I welcome this opening, thank you for the opportunity to teleport. Since this delightful memory popped up earlier today, I've actually been contemplating this very question. Tomorrow I embark on a brand new venture (outside of tech), one that has me again drawing outside the lines. And so of course, in this moment, I am given the opportunity to reflect on another time in my life where I did something outside the norm.

I don't think it's easy to appreciate just how "weird" it was to be in tech in 2004-2006 from our current perspective. I recall sitting in for a talk at UC Berkeley by PG in around 2004, promoting his "crazy" new idea. There were maybe a dozen people there at most. And I remember thinking "I don't really know what this startup thing is, but I know I want to be a part of this movement".

And doing something like starting a startup then was actually really hard. My family definitely judged me for making this choice, many of my friends didn't understand why I would go this route. But it was an excellent filter - the people who came to this space at that time were passionate about building something amazing. Very few of us had dollar signs in our eyes at the time, and yet many of the big names of today were forged in that fire.

None of us knew what we were doing, and that was the best part! Everything was new, exciting. But you also had to build most everything from scratch because the SaaS ecosystem wasn't there. In this early time, despite the challenge, there was room to explore and forge new paths. To make mistakes and be creative.

LikeBetter started as a dating app. The concept was simple - I thought that current dating apps at the time were stupid in that they asked users to fill out profiles (eHarmony, Yahoo Dating). You essentially had to trust that everyone was being honest, which was never the case. What if there was a dating site that "knew you" better than you even knew yourself, and matched you with people that were actually like you?

So we build a bifurcating personality classifier with the simple and addictive prompt "What do you like better?" and the choice between two distinct images. We had a responsive interface which felt unbelievably fast for the time, and people were just so drawn into this concept. We were featured on the front page of Digg (lol) and got a lot of press too.

We also launched with no data model whatsoever - we just presented "guesses" and allowed the users to correct us if we were wrong. But over time we were able to accurately guess all sorts of interesting things about a person's personality, just from their choosing between 20 or so pairs of images.

But as with many things, the course of my own life forged a different path. We were part of YC Summer 2006, back when it was in Boston. We relocated back to SF, my cofounder and I had a falling out, and we decided to shut down the company rather than raise capital. We had hit upon an exciting spark, but were not the right torch bearers to see it through.

The path in startup land that began with LikeBetter eventually led me to successful outcomes, and for that I am forever grateful. And it all started by being brave and joining a movement that I felt passionate about.

In your own life, it's so easy to follow the "head": what makes sense and will make me the most money? But I encourage you to look for those moments of passion and inspiration, even if they seem strange - for they will lead you to great things.