The Accidental Technologist: Caterina Fake

  • Before starting Flickr Catalina was a renaissance studies aficionado: I was planning on going into academia. I’m an accidental technologist. There was certain things about the internet that drew me to it.

  • Jorge Borges anticipated the internet in his writing: The Library of Babel is internet thinking before the internet. It’s beautiful.

  • After college Caterina moved to San Francisco and used her art background to get a job designing websites: She worked at Salon and Netscape before starting a gaming company with her husband Stewart Butterfield [cofounder of Flickr and Slack].

  • They created a game called Game Neverending: It was failing. They were broke. Only one person was getting paid. It was like The Donner Party.

  • Flickr was a feature of Game Neverending: As part of the game, they created an interface where players could create an inventory of objects they could pick up. It looked like a shoebox of photos. This turned into Flickr.

  • Time was running out. They were saved by a grant from the Canadian government: We got $175,000. That was supposed to go to the game but they used the money to work on Flickr. . . As entrepreneurs know, it is just a matter of staying alive until you get to the next level. It wasn’t called pivoting then.

  • When did you know Flickr was working? It was growing so fast that our servers were constantly about to collapse. [A hint of product/market fit. More on that from Michael Seibel below] 

  • Entrepreneurs hear no, no, no, no: When you hear a yes, you have to go after that yes as hard as you can. They needed investors. They wanted to go to a conference called PC Forum. PC Forum was run by angel investor Esther Dyson. They emailed Esther asking if they could go to the conference for free. She said no. A member of her staff replied to the same email and said yes. They went with the yes.

  • Yahoo offered $25 million: Stewart wanted to take the money and Caterina did not. She thought Flickr could go public like Shutterfly. The investors did not agree with her.

  • On making decisions with no data: The future is a blur. You can’t really see it. But somehow I think you can feel it. I think that there are a lot of decisions you have to make in spite of the data. In spite of received wisdom etc..

  • What would you do differently? I’m not a big believer in this woulda, coulda, shoulda scenarios. The way I think about these things is that is what happened. I try to live forward and not backward.

  • How was it to build a company with your husband? I read a book called Communitas: Means of Livelihood and Ways of Life that showed how men and women were divided. Women with the family and men at work. Instead of dividing work and family Caterina felt that you could have a life experience that everyone could participate in. Living, child-rearing and the work - all together - it could all fit together. 

  • More on working with your family: It is a more humane way of living. Many people’s work life is not humane. That’s a tremendous gift for you and your wife and your family. [The host of Without Fail is the founder of Gimlet. He also works with his wife.]

  • Working with your significant other from a historical perspective: I’m building Yes VC with my life partner. This is not something a lot of people understand or appreciate. They think it’s odd. But it was the way the work was always done. Throughout history, most businesses were family businesses. Most works was done collectively by the family unit.

  • A good way to evaluate technology: Does it divide us or bring us together? If it divides us don’t use it.

  • An interesting way to think about building a company: The most successful investments I’ve done they all had this feeling of finding a parade and get in front of it.

  • Full podcast here.