Diversity, Balance and Big Dreams: Michael Serbinis is in a League of His Own

When Michael Serbinis introduced League in 2014, he shook up the health insurance industry.

Branding itself as the “digital alternative to traditional health insurance,” League gives businesses a new way to deliver health benefits to their employees: completely personalized.

The platform expanded into the U.S. two weeks ago, offering small- and medium-sized companies its alternative to what League calls an outdated insurance model.

With League, users build a flexible health plan that suits what they need, whether that’s physiotherapy or fitness classes. Users can connect with trusted professionals, book health services and monitor payments all through the application.

League isn’t Michael’s first technology success. The serial entrepreneur worked alongside tech tycoon Elon Musk at Zip2 before founding—and selling—cloud storage company DocSpace and ebook business Kobo.

Now at the helm of League, Michael’s innovation is pushing companies to think differently about health and wellness.

In Canada, we have many entrepreneurs who are trying to make a positive impact on people’s lives. What influences your entrepreneurial efforts and worldview?

I learned this lesson a while ago: that I’m not good at everything, but the things that I’m really good at, I know I can make a difference on. I’m a big innovation, make the country better guy. And I spend a ton of time on that.

At League, we offer health and wellness benefits to people. A lot of people choose us—or use us—because in their traditional plans, there’s no mention of mental health. I kind of view it as our responsibility to be a part of the change that mental health is necessary.

Being a startup is not all ping-pong tables and fast lunches. It can be stressful.

In my interviews, the first question I ask is, “Why League?” And it’s a staggering percentage of people that say because I had or have a mental illness or I know somebody that does. Five or ten years ago, nobody would say that. So the conversation around mental health is changing and I think we have a role in what we do to be a part of that change.

What makes League’s feels more like a health and wellness brand more than an insurance company. Is that distinction intentional?

We didn’t start League to be an “insurance something.” We started this with this simple insight around the future of health: less bureaucratic, less institutional, and consumer first.

Our mission—which we wrote down literally on the first day of the company—was to empower people with their health so they can live the lives that they want to lead: happier, healthier, longer.

What we’ve learned along the way is that although our product is in the benefits or insurance category, these are benefits that you can actually use. It’s all about you in a personalized way, a preventative way, and a way that’s right for you.

Are we more of a super lifestyle brand? Yes, whereas I don’t think anybody thinks like that about their insurance company.

Traditional health insurance companies don’t give consumers a reason to engage with an app. What does League do differently?

We have this feature where your home screen is a news feed. So I get content every time I sign in. I might sign in because I want to check out a health provider that I’m interested in or I might want to snap a photo of a claim, but I always get a piece of content. And as it gets to know you over time, the content gets more targeted.

We’re constantly thinking about new ways to release content that is relevant for that young consumer based on general needs, but also in these very specific niches that are tied to your health. We’ve become a place that isn’t just where you snap a picture of a receipt or where you see how much is left in your plan. But also the kind of a place you go for your health, period.

You’re a director, a member of several boards and you head-up League. Does that become difficult to manage?

I think what changes over time is you get better at deciding what’s important and you’ve just got to be constantly doing that. For me the greatest achievement is not in any one company, but this realization that you can go after what you’re passionate about and live an awesome life with your family—and you can do it all. That is the achievement.

It just takes work to be constantly prioritizing, You can’t go to every single board meeting. So, you end up becoming ruthless with your time and end up thinking about where you can have big impact and where can you be unforgettable.

So you don’t assume the “work hard, play hard” mentality?

I don’t believe it’s all about work. I don’t believe the only way you can be successful is if you are 99% all the time. At League, “work really hard, play really hard” doesn’t really work. It’s not sustainable. You can do it for a year, but it doesn’t attract the diversity of people that you need to be successful.

We’re over 50% women. If it’s just a bunch of dudes hanging out all day, you’re not getting all kinds of people to want to play in that environment. The approach that we take to building the company is not one where we want to crush people. That’s what people think of startups. I don’t buy it.

There is an ongoing conversation of Canadian brain-drain to the valley. As someone who started their career in the US, what are your thoughts on young Canadians starting out abroad.

I think Canadians have an opportunity to head down to the valley, either to work on something new or something that’s been around for awhile and just drink the Kool-Aid. It provides an understanding for how the world works and the level of play. And then coming back—or being a positive contributor by not coming back—I don’t think that’s a bad thing.

I went through the valley, I did my 10 years, but then I came back and I created thousands of jobs. And I’m still doing that. Would I have been able to do that if I didn’t do my particular tour? Probably not. Not in the same way. I think we need to be a little bit more open minded, in general.

That said, you were also an early catalyst for the Vector Institute, which seeks to retain Canadian talent to enable and sustain AI-based economic growth in Canada.

With Vector, it’s like we found Kryptonite, and we don’t have it by accident. We have it because there’s 20 years of research grants and investments. The idea of creating Vector started on a dock in Muskoka two years ago where I said, “We can’t be great at everything. We are great at a few things, one of them is AI.” We’re going to bring incubators, accelerators and commercialization and call it a super cluster and that’s something we should be great at.

So you’re not only preventing some people from leaving, you’re attracting a ton of people. I put out this prediction at the beginning of the year that we’ll see at least 100 corporate AI labs show up in Toronto this year because of Vector. Hundreds of corporate AI labs will move to Canada and either bring people with them or hire local people and I thought that’s a good thing.

Your old pal Musk has plans to colonize Mars. What is your big dream?

Haha yeah. The moonshot maybe is transhumanism – living to 200 years. There’s new stem cell therapies actually being developed in this (MaRS) building and we’re one of the leaders in stem cell and regenerative medicine. We’re going to extend life. I don’t talk about this (laughing) this is actually the first time I’ve ever said this to anybody. I think there is this life extension moonshot that someone should own and no one has really claimed it yet.

Healthcare is going to become better, personalized, and you should be able to live longer out of that. And whether it’s 150 or 200 years, I just think we will. We were living until 40 until 100 years ago. Is it not insane to think that it’s going to go up? Real bio signals are starting to emerge from devices that are not only from devices that you wear, but devices that can be embedded in you – your blood, your eyes or your ears. We’re headed there. We’re going to become bionic. Those crazy ideas, the moment you set an intention, are not so crazy.

This interview has been edited and condensed for clarity by Kate CornickPhoto by Matt Odynski.