
What you get when you put a Master’s Degree in Entrepreneurship, a Diploma in Commercial Skydiving and a Certificate in Adventure Leadership together?
No idea? Neither did I until I spoke with Ben Calder; a Queenstown based entrepreneur, co-founder and CEO of Wherewolf, a company specialising in digital registrations and operational software for the tourism industry.
Calder holds this awesome medley of qualifications which have helped him in building and selling two successful ventures already, and to lead his latest venture as they look to revolutionise the way that adventure tourism companies operate.
His unique background and success make Calder an interesting and knowledgeable individual to discuss entrepreneurship with. Over the hour long interview, we discussed more about his latest venture Wherewolf, his experiences through the businesses heβs run, and some of the insights into entrepreneurship heβs garnered through 10 years in the game.
We started by deep diving a little more into what Wherewolf does, a company gaining solid traction in the adventure tourism market.
βWe create branded arrival apps that replace the traditional paper waivers for adventure tourism operatorsβ, he said. βHowever, our real specialty comes in our work on the business operations side. Weβve built a suite of products that can manage a whole host of tasks – such as equipment allocation, assigning staff and allocating people onto loads of jobs – that were previously managed by the βfor office use onlyβ section at the bottom of liability waivers or registration forms. The third part of the business is a tool which collates all the marketing data from the business, manages follow up emails to customers, and provides the insights that enable a business to grow.β

I continued asking questions around Wherewolf, interested to hear the story of how this unique company came to be.
βIt really got started from a desire to grow my own business. At the time I was working with Wulf Solter (the future co-founder of Wherewolf) on a web-app to gather the customer data at check in for Big Night Out.β It was this app that helped Big Night Out grow to be the second biggest Facebook page in New Zealand tourism, and Calder pretty quickly recognised the importance of word of mouth, and customer ratings and referrals, all things that they were able to influence with the app.
βI felt as though this app could be marketed and sold to businesses by itself and so we added a few more features to the app and began to sell it to local adventure tourism businesses.β
βThe interesting thing about Wherewolf was that it grew from client desire,β Ben says. βWe would sell it to a client with a few features not quite right, so weβd build those features into the product for them. We eventually reached a point where we had this wonderful suite of tools that served the majority of our target market. This allowed us to start speeding up the development time because a lot of the tools were already there for the businesses to use; whether it be trip manifesting, staff allocation or equipment manifests.β
As mentioned earlier, Calder has an interesting batch of experience, including some very unique qualifications, that have helped get him to where he is now. I asked him to elaborate on some of his experiences and what the some of the biggest learnings that came from it were.
βAs far as previous work experience, I was a youth development facilitator, an outdoor instructor and a freefall photographer for skydiving companiesβ; experience which clearly taught Calder a lot about the adventure tourism industry. In business, Calder has already built and sold two companies in his 10 years as an entrepreneur; Big Night Out and Vinyl Underground, a bar in Queenstown.
βI learnt an enormous amount from building these two businesses and it would be impossible to write it all down in one short summary,β Calder says contemplatively, βbut if I was to have to pick one learning it would be the ability to choose the right response. To have the ability to pause and think about which decision is going to put you in the best position; to negotiate, to retain respect, and to leave yourself with further options. Itβs everything from the conversations you have on Vodafone customer support calls, to negotiating with CEOβs and Angel investors. If you are able to slow down and choose your response, youβll end up in much better positions.β

On the topic of decisions, I asked what some of the hardest calls Calder had been forced to make were, and what gave him the strength to make these calls. For him it turned out it was actually quite straightforward. He said that, βall decisions are made out of necessity; itβs a sink or swim situation and you have to make these calls to stay alive. Itβs never easy to lay off workers, or put people on performance plans, but these decisions need to be made. For me,β Calder said βthe hardest call to make is starting in the first place. Am I going to commit the next βxβ many years to making this work?β
This answer really resonated with me; business decisions are much easier to justify with facts and figures, things that people can understand and reconcile. Itβs a lot harder to justify decisions that are made with some element of gut instinct, like starting a business so often is.
I was curious what motivated Calder to become an entrepreneur.
βAny entrepreneur knows youβre the last to get paid, and the first to extend the mortgage, or throw in savings to keep things going at times so itβs never just about the money. For itβs mainly the pursuit; a landscape gardener or builder could start with an empty canvas and create something, and for me business is very much the same. Thatβs why I love being an entrepreneur. Provided I can enjoy myself along the way, thatβs what has always motivated me as an entrepreneur.β
What did he believe separated a successful entrepreneur from an unsuccessful one? In answer, Calder shared a quote that his mother had sent him once.
βTough times donβt last, tough people do.β He continued; βResilience; try and try again until you find the formula that works. Yes, there has got to be a level of intelligence to that – not pursuing a failing idea and learning from those in front of you – but you will encounter your own problems that you have to overcome, and hence that quote always rings to me. Itβs the people that donβt listen to the bank manager or accountant who tells you to cut your losses and run. Youβre always a week away from collapse, youβve just got to push on and find a solution.β
Being an entrepreneur can often be a lonely game, I asked, what keeps you motivated when times are tough?
βIβve had companies as a sole director and as a team and I can tell you that I will always involve others in future ventures for this exact reason. If youβre in the same boat you can both paddle together. If youβre by yourself you either sink or swim. Youβve got no one that actually understand the consequences. Sure, you can talk to friends or mentors but they donβt have skin in the game, so their advice is taken with a grain of salt. Having a business partner is like having a gym buddy. If you go to the gym with a buddy the results are way different. You push each other along, give each other encouragement and you get each other through. Itβs the same in business.β

Calder and I continuing discussing the traits of good entrepreneurs, and it was clear to me that humility was one of his strong suits. He mentioned multiple times that he knows wholeheartedly that he will be βcrap at things, and thatβs okay.β This allows Calder to understand his weaknesses and mitigate those by building a strong team around him, the key to any successful business. Calder quoted Steve Jobs by saying, ββWe hire smart people, not to tell them what to do but so that they can tell us what to doββ, a quote that he seems to abide by in his own companies.
Furthermore, Calder says βIβve always maintained the ability to take on board and implement feedback. With that comes a certain amount of sifting and sorting, as not everyoneβs advice is gospel. I pick the gems from peopleβs feedback, but most importantly, I implement it. You can nod your head all you like but unless you actually put some of the suggestions into practice, then youβre not going to see the fruits from their seeds.β
βAt first ideas might not sound all that useful. But hold onto them, let them rattle around until they reveal themselves as the gems they truly can be sometimes. Keep listening. It might be the third or fourth time that someone suggests something to you realise the pearl of wisdom itβs been all along.β
On the subject of pearls of wisdom, I asked Calder for a couple of his before the conversation ended. I first asked him what he would tell his 20 year old self with the benefit of hindsight, and to me, Calder gave a great response.
βIβm not one for regret so Iβd say Iβd do it all the same; but remember your health along the way. Often that let me down. You get up early to go to the office and get those emails away and you forgo going to the gym. I certainly canβt complain at the speed Iβve tracked through a few things, but if I was to do it again I would always remember my health along the way.
To close I asked him for the one daily habit that he believe all entrepreneurs should adopt.
βObviously Iβve been one for quotes, so here is another one my brother passed onto me that I love; βThe difference between a millionaire and a billionaire is that a billionaire checks their goals twice a dayβ. I really really love that. Each day must have purpose. Thereβs always things to do, but are the things youβre doing getting you closer to your goal? If at the end of each day theyβre not, then you know youβre just busy being busy.β
You canβt argue with what Calder has achieved in his relatively short entrepreneurial career to date. In roughly 10 years heβs built and sold two businesses already, and is well on the way to turning his third into a roaring success.
Calder is patient, reflective and purposeful, and proves to me that wisdom does not just come with age. Combine this with his energy and enthusiasm for business and you realise that there are still a lot of exciting things to come from this #nzentrepreneur.β¦
[Editors Note: Wherewolf secured $NZD550k in angel funding earlier this year from Flying Kiwi Angels, part of which is earmarked for expansion into the US.]