15) We were on pace for vanilla mediocrity, we had to change
3. (21:00) What is the cost of?

Timestamps:

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

(00:30) Introducing John Joyce and CRS Technology Consultants

(02:45) How CRS Technology Consultants has evolved

(05:45) Purposefully shrinking the client list

(10:05) How the company operates today

(12:00) What do you look for in up and coming leaders?

(13:55) Core Values

(14:45) Learning from mentors and mistakes

(21:20) The Solid State Podcast

(23:50) 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.

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Yvonne is the founder and CEO of Workforce Development Partners, a nonprofit in the Tampa Bay region that connects high school students with trades and other companies. She’s also an entrepreneur, who has started and grown a branding company and talent agency, among other firms, and a dedicated and visible economic development cheerleader for the Tampa Bay region, especially east Hillsborough County and Plant City.

Business Observer Managing Editor Mark Gordon and Yvonne talked about how her work ethic was shaped by growing up on a farm and the lessons she learned as a child about leadership, resilience and integrity.

3 Takeaways:

1. (05:00) Soft skills are so important in upcoming members of the workforce
2. (17:00) Integrity is the most important characteristic of leadership
3. (19:13) Everything is done through a team

Timestamps:

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

(00:30) Introducing Yvonne Fry, CEO of Workforce Development Partners

(01:00) The genesis of this program and the benefits

(05:45) Growing up on a farm and finding this career

(10:20) Standout projects

(13:35) Leadership advice

(16:40) Characteristics of leadership

(19:45) Setbacks

(23:30) Looking forward to 2025

(25:30) 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.

Ron has been a prominent business and health care attorney in Tampa and Florida for more than two decades. He currently oversees Shumaker Advisors, a public policy firm that works with clients in Florida, as well as nationally and globally, on a host of regulatory and government issues. Ron is also known across Tampa Bay and Florida for his diverse civic leadership; he’s currently chair of the Tampa Economic Development Council and has top roles on myriad other boards, including Leadership Florida.

Business Observer Managing Editor Mark Gordon and Ron talked about his leadership mindset, and how it starts with integrity and honesty, revolving around problem-solving. They talked about how he knew he wanted to be an attorney — it dates back to a big win in fifth grade in New Jersey. And they talked about how Ron chooses the groups he volunteers his time with. Also, listen for the why behind Ron’s passion for a sharp necktie.

3 Takeaways:

1. (01:50) We all have a responsibility to lift up our community
2. (17:00) Understand the power of delegation and be self aware of your limitations
3. (19:35) If you find yourself doing everything, you will get nothing done

Timestamps:

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

(00:25) Introducing Ron Christaldi, President and CEO of Shumaker Advisors, plus a lot more

(04:20) What does Shumaker Advisors do? Plus his first experience changing a law

(10:00) The importance of connecting people

(13:00) First interest in becoming a lawyer

(16:05) Leading other lawyers

(20:14) Characteristics of upcoming leaders

(23:40) Shumaker Advisors in 2025

(26:05) 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.