Morning, Greg here! Welcome to Issue No. 27 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.
Also, a huge thank you to all the Inner Circle Members who joined us this week for our first live ‘How I See It’ with 29029’s Marc Hodulich. Forget listening to podcasts with fascinating, impressive men and feeling disconnected. With the Inner Circle, we invite you into the conversation. Dozens of members showed up, asked Marc questions and got real insight and personal, actionable advice they can use. We learned, we laughed, we connected and we’re just getting started. There is nothing else out there like this for midlife men like us. Don’t miss our next live event! Join us here.
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‘How I See It’ with Ryan Estis
You know those people who make you stop and think differently? The ones who shift your perspective without forcing it? That’s Ryan Estis for me.
I met Ryan a few years ago through Impact Eleven—he’s a partner, I’m a student. Since then, he’s been an invaluable mentor, resource, and teacher. But more than that, he’s just a great guy. The kind of person you want to be around. The kind who elevates any room he’s in.
Every time I hear him speak, read something he’s written, or watch how he operates, I walk away better for it. And here’s the thing—he’s not flashy about it. He’s not the loudest guy in the room. But when Ryan talks, you lean in, because you know he’s got something real to say.
He’s one of the top keynote speakers in the world, a renowned thought leader, and his work has inspired millions. His new book, Prepare for Impact, is no exception.
What I appreciate most about Ryan is how he takes big, complex ideas and makes them click. He doesn’t just talk theory—he shares his own journey. Whether it’s getting his health back on track, taking on new challenges, or learning to say “no” to the right things, he breaks it down in a way that’s honest, relatable, and—most importantly—useful. He’s got this quiet confidence that never tips into ego. Like a really smart friend who’s figured some things out and is happy to share what’s worked and what hasn’t.
That’s how this interview happened. It wasn’t even supposed to be an interview. We were just catching up on a call, and he started sharing what he’d been working through, how he was approaching it, and I stopped him mid-sentence—“Are you cool with me publishing this?” Because guys need to hear this.
I keep coming back to Ryan’s perspectives because they’re not just interesting—they’re actionable. And that’s why I wanted to bring him into this community. Because his way of thinking, his approach to life and work—it’s something special. Trust me, you’re going to want to read what he has to say.
How I See It with Ryan Estis
MLM: How have you been since we last spoke? Any big changes recently?
Ryan Estis: A lot of upgrades in terms of business—new brand, new website, book release, and a lot of momentum on the speaking side. On the personal side, I’ve taken additional steps to focus on my health. New doctor, deeper biomarker measurements, more supplementation, peptides—I'm starting to see the results. I feel stronger in the gym, my energy is improving, and I’ve reduced the inflammation I was dealing with. You hit your 50s, and it’s just not like being 30 anymore. I had to take a closer look at what was happening inside me, and I’m on a good path now.
MLM: That’s amazing. Everything you do, you set a goal and then map out how to get there. I’d love to get deeper into your process—how you found your doctor, what’s working. I think guys learn best by hearing from relatable, aspirational men who are at the top of their game but still face challenges.
Ryan Estis: I haven’t talked about this publicly yet, but I’ll share it with you. I wasn’t just feeling off—I was sick. Metabolic syndrome, thyroid dysfunction, stage two kidney disease, high cholesterol, high risk for cardiac disease. And this was happening to someone who works out five days a week, eats clean, and generally takes care of himself. I wasn’t eating junk, yet I was still inflamed and exhausted. It was a mix of environment, stress, past neglect, and aging. I went to three different doctors, and none of them could give me the help I needed. Finally, I found a holistic, integrative doctor who took a deeper dive. She told me the standard tests weren’t telling the full story, and she was right. Once I got the right protocols in place, things started improving.
MLM: That’s so important. And I love what you said about mental health—it’s not talked about enough. High achievers don’t want to admit they have low T or thyroid issues, but it happens. We work so hard to be the example, but we don’t talk about when we feel off.
Ryan Estis: It’s easier to just say, “I’m great, best year ever,” while secretly knowing something’s wrong. I might have had my best financial year, but if I was going back to my hotel room feeling like crap, what kind of wealth is that? I see it over and over again—whether it’s a billionaire hedge fund guy, a top speaker, or an entrepreneur. We project success, but when we peel back the layers, we ask: What actually makes us feel wealthy and healthy? The real success is getting my health back on track and feeling great again.
MLM: That’s why I love talking to you. It’s about redefining success. It’s not just money or applause—it’s feeling great, being on the right path, and enjoying life. And I think mental health conversations are getting glossed over. It’s become a buzzword, like “burnout” or “culture,” but real optimization happens when the conferences and masterminds are over. It’s about what you do when you go home.
Ryan Estis: The most important minute of a meeting is 8:01 the next morning—when you actually do the work. You have to ask yourself: If I feel like this now, how am I going to feel in five years? And I wouldn’t accept that this was just “getting old.” I saw guys like you, Troy Aikman, Kelly Slater—guys in their 50s still crushing it. So I found someone who could help me, and I got to work.
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How to Do NYC in 36 Hours
3,2, 1 go…Just wrapped up an all out blitz on New York last week and I actually think I nailed it this time if I do say so myself.
Flew in Thursday, claiming my signature spot — 7F/7C, the perfect aisle seat right after first class. I used my Marriott Bonvoy free night certificate to stay at The Edition hotel on 5th Avenue by Madison Square Park. Gotta love that $35 daily meal credit for Bonvoy members.
After checking in, I headed over to Bathhouse where Travis, the owner, gave me a private tour. Their facilities are next-level: sauna, cold plunge, steam room, and every amenity you could dream of. If you’re visiting NYC and value wellness, this place is a must.
Dinner that night was at Port Said with three of my high school best friends. The spread? Unreal. Bread salad and the potato appetizer were standout starters, the hummus was flawless, both Branzinos were cooked to perfection, and the steak was outstanding. I’m not a huge desert guy, but the cheesecake? Easily some of the best I’ve ever had.
I always stick to my wellness routine while traveling so I dropped into The Strength Club, owned by my good friend and top trainer Kenny Santucci. It’s like my home base for fitness when in the city. Started another day with a restorative session at Othership, combining guided sauna and cold plunge contrast therapy. Totally different experience from Bathhouse. This is more like the yoga class of contrast therapy; very spiritual and woo woo…Breakfast back at The Edition was next-level — salmon avocado toast with perfectly poached eggs hit just right.
I was there to work. Two of my 1:1 coaching clients are based in NYC and this was our annual planning time. We walked, talked, ate and then spent 4 hours crafting a midlife action plan, followed by another training session at The Strength Club.
I wrapped things up with a stellar dinner at The Corner Store with another client for his January review. These sessions are always better in person breaking bread. We went all in: shrimp cocktail, snapper crudo, and filet mignon with wilted spinach and grilled asparagus. The highlight of the night? Meeting Kevin Love and chatting about our mutual friend, Gunnar Peterson.
Here’s what I packed:
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.
This week: FUN
Why the Only Way to Truly Fail Is to Not Try At All
This is a guest post from Billy Mann, Grammy Award-Nominated Singer/Songwriter.
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Songwriters, not trying is failure.
It’s that simple.
The search for “perfect” is failure because there is no such thing as perfect.
No perfect song.
No perfect personality, professor, parent, partner, prime minister, or president.
Even a so-called “perfect score” is imperfect—subjective, scaled, hedged/biased by someone, somewhere imposing agenda, insecurity, culture, judgment.
Yesterday, I boarded a flight with the plan to tackle a mountain of emails during the hours in the air. I was caffeinated, ready, and armed with good intentions. After takeoff, I signed into the inflight Wi-Fi, only to learn it wasn’t working. So much for my “perfect” plan.
And there I was—staring out the window, untethered from productivity—until something compelled me to hit shuffle on my library of old song demos. Hundreds of tracks written over decades. Some with legends and superstars. Others with unknowns, fellow troubadours, or pop clones.
It was agony.
Bad songs. Cringe-worthy lyrics. Derivative melodies. Embarrassing moments that made me laugh out loud in humiliation—alone in my seat.
But just as I’d resigned myself to this painful nostalgia, a song would start. A just-in-the-nick-of-time gem that resuscitated me from the “songwriter’s hole of shame.” An original turn of phrase or an expected melodic leap of faith or foolish.
Dud after dud. Almost after almost. I couldn’t help but wonder: What was I thinking pitching these records? And yet…many of them actually got cut. Some even became hits. They charted, lifted me from the Ramen noodle grind of scraping by, and gave me the freedom to grow more music. And without even realizing it consciously, I recognized the question was less about having a “hit for everyone” and more about “is it a hit for someone?”
Isn’t that true about life? Happiness? Love? Work? Faith? Your food? Your hairstyle? Not everyone likes a “neat freak,” but maybe a messy person does. Not everyone loves their ballads with extra cheese and a key change, but maybe that lonely romantic in Little Rock does.
In today’s music market, the volume of songs released to consumers is staggering—hundreds of thousands, even millions, per week. Listeners choice never had more potency. Talk about sperm competing for the egg! Meanwhile, 80% or more of the songs on Spotify never get more than 10 streams. Let that sober truth sink in.
So why am I so precious now? Why all the self-judgment?
The truth is…
In Case You Missed It
CHECK OUT OUR MOST RECENT ‘How I See It’ INTERVIEWS:
Dr. Darshan Shaw on Practical Longevity Solutions
Author Jonathan Goodman on the Obvious Choice
Jacob Zemer on Reclaiming Fitness
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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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