The Perpetual Outsider: The Big Benefits of Not Belonging

Growing up, I never felt like I fit in. Born in the USA, moved to Canada when I was 1 year old. Vancouver at that time was a backwater and we were clearly the minority. Bear in mind this was before the wave of wealthy Asian immigrants from Hong Kong, Taiwan & China that came after 1986. I got used to being called Mr Kung Fu man. I also did not belong to the clique of well off Asian kids.

I was popular in high school though but I think this came from suppressing my true personality, interests, opinions and views. The best way to be liked is to just agree with everyone. I think this is the main reason I found and still find Canada so stifling for me. Probably Also why I left as soon as I graduated university. (UBC: The University of British Columbia aka University of a Billion Chinese :)

I traveled through Europe and then lived in Taiwan for a few years after where despite being of Taiwanese heritage, I was seen as a banana: yellow on outside, white on the inside. Then my move to San Francisco in 1999. Definitely an outsider without the Stanford or Berkeley or Ivy League background & relevant business background.

Frankly even now, I still don’t feel like I belong.

I recall a conversation with my friend Itai in Hong Kong where he said “you’ll never belong in Silicon Valley because you are way too international” which he meant as a compliment.

But in my older age, I’ve come to embrace it. There is a power to not “belonging”.

There is a term called “Third Culture Individual”: According to Wikipedia, people who were raised in a culture other than their parents’ or the culture of their country of nationality, and also live in a different environment during a significant part of their child development years.

There is this great scene in “Billions” where Axe is trying to hire the young transgender genius Taylor Mason. He says to her “Sometimes you catch yourself watching all people like they are some other species. So you retreat behind your aquarium walls watching. But you don’t realize. That glass is not a barrier. It’s a lens. It’s an Asset. It’s what makes you good. You see things differently: That’s an edge.”

This really stuck with me. Social cues are overwhelming but most of the time the crowd is wrong or usually late. I now actively resist the pull of hype and crowds. As a VC I saw how many investors, myself included, invested in some bad deals (or crowded trades as they call it on Wall Street) due to the need to follow a trend and not get left out.

If I look back, this resistance has served me well in my career and in my investments. Some of my best career moves were completely unconventional or questioned. Ie. Joining a startup in 1999, running Sales Operations for International in 2003, joining the Emerging Markets group in 2007. Also Investing in startups overseas, especially in Europe and Africa before it was cool to do so, as it seems to be now. Most of my best performing investments were derided or misunderstood. When I suppressed this resistance or gut feeling, it came back to haunt me.

So my point is that in our now vanilla monoculture world, embracing your own difference and outsider-ness may be what actually helps you win.