Engineering for Serendipity / by Nate Westheimer

Fred Wilson blogged about his experience hosting Office Hours (and a bit about the Ohours platform itself) today. While he didn't mention the word "serendipity" once, in the comments the word came up 8 times, mostly from current Ohours users. I thought I'd write a bit about serendipity and Ohours here. One of the things I've enjoyed most about hosting Ohours is the serendipity involved in who I meet and what I learn from meeting them. In the past 2 years, I've met one person I've hired, some people I've found jobs for, and others who have become friends. Every week I do Ohours I learn something new.

Historically, the randomness of who would reach out and sign up for my Office Hours made it so I would meet new people and interesting people. Adding to the serendipity, the folks who found a little link on my blog saying I did "Office Hours" would people quite different than the folks who would reach out through other channels. Serendipity was high.

One thing that's happened over time, however, is that demand for my Ohours have gone up. Building the Ohours platform itself has had this affect, and of course my profile within the greater NY Tech community adds to things.

Now when I create new Ohours, 60 plus people get an email saying I've opened new slots. The folks who get a slot start to trend towards folks who try the hardest. Of course there are other factors which boost randomness, like if someone happens to be by their computer), but anything that changes a trend means serendipity goes down.

So, what's clear about my experience, and hearing about the experiences of folks with much more demand for their time, like Fred, is that that even with a platform (generically speaking) like Office Hours, serendipity takes a hit when demand for an individual when demand goes up.

Bad thing? Not necessarily. You want to reward fast-movers. But it's not necessarily the best outcome or why you'd want to open up time in your schedule in the first place.

Ohours is at its best when people are finding ways to meet with a "type" of person, rather than a specific person.

This has gotten me to think about how to better engineer serendipity.

One idea is that perhaps I should create "ghost mode," where everyone on the platform are only known by what they're "good at giving advice on," so that you don't know who you're getting, and serendipity goes up.

I don't know if "ghost mode" is the right answer. It's just a quick idea.

Would love to hear other ideas from folks on how to better engineer serendipity, for Ohours or anything else.