Steven Siebert: “Here Are 5 Things I Wish Someone Told Me Before I Became CEO of Uomo Sport”

As part of my series about the leadership lessons of accomplished business leaders, I had the pleasure of interviewing Steven Siebert. Steven has been playing and loving the sport of tennis since he was six years old. Now he’s taken his love for tennis and turned it into a luxury athletic wear line called Uomo […]

As part of my series about the leadership lessons of accomplished business leaders, I had the pleasure of interviewing Steven Siebert. Steven has been playing and loving the sport of tennis since he was six years old. Now he’s taken his love for tennis and turned it into a luxury athletic wear line called Uomo Sport.

Thank you so much for joining us! Can you tell us the story about what brought you to this specific career path?

The short of it is as a young boy in the 70’s my brother and I were fortunate to receive club house passes to The US Open in Forrest Hills New York (Westside Tennis Club) which was then played on grass courts. There was an aura of the coolest looking players that had the best sophisticated distinct individual style dressed predominantly in Italian made tennis apparel tailored to perfection.

My two boys both played high school tennis and my younger son played USTA tournaments. The high school team composed of some of the smartest kids in any sport had no idea how to dress on a tennis court. I wanted to create a brand and dress the team. Well, that took longer than I expected. I began soaking up knowledge from players, coaches, officials, agents, tournament directors all deeply rooted in the sport who all helped shape this brand.

I wanted to create the ethos of an authentic heritage brand embraced by the tennis world.

Brands lost sight of what they once were and steered off path. I saw a missing space. Uomo Sport aims to revitalize the prestige of the sport and bring back style. That experience as a young boy in New York has had an ever-lasting impression that continues to inspire me.

Can you share one of the major challenges you encountered when first leading the company? What lesson did you learn from that?

Finding the right, genuine people to produce the quality that I knew Uomo Sport needed. The lesson I learned while searching for that quality was to stick with your gut or intuition and not settle for less. I knew what I expected, and I wasn’t going to sacrifice my needs over time or cost.

What are some of the factors that you believe led to your eventual success?

Drive, ambition, perfectionism. Constant hard work. Never taking “no” for an answer.

What are your “5 Things I Wish Someone Told Me Before I Became CEO”? Please share a story or example for each.

It can be a very lonely road being an entrepreneur. You’re on your own. Not a lot of resources. Sometimes people don’t believe in what you’re doing.

No training manual; there is a ton of problem solving.

No one wants to take your calls, but it is rewarding when you get through all of that. Sometimes, it took months of calling and following up with a shop or club in order to have the product visible in a location.

You’ll always be working what feels like 24/7. You can never really get away from your work. Even when I am on vacation with my family, I am answering calls, texts, and emails taking care of things that need attention. But there is also a balance.

What advice would you give to your colleagues to help them to thrive and not “burn out”?

Balance lifestyle. You can’t just work 20 hours a day. Exercise and eat healthy. Get some fresh air.

Go after things that you enjoy and feel good about. Not just the things that pay the most. Do what you love. Work as a team. Collaboration produces better. Don’t be afraid of failure.

Don’t be afraid to ask for help when you need it. No one can do everything on their own, and I understand that. Set both short-term and long-term goals, give yourself reasonable timelines and stay focused to work through each task.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

My mother Sylvia. She is a hard-working woman who is now 86 and still wants to work her butt off. She instilled in me the very principles, discipline, and habits that I have today. For years, she owned and ran a very successful party rental business, and I saw her work ethic, consistency, and drive. I wouldn’t be where I am today without my mother.

What are some of the goals you still have and are working to accomplish, both personally and professionally?

To sign the best 17-year-old in the world

I want to make the brand into a total style destination.

What do you hope to leave as your lasting legacy?

What I hope to leave is an example of consistent hard work really paying off and that following your dreams can yield amazing results as long as you stick with it.

You are a person of great influence. If you could start a movement that would enhance people’s lives in some way, what would it be? You never know what your idea can trigger!

Ultimately, I would like to have Sprinters across the globe that people can visit to freshen their gear, buy new items, string their racquets, and just hang out to hear professionals of the sport speak and give training and playing tips. Everyone knows the craze of food trucks; I imagine that it can sort of be like a popup for tennis enthusiasts and people that want to learn.

How can our readers follow you on social media?

Uomo Sport can be found on Instagram @uomo_sport, on Facebook at uomosport2016, and our website at We also have a blog that we run on our site.

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