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John Winsor

@jtwinsor

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My latest Substack. https://johnwinsor.substack.com/p/the-right-place

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A buddy of mine saw a post about the Midlife Male Excellent Adventure Club and said, “Dude, this is great. Whenever we have vacations, I do everything. I schedule it, I plan it, I pay for it. It’d be awesome as a dad to just have a group of guys say, it’s all taken care of. Just get here.”⁣
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That’s exactly what it is.⁣
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It’s all taken care of. All you have to do is book a flight and a hotel. You don’t have to do all the stuff you normally do for vacations. You don’t even have to think about what your next adventure is, or who the guys are that are going to be there. Want to invite a friend? Bring them.⁣
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We’re bringing happy, healthy and successful guys together for adventures and experiences that they look forward to on their calendars. Our members are Execs, founders, CEO’s, Professionals, writers, authors, speakers, retired athletes, doctors, attorneys, even a grammy nominated songwriter. ⁣
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Guys who are relatable, credible and aspirational as husbands, fathers, providers and men and where the conversations about life, business, health, and family happen organically through amazing shared adventure experiences; combined with lux accomodations and great food.⁣
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We don’t have to say what we’re not, but we know what we’re not. There’s no sitting in rooms for hours. There are no speeches or presentations, there’s no sitting in circles and there’s no white board. ⁣
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We just do cool sh*t, with cool guys. ⁣
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For years, I denied myself these types of experiences and opportunities while I built my companies. I’ve now realized that this is what makes life worth living. I’ve done things recently that I’ve never done before and didn’t think I was capable of, or had the time for, or that I was somehow not prioritizing the right things if I wasn’t staying put and grinding away.⁣
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If you really are the sum of the five or 10 people you surround yourself with, imagine if you had a network of it 100 of those people. ⁣
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That’s what the Midlife Male Adventure Club is. Men who really want to make a difference in their lives, and they actually do it. ⁣
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Is this real? Yeah. It is.⁣
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Link in comments to learn more. Membership is by interview/application only.

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A few weekends ago I got to have the most epic experience hiking up to Gray’s and Torrey’s Peak with old and new friends. THANK YOU, @sterling_hawkins @havilandhawkins and @gregscheinman for organizing such a thoughtful and fun 48 hours. We pulled an all nighter to get to the trail head by 230am, an all nighter in your 40s with this crew looks different to one in your 20s. I loved talking to everyone as we made our way up in the dark. The weather turned as we made our way to the summit but that is all part of the fun. We got back down around 1pm and has the best Burger in the most beautiful setting. I love these experiences and the people I get to meet on them. Looking forward to the next one!

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Life lately has been very full.

Retreats all over the world. Keynotes all over the world. Mountains, airports, hotel rooms, long conversations, new faces, old friends.

There’s been a lot of movement. And a lot to be grateful for. Gratitude doesn’t begin to cover it.

I’ve gotten to watch people do things they didn’t think they could do. Sit with things they’d been avoiding. Make decisions that changed the direction of their lives and businesses. And I’ve gotten to do it alongside some incredible people.

I don’t take any of that for granted.

There’s still a lot ahead for No Matter What. But for a minute, I’m just taking in how awesome these last few months have been.

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When you put me and @gregscheinman together… you know things are about to get interesting.

Grays and Torrey’s Peak gave us rain, wind, cold, and a whole lot of good people willing to keep going.

No perfect conditions. No checking a box. Just a mountain, a crew, and plenty of opportunities to actually practice getting real, No Matter What.

@themidlifemale x No Matter What

No Matter What Adventures | Retreat | Colorado | Denver | Mountaineering

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The photos show the epic places of where we went. But the words from the people who came with us tell you what actually happened.

No Matter What Adventure Retreats | Growth | Leadership

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Connection + Renewal
I joined the No Matter What Leadership Immersion to climb my first.

I didn’t to do it to prove anything. I wanted to meet myself at the edge of comfort for discomfort.

The real climb began before we started. Prep, facing limiting beliefs, having the unknown, and choosing to do it anyway.

Before we began, Sterling grounded us by reading from ‘Die Wise’. We set our intentions and off we went.

The reading stayed with me. Living wisely isn’t about avoiding heartbreak or rushing past it. It’s about allowing heartbreak to shift us. Deepening our capacity to love, releasing what we need to ascend and be fully alive and aligned.

So often, we want to take big steps forward and hurry through heartbreak or whatever else. But our guides reminded us that the easiest way up isn’t with big steps; it's with small ones.

Slow. Intentional. Steady.
Healing and goals work the same way.

Then, 60mph wind 🌬️😅.
It didn’t ask to be stronger, brace against it, avoid it, or pretend it wasn’t assaulting at times… lol. It simply asked to pause, move through us like a kite and pass while we kept climbing up.

Somewhere b/n the REAL convos, wind, laughter and silence, I realized the greatest gift wasn’t standing above 14,000 feet.

It was remembering that growth often begins when we let our hearts break open. When we release the stories, fears, situations and identities we’ve been carrying, the ascent becomes lighter.

The greatest gift wasn’t the summit.
It was a group of “strangers” willing to commune in unity (community), to walk beside and encourage one another. We became something more together than we could have been alone.

Here’s to the mountains that humble us.
The heartbreaks that keep us open.
The people who make the journey childlike and filled with wonder.

The Spark isn’t found at the summit.
It’s recognizing we’re never meant to make the climb alone and becoming the kind of person who keeps climbing.⛰️✨

I'm deeply grateful! ❤️

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Real experience has never mattered more.

You can get a framework, a strategy, a leadership philosophy in seconds. Ask ChatGPT. Ask Claude. And you’re there.

None of it can walk you up a mountain though.

Saturday we took a group up Mount Sherman for our retreat here in CO. 14,000+ feet. 60 mph winds.

No performing up there. No hiding. Just the next step and what’s true.

One person went 68 minutes without checking his phone… the longest he could remember.

Someone else let go of something she’d carried for years.

@ericka.jones_ said it best: inside the word community is the word unity.

You cannot prompt your way into that. You have to live it.

The mountain tests what you say you believe.

Being witness to it happening in someone else is one of the greatest honors of my life.

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AI is accelerating a shift that was already happening.

In our latest conversation with @jtwinsor, he talks about the rise of freelancers as micro-entrepreneurs — people who combine global talent, new tools, and their own perspective to build work in entirely new ways.

AI lowers barriers, but the real edge still comes from human things: judgement, trust, and taste.

For freelancers, the signal is often the friction you feel in your work. The slow processes. The broken workflows. The things that should be easier.

Those are often the places where the next tools and opportunities emerge.

👉Full conversation in the Hence Journal.

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From newsroom kid to founder of Victors & Spoils.

@jtwinsor has spent his career challenging how creative work gets made.

Now he’s focused on AI, open talent, and what actually gives freelancers an edge: Judgment. Trust. Taste.

Full interview live on Hence Journal.

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Voice of the Mountains Season 2 Episode 7 is now live: Brilliance is Abundant 🎧

Steve House and John Winsor explore what it means to live with an explorer’s mindset—carrying lessons from the mountains into business, loss, and life. From high-risk environments 🧗‍♂️ to letting go of legacy, this episode is a powerful reflection on courage, presence, and freedom.

Listen now wherever you get your podcasts or at uphillathlete.com/voiceofthemountains 🔗

#VoiceOfTheMountains #UphillAthlete #ExplorersMindset #Resilience #HumanStories

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Brilliance is Abundant✨

Coming soon on Voice of the Mountains: Steve House sits down with entrepreneur and Harvard researcher John Winsor to explore the explorer’s mindset—from FKTs on Kilimanjaro 🏔️ to surviving avalanches ❄️ and navigating profound personal loss.

A conversation about risk, resilience, and embracing the full spectrum of being human. Go to uphillathlete.com/voiceofthemountains tomorrow to hear the full episode🎙️

#VoiceOfTheMountains #UphillAthlete #ExplorersMindset #Alpinism #Leadership

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“Open Talent: Leveraging the Global Workforce to Solve Your Biggest Challenges” by John Winsor (@jtwinsor) and Jin H. Paik

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