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- 116,116 Steps Up ‘Everest’: Pain, Perspective & Personal Progress at 3AM Climbing Jackson Hole
116,116 Steps Up ‘Everest’: Pain, Perspective & Personal Progress at 3AM Climbing Jackson Hole
PLUS: How I Approach 29029 (and Why it Works), The Million-Dollar Investment in Your Closets, The Book that Will Kick Your Ass (In a Good Way), and more

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Morning, Greg here!
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In Today's Issue of Midlife Male:
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116,116 Steps Up ‘Everest’: Pain, Perspective & Personal Progress at 3AM Climbing Jackson Hole
I'm 52 and wearing a black bib, the color they give you after completing the 29029 Everesting challenge three times. This is my fourth year. When people see it, I think they assume this comes naturally to me. That I've always been the guy who does stuff like this. But that's not true. Five years ago, I was making the same excuses most of us make. Too old to start something new. I’m not in shape for this. I don’t do 36hr endurance events. I don’t even like 5k’s. I’m too busy to train for this anyway. I genuinely didn't think I had this in me. Not once, and definitely not four times. But I was intrigued. And there was something pulling on me to say yes to what I've always said no to.
Here's what I learned: the difference between the guy I was and the guy standing here today isn't talent or luck. It's showing up consistently when you don't feel like it. Making the choice to try something that scares you a little (or in this case, a lot). And discovering that the voice in your head telling you "you can't" is usually wrong. That's what I want to talk about—not the achievement, but the process. Because if this is what’s happening to me from 47 to 52, maybe it can happen for you too. It’s evolution. It’s growth. But don’t for one second get the impression that it's easy or routine. It's anything but.
I talk a lot about progress being a process and about setting standards for yourself, even above goals. Well, let me backtrack to five years ago, when I first heard about this event. I said, "Wait a minute, I can climb the equivalent of Mount Everest? Do people do that? I don't do that. I've never done anything like that. And wait, the average age is 46 years old? That's me. What kind of shape do you need to be in? What does this cost? What kind of commitment do you need to make? It's certainly possible because there are people doing it, but is it probable for me?”
At that moment, I decided to make the commitment, because if you don't take the leap, and start, it'll never happen.
One of the best decisions of my midlife.

The First Climb Was a Mess (And That’s the Point)
Here’s how I approach risk…
29029 Timeline - How I Do It (And Why It Works)

Arrive Wednesday
I like to get in early and acclimate. See Jackson Hole, preview the mountain. We had lunch in town at Local, which was excellent for steaks and burgers.
Thursday
Slept in and then went for breakfast at Persephone Bakery. This place is fantastic. The pastries, coffee and the entire menu was delicious (we way over ordered). Then we went to see the Tetons. The aerial tram ride was beautiful and the views from the top of the mountain were gorgeous. They even had a waffle stand at the top and we had these amazing hot, buttery waffles.
Back to the hotel and hit the spa for a sports massage, followed by infrared sauna, and hot tub. Then there was the opening ceremony, where I received my black bib (for completing 3 or more events) that I got to wear on the mountain. Passed on the buffet dinner with the group and went into town with Kate for date night at Kampai for sushi.
Friday - Saturday
The event starts at 6am.
As a “veteran”, I’ve figured this out now. I get as much sleep as possible, get up at 5:45am, and I’m dressed and at the back of the starting line pack by 6am. I hydrate, don’t eat breakfast and use the first ascent to warm up. I eat my first “meal” at the top of the mountain aid station.
First break for breakfast around 8am after 2 ascents. Continue hiking through lunch and break at noon for no more than 30 minutes. Key is to use the aid stations for small nutrition/hydration and the gondola down for rest. Hiked through 10pm and completed 12 ascents.
Shower, eat, and sleep until 230 am.
Get up, dressed and back on the mountain by 3 am with a headlamp for night hiking. Completed 13-16 from 3 am to 6am and then took a break for breakfast.
Back out on the mountain by 8 am and finished 14-19 by lunchtime. Showered, clean clothes, food and gondola to top of mountain to cheer on the other participants finishing. Closing ceremonies at 7p and felt great.
Back into town with friends for Italian at Orsetto. The pastas and salmon were delicious. Dessert was earned so we hit Moo’s; which is legendary for ice cream. I went with the award winning Wild Huckleberry.
Sunday
Slept 9 hours, then back to Persephone Bakery because it was so good the first time. Checked out of the hotel and got on a 3 pm flight to Denver. We arrived at 5.30pm, picked up a rental car, drove to dinner, our son met us at 6: 30, ate and got to Empower field by 8:15pm, parked and in stadium seats by 8:30p, Metallica hit the stage at 8:50pm.
Epic days.

The Million Dollar Investments in Your Closet
By Ron Speaker
As a mid-life investor, I’ve discovered that some of the best investment opportunities are literally staring me in the face, or more accurately, wrapped around my wrist, hanging in my closet, and sitting in my shopping cart. In fact, I’ve come to view the products that have infiltrated my daily routine as potential goldmines that I’m already beta-testing with my own wallet.
The Power of Investing in What You Know
Peter Lynch famously advocated for investing in companies you understand and use. This philosophy resonates deeply with me because I’d naturally like to invest in brands I know and use. When I’m obsessively checking my recovery metrics or explaining to my wife why I “need” another pair of expensive workout shorts or shoes, I’m essentially conducting market research disguised as midlife crisis purchases.
Fitness and Wellness Technology
The wearable tech movement has created remarkable companies that we interact with daily, or, in my case, obsess over their data like a day trader watching stock tickers. Whoop (private) has revolutionized how I track recovery, which is a fancy way of saying it tells me I’m too old to party like I’m 25 but too stubborn to listen. Oura (private) provides similar insights through its elegant ring design, tracking sleep patterns and more while Garmin (GRMN) has a wide range of GPS-enabled wearables covering diverse markets.
Over time, these gadgets become health companions with sticky, subscription-based business models. The data they collect becomes more valuable the longer you wear them, making them increasingly indispensable. If Whoop or Oura become public I’ll be ready, and sometimes…
College Drop-Off Just Got Easier (Thanks to This Guy)
Have kids in college? Nearing that time? One of the most valuable resources we've found is Harlan Cohen. He's a NY Times Bestselling author & journalist, has an amazing Instagram with 727k followers and he loves to help. If you've got a kid in college or are about to, make sure you’re following him.
Breathe Better, Move Smarter, Feel Younger
No two things will make a more positive impact on your overall fitness than breathwork and mobility. The app that incorporates both into our regimen is XPTlife. It's $99 for the year and we use it every day. There are tons of options, and time domains to choose from along with various coaches, styles and everything you need to breathe well and move well. We really like how it syncs with your Spotify or Apple Music as well.
This Book Will Kick Your Ass (In a Good Way)
Shoveling Shit! We love this book. The authors, Kass & Mike Lazerow ; founders of Buddy Media, deliver hard-won insights about entrepreneurship's messy path to success with sanity and a sense of humor. The foreword by Gary V is so good that MLM Founder Greg Scheinman regularly shares it to inspire friends, family and the MLM crew to strive to have someone talk about us like this in business and in life. Order your own copy HERE
The Sweet Stuff That’s Actually Good for You
We're off sugar (for the most part) and our latest thing is Manuka Honey. This premium New Zealand honey offers genuine health benefits beyond regular honey, including antibacterial properties and digestive support. Worth the investment for your morning routine or as a natural remedy for seasonal throat irritation. We use it on our pancakes instead of syrup, with greek yogurt and fruit and even put some in our smoothies.
Old-School Style That Still Turns Heads
PF Flyers Classic American sneakers combine retro style with surprising comfort for the guy who wants something different from standard athletic brands. The canvas construction and vintage aesthetic work equally well for weekend errands or casual Friday. We're wearing the high-tops right now.
Pretty in Pink Still Hits Home
If live music is one of your outlets, get out there and see bands as often as possible. Here’s who Greg’s catching this week:
“The Psychedelic Furs are in Houston this week. We enjoy catching these "older" bands that we came up with live. These new wave legends still deliver the atmospheric energy that made them essential listening in the '80s. This tour showcases both classic hits and deeper cuts with the polish that comes from decades of performing. Who didn't love Pretty in Pink?”
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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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