Michael Serbinis | Crain's Toronto

In this ongoing series, we ask executives, entrepreneurs and business leaders about mistakes that have shaped their business philosophy.

Michael Serbinis


League takes a “sharing economy” approach to health insurance, allowing companies of all sizes to provide coverage by offering employees a set spending limit, then connecting them with care and service providers at their discretion.

The Mistake:

Staying on too long.

In one of the companies that I built and ultimately transacted, I stayed too long with the acquiring company. We were in a time of chaos, it was post-2000 with the dot-com bubble bursting, and we were a growing company with good things happening. But the market really turned. And while I did a lot to fix it and get the company profitable and on its feet, I probably stayed too long after that.

And one of the first things I did when I finally left was I started a new company, which ended up being a company called Kobo, which was in a totally different industry, but was started from a moment of inspiration. We became the Amazon Kindle's No. 1 competitor worldwide, No. 1 or No. 2 in almost every market. 

Turning the Titanic even one degree is tough.

The Lesson:

You can be in the greatest boat ever, let's say it's a rowboat, and you can be really strong and great at rowing, But if there's a tidal wave coming at you, it won't matter how good your boat is, or how good the people rowing the boat are. You’re not going to make it. That's what I experienced with this particular situation, where the market just completely changed. It didn't matter how well we put Humpty Dumpty back together again, because the long-term prospects didn't really make sense or weren't attractive any more.

So staying too long post-acquisition and doing "the admirable thing" sometimes just doesn't yield any results. I realized I was pretty good at building these transformative digital companies, and it didn't really matter whether it was search or storage or books or messaging … that approach worked in pretty much every industry.

Turning the Titanic even one degree is tough, and in the health insurance industry you’ve got antiquated systems that you could spend 360 days of your 365-day IT budget on, just maintaining your existing infrastructure and keeping it ticking, versus building something complexly new and disruptive.

Follow Michael Serbinis on Twitter at @mserbinis.

Pictured: Michael Serbinis. | Photo courtesy of LEAGUE.

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