Eternal Summit: Tyler’s Endurance and Entrepreneurial Journey

For Tyler Schmoker, the eternal summit has always called to him, whether it’s the peak of a towering mountain or his current status as an entrepreneur. This drive, forged through his experience in military service, has propelled him to take on some of the biggest mountaineering adventures in the US while building a thriving consultancy business.

The Foundation for His Future Pursuits

Tyler’s journey began in the U.S. Army, where he spent approximately 9 years on active duty and nearly 21 total in service, including deployments in the aftermath of 9/11. “For all intents and purposes, I was doing purely military stuff as a full-time job through different components for the first nine years of my career,” he explains. Tyler then transitioned into the National Guard. The skills he honed – physical toughness, strategic thinking, and a relentless will to persevere – would become the foundation for his future pursuits.

I Want to Climb a Mountain Someday

During a work activity that led to a conversation about dreams, two of Tyler’s friends mentioned marathons and mountains. “One of them said, ‘Well, I want to climb a mountain someday,'” he recalls. Curiosity and looking for the next step after military life led Tyler to the internet. The seed was planted, and Tyler found his way to Mt. Elbert, a peak in the Rockies that is the 2nd highest peak in the contiguous US. Then, his path intersected with the ultra-endurance world.

Arrowhead 135

It was the Arrowhead 135, a 135-mile winter ultra endurance event in northern Minnesota, that became Tyler’s biggest test of fortitude. “Last year, real temps were like negative 44, so with wind chill, negative 60,” he says of his first attempt in 2022, which ended in a medical scratch due to frostbite after 61 miles in the bitter cold. Undeterred, he returned in 2023, only to face a new challenge – freakishly warm temperatures rendering the snowmobile trail nearly impassable. “You’re literally pushing through tree saplings, and it’s ungroomed,” Tyler describes. Despite numerous crashes from the tough conditions, he persevered for over 18 grueling hours before his bike became inoperable, forcing another DNF.

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Adapting and Applying

Through Tyler’s mountaineering adventures and Arrowhead 135 experiences, a pattern emerged. Tyler would not back down, adapting and applying the gritty mindset that he forged in the military to his current adventures. “I’m willing to put my foot on the line and go try some things,” he states. “I’m definitely like a professional dilettante, and I just try a bunch of different things.”

Entrepreneurial Endeavors

This ethos shapes not only Tyler’s athletic exploits but also his entrepreneurial endeavors at Winsly, his consultancy firm. “I’ve integrated a lot of different sociological and psychological aspects into it, like just proof concepts that work,” he explains. His approach involves blending real-world experience from his military and intelligence background with modern business tactics.

The Lens of Military Strategy

His “LinkedIn Tradecraft” course teaches professionals to master the social media platform through the lens of military strategy. “How do you communicate better? How do you execute a strategic communications plan? How do you target opportunities?” Tyler asks, then provides the “cheat codes” derived from his unique experiences. Just as extreme athletic events like Arrowhead require resilience, entrepreneurship demands the ability to persevere through setbacks.

Eternal Student

At 44 years old and still chasing summits, Tyler displays the “eternal student” mindset – always striving, always learning, always evolving. He may have fallen short at Arrowhead, but you can be sure he’ll quickly find the next challenge. “I’m really more of an indie dirtbag climber who occasionally gets into an event to train for it,” Tyler jokes. Whether it’s mountaineering or entrepreneurship, Tyler’s mission remains the same – that eternal summit. He wants to test his limits and transcend what he’s accomplished before. It’s an obsession that will surely lead him to greater heights.

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