Jeff has been a leader at two family-run homebuilding businesses in the Sarasota-Manatee market. The first was Eslinger Homes, which operated from 1991 to 2010. In 2017, he co-founded E/M Custom Homes. On this episode, Business Observer Managing Editor Mark Gordon and Jeff talked about the leadership lessons learned in shutting down one company, when the housing market collapsed in 2008-2010 and launching a new one. He also talked about what he learned from his mentors in the business.

3 Takeaways:

1. (07:30) Patience and good listening are must-have leadership characteristics
2. (09:30) There is only one way to do things, the right way
3. (16:05) It’s not about you, it’s about who you surround yourself with

Timestamps:

(00:00) Introducing Jeff Eslinger, president, E/M Custom Homes

(04:35) What is E/M Custom Homes?

(05:40) An opportunity but no company

(07:25) Must-have leadership characteristics

(08:30) Balancing patience and decision making

(10:10) Jeff’s leadership influences

(12:15) Lessons from Jeff’s grandfather

(13:40) Hard decisions

(16:05) Best leadership advice

(16:35) Hard feedback

(18:00) What is coming up in 2026?

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Jack Cox has been with Sarasota-based Halfacre Construction since 1985 and is now president and owner. He’s also chairman of the board at Lakewood Ranch based-FCCI Insurance. On this episode, Business Observer Managing Editor Mark Gordon and Jack talked about Halfacre’s long history of projects in the Sarasota-Manatee region and his role in continuing the company’s legacy. He also talked about what he looks for in hiring and promoting leaders, and what he’s learned about leadership from being on community nonprofit boards

3 Takeaways:

1. (09:00) Leaders need consistency
2. (10:00) Set the vision by giving guardrails, let employees do the rest
3. (13:00) Learn from others and adapt your leadership approach

Description:

(00:00) Introducing Jack Cox, president and owner, Halfacre Construction

(04:25) About Halfacre Construction

(06:45) Landmark projects

(08:00) Why be involved in nonprofits?

(09:00) What does every leader need?

(10:00) Setting the vision

(13:00) Leadership approach

(14:10) Accepting feedback

(15:30) Making tough decisions

(16:30) Leadership legacy

(18:10) Halfacre Construction in 2026

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A nationally recognized workplace expert, Linda, based in Sarasota, is the architect of the Spectator-Free Workplace methodology, which fosters shared ownership of performance and revitalizes engagement, productivity and morale. Linda worked in journalism and corporate communications, with GE and AlliedSignal, before starting her own firm. Business Observer Managing Editor Mark Gordon and Linda talked about her work in helping leaders break down silos and become better listeners to the entire team. She also talked about some key lessons learned from her entrepreneurial parents to legendary GE executive Jack Welch.

3 Takeaways:

1. (04:50) People make the success in business
2. (07:30) You can’t lead with a void of knowledge
3. (12:45) Use AI to spark creativity

Timestamps:

(00:00) Introducing Linda Dulye, founder, Dulye & Co.

(04:30) What is Dulye & Co.?

(06:40) How do you advise your clients?

(09:00) Creating a better culture

(10:20) AI-proofing your career

(12:30) Using AI as a tool

(14:30) Linda’s career trajectory

(17:30) Must-have leadership characteristics

(19:00) Using feedback

(20:10) Mentors

(23:30) Syracuse Basketball and Dulye & Co. in 2026

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Michael Arrieta founded Garden City Equity after working in Silicon Valley for tech companies, including a stint as a global vice president and chief of staff to the CEO at DocuSign. Garden City, he says, is dedicated to making people-first investments in family and founder-owned businesses in the Southeast. One of its recent investments is in Venice-based outdoor aluminum and pool cage material manufacturer Commercial Residential Aluminum. On this episode, Business Observer Managing Editor Mark Gordon and Michael talked about key business and leadership lessons he learned from DocuSign and other tech companies. They also talked about his mentors and his vision on what makes for a strong and sustainable company culture.

3 Takeaways:

1. (11:20) Give employees a clear path of growth
2. (13:15) People support what they help create
3. (14:45) To be a good leader, you need to be a servant

Timestamps:

(00:00) Introducing Michael Arrieta, founder and managing partner, Garden City Equity

(03:40) What is Garden City Equity?

(05:55) Michael’s career arch

(08:40) What is a good company culture?

(13:00) Clarity is kindness

(14:45) What made you the leader you are today?

(16:55) Lessons from Docusign

(18:20) Vulnerability

(22:00) Leadership legacy

(24:00) What's coming up for Garden City Equity?

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Aakash Patel founded Elevate Inc. in 2012. The firm provides community relations, targeted networking, and social media consultation. Aakash is also on the board of Hillsborough College and the Early Learning Coalition of Hillsborough County. On this episode, Business Observer Managing Editor Mark Gordon and Aakash talked about his unique backstory in launching his company and his tricks and tips for networking. They also talked about his mentors and role models and what motivates him to give back to the community in nonprofit board roles.

3 Takeaways:

1. (06:45) When people are giving you guidance, it is because they care
2. (07:05) Good leaders communicate well and listen well
3. (13:30) Lead with integrity

Timestamps:

(00:00) Introducing Aakash Patel, Founder and President of Elevate

(02:30) What is Elevate, Inc?

(04:20) How did you build this network?

(05:20) Learning from mentors

(06:30) Responding to feedback

(07:05) What characteristics make a good leader?

(07:45) Community involvement

(09:40) Advice for those interested in joining boards

(10:40) Running for office

(12:10) Making tough decisions

(13:30) Best leadership advice?

(14:35) What do you hope people remember about Elevate?

(15:15) What is coming up in 2026?

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Bruce Cassidy has owned the Concession Golf Club in east Manatee County since 2009. The Concession has been in the news lately, as it is hosting the 2026 Senior PGA Championship in April. Prior to the Concession, Bruce ran global manufacturing and mining businesses in Ohio. On this episode, Business Observer Managing Editor Mark Gordon and Bruce talked about how he ended up owning a golf course — which at first was the last thing he wanted to do. Bruce also talked about what he looks for in building high-performing teams.

3 Takeaways:

1. (08:00) As a leader, you have to look like the house is not on fire
2. (10:40) Focus on what you can control
3. (12:00) Hiring a great team is the most important aspect of leadership

Timestamps:

(00:00) Introducing Bruce Cassidy, Owner, Concession Golf Club

(02:30) How did you come to own Concessions Golf Club?

(04:15) Hosting the Senior PGA Championship

(06:40) Bruce’s career before Concession Golf Club

(07:20) Leading as a manufacturer

(09:00) Leadership influences

(10:25) Leadership lessons

(11:20) How do you give feedback?

(13:00) How do you know an employee is not the right fit?

(16:00) What is the story behind the name “Concession?”

(17:20) Stories from the course - Playing with Jack Nicklaus

(19:35) What is coming up for Concessions Golf Club?

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Chuck Wolfe has been CEO of the Chiles Group since 2018. The company oversees several assets, including the organic Gamble Creek Farms in Manatee County. The company previously owned and operated three waterfront restaurants in Manatee. Prior to hospitality, Chuck was in politics and strategic planning, including a 12-year stint as CEO for the Victory Fund, a national advocacy group supporting LGBTQ candidates. Chuck was also a senior aide to the late Florida Gov. Lawton Chiles for seven years. On this episode, Business Observer Managing Editor Mark Gordon and Chuck talked about leadership — and life lessons — he learned from everything from the boy scouts to political campaigns. They also talked about his process for making key decisions and how he overcomes setbacks.

3 Takeaways:

1. (15:10) Listen more than you speak
2. (16:45) Direction is more important than certainty
3. (23:50) Hiring is the most important thing you can do

Timestamps:

(00:00) Introducing Chuck Wolfe, CEO, Chiles Group

(07:30) What is the Chiles Group?

(10:00) Working with Lawton Chiles

(13:30) What did you learn from Governor Chiles?

(15:55) Leading with certainty when so much is uncertain

(20:05) Who influenced your leadership?

(23:10) What leadership characteristics do you look for?

(27:45) What is coming up in 2026 for the Chiles Group?

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Toni founded her fractional CEO firm, The C Society, in June 2025. One of her goals is to bring high-level leadership to restaurant and hospitality companies with the overhead. She was previously president of restaurant brand Perkins and managing director for Little Ceaser’s Pizza, Canada. On this episode, Business Observer Managing Editor Mark Gordon and Toni talked about her career, both with large brands and now, leading a consulting firm. They talked about how she builds high-performing teams and how leadership is more than a position, it’s a seat at the table that shapes the entire organization.

3 Takeaways:

1. (09:30) Great brands and great leaders do not grow on their own
2. (13:15) Root your strategy in data
3. (20:40) Feedback is a gift, but consider the source

Timestamps:

(00:00) Introducing Toni Ronayne, founder and fractional CEO, the C Society

(07:00) What The C Society?

(10:05) Toni’s role at Perkins

(12:35) Handling the visioning of a legacy brand

(15:50) Leadership mentors

(19:30) Imposter Phenomenon

(20:30) Valuable feedback

(26:32) What is coming up in 2026 with The C Society?

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