The Island of Misfit Toys

I was asked to speak to the Tech Club at the UW Foster School of Business tonight (thanks again for the invite, Saurabh).

During the discussion, one of the students in the group asked how I planned my career. My off-the-cuff response was that there wasn’t a lot of planning in it — I actually tried to follow a traditional corporate career path and just didn’t feel like I fit in any of the big companies I tried.


I kept switching to smaller and scrappier gigs until I found my real home in the company of entrepreneurs.

This got me going on the topic of the entrepreneurial community, and the incredibly warm welcome typically extended to anyone who shows up with a sincere desire to make a difference. My analogy — which may not make sense to anyone who didn’t grow up watching those stop-motion animated Christmas specials from the ’70’s — was the “Island of Misfit Toys” section from Rudolph the Red-Nosed Reindeer.

In my experience, entrepreneurs are the “misfit toys” of the corporate world. At first glance, we look like anyone else in business — we believe in markets and capitalism, we sing the praises of job creation and innovation — but spend a little more time with us and our imperfections come in to view…

We’re impatient and demanding… we value autonomy and creative freedom more than money… we think the world can be a better place, and we’re just naive and egotistical enough to believe that we can help make it that way. 

Strangest of all, when we find other people who think the way we do, rather than look for ways to compete with or cut down what they do, we look for ways to help.

A few weeks ago Micah Baldwin wrote a great piece on the same theme called A Weirdo’s World. He said a lot of true things in that post, but the idea that stuck with me the most was this one, describing the community of software entrepreneurs:

We are an offer help first culture, and that mentally is finally beginning to seep into the world at large.

I don’t know if Micah’s right about the back half of that sentence but he’s dead-on right about the first, and that’s why I’m so glad I found my way to the Island of Misfit Toys.