On February 26, 2025, under the bright lights of Fairfield University’s Leo D. Mahoney Arena, the Staples High School boys basketball team made history.
They hadn’t won an FCIAC title since 1963. That’s 62 years. But this year, they did it—beating top-seeded Ridgefield 68–58 in front of a sold-out crowd of 2,200.
They did it without their leading scorer, who was sidelined by injury.
They did it after two straight seasons as runner-up.
They did it with grit, with teamwork, with resilience—under the leadership of Head Coach David Goldshore.
Watching the footage, seeing the emotion on the court and in the stands, reading how Dave rebuilt this program—not just technically, but culturally—hit me hard. He’d just lost his own father. He coached through it. He showed up. He led. And he won.
That’s when I reached out.
Dave and I went to college together at the University of Michigan. Same fraternity. Same circle. Friends—but not close. To be honest, I wasn’t capable of letting anyone get close back then. I was 18, reckless, grieving my dad, and coping through all the wrong things—alcohol, women, distraction. I didn’t know how to be a good friend, let alone a good man.
It’s a time in my life I’m not proud of.
I didn’t keep in touch with many people from those years. Not because I didn’t care—but because I didn’t think I was someone worth staying close to. There’s always been a quiet voice in my head saying, You weren’t great then. Why would anyone want to reconnect now?
Then I saw what Dave had built.
From the national championship game in Houston. I hadn’t seen some of these people in 30 years. -Greg
The connections he’s kept. The community he’s led. The culture he’s shaped. The family he’s prioritized. The success he’s earned—not in titles or trophies, but in impact. And it moved me. Deeply.
So I reached out. Told him I was proud of him. And he was gracious enough to say thank you—and yes—to this interview.
Because what Dave is doing now is what so many of us think about and rarely do. He became Coach Goldshore—not just Mr. Goldshore. And in doing so, he’s elevated every part of his life: his health, his family, his business, his purpose.
He’s living his legacy. And he’s leaving one, too.
It’s rare to reconnect with someone from your past and be inspired by the man they’ve become. It’s even rarer to realize—maybe, just maybe—you still have time to become a man worth reconnecting with, too.
Enjoy this week’s How I See It with Coach David Goldshore.
On Finding Purpose
“It’s not about cars, big houses, fancy trips—it’s waking up daily, same bed, same life, with a smile, passion, purpose.”
On Coaching as a Calling
“Hearing ‘Coach’ from my players, their parents, the folks at school? That’s the good stuff. It hits different than ‘Mr. Goldshore’ or ‘David.’”
On Business Partnership
“It’s been a 15-year marriage—bumps, sure, but solid. Tough talks, transparency, and knowing our strengths. Like any marriage, it’s work.”
On Balancing Coaching & Family
“It’s a balancing act, no doubt—family comes first, but shaping these 15- to 18-year-old guys is a big part of what I do.”
On Midlife Reinvention
“You don’t have to pick one path or think success looks one way. Coaching’s made me more than one thing, and that’s the key.”
On Mental Health & Burnout
“Moved out [to Chicago], but it crushed me. I was mentally unready. Panic attacks, heavy stuff. Lasted six months.”
On Parenting with Boundaries
“I wasn’t gonna hand them spots just ‘cause they’re my kids, especially if other players were grinding harder.”
On Mentorship
“Coaching’s my chance to pass it on. My football and basketball coaches were huge in my life—I still talk to them today.”
On The Grind
“Follow your passion, but know it’s not overnight success. It’s a grind.”
On Coaching Impacting Business
“It’s no coincidence our business has taken off since I got deep into coaching. Coaching gives me stories, value, something different.”
On Sacrifice
“We haven’t taken a family vacation in eight years—not because of money, but because Christmas and February breaks are game time.”
On Living Your Legacy
“If my legacy ends up being about doing this well, building up young guys, and making a difference, that’s awesome.”
On Doing It for Yourself
“Going for what I want has made me better for everyone else.”
On the Value of Time
“Coaching’s like teaching a class 20 nights a year in front of 500 to 750 people. You’re constantly judged. It’s soul-searching.”
On the High Point
“I spotted Lauren in the student section, pointed at her, and she pointed back. That moment tied everything together—personal, coaching, all of it.”
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Greg Scheinman
Founder, Midlife Male
52. Husband. Father. Entrepreneur. Coach
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