Post-startup school thoughts
This weekend was Startup School (thanks to Jessica and the YC team for organizing). The event was thought provoking in a different way for me this year. Usually it’s a raw feeling of inspiration and wanting to build a successful startup so one day I can be a speaker and not an attendee. This time it left me more reflective. Differences in the talks this year were Tony Hsieh and Mark Pincus going into the psychology of why people start companies and Paul Graham talked about what startups are really like i.e. for the most part they’re a brutal experience.
My motivations for doing my first startup were simple and mercenary. I wanted to get never-have-to-work again rich and thought a startup represented the best chance of achieving that goal. I didn’t question that motive in any great depth. I’d never had much money growing up and the desire to be rich was hardwired in me since as far as I could remember.
The time I spent on a startup was by far the most intense and stressful period of my life. I’ve now seen first hand just how hard building a business is and I’ve been around enough failed startups to confirm it. The net result of this is I can’t use mercenary motives to justify doing another startup. My brain just won’t let me delude myself on the chances of that outcome like it used to. We were incredibly lucky to be in the group of first time entrepreneurs to get a profitable exit. It wasn’t never-have-to-work again profitable but it significantly changed our financial positions. It still doesn’t change the reality though. Startups are hard and big exits are rare.
That’s where my thinking was at before going into Startup School. In this context, these parts made me think the most:
- Tony Hsieh presented an interesting thought experiment. Ask yourself what one of your goals is. Then ask why. Then ask why again and keep going. It should end with to be happy. We set goals and do things because on some level we think they will make us happy.
He touched on the ideas presented in Stumbling on Happiness (a fantastic book I found via Kul) namely that although we do things because we think they’ll make us happy, humans are notoriously bad at correctly predicting which things will actually make them happy. Unless you’re fortunate (or have a low bar for happiness, which is arguably in many ways a good thing), knowing which things and actions will make you happy is not a trivial exercise. It’s something everyone should spend time thinking about but especially in the context of startups and founders, not enough of us do. There’s so many external forces pushing us (peer pressure, societal expectations, family, circumstances, etc) that make it hard for us to listen to our inner voice when there’s so much value to be had in doing so.
- Mark Pincus talked about how even after selling a few companies and being successful he still had the desire to start another one. I spoke with Mark after his talk and he articulated why selling a company can be an anti-climax. Once you sell, you reap the financial rewards but if it wasn’t a product that really mattered you’re left with nothing to really show for it. That’s what drove him to start Zynga - he wanted a product that really mattered to people.
So far I’ve managed to distill two (very vague) motivations/goals that I want to optimize around for whatever I do next:
- Work on something that positively impacts a significant number of people’s lives.
- Work with people who can improve me
I’m curious to see where the thought process will take me. If anyone is/has been in a similar position, I’d be interested to hear about your experiences.