I spent the past weekend out in the San Francisco bay area taking part in Y Combinator’s  (YC) Startup School. Startup School is an event that YC has been hosting for the past 10 years. They bring in founders and investors from some of the most successful technology companies and give them each 30 minutes to talk to a room of 1500+ potential entrepreneurs. The talks range from honest stories about failures to funny antidotes. In the past year YC has added startup schools on the East Coast and in London, so they must be doing something right. 

The last time I attended Startup School in 2012 I had just barely started my company. I was wet behind the ears and I thought that I was going to come away from the event with a new understanding of how to run my company. The event was nice, but I didn’t feel like I learned anything actionable. 

This year I’m in a very different place. I’ve learned a lot of hard lessons in the past two years. I probably wouldn’t have attended Startup School this year based on my past experience, but I was invited to a dinner the night before and I had a few other contacts I wanted to re-connect with, so I made the trip out to California.  

The lobby of one office building I visited had two solid walls of plants. I wonder if there's a startup that could make a product for that...

The lobby of one office building I visited had two solid walls of plants. I wonder if there's a startup that could make a product for that...

I was pleasantly surprised when a large number of the talks took a different path from those in 2012. Instead of just telling a sugar coated story about going from obscurity to running a billion dollar company the founders were very consistent about mentioning ways they had failed early in their careers. Some of them tried multiple different versions of the same idea before making it work, while others had to jump around from one company to another before they built something that solved a real problem. 

My own experience with my company hasn’t quite wrapped up yet, but I think it is safe to say that the current prospects don’t match up with what I originally wanted. It has been hard to see the company shrink slowly over the past six to eight months. As things have been wrapping up I’ve spent a lot of time thinking about why we didn’t win and it has been pretty depressing. I’ve touched on some of those stories in past blog posts and I’m sure I’ll go into more detail here in the future, but for now I think it is safe to say that I’ve been coming to realize that I’m the main reason we didn’t succeed. 

With that realization in hand I’ve been pretty doubtful about my ability to run another technology company. Outwardly I’ve been saying that I am definitely going to start another company one day, but in the back of my mind I constantly question that assertion. Hearing about how others have overcome similar challenges and persevered in the face of failure was incredibly encouraging. It’s was so relieving to be in an environment where failure is not just tolerated but celebrated as a step toward success. 

I hope that one day I’ll be able to share a similar story about going from an initial failure to a big success. But for now I’ll just remember the stories of others and draw encouragement from the fact that I’m not the first person to run a business poorly and survive it. 


There are dozens of people who take fantastic notes at these and publish them online each year. If you’d like to get a better idea of what the talks are like you can check out these great notes or just watch the talks online here