Jake Haulsic has some 15 years of experience in technology sales, with Velosio and Tribridge. He founded Trofeo, a fast-scaling cloud consultancy specializing in Microsoft Azure, in 2024. On this episode Business Observer Managing Editor Mark Gordon and Jake talk about how he built his company, not only around product and service, but culture. He also talked about some early decisions at Troefo that helped shape its trajectory, and his mentors that have helped guide the business along the way.

3 Takeaways:

1. (11:50) Leaders need to trust their employees
2. (12:40) The best leaders practice patience
3. (14:50) Every failure needs to be a learning opportunity

Timestamps:

(00:00) Introducing Jake Haulsic, Trofeo, founder

(02:55) What is Trofeo?

(05:10) Jake’s mentors

(06:50) What did you learn from Tony DiBenedetto?

(09:00) What does culture mean to you?

(11:40) Leadership characteristics

(12:20) Best leadership advice you have received

(13:15) What role does storytelling play in Trofeo’s growth?

(14:00) Resilience

(15:50) How do you want to be remembered as a leader?

(16:45) Trofeo in 2026

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Tom Hall is a longtime advertising executive, with work across Florida and the Southeast. In addition to Tucker | Hall, a strategic communications firm with offices in Tampa, Jacksonville, Orlando and Tallahassee, Tom launched Creative Seminars, a prominent speaker series, which Adweek magazine acquired. On this episode Business Observer Managing Editor Mark Gordon and Tom talk about the origins of the firm and how he and the team led it to national prominence. They also talked about Tom’s book, “Ruthless Focus" and the lessons he learned about leadership writing it.

3 Takeaways:

1. (05:50) When in crisis, tell the truth, tell it all, and tell it right now
2. (13:30) Ruthlessly focus on what you do extraordinarily well
3. (15:10) Create an atmosphere where people can think their best

Timestamps:

(00:00) Introducing Tom Hall, Chairman, Tucker | Hall

(03:40) What is Tucker | Hall?

(05:30) What do leaders need to do when in crisis?

(06:40) Creative Seminars

(09:00) What did you learn from Creative Seminars

(11:55) Who does a good job advertising these days?

(12:55) Learning from “Ruthless Focus”

(14:30) Keys to leading a firm

(16:15) Leadership mentors

(19:15) How do you handle conflict as a leader?

(20:30) Starting the Florida Aquarium

(24:30) What is coming up in 2026?

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Sinead Runyon runs Express Employment of Sarasota, which she founded in 2020 along with her mom, Josephine Carr. In 2024, she and her husband, William Runyon, opened a Made in the Shade window treatment, blinds and shades franchise in Venice. On this episode, Business Observer Managing Editor Mark Gordon and Sinead talk about her entrepreneurial mindset, what she learned from her mentors and how she resolves conflict as a leader. She also talked about the second business she launched while running the first business.

3 Takeaways:

1. (11:15) The bus is moving forward, stop comparing yourself to others
2. (20:55) Good leadership is owning your mistakes
3. (23:00) Be there with your client

Timestamps:

(00:00) Introducing Sinead Runyon, co-founder of Express Employment of Sarasota

(04:50) What is Express Employment Professionals - Sarasota?

(06:25) Door pulls

(08:20) Building up the stamina

(09:40) Leadership mentors and lessons

(12:40) Learning from other entrepreneurs

(14:50) Truly showing up for your clients

(16:45) Owning and fixing mistakes

(19:25) What is Made in the Shade?

(20:55) What is good leadership?

(21:55) Handling conflict

(24:30) What is coming up in 2026?

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Ashley Ljesevic has led marketing, sales, and development initiatives for a variety of organizations over the past decade, working in sports, travel and nonprofits, among other fields. She also has a podcast, the Endurance Diaries, which interviews athletes, artists, entrepreneurs and others to share stories of resilience. On this episode Business Observer Managing Editor Mark Gordon and Ashley talked about striving for — and pivoting when necessary — for big goals and how she does that in her personal life. They also talked about the lessons she’s learned from Endurance Diaries guests.

3 Takeaways:

1. (08:30) “Can you enter a process where there are no outcome goals attached?”
2. (12:45) What we see on the surface is not the full story
3. (17:30) When things are tough, focus on the next step

Timestamps:

(00:00) Introducing Ashley Ljesevic, Host of Endurance Diaries podcast

(04:50) Ashley’s 10x10 journey

(07:45) What is Endurance Diaries Media?

(11:45) Who have you learned from on Endurance Diaries?

(14:45) What is endurance to you?

(16:00) Overcoming adversity

(18:20) What leadership characteristic does every leader need?

(20:55) Imposter syndrome

(24:30) Endurance Diaries Media in 2026

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Dan is the CEO of Moorings Park, a nonprofit senior living organization with three campuses in Naples. He has been with the organization for nearly 20 years, first as CFO. Before that he ran his own packaged delivery service small business in Ohio. On this episode Business Observer Managing Editor Mark Gordon and Dan talked about how the concept of VUCA — leading through Volatility, Uncertainty, Complexity and Ambiguity — has helped make him a better leader and the organization stronger. They also talked about how Dan hopes his team sees him as a leader.

3 Takeaways:

1. (05:30) Leadership is humility and professional will
2. (08:10) Mission driven organizations focus on the end result
3. (09:20) Separate success from leadership

Timestamps:

(00:00) Introducing Dan Lavender, CEO, Moorings Park

(03:15) What is Moorings Park?

(04:00) How did you get into senior living?

(05:10) What defines good leadership?

(07:20) Leadership influences

(08:45) Learning from residents at Moorings Park

(10:30) Decisions that shaped you

(11:35) Balancing short and long term wins

(13:40) Handling conflict

(14:40) Resiliency as a leader

(17:10) Your leadership style

(18:15) Moorings Park in 2026

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Eleni founded Gates Hospitality Group, which handles brand building, corporate communications, public relations and more for restaurants and other businesses, earlier this year. She was previously head of investor relations and corporate communications for East Manatee County-based First Watch Restaurant Group. On this episode Business Observer Managing Editor Mark Gordon and Eleni talked about what she’s learned from some important hospitality mentors on company culture, motivating teams and more. They also talked about her big step in working for corporate brands to going out on her own and going back to school for her MBA.

3 Takeaways:

1. (05:50) Be intentional about how you communicate with specific audiences
2. (16:00) A leader is never above any work in the organization
3. (17:00) Be a human, not the boss

Timestamps:

(00:00) Introducing Eleni Gates, Founder and Principal, Gates Hospitality Group

(04:00) What is Gates Hospitality Group?

(06:15) Starting at First Watch

(08:20) Working for Chris Tomasso

(09:30) IPO-ing with First Watch

(13:00) Dealing with imposter syndrome

(14:30) Learning from Ken Pendery

(17:25) What is good leadership?

(19:00) Leadership advice

(20:30) Learning from her parents

(23:00) Storytelling in leadership

(24:20) Gates Hospitality Group in 2025

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AG Lafley is the former CEO of consumer products giant Procter & Gamble, where he ran the company for 15 years over two different tenures. Since retiring and moving to Sarasota, he has worked with small businesses and nonprofits, and also led the development and operations at the Bay Sarasota. On this episode Business Observer Managing Editor Mark Gordon and AG talked about how he overcame difficulties and challenges at P&G, and why leading with a customer-first mindset, even in such a large organization, was a priority. They also talked about why it was important for him to be a “say do” leader.

Key Takeaways:

(05:30) Crisis is opportunity

(05:45) Leadership is not genetically determined, it can be built

(12:35) Great leaders take accountability and create accountability

(17:30) Leadership is a navigation job

(19:40) Know yourself, be yourself, and play to your strengths

(20:40) Understand the art of going slow to go fast

(21:20) Leadership is thinking, decision making, and doing

Timestamps:

(00:00) Introducing AG Lafley, retired CEO, Procter & Gamble; founding CEO, The Bay Park Conservancy

(05:00) Keys to being a great leader

(06:30) Seizing leadership opportunities early in life

(09:00) Becoming CEO of Procter & Gamble

(12:00) Decisions made in the first 100 days of being CEO

(17:15) What is leadership?

(19:25) Leadership advice

(22:00) Learning to ‘go slow to go fast’ from the Japanese

(27:45) AG’s leadership legacy

(31:30) What is coming up at Bay Park Conservancy?

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Darla has more than 20 years of experience in everything from corporate sales and operations to leadership development. She currently runs Darla Bonk Consulting, and, with her husband, Architectural Metal Flashings. Two more biographical nuggets: She’s a Fort Myers city councilwoman and she hosts a weekly podcast, “On Your Way.” On this episode, Business Observer Managing Editor Mark Gordon and Darla talked about her diverse and winding career, what she learned from her parents about leadership — who have been married for 70 years — and how the power of being intentional in all her communications has helped be a better leader.

3 Takeaways:

1. (08:15) Listen for cues to get consensus
2. (14:00) Leaders need the ability to pivot
3. (15:30) Communication is everything

Timestamps:

(00:00) Introducing Darla Bonk, CEO and founder, Darla Bonk Consulting

(07:45) What did you learn about leadership being on the City Council?

(10:15) Learning from leaders in Darla Bonk Consulting

(11:30) Growing up as Darla Bonk

(13:50) What do you look for in leaders?

(15:25) Leadership advice

(16:00) Storytelling in leadership

(17:00) Balance short term wins and long term planning

(18:10) Imposter syndrome

(19:00) Lessons from her parents

(20:45) Darla’s leadership legacy

(21:30) Darla Bonk 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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