The Red Sox, Venture Capital and ‘Pocahontas’

This week, I was filmed for a Harvard Business School video. The interviewer asked me, “What’s the most important piece of advice you would share with students?” My answer: “Take more risks in your life.”

I’ve been thinking about that line all week, and it made me think about being open to “the unexpected.”

For example, the Red Sox last year completely bombed.  Now, they’re in the playoffs (I’m going later today, and it will feel like Christmas Day to me). What a difference a year makes.

All the pundits had picked the Red Sox to finish last in their division. Nobody predicted a season with 97 wins. From zeroes to heroes, from worst to first. It’s yet another data point that shows how tough it is to predict the future.

Similarly, in my experience, the start-ups that seem the most promising early on almost never are the fund-makers. Those usually are the controversial investments, or the really wacky ones whereby a partnership says, “Well, it’s so weird, but the team is so strong, why wouldn’t we just see what happens?”

I see this dynamic in other parts of life. Many friends met a life partner when they weren’t looking for one. The best fly-fishing spots, when you visit a river for the first time, come up around the bend unexpectedly, out of nowhere.

My exec. coach recently mentioned a particular song from the Disney movie Pocahontas.  She did so to give an example of risk-taking, about which even children know. Yeah, that’s right, I’m now going to quote from a Disney movie:

What I love most about rivers is:
You can’t step in the same river twice
The water’s always changing, always flowing
But people, I guess, can’t live like that
We all must pay a price
To be safe, we lose our chance of ever knowing
What’s around the riverbend
Waiting just around the riverbend

Life is such an adventure if we let it. You never know what’s around the bend when you push ahead and keep an open mind. “Staying put” feels safe. But, it really just kills upside.

The Pocahontas song is below, or you can click here.

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