Thomas O'Riordan, 34

If Thomas O’Riordan hadn’t had his father, Tom, to turn to as a mentor, there’s a good chance he wouldn’t have become an entrepreneur. “It definitely would have changed my life completely,” he says. “I’d probably be working at a large corporation and not having the freedom that I have working for myself and owning my own businesses.”

O’Riordan’s latest venture is coworking space Collier Capital Club in Naples, which offers everything from day passes to dedicated desks to private offices for members. He’s also the founder of customer experience and intelligence firm CXCI and activewear e-tailer Ensō.

His father, an entrepreneur and retired Fortune 500 CEO, has been a trusted source for advice and guidance throughout his career. “He’s very good at giving different angles and views on things that have helped my perspective grow over time,” says O’Riordan. “But he never pressured me to feel the need to be as successful as he has been in his career. Whatever I wanted to do in my career he always supported, whether that was to become a teacher or entrepreneur or anything in between.”

Being a serial entrepreneur requires an ability to know when you have the bandwidth to take on something new. O’Riordan’s father has helped him assess if it’s the right time to get involved in another venture.

“Generally when I have something that’s kind of new and outside my scope, I’ve gone to him and talked to him about it,” he says. “He’ll give me a good lay of the land of whether he thinks I have the time or availability to do a new project, or whether I need to find somebody who can help support parts of the puzzle to make a project happen.”

A major lesson he’s learned from his dad? Do things right the first time. “If you’re doing it wrong to begin with, you’re always going to be treading water instead of being focused on the next step in the process,” he says.

O’Riordan’s now someone Collier Capital Club members can bounce ideas off and ask for advice. He knows it’s important to get past any fears about reaching out for help. “Have the humility to ask questions,” he says. “You might not like the answers to them, but it’s better than not getting an answer and not knowing.”

Name: Thomas O'Riordan

Age: 34

City of Residence: Naples

Employer: Collier Capital Club Inc.

Title: Founder & President

Birthplace: New Jersey

Years in the area: 10

Marital Status/Children: Engaged / No Children

Alma Mater/Degree: Chapman University - B.S. in Business Administration, Entrepreneurial Studies

What community group or organization are you most involved with? St. Matthew's House

What's the weirdest job you've ever had? My first job at 14 years old - Miniature Golf Course Attendant

What's your top tip for being productive? Post-it Notes. Lots of Post-it Notes. Whether it's a note for following up with a new business lead, to complete a back-office task, scheduling an appointment, or finishing a proposal. Knowing when to pivot is essential and having visual aids on your desk with immediate information is key. You can always update your task management software later to update your team, but having information in view without having to switch between apps or browser windows.

If you could have a side hustle, what would it be? Amazon reseller.

What's your favorite off-hours activity? Networking

Have you gone to the movies in 2021? If yes, what did you see? No

What's the top item on your bucket list? Showing a car at Pebble Beach Concours d'Elegance.

What's your favorite podcast? The Tim Ferriss Show

Where is your happy place? The beach!

Describe yourself in three words: Compassionate, dedicated, trustworthy.

Who is your mentor for your career and why? My Father. He's a fellow entrepreneur, retired Fortune 500 CEO, and provider of trusted advice any time I need to bounce ideas off of him or guidance on prioritization.

What are the biggest lessons you have learned from your mentor? Do things right the first time even if it takes longer because patience allows you to focus on your goals instead of fixing problems that arise from impatience. Always do the right thing and don't be afraid to ask for help because having high morals and a sense of humility when you need it allows you to accomplish more and sleep soundly.