Mogul in the Making
Focused, disciplined, and thoughtful beyond his years, 19-year-old Hayes Benzan is applying lessons from soccer and his business to shape a community-minded approach to leadership.
By Laura Grunberger
Photographs by Jonathan Kozowyk
By the time Hayes Benzan ’25 graduated from Milton, he had already launched his first business, BenzBoots, an online marketplace where young soccer players could buy and sell cleats.
Now a first-year student athlete at Boston University’s Questrom School of Business, Benzan is balancing the demands of college life with running a digital marketing company. His video series about leadership and entrepreneurship has spotlighted Massachusetts business and civic leaders—including Milton alumnus and former governor Deval Patrick ’74. Somewhere in between, he is also managing a steady stream of client projects (including work for Milton Academy) and content creation.
In this conversation with Milton Magazine, Benzan reflects on starting a business as a student, lessons from soccer, and why his father’s advice to “take imperfect action” has shaped how he approaches life and entrepreneurship.
HOW DO YOU BALANCE STUDENT LIFE, ATHLETICS, AND RUNNING A BUSINESS? WHAT DOES THAT LOOK LIKE DAY TO DAY?
I use Google Calendar a lot! I’m pretty structured with my schedule—what time I wake up, when I go to bed, and how I plan my day.
It was an adjustment at first, especially going from having the first four hours of my day open to suddenly dedicating that time to soccer training. The best advice I got was that no matter how many scheduling tools you use, you still only have 24 hours in a day. You have to decide what matters most to you and who you want to spend your time with.
WHAT MOTIVATES YOU ABOUT MARKETING AS A CAREER?
Part of it comes from seeing how hard small business owners work and how much they struggle sometimes. Businesses give people autonomy and a chance to create something for themselves. Marketing plays a huge role in whether those businesses succeed.
If I can help someone market their business better, they can make more money, support their family, and provide value to their community.
HOW DID YOU LEARN THE SKILLS YOU’RE USING NOW?
A lot of it came from Milton. I took film classes every year I could. For my senior project, I interviewed business owners, edited the videos, and posted them on social media.
That class taught me video editing, which turned out to be one of the most valuable skills I learned at Milton. Even the work I do now helping Milton with admissions videos comes directly from those skills.
YOU’VE INTERVIEWED MANY BUSINESS LEADERS FOR YOUR VIDEO SERIES. DID ANYTHING STAND OUT TO YOU FROM THOSE CONVERSATIONS?
I’ve interviewed business owners and leaders from many different industries—architects, stylists, event producers, even a former governor.
One piece of advice that stuck with me came from Governor Deval Patrick. He told me: “Once you figure out that you can figure it out, you’ll be okay.”
YOU ONCE SAID THAT YOUR FATHER ENCOURAGED YOU TO “TAKE IMPERFECT ACTION.” WHAT DOES THAT MEAN TO YOU?
My dad and I are really close. He always says two things: “Take imperfect action,” and “If it were easy, everyone would do it.”
To me, taking imperfect action means moving forward even when you’re not sure everything will work out. A lot of the time you’re stepping into the unknown. You might fail, but you still take the shot.
HOW DO YOU DEAL WITH SETBACKS OR OBSTACLES?
I try to remind myself to be grateful. Every morning I write a short journal entry, and at the end I write down one thing I’m grateful for—even something simple like seeing the sun or spending time with family.
My parents also emphasized effort over results when I was growing up.
WHAT HAS SOCCER TAUGHT YOU ABOUT LEADERSHIP AND RESILIENCE?
Soccer has shaped a lot of who I am. I’ve been playing since I was 3 or 4 years old, and I was captain my senior year at Milton.
One big moment was when I broke my leg as a freshman. I fractured my tibia and was out for months. That experience made me appreciate things I took for granted, like simply being able to walk.
It also showed me how supportive the Milton community is—coaches and teammates visited me while I was recovering.
WHAT DID YOU LEARN FROM RUNNING BENZBOOTS, AND HOW DID THAT EXPERIENCE SHAPE THE WORK YOU’RE DOING NOW?
When I started BenzBoots at Milton, it felt like a huge project. Looking back, I wouldn’t call it a big success, but it gave me the experience of launching something and learning what it takes to get people interested in an idea.
While I was building the business, I experimented with a lot of different things—a podcast, events, and even a five-on-five soccer tournament where local players paid to participate. But the core idea—selling cleats—didn’t take off the way I expected. It taught me an important lesson, which is: It doesn’t matter how much you believe in a product if there isn’t real demand for it.
Around that time, I went to an event hosted by my mom’s hairstylist. I noticed none of it was being documented or shared online. With BenzBoots, one thing I had done well was documenting everything and building an online presence, so it made me realize that many small businesses struggle with digital marketing.
I ended up helping her with her online presence. I built a website, ran Facebook ads, created social media content, and sent emails. She paid me $200, and at the time it felt like a fortune! More important than the money, the gig showed me those skills had real value.
DO YOU THINK YOUR GENERATION HAS A DIFFERENT PERSPECTIVE ON WHAT DRIVES SUCCESS IN BUSINESS TODAY?
Technology and AI are going to change everything, just like the internet did. But I think what will separate successful founders is being mission-driven, tapping into a personal brand, and human connections.
Anyone can learn technical skills today, like editing video, posting content, or running ads. What really matters is how much you care about people. Can you bring that little bit of magic, that human touch?
IF YOU COULD GIVE ADVICE TO YOUR YOUNGER SELF AT MILTON, WHAT WOULD IT BE?
Try a lot of different things. Milton offers so many opportunities: classes, activities, people to meet.
But once you discover something you truly enjoy, double down on it. It’s better to go deep on something meaningful than to join dozens of clubs just to list them on an application.
YOU’RE ONLY 19 AND ALREADY DOING A LOT. HOW DO YOU THINK ABOUT THE FUTURE?
I still have a lot to learn. I’m just getting started. It’s exciting to share what I’ve experienced so far, but I know there’s much more ahead. This definitely feels like the beginning of the story.