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(How) Am I Biased as an Investor?

Reflecting on my investments to date, I’ve been thinking about my biases. The question isn’t am I biased? Honestly, the question is how am I biased?

I started investing in African start-ups in 2016. 700 coffees and 25 investments later, there are now enough data points for me to reflect on how things are going. (I share 25 lessons here). What have I learned, and what do I want to do differently?

One of the most interesting dynamics in my investing journey is this:

  • The first 5 investments I made in Africa are all led by expat male CEOs.

  • The middle 5 investments I made are all led by Kenyan male CEOs.

  • Of the last 7 investments I’ve made, 5 are led by Kenyan female CEOs.

I wasn’t necessarily trying for any “type” of CEO profile. I was busy meeting entrepreneurs, and this is the first time I’ve been able to lift my head out of the muck and reflect. What does this say about my biases?

First of all, it says that I am biased. I am a product of my environment and my experience. Despite experiencing a lot in the world across 4 continents - from the mountains of Kenya to the slums of Haiti to the high-rises of Taipei, my set of experiences is still extremely limited. In the end, I am most comfortable with those most similar to me, and I am networked to those who have the most in common with me.

However, I also wonder if those who have the most in common with me are starting to shift — from superficial commonalities to deeper values and aspirations. As in, I might seem to have the most in common with another 2nd-generation suburban Asian-American. But my “people” these days tend to be builders / connectors who want to change the world though business and tech. In other words, it’s not the people who look like me, but the people who are traveling a similar journey as me. Maybe having a similar future is starting to overtake having a similar past.

Here, I wonder if being Asian-American has been helpful — even an asset. Straddling two cultures and two languages from an early age hasn’t always been easy. If you’re not careful, you might feel like “the other” no matter where in the world you are — geographically homeless. Even worse, as China & the US compete further on the world’s stage, you could even be seen as “the enemy.” But on the positive front, this upbringing innately made me more curious. Very early on, there was a sense that life can be lived in many different ways and… people are interesting! People are almost always not who they initially seem to be and are quite multi-dimensional. Like a diamond, depending on how you look at it and at what angle the light catches, you’ll see beautifully different shades.

The other bias is less about my family/ethnic background and more about my “entrepreneurial background.” As someone who’s started seven companies, I now have a set of assumptions of how companies are supposed to be run. And yet, I’m learning there is more than one way to succeed (and many more ways to fail). The entrepreneur in front of me isn’t me, operates a business different than my own, and works in an environment different than mine. So, they will likely succeed in some ways very different than me. They might not apply all of the “best practices” I found to be instrumental. Maybe there are some commonalities of how entrepreneurial success is earned — great well-balanced teams, consistent hard work, well-executed pivots, etc. But more often than not, there are exceptions — or at least nuances. And it’s the differences in the journey that make it so fun.

A lot of “rules of thumb” don’t work for people using the other hand — advice always has context. For example, having a well-balanced team doesn’t necessarily mean one technical founder and one business founder. It could be a technical founder with a strong commercial board. The principle is to have as many bases covered as possible. Another one: the workaholic CEO doesn’t need to work harder, but work less. Rules are mental short-cuts that make nuanced principles easy to remember. I wonder if stereotypes are exactly the same thing.

I’m still working through my biases. There are likely more that I don't even see yet. I’m trying to remind myself: The person in front of me will teach me something new today — if I ask the extra question and stay curious. And if I’m willing to re-examine what is truly common amongst us.

The question isn't "am I biased?" It's "how am I biased?" Our environments and experiences are all bubbles that need to be popped -- over a lifetime. The people I like working with the most aren't unbiased. It's just that they are aware enough to know they are biased and curious enough to keep growing.

Today I got a WhatsApp message from one of my most precious friends in the world, who happens to be a rural Kenyan farmer / single dad who didn’t finish middle school. What we have in common: trying our best to raise good kids, using our talents to help others, and learning/marveling about a really interesting world.

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