Canadian-born Steve Dubbeldam has been described as a “serial entrepreneur”, having begun multiple fashion collections and co-created an online magazine with his wife. His latest venture is Wilderness Collective, supplier of “Legendary Adventures for Men”. Learning, facing fears, and forming lasting memories and stories to tell for years to come are just a few of perks included a trip; higher testosterone, a wizened perspective and increased frequencies of philosophical musings are potential side affects.
We sat down with Steve to discuss his approach to adventure, what men stand to gain from the trips he arranges, and what went into starting a company built to satisfy man’s thirst for exploits.
Q. What’s one thing every man should know?
How to troubleshoot. So many broken things can be fixed and threatening situations resolved by the simple and practiced art of mentally slowing down, critically looking at what’s wrong and then forming a plan.
Q. What’s the hardest thing you’ve ever done?
My first instinct was to talk about a grueling hike in the Sierras to 12,000 feet, or when a friend and I sailed my $500 catamaran to the Channel Islands with only a drug store compass, but those are all too predictable.
I believe that there are much harder tests thrown at men in life than the mere physical. One of the hardest things I’ve ever done was rebuilding a 1975 Honda CB450 in my downtown LA loft. I had never rebuilt a motorcycle before and to find the problem I had to keep taking it further and further apart until I literally couldn’t take it apart any more. It was completely overwhelming to look at this giant mound of parts and realize I had just ruined my motorcycle. The only way I’d be able to finish was to just slow down and tackle it bit by bit. I couldn’t call my dad, my friends didn’t know what a torque wrench was and I didn’t have the cash to bring it in. At long last I ended up finding the issue, which was a $3 spring deep in the bowels of the engine. I replaced the spring and about a month later started the bike up and much to my surprise it worked perfectly. For me it was a huge lesson in mental perseverance, patience, and doing something I had no idea how to do.
Q. What are you working on right now?
Right now I’m planning the next 3 WC trips (Channel Islands, Mt. Baker, and Eastern Sierras) and producing Issue 4 of the women’s magazine my wife and I created called Darling.
I believe that there are much harder tests thrown at men in life than the mere physical.
Q. Name one thing you can’t live without.
My Leatherman. If I have that on any adventure I literally feel much more at ease.
Q: Who or what influences you?
My wife, my community of uber-entrepreneurial friends in LA, my father and my crazy grandfather who built a trimaran by hand out of airplane fuselages and sailed it from New York to Florida and back with his 7 kids.
Q. What are you reading right now?
A. The Last American Man
Q. Name one thing no one knows about you.
Q. It’s your last drink and meal on earth. What’ll it be?
A Sazerac and a steak dinner.
Q. If you could go back and tell your 16 year old self something, what would you say?
Try and execute 90 percent of the ideas that come into your head.
Q. How do you want to be remembered?
As a man who was kind, generous with my time, and who had the courage to pursue dreams that leave the world better.
Q. What is your ideal adventure — one you’ve not done yet?
I’m dying to ride dual sports along the continental divide as well as through Central America.
Q. Any advice on how to properly prepare for a trip?
You always pack too many clothes, not enough water and rarely enough quality tools. Also over-preparing sometimes takes the adventure out of an adventure.
Q. What should guys take away from an adventure?
A good adventure is an opportunity to learn, but you have to take it. If guys come on my trips and leave feeling like they’ve done a few things they didn’t think they could do, shared a few fears and feelings they never thought they would, and go back to their lives with a story to tell and a new hobby to bring balance to their life, then I’m more than happy.
Q. Why is it important for guys to get off the grid?
Herbert Simon said “A wealth of information creates a poverty of attention”. I craft these trips very intentionally to keep guys present in the moment. I don’t want guys to feel the urge to pull out their phone and capture every moment so they can upload it, I just want them to be in that moment and have enough mental space to actually take something away from it. And there’s nothing worse than being in the woods for two days, climbing a ridge and all the sudden getting cell service and a bunch of emails all pulling you back into the hustle. The whole “digital detox” rule has actually become a favorite part of the trip for the guys. Many try to leave their phones off for as long as they can after the trip.
Q. Were you an outgoing kid?
As a kid I was outgoing, then I got more and more shy for some reason, now I make big mental efforts to not just be outgoing but to be intentional when I meet people.
Q. What’s the worst experience you’ve had on a journey?
On the beta trip we lost two riders for about two hours due to some radio miscommunication. That was a bad experience for me as the leader, though those two said their wrong turn led to some of their favorite riding in the whole trip.
Q. Does anything make you uncomfortable?
Conflict, admitting I’m wrong, surfing in cold water, untangling hoses, and tackling things I have no idea how to do.
Q. Why did you start WC?
Being born and raised in Canada, I’ve always been very adventurous, but only after moving to LA nine years ago did I realize how much balance those adventures bring to my life. I can be hustling on five ventures at a time, but if I carve out time to be in nature with people, it always seems to give me the fuel to keep going. I saw an opportunity to create a brand that encourages and enables successful, ambitious and entrepreneurial men to reconnect with that original source of inspiration that got them to where they are. I have many friends who will never plan an adventure for themselves, but once they are out there they gain so much from the experience that it’s become an important rhythm of their lives now. Also, there’s an aesthetic and story quality that is lacking from many other adventure outfitters — and I’ve got a hunch that there’s plenty of guys out there who appreciate that.
Q. How is WC different than other travel outfits?
We work hard to build an environment that will not just be adventure for adventure’s sake, but a trip that gives opportunities to become a better man while having a legendary trip. Chances to face fears, engage in deep conversation and to grow closer as friends, brothers, fathers and sons. I’ve also got a lot of schemes for the future of WC. What people see now is just the tip of the iceberg.
Q. How much does your insurance company/legal team hate you?
I’ll just say that of the 50+ insurance companies my broker ran my policy by, only ONE was brave enough to insure me. That said, my current mortality rate is 0 percent, so I’m proud of that.
Wilderness Collective is constantly developing new adventures of every type for men who want to experience ultimate thrills — scaling mountains and sailing the high seas, to name a couple — and also for footwear enthusiasts who want to do the same. The winner of UGG Australia’s current sweepstakes on their Facebook page will win a spot on an upcoming Wilderness Collective adventure. If you’re not lucky enough to win a spot, you can always book one on your own. Spots are still open on current trips. wildernesscollective.com