Shu Uesugi

Anyone Can Lead

If you haven’t watched these three videos of Jack Ma, cofounder of Alibaba and currently China’s richest man, do so now:

Anyone Can Lead

As far as I can tell from these videos, Jack Ma is a very different kind of a technology leader. Compared to how other tech heroes of our time came to be, Jack’s background is a complete outlier. He even says that he doesn’t understand technology.

Jack makes me believe that anyone can lead. Let’s say that before knowing about him, I assumed that the set of traits required to become a great technology leader had X elements in it. Now I think that the size of this set may actually be X2, or even X3.

This might sound obvious, but it wasn’t to me. It certainly helped me make sense of how I had made my career decisions in the past.

I </3 Entrepreneurship

In early 2012, I left my designer role at Quora in Silicon Valley, and began looking for a startup job in Tokyo. I met lots of great founders, but I simply didn’t want to work for any of them. It wasn’t because the Japanese startup ecosystem sucked (although this still is true, at least when compared to Silicon Valley).

What turned me off was that almost every startup founder I met in Tokyo was obsessed with the idea of entrepreneurship. They seemed to believe that the equation Entrepreneurs > Others held true. Of course, none of them explicitly told me so, but I could tell.

And I didn’t want to work for any of them. My reasoning was as follows, although I couldn’t articulate it clearly back then:

  1. I eventually began to assume that being obsessed with the idea of entrepreneurship was a key trait to becoming a great technology leader.
  2. I didn’t want to admit that this was true, because I not only lacked this “I <3 Entrepreneurship” mindset, but I also didn’t want to acquire this mindset. I couldn’t see myself becoming someone who thinks Entrepreneurs > Others.
  3. If I help those founders become successful, it would validate (1), which would make me feel bad because of (2). So I didn’t want to help them become successful.

I was never jealous that those founders were onto success; I was jealous of their personality that I’d never have.


After six months of unsuccessful job search in Japan, I met Betsy Corcoran, co-founder and CEO of EdSurge, the company I now work for. I can go on and on about how amazing she is, but for the sake of simplicity, let’s just say that she’s the most humble entrepreneur I’ve ever known.

Shortly after starting at EdSurge, Betsy and I drove down to an education meetup in San Jose. The keynote speaker asked people to raise their hand if they identify themselves as an entrepreneur. Well after ~30 people in the room confidently raised their hand, Betsy looked at me, raised her hand only halfway and modestly said, “…I guess I’m an entrepreneur too?”

This might be a cheesy story, but this was the moment I realized that her success would lead to my happiness. Humility, I believe, is the key quality to become a successful technology leader, despite so many counterexamples you see on the press.

Again, Anyone Can Lead

I might sound obsequious, but I’m not trying to be. My point is simple: I’ve always thought that I’d never be successful in the technology field. I’m missing certain “entrepreneurial” traits, and therefore nobody would follow my lead.

However, now I know that leadership can take vastly different shapes and forms. If you look into the set of traits required to become a great technology leader, they may contain traits that are outside of your imagination. To my knowledge, Jack Ma is a great example of this.

All one needs to do is to decide to lead. If I decide to lead, I might actually get support from people who also lack the same “entrepreneurial” traits as I do, but want to believe that those traits are actually unnecessary. My success would be their happiness.

I could become the symbol for the course of thought that anyone can lead, regardless of how different they are from the group of stereotypical technology leaders. And that gets me really excited.