The #1 Most Important Conversation Dads Need to Have

Morning, Greg here! Welcome to Issue No. 20 of Midlife Male, the lifestyle magazine for midlife men, by midlife men. I wanted to personally welcome all our new readers, and if this newsletter was forwarded to you, subscribe below.

This December, we’re proud to be partnering with mindbodygreen. MBG is one of our Midlife Male Approved brands and my family and I use their products daily. I’m very picky about what I put in and on my body, and I trust mindbodygreen, as well as the people behind the products. My personal go-to’s are the daily Multivitamin, Creatine (and I love their new travel packs), Omega 3’s, probiotics and their protein powder.

Learn more about MBG here, and use GREG10 to get 10% off your next order.

How I See It With Billy Mann

Billy Mann is one of my favorite people—and that's not just a casual statement. I've had the pleasure and privilege of knowing Billy for the last few years, having been introduced by his wife Gena, a childhood friend of mine. 

To simply list his accomplishments—Grammy-nominated songwriter, publisher, producer—feels reductive, though impressive. He's also a devoted husband, father, and passionate Philadelphia Eagles fan. But what truly sets Billy apart is his generous spirit and thought-provoking nature that has made him one of the most genuine individuals I've met.

As one of the earliest guests on our podcast, Billy shared a mantra of his that helped to reshape my perspective on midlife: "Chase the hit life, not the hit song." It's this kind of maturity that exemplifies who Billy is—someone who consistently pushes himself to grow emotionally, physically, spiritually, and creatively.

Recently, Billy undertook a really cool journey; a guys' trip to Guatemala. When he shared a recap of his experience with me, I was touched by both the challenge he embraced and the deeper meaning behind it. As someone who strongly believes in the value of “the guys trip”; it’s a full chapter in my book —whether through physical challenges like hiking mountains, or  my recent trip to Naples with my fraternity brothers which consisted of nothing more than boating, pickleball (yes, I played), great meals, and big laughs— Billy's experience landed with me; and I just enjoy learning about new things and maybe add them to my list. 

Billy's detailed account of his Guatemala expedition—from his friend Dan who organized it for his 60th birthday, to the lessons learned and the bonds formed with his fellow travelers—was so compelling, somewhat scary and pretty fuckin funny, in a “we survived” kind of way,  that we invited the entire group onto a Zoom call to record a podcast episode, which I'm excited to share with y’all soon. 

Billy sees things through a unique lens – his viewpoint, perspective, and philosophies shapes his artistry and how he interprets the world around him. In this edition of "How I See It," I'm honored to share the insights of my friend, Billy Mann, a man who truly embodies what it means to not only chase the hit life, but to actually be living and enjoying it. This interview combines a post he sent me and our conversations about the trip.

MLM: Conversations like this inspire me. A few years ago, I never would’ve imagined doing this—sitting down on a Monday morning, talking with someone like you. It’s incredible. And of course, I’m dying to know why you decided to get on board with this insane Guatemala trip?

Billy Mann: Last year, my friend Dan invited me to join him and a group of his pals for what he called a “not a joke” Guatemala Trek. The plan was to travel to a remote Mayan country and hike 8 or 9 miles a day, mostly…UP. 

I thought I understood what “up” meant, but I learned very quickly that I did not. By the time I was shortening my walking sticks to negotiate the space between climbing and crawling—for hours—I was wondering why anyone would consider this a leisure activity. By the first hour of the first day, I was already asking myself existential questions like, “Why am I not on my couch waiting for UberEats to bring me sushi?” But there I was, at 7,000 feet, dizzy from the altitude and breathing in a thin air cocktail of orange, earthy dirt, volcanic ash, and whatever else nature decided to throw my way.

MLM: Just you versus nature. How difficult was that first day overall?

Billy Mann: Grueling. None of us copped to the agony of that first day, that first hour, or the mental negotiations we were all silently having between time and benefit. We were a group of a dozen men—mostly Americans, plus a Swede, a Brit, and an Israeli—brought together by Dan. Different backgrounds but all successful, Type A, achiever types. No one was going to complain or whine. Light encouragement? Sure. But we were not the empathetic type. We even had two ranking soldiers among us, and only one musician. This was not a group for glamping.

At night, temperatures dropped into the 30s, and we huddled around a teepee firepit to reflect on the day. Guides handed us hot water bottles—“babies,” we called them—to keep warm. It was so cold, we clung to them like lifelines. Around the fire, I strummed a guitar, which anchored me in a way nothing else could after hours of endless climbs and descents, surrounded by brush, ash, and the humbling reality of aging bodies. That first night, I finally drifted off to sleep when I heard a growl outside my tent.

MLM: A growl? Oh shit. What happened with the growl?

Billy Mann: Startled awake, I held my breath. This growling sounded ferocious. I was convinced a wolf—or worse, a jaguar—was right outside my tent. I grabbed one of my walking sticks and retracted it into a spear-like weapon. “Great,” I thought, “I have to kill a wild animal now.” Armed with my headlamp and “weapon,” I unzipped the tent, crouched down, and stepped outside into the pitch-black night, my heart pounding like a techno beat.

I spun around, shining the headlamp in every direction. Nothing. I hissed to scare whatever it was. Nothing. Finally, I stood to pee, and there it was again—the growl. Louder this time! I spun around with my walking stick, ready to fight for my life. And then…I realized the terrifying beast was the Swede in the adjacent tent, snoring like nothing I’ve ever heard. So much for my Indiana Jones moment. I confessed the ridiculous episode the next morning and got some good laughs.

MLM: What surprised you about the trek?

Billy Mann: Over the days, I got to know Dan’s friends—people I likely would never have met in my day-to-day life. We shared stories about families, habits, and experiences. Nature has this way of mentally lubricating conversation, and standing eye-to-eye with a volcano as it erupts does wonders for perspective.

The most humbling moments came from the locals. Mayan villagers, some as old as 70 or as young as 7, would pass us wearing sandals, carrying heavy stacks of wood or baskets of supplies, moving effortlessly while we labored in our fancy hiking boots and daypacks. They weren’t nearly as tall as us, but they moved like they were floating.

MLM: Did you face any unexpected challenges?

Billy Mann I got food poisoning the first night, which was not ideal for a trek with no bodega for Pedialyte or urgent care. I felt self-conscious about holding the group back and being perceived as weak. But I pushed through, swallowing my embarrassment when my condition caused delays. It was a tough balance—wanting to be strong while knowing my body had other plans.

MLM: What did you take away from the experience?

The Conversation Every Father Needs to Have, About the Word Nobody Wants to Mention

Last Thursday night, I got a call from our son who is a junior at the University of Colorado, in Boulder. He's a member of a fraternity, and he's seemingly thriving. His grades are solid. He has a wonderful girlfriend, roommates, and brothers. He's also 21 years old, having fun making mistakes, living and learning, and from all I can seemingly tell, doing far better at his age and stage than I was.

This is not a positive story though. Far from it.

When my son called last week he told us that one of his fraternity brothers had died. We didn’t know at the time how, but it has since been determined to be a suicide.  Suicide. Let that sink in.  A 19-year-old freshman who was recently initiated into the fraternity, who had his entire life ahead of him, went out to a local park  in the dark, never came out and they found his body the next day.

My heart instantly sank. I can't even imagine losing a child. I can't fathom how, and with no warning and hearing so much about this promising young man, this could happen. 

While at the same time, I feel so awful, hollow and sick because this gave me flashbacks to when I was 19, and I've never admitted this before, but I get it.  I understand. And that doesn’t mean I accept it. And it's not to put myself in anyone else's shoes, or that I'm trying to associate myself with anyone else’s  particular situation or circumstance. But rather, it very much made me think about myself, and where I was at that age and stage of life and how lucky I am to be here today. 

You can’t maximize middle age, without making it to middle age. 

While my son didn't know this boy all that well, he described to me what the fraternity chapter was doing, what the Chabad was doing, what a local rabbi was doing, what his friends and families were all doing – coming together and being together in this time of tragedy. This is not the experience that college prepares you for. It's not an experience life prepares you for.

Over the past few days we've been on various group texts and emails and correspondence from the chapter. I watched the funeral on zoom and watched this young man's father speak with poise, composure, passion, empathy, grief and questions. It's one of the most powerful things I have ever watched.

Millions of stories are posted online every day and 99.9% are noise. We sifted through the nonsense to find experts and thought leaders who will share deep dives in one of our 6Fs every week: Fitness. Family. Finance. Food. Fashion. Fun. These are powerful essays by our team or guest writers designed to make you think, grow and maximize your midlife starting now.

FINANCE

How to Turn Your Biggest Expenses into Your Next 10x Investment

By Ron Speaker

The “Follow the Money” catchphrase was popularized by the 1976 docudrama All the President’s Men, suggesting that political corruption can be exposed by following the money trail.

When I “followed the money” in my own life by examining our family spending data on public companies, I realized great ideas were staring me in the face. As a professional money manager, it was embarrassing to admit that I had supported many excellent companies with my spending and wasn’t a direct shareholder. I was helping them get rich, and their stocks went up, yet I wasn’t in the game. This has been the most problematic habit to correct, and it is still a work in progress.

To help with my analysis, I categorized my spending into seven broad categories: technology, financial services, healthcare/utilities, travel, food, entertainment, and retail. Here is a snapshot of the companies I support as a customer in these categories.

Your list will carry important information because repeat customers develop an opinion about a company and love (or not) for the products. This is called conviction and can be the decisive force keeping you invested in a stock during volatile times.

I met Jeff Bezos in 1997 when he was on the initial roadshow for Amazon's public offering; he had been losing money for years, which kept a lot of investors out of his stock but had grown sales yearly. Amazon packages began slowly appearing at my front door back then and over the past twenty years at an alarming pace. We have all helped Amazon become the company it is today. How dare we complain about Amazon stock going up if we didn’t own it when we helped them become profitable! Notice from the chart that Amazon hits two of my spending buckets and is a major vendor in my total budget.

Several years ago, I noticed my wife wearing a new brand of workout shoes called On Running (ONON). She bought several additional pairs the same year, and I received one for my birthday. They were trendy, stylish, and, most importantly, comfortable. We were making an important consumer decision, and I encouraged her to put our investment dollars alongside our spending.

After watching this happen multiple times over the prior decades, I established a new rule in my family investment policy. If we spend significant money with a company because we love their products, then we need to invest in their shares each time we purchase

Last month, I bought a new iPhone 16 and invested more in its shares. My wife bought another pair of On Running shoes for $160 and purchased more than $160 worth of shares. This simple rule helps us stay in the game and dollar-cost average with the companies we love. Keyword: companies we love.

We also own a Peloton from lockdown, and my wife bought the stock. Then we had some issues with the software and updates, and we lost our love, especially when the famous Kendall Toole left. Goodbye shares. If you fall out of love with the product, exit the stock. Sonos has also had tech issues in our gym. As consumers, we are constantly evaluating products. Let’s also use that information to help us invest.

We at MLM believe that guys’ trips are essential. You need time away from being a dad and husband to simply be a guy around the men who know you best. Goofing off. Talking shit. Doing cool stuff.

Listen to the audio book of Midlife Male, read by author/founder Greg Scheinman, on Audible today!

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