We’re looking forward to introducing you to Stan Rudman. Check out our conversation below.
Hi Stan, thank you so much for joining us today. We’re thrilled to learn more about your journey, values and what you are currently working on. Let’s start with an ice breaker: What makes you lose track of time—and find yourself again?
Work truly makes me lose track of time. Before I know it, it’s already time to head home. When you love what you do and stay focused on achieving positive results, every moment feels worthwhile. I juggle quite a few roles — from serving as a CMO and a realtor to spending more than 25 years as co-chairman of the Miami Dolphins Foundation’s Fins Weekend, and an Art/Watch Collector. Each role gives me purpose, keeps me motivated, and reminds me how rewarding it is to make a real difference in the community.
Can you briefly introduce yourself and share what makes you or your brand unique?
My name is Stan Rudman, and I’ve always believed that success is about passion, purpose, and people. I wear a few different hats — as a Chief Marketing Officer, a realtor, a collector of the Arts and for more than 25 years, the co-chairman of the Miami Dolphins Foundation’s Fins Weekend, one of South Florida’s most impactful charity events.
I serve as the CMO and owner of two major apparel brands, Hook & Tackle and Weekender, which have been family-run and proudly established for more than 63 years. These brands celebrate the coastal lifestyle, combining innovation, comfort, and sustainability — and it’s incredibly rewarding to see how they’ve continued to evolve while staying true to their roots.
In addition, I’m a managing partner in Rudman Enterprises, which owns and manages multiple warehouses in the Little River Business District of Miami, just north of the Miami Design District. This area has quickly become one of the world’s most exciting emerging neighborhoods. Our properties sit along the soccer park and will soon neighbor the Magic City Innovation District, featuring residential towers and modern office buildings. A new rail station is set to open just blocks away, and several top restaurants — including the acclaimed Sunny’s Steakhouse — have already begun to open. It’s an incredible time to be part of Little River’s transformation and growth. We thank the Mayor and our city commissioner for renaming a street in the heart of Little River (NE 2nd Court) to Rudman Way. Such an honor for my grandfather and dad, we are so proud of our legacy that will forever live here in Miami.
What makes my work special is the ability to connect business with purpose. Whether I’m developing marketing strategies, helping families find their dream homes, or contributing to Miami’s evolving landscape, my goal remains the same: to create meaningful experiences and make a lasting, positive impact on the community I love.
Appreciate your sharing that. Let’s talk about your life, growing up and some of topics and learnings around that. What’s a moment that really shaped how you see the world?
A major influence in my life has always been my dad. He’s been my greatest mentor — both in business and in life. From an early age, he taught me the importance of integrity, hard work, and treating people the right way. Even now, he continues to inspire me and remind me that success isn’t just measured in accomplishments, but in how you impact others along the way.
Those experiences — giving back through Fins Weekend and learning from my father’s example — have shaped everything I do. They remind me that when your work comes from the heart, it doesn’t just change your life; it can help change the lives of others too.
What did suffering teach you that success never could?
I’ve been blessed in many ways — I haven’t personally experienced the kind of suffering or hardship that my parents and grandparents did. But their story, their perseverance, and their ability to rebuild — not once, but twice — taught me lessons that no amount of success ever could.
My grandfather fled Eastern Europe in the 1930s, escaping Poland with hopes of reaching the United States. When immigration was full, the ship was rerouted to Cuba, where he started a new life with my grandmother. A skilled tailor, he took his trade to Havana and began working to support his young family. My father joined him in the business, and together they built a men’s clothing company that became the licensee for Palm Beach suits. Their operation grew to 700 employees, serving customers from across the country — even government officials came in for fittings.
In the early 1960s, Fidel Castro himself walked through their factory. At the time, no one could have predicted the drastic political changes to come. My father, only 19 and newly married to my mother, realized their lives were about to change forever. With the help of friends in high places, he managed to get the entire family out of Cuba — arriving in Miami in January 1961.
Imagine immigrating twice in one lifetime, leaving everything behind, and starting over from scratch — again. My grandfather became a tailor at Saks Fifth Avenue on Lincoln Road, and my father went to the University of Miami, becoming a CPA. In 1963, the two of them started Sportailor, Inc., creating the Weekender brand, known for its Guayabera shirts and cabana sets that are still popular today. My father would walk through downtown Miami, selling to local retailers, slowly building a business that grew into partnerships with JCPenney, They were also the licensee for YSL men’s swimwear for the United States.
By the 1980s and 1990s, as my brothers and I joined the family business, we expanded into new ventures, launching Hook & Tackle, a sun-protective apparel brand for anglers and boaters — a brand that carries forward the same entrepreneurial spirit my grandfather began with a single needle and thread.
Their suffering taught me the value of resilience, gratitude, and hard work. It taught me that success isn’t measured by what you have, but by what you’re willing to build again when everything falls apart. And it reminded me that true strength comes not from comfort, but from courage — the kind my family showed every step of the way.
Alright, so if you are open to it, let’s explore some philosophical questions that touch on your values and worldview. What would your closest friends say really matters to you?
I’ve been lucky to have friendships that span every chapter of my life — from childhood and college to the incredible group of friends I met about sixteen years ago. It all started when my buddy invited me on a trip to Vegas, and from that moment on, the rest was history.
What began as a fun getaway turned into a lifelong bond between more than a dozen of us. We built an amazing crew — all of us living in the same building in South Beach, and weekly dinners where we’d cook for each other and watch shows like 24. We traveled together across the country and even through Europe, creating memories that still come up in conversation to this day.
I think my friends would say that what really matters to me is loyalty. I’ve always believed in showing up for the people I care about — whether it’s a wedding, the birth of a child, or simply being there when life throws curveballs. Even though many of us have since moved and settled in different places, that bond will never break. True friendship is one of life’s greatest gifts, and I’ll always value those connections above all else.
Okay, so let’s keep going with one more question that means a lot to us: What is the story you hope people tell about you when you’re gone?
I hope people say that I lived a life of purpose, integrity, and generosity — that I worked hard, loved deeply, and always showed up for the people and causes that mattered. I’d like to be remembered as someone who didn’t just build businesses, but built opportunities; someone who used his success to give back and lift others up.
I hope my friends and family tell stories about how I was always there — for the big milestones and the small moments — and that my loyalty and friendship meant as much to them as theirs did to me. I hope my colleagues and community remember me as a connector, a mentor, and someone who believed that success and service should go hand in hand.
Most of all, I’d like the story to be that I carried forward the resilience and entrepreneurial spirit my family started generations ago — from my grandfather the tailor to my father the businessman — and used it to make a positive difference. If people say I left the world a little better than I found it, both in business and in my community, that would mean everything.
Contact Info:
- Website: https://www.sportailor.com
- Instagram: https; https://instagram.com/stanrudman
- Linkedin: https;//linkedin.com/stanrudman
- Facebook: https;// facebook.com/stanrudman
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