Harley Finkelstein, Chief Platform Officer of Canada’s tech darling Shopify, took on a second job this year as a judge on CBC’s Next Gen Den, the web-only version of the hit show Dragon’s Den, featuring younger entrepreneurs and riskier deals. Canadian Business talked with Finkelstein about his experience judging business pitches on the show, the best pointers about how to pitch a business idea, and how to get him to make a deal.

You already had more more than enough to do at Shopify. Why go on Next Gen Den?

A couple of things. First and foremost, the values that Shopify exemplifies is all about the idea of entrepreneurship and creating as many entrepreneurs as possible. We do it with our Build a Businesscompetition and creating software that allows anyone to create their own company. I felt that helping entrepreneurs through Dragon’s Den is just a great extension of what we are already doing.

Secondly, and most importantly, is that there are still people out there who view entrepreneurship as this very scary, intimidating thing. If you go back a decade ago, even the term entrepreneur is a dirty word. People wanted to become professionals and not entrepreneurs. I personally believe that entrepreneurship is this wonderful thing that allows anyone with a passion and product to do something with that, and get that product into the hands of people around the world. And I thought that by going on the show, which gets a lot of publicity, I might be able to inspire a new cohort of entrepreneurs and reduce some of the anxiety and risk-aversion that most people have about starting their own company.

Next Gen Den is sort of the perfect venue for a lot of this. It’s all about the creation of entrepreneurs that are under the age of 40, just getting started, looking to raise up to $100,000. It has the opportunity to make entrepreneurship seem far more accessible. That’s really what I care most about.

What’s your favourite pitch so far?

Only six episodes have been aired from the second season, and there’s quite a few more coming, but PopRxis my favourite so far. Here are two entrepreneurs who were constantly looking at their industry. The pharmaceutical industry is very traditional; there hasn’t been much innovation there. We have two young entrepreneurs, one of them is a doctor with a lot of experience in the industry, who looked at the way that prescriptions are being delivered and decided that there must be a better way. PopRx is a company that is trying to change the idea of prescription delivery. This is not only good business, but it also has incredible implications for those that may need prescriptions but may have accessibility issues to go out there and get them. I just think it’s an incredible idea. It’s my favourite one so far, and I’m excited to invest in the company.

Can you give entrepreneurs a few tips on pitching on the show?

Something that’s really important is to tell us your story. Explain to us why you have this idea: why do you want to start this company? What was the catalyst? What was that spark? A lot of the entrepreneurs just very quickly get into their pitch and what they are doing and how they are doing it, but they don’t talk about thewhy. And I think the why is so important. I, as a Dragon, am investing in people, not companies. I’m backing entrepreneurs, not their businesses. Their business may change 150 different times. In a pivot, they may decide to go a different direction. All that stuff is the normal course of action when it comes to building a company. But what is fascinating is that when they tell us their motivation behind it, that’s what gets me really excited because now I understand their story. So going back to Wove and Grain, the apron company, I didn’t invest in that company for a number of reasons, but I loved this entrepreneur because he took something that was so blatantly broken and made it better. That’s what entrepreneurs are.

How can entrepreneurs get you on their side?

Certainly doing your homework is really important. Understanding the type of things I’m into helps. For example, on the Wove and Grain pitch, the entrepreneur knew that my wife is a psychotherapist but also a food blogger on the side. As a part of his pitch, he referenced the fact that my wife, as a food blogger, may also cook quite a bit. This way, he made it personal for me. Doing some research in advance shows that they really cared and they’ve invested time to make sure their pitch is as strong as possible. Having a ton of conviction is also very important. Not every deal is going to get done, but I want to see an entrepreneur who has conviction. If Dragons are asking tough questions, I want to see that the entrepreneur has the right answers. And even if the answers aren’t exactly what I want to hear, I want to see that they are showing a lot of hustle and a lot of grit. That they truly believe in what they’re doing. I think that’s incredibly important.

What would you say is your unique style as a judge that sets you apart from Nicole and Michael?

I’m sort of the entrepreneur’s entrepreneur. In the past episode I called Michael “mean,” because I thought he was being a little bit rough on the entrepreneur. I’ve been an entrepreneur since I was 13 years old. I started a DJ company, later on I started couple of T-shirt businesses, so I’ve been an entrepreneur for most of my life. And I think I have a lot of empathy for what entrepreneurship is all about, having come from the trenches of entrepreneurship. I don’t know what my “personal brand” is, but I love entrepreneurship. It’s not only my job, but also my hobby and what I think about. My father and grandfather were both entrepreneurs. And because of that, even if I don’t invest in their company, I want them to leave the show with some insight or some perspective, and hopefully additional motivation to keep going. Because some of these people may come to me a year later and send me a tweet and say “Hey, I think your advice helped, and here’s how the company’s doing,” and I may actually subsequently invest in that company. But I want to see grit.

Do you think you’ll find the next Shopify on the show?

I sure hope so. It’d be wonderful to do that. These sort of shows didn’t exist in the early days of Shopify, so that wasn’t an option for us. But I can tell you that I’m on the look out for the next great Canadian entrepreneur and the next great company. Dragon’s Den just provides me with this wonderful platform which I can get a really great bird’s eye perspective on what entrepreneurs are building across Canada. I’m lucky that CBC asked me to be on the show. I’m having a great time with it.