How to Pitch Next Gen Den

Shopify's Harley Finkelstein is one of the judges on the youth-focused spinoff of Dragons' Den. What he's looking for

Written by Murad Hemmadi
Shopify Chief Product Officer and Next Gen Den judge Harley Finkelstein. Photo: CBC

Harley Finkelstein, Chief Platform Officer of Canada’s tech darlingShopify, took on a second job this year as a judge on CBC’sNext Gen Den, the web-only version of the hit showDragon’s Den, featuring younger entrepreneurs and riskier deals.

We talked withFinkelstein about his experience judging business pitches on the show, the best pointers abouthow to pitch a business idea, and how to get him to make a deal.

You already had more more than enough to do atShopify. Why go onNext 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 withourBuild a Business competition and creating software that allows anyone to create their own company. I felt that helping entrepreneurs throughDragon’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 sixepisodes have been aired from the second season, and there’s quite a few more coming, butPopRx is 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 italso 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 toWove 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.


Have you watched Next Gen Den? How does it compare to the original Dragons’ Den? Share your thoughts by commenting below.

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