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

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.

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?

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.

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?

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.