League Updates

Skate to where the puck is going

by: | December 1, 2016

A couple of weeks ago, I was invited to speak at the Prime Minister’s long-term capital summit, organized by BlackRock. Trudeau, members of his cabinet, BlackRock’s Laurence Fink, and investors who are responsible for over $20 trillion dollars were in the room.

When have you ever been in a room with a trillion dollars?

It was a pretty awesome affair—an illustration of long-term thinking with action today.

I spoke about League and the massive market opportunity we are going after: a trillion-dollar market worldwide, with hundreds of billions in North America alone. I spoke about disrupting an age old insurance industry with a new philosophy focused on empowering people to be healthy, every day. I spoke about building a new industry giant that the world needs, a life optimization company that offers a new kind of health benefits product to employers to give to their employees.

That’s long-term thinking.

As a startup CEO, you need to balance the long term with the short term.

Short term, you are building product, fighting fires, hiring, firing, landing the next customer, meeting payroll, meeting investors, partners and more. It never stops, and it is pretty easy to get caught up in the short term. But you have to keep your eye on the prize. I do that by having very clear long-term objectives that I repeat over and over to myself and the team. We regularly review our plans, and brainstorm: What’s it going to take? What are the risks/opportunities? What is the competitive response?

And then we make some bets on infrastructure.

As CEO, you cannot be consumed by today.

You need to be putting “infrastructure”—that is going to help you succeed, that is going to help you scale—in place. You also need to be setting up enablers that will help your team 3, 6, 9, 12 months out.

Right now at League, that involves making critical hires that bring skill sets that we need: finance, underwriting, product management, machine learning to name a few. It also means investing in our sales machine—with tools, technology, training, automation—not only for short-term productivity gains, but for medium to longer term scaling needs. Signing millions of dollars of contracts per month is one thing. We can do that. Signing $10, $20, $50 million is quite another.

I want to be ready for those months. They’re coming.

Remember to set long-term objectives and make bets on the “infrastructure” investments that are going to help you succeed tomorrow.

Or as The Great One once said, “skate to where the puck is going.”

  • Great write-up paired with excellent insights.

  • Madison Dias

    Well said! The great one also said “You miss 100 percent of the shots you never take”.

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