July’s Dad of the Month: David Rollo

July's Dad of the Month David Rollo breaks down why leading with imagination is the ultimate gift for your kids and how boxing sharpens his parenting edge

By Your Bro · Mon Jul 20 2020 · Guy Stuff

Being a father in a city that never sleeps is an endurance sport that makes a twelve-round prize fight look like a nap in a hammock.

The Manhattan CEO with a Toronto Heart

Entering Manhood is pleased to announce that July's Dad of the Month is David Rollo (@irollo). One of NYC's most eligible bachelors, Dave is the CEO of a global digital advertising agency and a passionate fan of boxing. Originally hailing from Toronto, he is a father of a teenage boy and girl. Watching a man run a global agency while keeping his head on straight in the New York rat race is one thing; watching him do it while raising two teenagers is another entirely. You have to be part strategist, part enforcer, and part diplomat.

Dave doesn't just manage budgets and creative briefs; he manages the development of two human beings in an era where attention is the rarest commodity on earth. It is easy to get lost in the spreadsheets and the client calls. Most men let the job become the identity. Dave treats the job as the engine, but the family as the destination. It is a distinction that separates a guy who merely provides from a man who actually leads.

The Power of a Loaded Imagination

Dave’s parenting style is one that leads with imagination. "Nurture a child’s imagination and that’s a gift that will last a lifetime," he says. He believes that imagination and creativity can lead to a wide array of options, ideas, and pathways to both happiness and success. Opening a child's mind can help them find their passion and reach their full potential. This isn't about finger painting and make-believe. It is about cognitive flexibility.

When you teach a kid to look at a problem and see four different solutions instead of a dead end, you are giving them a survival kit. According to research from the American Psychological Association, creative play and divergent thinking in the developmental years are linked to better emotional regulation and problem-solving skills in adulthood. If they can imagine a better world, they can build one. If they can't, they just end up working for someone who can. I mentioned some of these concepts when discussing thirty fatherly rules for the next generation.

Connection as the Engine

Dave's favorite thing about being a dad is "connection." He says the connection he has with his kids is a thousand times stronger than anything else in his life. "That connection drives me, inspires me, and enriches my life daily," he admits. In a world of digital distractions, a real bond is the only thing that doesn't depreciate. You can have the $8 million net worth and the corner office, but if your kids don't want to take your call when they're twenty, you've failed the most important KPI of your life.

I remember a buddy of mine who was a high-level litigator. He never missed a billable hour, but he missed every one of his son's baseball games for three years. When he finally showed up to one, his son didn't even look toward the bleachers. He had stopped looking for his dad a long time ago. The connection was severed, and no amount of tuition money could patch the hole. Dave gets that you have to be in the room—physically and mentally. We've talked before about how your time is bigger than money, and Dave is living proof of that priority.

Lessons from the Square Circle

Being a fan of boxing isn't just about watching guys trade leather. It is about the discipline of the camp and the grit of the late rounds. It’s a metaphor for life. Dave takes that same intensity into his daily routine. You don't get to be a CEO or a present father by being soft. You have to take the hits and keep moving forward. Boxing teaches you that you're going to get tagged; the trick is not letting it ruin your plan.

The Mayo Clinic has noted that regular physical activity and a focus on high-intensity training can significantly reduce the physiological markers of stress. For a guy like Dave, the ring is likely where the noise of the agency fades away so he can focus on being the man his kids need. There is a clarity that comes after a hard workout that you can't get from a meditation app. It’s the kind of grit I explored when talking about lessons for men from the world of boxing.

The Responsibility of the Modern Mentor

Dave represents a shift in what it means to be a modern father. He isn't the silent, distant provider of the 1950s. He is an active participant. He understands that his children are watching how he handles pressure, how he treats his staff, and how he carries himself in the city. You aren't just raising kids; you are training the people who will replace you. That is a heavy lift, but men like Dave make it look like a privilege rather than a chore.

We're with you, man. Being a father is truly a blessing. It is the hardest job you will ever love, and it is the only one that actually matters when the lights go out. Congrats, Dave. You are July's Dad of the Month.

—Your Bro