How David Goldshore Built a Champion

PLUS: When 5AM Wake-ups Are Dumb, Protect Your Time At All Costs, Fashion Tips After 50 and more...

Author

Greg Scheinman
May 11, 2025

Morning, Greg here!

Welcome to Midlife Male, the fastest-growing, #1 newsletter and lifestyle brand for men 40+. Hundreds of readers are joining us every day for actionable, relatable columns, exclusive interviews and stories you’ll find nowhere else to help you maximize the rest of your life. If a fellow MLM reader shared this with you, subscribe here:

In Today's Issue of Midlife Male:

Let’s get to it!

David Goldshore on Winning, Mentoring, Parenting and the Value of Coaching

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.

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.

Protect Your Time Like Your Life Depends On It

Do you know what the most valuable thing I own is?

It’s not my car.
It’s not my business.
It’s not my followers or reputation.

It’s my time.

And if you’re a man in midlife—juggling your family, your fitness, your finances, and your future—you already know this:

Time is the most valuable thing you’ll ever own.
Not because it’s rare, but because once it’s gone, it’s gone forever.

Here are 5 lessons I’ve learned about time and why I protect mine like my life depends on it:

1. Every ‘Yes’ Is a ‘No’ to Something That Matters More

When I give you an hour of my time, that means I’m not spending it with my wife or sons. I’m not training. I’m not writing. I’m not working on my business. I’m not walking my dogs, calling close friends, or reading a book that fuels me.

So no, I can’t “hop on a quick Zoom” or “grab coffee to pick your brain.”

Not unless there’s mutual value, shared purpose, and aligned priorities.

That’s not rude.
That’s reality.

2. You Don’t Deserve Time You’re Unwilling to Earn

Why 5AM Workouts Are Great, Until They’re Dumb

The 4AM or 5AM morning routine has received a lot of media attention lately because one lunatic’s 2-hour morning routine that begins at 4 in the morning went viral. The Wall Street Journal even wrote a profile here on how Tim Cook and Bob Iger famously wake up early to workout and start their day while everyone else is sleeping.

Is this some secret hack? A productivity cheat code? Is it worth it? Is it stupid?

The answer to all of these questions is, incredibly, yes.

This may sound contradictory, but I lived that 5AM workout life for nearly a decade (worked great) and recently ditched it (so glad I did).

Here’s my story that will help you decide which side of the 5AM wake-up you should be on now – and which side you should be on in the future:

“Just because something works, doesn’t mean it’ll work forever.”

This feels like a famous quote from a famous thinker, but it isn’t. I can’t find its origins anywhere and maybe it’s close to a movie line I can’t quite remember so if it is, hit us up and let us know. Until then, let’s just roll with it because it’s true and it speaks to an increasingly common issue I’ve talked about with friends around our age – and that’s the idea that after 40 we have to actively assess why we do what we do.

In particular, how we structure our days.

When was the last time you sat down and really thought about your day?

Why do you wake up at the time you do? Why do you workout when you do? When did you decide what your average bedtime would be?

When you really think about it, you’re likely to stumble on this fact: you never actually think about it – or at least you haven’t in a long time. Also, the answer to many of these questions is uncomfortable. 

Why? 

Because most likely you didn’t decide any of them, they just sorta happened as you played life defense as a midlife male.

What’s life defense?

5 Steps to Overcome Limiting Beliefs

We love this LinkedIn post from Ryan Estis about overcoming limiting beliefs. Powerful stuff.

He writes:

Overcoming limiting beliefs requires intentional effort and a willingness to challenge the narratives you’ve accepted as truth.

One of the biggest hurdles in overcoming limiting beliefs is recognizing that they aren’t absolute truths. Beliefs are just thoughts you’ve repeated enough to feel certain about. When you challenge these “truths,” you create room for growth and new possibilities.

Here are a few of my favorite tactics to break free of their hold.

How to Dress When You’re Past 50

While I disagree with some of these outfits, I completely agree with the sentiment in this post. You should care about how you look and have certain guidelines for yourself.

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Interested? Hell yes, you are. And we’ve got a great deal for you through Midlife Male if you sign up today: $300 off with code MidlifeXPT. Use this link. Spots are going fast!

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Some have been married for decades, others are divorced, most are fathers. All of our members seek improvement, access, insights, and support in a group of like-minded men. They are committed to making the next phase of their lives, the best phase of their lives, living happier, healthier, wealthier, stronger and having more fun in business and in life.

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“You either define midlife, or it’ll define you.” - Greg

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“It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again, because there is no effort without error and shortcoming.” - Teddy Roosevelt

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