When I was about 14 one of my best friends and I delivered newspapers over the summer and learned about starting and running a business, and how to make a profit. As we built out the business we started testing out other related services—anything. We picked up garbage, did pizza delivery, grocery shopping, anything we could think of to add more value for our customers. We actually ended up starting our own newspaper called the Lake of the Woods Post, a community-type flyer that was inserted into the Winnipeg Free Press, Globe and Mail and the National Post, the three papers we delivered at the time. I remember going up and down to every single local business in Kenora selling advertising for our little publication. A friend of ours was going to be studying journalism in university, so we recruited her to write a weekly column. We included the weather, movie times, things going on about town. It was all very fun and we did well with that. We also had ambitious plans to build out an app—perhaps we got a bit ahead of ourselves! But those were the terms we were thinking in. I had a wonderful time with it, and I learned that if you go out on your own, thoughtfully with a plan, there’s a lot more opportunity to create for yourself than if you just accept the jobs that are out there for you. Back then, the alternative for me was doing what everybody else was doing, which was bagging groceries or pumping gas at the gas station. Neither of those seemed like very much fun, so that’s when I got thinking that I wanted to start something. At a young age, I started thinking in terms of, when you see a need or something that’s not being met, it’s not about saying, “Somebody else will do that,” it’s about thinking to yourself that maybe it’s something you can do—if you’re feeling this need then presumably other people are too and there could be a market there.

As you went through this process of running a successful business and becoming a young entrepreneur, what was the drive that kept you going to overcome challenges and keep heading toward your goal? I just enjoyed the challenge of it. Financially it was rewarding but when you’re that age you don’t really spend that much money, so that was just a by-product. It was more just the fun of figuring things out. We would have our newspapers brought in to Kenora from Winnipeg every morning on the 5 a.m. Greyhound bus. I remember one year Greyhound cut that 5 a.m. service, which would mean our papers would come a day late, which wasn’t acceptable for us: it would be bad service for our customers. We called everyone we could think of to figure out a solution and ended up finding a pharmacy that had their medicine delivered every morning from Winnipeg to Kenora, so we offered them money to take our newspapers. That was a great solution, we got our newspapers to our customers the day of and none were any the wiser of what it took to get them the paper. That was fun, but I remember it taking hours and hours, so many phone calls, to find that solution. But we took a lot of pride in solving that problem. I’ve had the privilege of spending time with Sir Richard Branson, who is one of my biggest mentors and I know is a great friend of WE. And what he said is that business should be fun. And it is—if your customers are happy, your employees are happy and you’re making money. What’s not to smile about?

You mentioned the mindset around entrepreneurship in Canada being different from what you’re setting out to do. What are your thoughts on the landscape of social entrepreneurship in Canada? I think there’s a great need for what we’re trying to do here, which is why it’s so exciting. When [former Liberal cabinet minister] John Manley spoke about the WE Social Entrepreneurship Centre, he touched on a lot of these things as well. On the most basic level, I really think we need to be doing more to encourage general entrepreneurship across the spectrum among our young people to just start things. In my experience, that’s not a skill set or mentality that’s taught in schools: in fact it’s the opposite. It’s a very passive attitude that I don’t think serves our country or anybody well, so it’s a powerful thing when you can get that mind shift into young people that they can start something just as easily as anybody else—why not you? I remember there was an award I won in high school, the Albert D. Cohen Entrepreneurial Scholarship. I was thrilled to have won it, but I also don’t know how much competition I really had. From what I’ve experienced, young people just don’t have that mindset to take initiative—and it’s not their fault, there’s just nothing out there to encourage them. It’s not present in the public school system and there aren’t many organizations out there that would be natural for them to turn to. That’s why I thought WE would be perfectly positioned to do so. They’re already engaging with youth in so many ways. In terms of social entrepreneurship, I think that’s where we’re into some really interesting, exciting territory. It’s the future. When I first talked to Craig and told him what I wanted to do with this project, I talked about how the line between business and nonprofit is coming closer and closer together in that businesses are operating much more socially than they ever have. As well, nonprofits are running themselves like businesses, in the sense that they have stakeholders to be accountable for, they have transparency in how they manage their money and they deliver results. I think the congruence between the two is very exciting. I told Craig that he and Marc should be considered among the top entrepreneurs to come out of Canada in the last 20 years, because to start something like WE is truly a feat—WE has operations in multiple countries, hundreds of employees and manages a lot of money, which is all business and no different to running a company. To me, the skills to start a non-profit, versus a traditional business, versus a social enterprise, it’s all the same—the outputs may be slightly different, but at the end of the day it goes back to what I was saying before. I think we’ll be really amazed at what young people can do if you just give them the tools to do so and be in the driver’s seat to solve problems—giving them that mindset to take action. It’s basic financial literacy, how to market yourself and what you need to do to get going in terms of simple incorporation, starting an entity and hiring people. I was fortunate to have someone like my dad at the dinner table to help me with all these concepts I was coming across, and to give me some coaching on how to start a small business. Simple things like, “If a newspaper costs you this much then, after your variable costs, overhead, labour, etc, you have to sell it for that much to make ‘X’ profit.” It’s concepts that aren’t hard to grasp, but someone has to teach young people about them for them to be able to go out and use them. Because my dad is experienced in business, he could give me the basic skills I needed to get going. The same skills that it took to start a small paper route are ones I deal with every single day in running a multinational business—margins, routes to market, effective marketing and managing a P&L—all the same in essence, just on a larger scale. I think WE is perfectly equipped to get young people thinking in a different way and to give them these skills that they need.

If the viewpoint is that jobs are just going to create themselves and problems are going to solve themselves, we’re in big trouble. From a Canadian viewpoint and from a generational viewpoint, we need to be continually innovating, creating new industries and new solutions.

When you traveled to Kenya with WE in 2017, you and Craig took a morning walk together where you shared thoughts about what it would mean for you to not only build a legacy, but to curate a really meaningful philanthropic journey as part of your life goals. Can you tell me more about this, and how it led to making a landmark gift in support of the WE Social Entrepreneurship Centre? When I made the decision six years ago to pursue an entrepreneurial opportunity and turn down a Bay Street law job, I didn’t know how it was going to work out. It ended up working out very well and I knew I had an opportunity that not many under 30s have. I felt very fortunate, but I also felt that what put me in that position was all things we’re talking about: my entrepreneurial experience as a kid. Well before we sold the company, I had thought about how I wanted to give back in the form of helping more young people become entrepreneurs. When I travelled to Kenya in August 2017, we were in the process of closing the sale of the company and I was still mulling it over and thinking through how I would do this. It kept occurring to me that WE is the perfect organization to do this with—it’s engaging with young people and it in itself is so entrepreneurial in how Craig and Marc have created it and continue to reinvent it. So on that trip to Kenya, I told Craig I wanted to go on a walk with him. We met at seven in the morning, got our coffee and went for a walk, where I said to him, “I want to talk to you about something I’ve been thinking about and it’s very timely given the sale of the company. And I’m in the position to stand behind this idea in a very meaningful way if you think it’s something that WE can do.” I told him about my ideas, my experiences as a young person, how I thought WE was the perfect organization to help fill this need. I could tell right away he was all over it—at the time Craig was just finishing writing the book WEConomy with Holly Branson and Marc, which mirrored a lot of the things I was talking about. It was very clear that it clicked with him. I was really hoping that Craig would be receptive to the idea, and not only was he receptive, he was incredibly enthusiastic and really took the ball and ran with it in ways I could never have imagined. I’m just so impressed with him and the whole WE organization for going full speed and putting a ton of resources behind launching the WE Social Entrepreneurship Centre. I’ve been absolutely blown away, and on that walk I had a tingling feeling that we had just started something special.

I really do believe it’s going to continue to evolve and we’ll be pleasantly surprised with the outcomes we get and the kind of young people we get through to the centre. I’m excited for the programming element and getting entrepreneurial education into the WE Schools program and igniting that movement. That will go toward changing the perception and mindset that I talked about earlier, in terms of getting people thinking, “If you see a problem, think about how to fix it.” I’m also very excited for the actual WE Social Entrepreneurship Centre building. It will be incredible to have a brick-and-mortar space for young people to really get their hands dirty and to have industry-leading professionals coming in, having other entrepreneurs to come give support and engage with them, and to really watch social enterprises grow right in front of us. To have a physical space where we can foster all that is, first of all, unlike anything else in the world, let alone in Canada, and right next to the WE Global Learning Center, which is a world-class building. I love walking through the doors of the WE Global Learning Center—I always have a smile on my face; it’s great energy. Just to imaging that for the new center is really exciting.

The first step is the hardest. If you can thoroughly analyze something and understand all the components of it, what you’re bringing to the market, how thought out your business plan is—if you’re fully confident on that, if you can get people around you that are confident as well, and get people that are willing to give you candid feedback and poke holes, and if after all that you still have something you believe in, then go for it and start it. That’s the first thing, to take that risk, because you don’t really know what you’ve got until you get going. The first step is the hardest because it’s outside of everybody’s comfort zone. There’s no safety net. There’s nothing to fall back on. It’s just you and your team. I think the most important thing is to just take the risk, and I think everything stems from that. It’s equally important to keep going and always be willing to adapt and adjust, but that first step is the hardest.