Reflections on Startup School

Exactly two years ago, I spoke at Startup School.

It was my first public appearance since the ugly demise of the company I had spent the previous ~7 years building.

To be perfectly honest, I was deeply dreading giving the talk. When Paul Graham first invited me to speak, I pointed out to him that publicly rehashing all of the things I learned about the music business seemed a self-destructive thing for me to do: I was afraid my talk would be seen as “sour grapes” or perceived as an attempt to blame others/make excuses for my failure. I had trouble sleeping in the days leading up to the talk.

After years of having my public persona mediated by marketing and PR, I had been trained as a founder to never be controversial, to tell audiences what they want to hear, to hide my true feelings behind carefully-crafted soundbites. Sometimes I would read quotes attributed to me in press, and not recognize the words as my own. That aspect of the job always made me uncomfortable, but I was under the impression it just came with the territory.

So, I made a promise to myself that if I was going to accept the invitation and speak at Startup School, I would consciously reject my prior training, and do my best to tell the Complete Unvarnished Truth. I convinced myself that I would go out there and pour my heart out, and the audience could choose to take it or leave it. Perhaps this was a self-destructive way to think, but that was my state of mind at the time.

After my talk was over, rather than being ripped to shreds in the ways that I was predicting, I experienced an outpouring of appreciation and support.

There are a number of different ways that I could have changed my behavior as a consequence of failure. That talk was a defining moment in my attempt to explain my failure to myself… to give my failure meaning. The Startup School audience rewarded me for telling the truth, for not “dumbing down the message”, and for being willing to admit and display weakness in public.

As I reflect on that what I learned that day, it’s now clear to me that the person I was on stage that day was and is my true self. I found my voice.

Thank you PG, and thank you Startup School.