Tom Benson is the CEO of Wildplay, a company that provides adventure and team-building environments for adults and children alike. The focus of many of the outdoor-based stations is for adventurers to face their fears. Benson knows business people face similar fears. He has experienced panic from a personal as well as an entrepreneurial lens. He speaks of how risk is his “Primal Passion” frequently, an element he faces both as  a businessman and an outdoor adventurer. 

Tom Benson, CEO of Wildplay. Image courtesy of LinkedIn

“‘Primal passion’ refers to that gut feeling when you’re frightened or faced with something that is uncomfortable,” Benson says. “Our passion, in that mix, is to help folks move beyond that, do the thing that they are uncomfortable with, and see what that unlocks for their future.”

“The primary focus of our company is to help folks overcome fear.”

When it comes to overcoming gut fear, Benson knows how it feels to take the leap, whether it’s bungy jumping, or leaping into a new venture. His advice to people considering a starting their own company, or owning a franchise should be aware of their limitations, and not be afraid to fail.

“I think if you aren’t able to be okay with failure, don’t do it. I really believe a lot of entrepreneurship is about failing forward, and folks that are looking for the sure-fire bet without failure are probably going to be disappointed.

“I think the key is to able to learn from mistakes, or those failures, and turn those outcomes into a success. So, if you’re sitting there, and thinking ‘oh, I want to be an entrepreneur,’ I think you need to go for it for the right reasons. If you see something where you can make a difference in your life, or in society, but thinking that you’re your own boss, or are about ease, are probably a mistake.”

Neither Wildplay nor Benson believe in taking the easy way out. For those who want to zipline across a gorge, going through the terrain on foot is not an adventure, nor will it give you the same experience. Benson explains how entrepreneurs make the mistake of romanticizing business ownership:

“I don’t think entrepreneurship is easy, and sometimes, folks look at it through a lens of, ‘oh, I’ll be able to be my own boss,’ and ‘I’ll be able to make my own hours,’ ‘I’ll get to decide when I get to go on vacation, when I’ll work and what I’m going to work on…

“The reality is, the endeavour drives you a little more than you might imagine. So I think it’s important to do it for the right reasons.”

Benson makes an analogy to between high-risk sports and business: Children are more likely to get more out of playing without considering the risks than an adult, as adults (and most business owners) tend to overthink the process.

Bungy jumper image courtesy of Wildplay

“Bungy jumping really is a sphincter-tightening experience. It is very exhilarating, it creates quite a bit of fear in folks. I’ve done a lot of high risk activities, and I avoided bungy jumping like the plague, until my 50th birthday, actually. Even though we had this business, it made no sense to me to jump off a perfectly good bridge, when I spent my whole life trying to stay on things, and to stay in control of things. I kind of missed the point, about the bungy jump.

The whole process is really about releasing yourself into a thing that is kind of out of your control.  There’s not much you can do once you leave that bridge: It’s all going to be what it’s going to be.

“However, if you take that, peel the layers and go backwards to decisions about moving forward in entrepreneurial endeavors, there’s real risk, and perceived risk. In bungy jumping, in a professional operation, the real risk is minimal to almost non-existent as long as everyone does what they’re supposed to do, which is generally the case.

“We’ve done hundreds of thousands of jumps without incident. Things should go without a hitch. But, when you’re standing at the edge of that platform, thinking that you’re going to jump off, it’s not the real risk that’s in your mind, i.e., it’s not ‘yes, it’s perfectly safe, and all these people have done it all before you,’ everything that’s primal about you is saying, ‘you’re at risk.’ That’s just perceived risk.”

As Benson is careful to run an enterprise whose main concern is safety, he also believes that risk must be tempered with caution. Research and gauging your environment before taking the leap applies to both adventure sports and business. He cautions people to recognize the difference between actual risk and perceived risk, then overcome a false perception as a fear to conquer.

“If you just do it blindly, that’s just as foolish as anything else. You need to consider it. You need to identify what the real risk is to decide to do it or not.”

“I think there’s a parallel to [bungy-jumping] and being an entrepreneur, that we could learn from in that process. ‘What is the real risk in this thing that I’m gonna do? What is the perceived risk?’ I think a lot of people going into entrepreneurship are presented with everyone else’s sense of perceived risk. ‘Oh, my god, you’re crazy, here’s why…’ and you’ll hear all the stories of why you shouldn’t do something.”

Benson advises bungy-jumpers and new entrepreneurs alike to to “carefully evaluate what’s going to happen,” ask themselves what would be the most likely outcome, and have the jumpers or entrepreneurs ask themselves what they are going to do about it.

“With that kind of mindset, you have a better chance of being a good risk manager in the business of being an entrepreneur.”

Benson thinks that we tend to become more conservative for a variety of reasons. He speaks of creating a more positive inner dialogue when fear comes creeping in during a decision making process. He calls the negative dialogue, “stories” that we tell ourselves, and he suggests entrepreneurs and extreme sports enthusiasts check literal and proverbial safety lines before taking the leap.

“Adults are generally more concerned about their mortality, about being hurt, everything that comes out of a little indiscretion, ‘well, I hurt my ankle so I can’t go to work.’‘I’m afraid of heights.’

“No, you’re not afraid of heights, you’re afraid of falling. If you have something that’s preventing you from falling, why are you still afraid? We start to tell ourselves stories.”

“We tell ourselves stories that end very easily. We get scared very easily. The other thing that happens with adults is that if we considered curiosity as a muscle, that muscle gets weak as we get older. Play, and exploration like that is really about curiosity. “What will happen if I do this? How will this be…?

“I don’t think that changes much as we get older, we just drop the curiosity, we don’t reach out to learn and play. When you meet people that are going out there doing adventurous stuff, you’re struck by their sense of curiosity. Entrepreneurs are often very adventurous and very curious.”

Naturally, we asked Benson what his greatest fear was when he was about to take that proverbial leap. What were some of the risks he evaluated before starting Wildplay?

“Here we are, ten years into this thing, and had you asked me that question in Year One, I probably would have identified the risk of it being kind of a fad, that it didn’t have legs, it wouldn’t last. But, I think in reality, the biggest risk that we faced was twofold: It would be capitalization; having the amount of money you need to grow match your growth plans. That’s a massive risk, and if you’re out of sync when you’re growing quickly, you’re constantly under stress as an organization.

Both Benson and his business partner, Gordon Ross, shoulder the concerns of a business based on high risk activities, as well as dealing with the challenge of looking for support when they are the groundbreakers in their field.

“It’s not like you can look around in our industry and go, “hey, what is the model for that?” In a lot of ways, we are the model. When you’re breaking ground like that, you feel a little bit alone sometimes, it’s not like there’s a playbook. And it’s a risk, not having the rest of the industry to compare to. Now, that’s changed a bunch, there’s a lot more people in the industry out there, and I think that part is dissipated.”  

Finding good information and training for unconventional companies can be a challenge. Benson adds that getting advice from a peer can go a long way towards easing some perceived risks, and once a new start-up has a chance to connect with experts, it can ease the primal fear of jumping right in.

Tom Benson, image courtesy of Greater Victoria Chamber of Commerce website

“I belong to an organization called Entrepreneurs Organization…and that organization is one where I have a peer group that I meet and I can walk through any difficulties that I have with my forum. That’s a group that I meet with on a monthly basis, and it’s probably one of the best support mechanisms that I’ve had.

“I also have an incredibly supportive wife, she’s way better at business than I am. I can go to her and say, ‘oof, I think I’m out of my field here, and what do you think?’” Benson laughs, “she’ll say, ‘yes, you are,’ or, ‘no, you’re not.’ I think I’ve got a good care group, and that’s been great.”

”Surround yourself with peers that you can go to for specific expertise. Surround yourself with peers that are not going to tell you ‘yes,’ just because they love you. They should give you good, objective feedback.”

“I think having that network around you, the people I’ve seen who’ve done that are more successful. It’s a key part of their success, that they’ve not been afraid to surround themselves without ego, with people that could give them good advice, that they could capitalize on that and vault their businesses forward.”