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These three executives traded an all-inclusive resort for spearfishing for their food on desert islands, learn why they did it below.

Entrepreneurs Are (Intentionally) Stranding Themselves On Desert Islands

When Davis Smith was 11, his father took him and his brother on an adventure into the Caribbean wilderness. Armed with nothing but homemade spears, the trio underwent a week-long effort to see how well they could survive. They lived off the land—sleeping on the earth and eating whatever they could kill. 

This was the first in a series of six survival excursions that Mr. Smith has embarked on throughout his life. And as CEO of Cotopaxi―a company whose slogan urges consumers to “believe in the power of adventure to make the world better”―Mr. Smith is definitely living his brand. But he’s not the only one willing to forgo the comforts of contemporary existence for the sake of braving the extreme. Survival trips are becoming increasingly popular, especially among entrepreneurs, executives, and even politicians. 

There seems to be something inescapably alluring about confronting the wild with nothing but the clothes on your back and a crude weapon in your hand. After all, the very notion of man versus nature is imbued in our collective consciousness—it’s always been at the forefront of what it means to be alive. But why are these trips gaining popularity now? Why would anyone—especially someone with the weight of a startup on his back—choose to go? 

Perhaps, the answer lies in the immediacy of our tech-driven society. With the touch of an app, we can hail a ride to any destination at any time. The yearn to purchase luxury clothing has been quelled by platforms that allow us to rent anything we could possibly want to wear at a fraction of the retail price. Between Instagram, Netflix, and Hulu, there is enough content to entertain us until the end of time. 

These three executives traded an all-inclusive resort for spearfishing for their food on desert islands, learn why they did it below.

Tech has undoubtedly made every experience more accessible—however, it may be this accessibility that strips us of the things that truly sustain us: the challenges we face that allow us to learn and grow, the bonds we build with others through our collective efforts to survive, and the unadulterated experience of being alone in the midst of a savage expanse. Maybe, our society’s game has gotten a little too easy.  

Whatever the reason may be, there is something about returning to nature and conquering the physical universe that is increasingly compelling. However, I wanted to know what underlies that compulsion. What really urges someone to extend himself beyond the limits of civilization? What would drive an individual to leave his daily life and face the ultimate challenge of existence? 

In pursuit of an adventure

“We went to a small island in the Marshall Islands called Jabonwod,” says Eric Rea, CEO of Podium. “It is on a lagoon that had fish you can eat as well as crabs that you can hunt on the island. It really was a unique experience to be on a 20-acre island in the middle of the ocean.” 

He, some of his Podium team members, and former Senator Jeff Flake spent six days on the island. “We each took a hammock, machete, magnifying glass, a water desalinator pump, a spear for fishing, a satellite phone for emergencies, a basic first aid kit, and that was about it.” 

Mr. Flake has been, in addition to his trip with Mr. Rea, on three of these excursions throughout his life. He credits his draw to survivor trips to his inherent and deep love for adventure. “As a kid, I loved reading adventure [stories], especially sailing adventures gone bad—that was my favorite genre,” he says. “I always wondered, if I were marooned on a deserted island, could I survive with minimal tools? 

“Finally, after years and years of talking about it, my wife said: ‘Why don’t you get it over with if this is your midlife crisis? Maroon yourself already!’ So, ten years ago, that’s what I did… It was an incredible experience. I did that for a full week, seven days, seven nights [by myself with] no food, no water, [and] minimal tools—just a pole spear and a magnifying glass to start fires.” 

In pursuit of a more difficult existence

Joe Staples, CMO at Motivosity, went on a survival trip in March of this year with both Mr. Smith and Alan Matheson, director at the Point of the Mountain State Land Authority. When I asked Mr. Staples why he would choose to go on such an extreme journey, he explains, “For me, the real motivation was… [to] come outside of your element… the exciting thing was to try something hard.” 

Mr. Staples went on to describe his trip in detail, saying that the group went together on “the equivalent of a rowboat with a sail” through the hundreds of islands and thousands of cays that make up the Bahamian archipelago—the majority of which are uninhabited. “We brought no food,” he says. “Our plan was to spearfish for the food we would need. Spearfishing is interesting, and there are not a lot of options to practice it. We were not sure how successful we would be.” 

On Mr. Rea and Mr. Flake’s trip, fishing was hit or miss. “On the first day we got there, Jeff was able to spear a 40-pound grouper,” says Mr. Rea. “We were all thinking that this might not be so difficult after all. Then we then went the rest of the trip unable to hunt anything near as large or great tasting.”

Mr. Staples’ group came up against the same dilemma, they were able to catch seven fish but all within the first two and a half days. They weren’t able to catch any fish the last one and a half days, which was when hunger set in. “Talk about having to adapt,” Mr. Staples said. The group subsisted off of coconuts they’d previously collected from another island—one of which poisoned Mr. Smith with salmonella. To combat his hunger, Mr. Matheson opted to eat termites from a nest he’d discovered. 

But for Mr. Staples, it was these very circumstances that pushed him to embark on a survival trip in the first place: “I like challenges. I like things that push me to certain limits. I like things where I don’t really know the answers going in and I have to go figure them out.” 

In pursuit of meaning

There is something that philosopher, Joseph Campbell calls “the experience of being alive” that has always fascinated me. But being able to truly live that experience feels heartbreakingly elusive because it’s often buried between the responsibilities and distractions of our everyday lives. However, Stephan Jacob, COO and cofounder at Cotopaxi, explains that the survival trips he’s been on have helped him “[generate] an appreciation for how amazing life is,” bringing him back to the essence of what it means to be a human being. 

These three executives traded an all-inclusive resort for spearfishing for their food on desert islands, learn why they did it below.

On one of Mr. Jacob’s trips, he, Mr. Smith, and six other entrepreneurs spent 100 hours on a deserted coast of Mexico’s Yucatan Peninsula. They built a shelter on the beach from whatever materials they could collect, and they used palm fronds to grill the fish they caught over a fire started without the help of any matches. 

When I asked Mr. Smith about his adventure in Mexico he says: “It turns out, when you are a hunter-gatherer, your whole day is spent preparing the meal or cleaning up the last meal and then going out and doing it again. There’s not a lot of free time. All you’re doing is figuring out shelter, figuring out food, and that’s it.” That pinpointed focus is something that allowed Mr. Smith to be incredibly grounded throughout his trip—save for one thing. 

“When you strip down your existence to what you really need, and obviously from a nutrition perspective, we need so much less than what we put into our bodies, that to me is always a cathartic experience,” says Mr. Jacob. “Let’s reduce things to what’s truly necessary to sustain life. And realize how much of the things we have access to and take for granted on a daily basis are really superfluous and not necessary… that simplification of life leaves a mark.”

In pursuit of community

“In the end,” says Mr. Staples, “If you think about why you do this, why you sign up to do these things, doing them with people that you’re close to, that’s a big part of the attraction to this. All three of us had individual challenges that we faced, and being able to rely on the other two to look after you and make sure you didn’t die—there’s a lot of confidence there.” 

Mr. Staples was not the only individual whose bonds were strengthened with those he went on his journey with. Mr. Jacob explains that “because you’re stripping away phones, you’re stripping away any type of distraction,” you find that, “[with] the people that you do these trips with, you have these intense moments of togetherness where you’re just genuinely focused on each other.” That very sense of togetherness may be what makes these adventures so appealing.  

These three executives traded an all-inclusive resort for spearfishing for their food on desert islands, learn why they did it below.

Mr. Rea’s group also grew closer together through working together. “Jeff and Brad were great fishing in the water. Josh was the tool creator. Dennis and I hunted for coconuts and crabs. JT was making sure everyone was healthy. It all happened so naturally,” he says. “The takeaway for me was when you are forced to eliminate all distractions and focus on the basic needs of survival— food, shelter, protection, etc.—things become very clear.”

“One thing that I’ve realized on these trips is that nothing ever goes right the whole time,” says Mr. Smith. “This is not what we’ve planned; this is not fun. Those things bring you closer together and you find that you really rely on each other. It’s a team effort. You can go do something hard together.”

In pursuit of a better world

Both Mr. Smith and Mr. Jacob encountered a tragic reality on the desolate shoreline of their chosen destination: piles of plastic littered almost every inch of the sand. Mr. Smith recalls “toothbrushes, flip flops, doggie toys, plastic bottles, and caps” while Mr. Jacob notes “an Aunt Jemima syrup bottle” among the debris. “Having experienced that and seeing that really made us, as a company and [as individuals], be responsible [about] what we do to this planet,” Mr. Jacob explains. 

What’s interesting is that it may have been this very nascent sense of responsibility—not yet fully awakened until witnessing the sight of the plastic on the beach—that enticed Mr. Jacob to undergo a survivalist experience in the first place. “You can get that [feeling of being off the grid] in other ways: yoga retreats, other retreats where you don’t speak, things like that,” Mr. Jacob explains. “But [survival trips create] this feeling of complete self-sustenance where you let go of all the comforts of modern life that we automatically get accustomed to.”

Mr. Rea also came away with Utopian visions. “In about 80 years, if things continue as they are now, the island we stayed on will no longer exist,” he says. “The entire island chain will be underwater. We are a growing, but still small software company in Lehi, Utah. We understand that our impact on something as large as global warming is limited, but we wanted to do our part to raise visibility to that issue.”

In pursuit of risk

One thing is definitely clear when I speak to each of these individuals: they’re all risk-takers. In business and in life. 

“If you look at an entrepreneur who steps out into the dark with, ‘Okay, I don’t have any money and I have a house payment to make, but I’m going to start this business,’ that’s pretty scary stuff,” says Mr. Staples. “Contrast that with people who, at the top of their career are looking for something that’s safe. I think those are two very different types of personalities.” 

“It’s not only founder/CEOs,” Mr. Smith adds. “Joe, for example, is a CMO, but he is very entrepreneurial. He left a big, big company to go join as one of the first 10 people at a startup. He has a willingness and tolerance for risk that’s unique. ‘Entrepreneur’ doesn’t necessarily mean founder/CEO; it just means someone that’s entrepreneurially-minded.” 

Perhaps the basic reason underlying the rise in popularity of these survivalist expeditions has more to do with our society’s fascination with entrepreneurialism than anything else. As individual citizens become increasingly inspired by the opportunity to change our cultural landscape through the latest innovation, it seems that risk-taking is becoming more and more a part of our everyday existence. Perhaps survival trips are just one way that collective thirst for risk-taking can be quenched.  

There is so much to survival: the potential to do more than we’ve ever thought physically possible, the promise of real and immutable human connection, and the ability to experience everything that life has to offer are only some of the reasons that people choose to get lost in the wild. So, if you find yourself called to go off on one of these journeys, do it. Dare yourself to go outside the bounds of everything you’ve ever known. 

The wild world is waiting.

These three executives traded an all-inclusive resort for spearfishing for their food on desert islands, learn why they did it below.