Caterina Fake on the Pressure to Avoid the Startup Sophomore Slump

Athletes and musicians aren’t the only people who need to worry about the dreaded ‘sophomore slump.’ Flickr co-founder Caterina Fake says it applies to entrepreneurship as well, and that it’s a risk every entrepreneur faces after a successful exit. “You have to be aware of it and you have to not be afraid to fail. You end up having all of these interviews with reporters who are crediting the reason you’re getting all this attention not to what you’re currently working on, but for the past success,” she says. “The expectations are high, and everybody’s watching what you’re doing. To fail is even more risky than when you did it the first time around because the expectations are such that ‘founder of well-known company X is now doing a new thing, and maybe it’s not actually very good’ and that’s actually a greater fall from grace than if nobody knows who the heck you are and you’re just starting out.” She says it sets you up in a position where there’s more to lose, and when there’s more to lose, people tend to take fewer risks. “It’s something you have to be perpetually looking out for. You have to keep on doing what you do.”

Fake says she started taking business risks when she was a little kid. “I was one of those kids that always had a lemonade stand, a newspaper route and a little business that I created of selling knick-knacks that I had made,” she says. “I think that it was always an impulse that I had, and the manifestation of that was also that I wasn’t a good person working at a regular jobs that had a start time and an end time. I wasn’t very successful at that, so it trended naturally that way.”

She spent time living in Vancouver, which is where she started photo-sharing site Flickr. She launched the site with co-founder Stewart Butterfield in February 2004, and it was acquired by Yahoo in 2005 for a reported $30 million. Fake has said that the company kept its heart even after it was acquired, and credits the Yahoo team. “I think it had the good fortune of good caretakers, the people who were managing it afterwards understood what it was and had a good understanding of what the heart of it was,” she says. “That’s a very important thing when your company has been acquired, you want to make sure that the heart and soul of it don’t get lost. It’s a very common thing for a company to come in and impose whatever the local culture is. The people at Yahoo really understood what it was.”

She also credits the Flickr community with maintaining the culture. “It’s a really strong community, and it’s a really strong culture, and a lot of that was also because the contributors to Flickr were very strong as well,” she says. Today Flickr is hosting more than five billion images, and counts U.S. President Barack Obama as a user. Fake says she always hoped the company would reach the level it’s at today. “You always hope that when you build a company it will thrive as it has. I think the lifespan of it is quite impressive,” she says. She also says it’s been amazing to see photos on Flickr of President Obama with his family. “The Obama administration especially has been very active on Flickr, which is a wonderful thing to see. From the campaign through the inauguration,” she says. “Throughout his administration there have been some amazing photographs put on Flickr.”

Fake joined Yahoo after the acquisition in 2005 and stayed until early 2008. She launched her latest venture, Hunch, in 2009. The company provides recommendations based on users’ preferences, and is trying to build an online ‘taste graph.’ Though Fake’s role has come in to question in recent months, she says she’s pleased with the direction the company went in after it pivoted. “I think that the product itself is very much about user-generated content, so I’m very pleased that that has carried through into the present day,” she says. “All of the recommendations that you see on Hunch are contributed by users, and I think this is a really important part of the service because if you are able to capture human activity you’re always able to make technology work in a much better way than it would without the human input.” She says she’s proud to have contributed to the community aspects that carry on to this day. ”We’re centring on a theme here of setting things up well in the beginning,” she says. “I think that’s a really important part of everything that you do. Constantly putting good back into the products that you build and the life that you lead is a very important thing to do.”

Though she could be comfortable with a big exit under her belt, a new startup and investments in companies including DailyBooth and Etsy, Fake says it’s important continue to take risks as an entrepreneur. “It’s about doing things that you haven’t done before, where you’re still kind of a beginner, and not resting on your laurels,” she says. “It’s a hard thing to do – there’s a ton of research that’s been done that shows that people are more afraid of losing what they’ve already acquired than of taking a risk and building something new. This is a really common quality, that you want to hang on to what you’ve already got.”

Flickr is credited with pioneering many of the user-generated content features associated with social networks today, like tagging and marking photos as favorites, and Fake’s background is online community and user-generated content. Now that she’s an active angel investor and partner at Founder Collective, she says she’s drawn to companies that incorporate community participation, a “human” aspect as she calls it. These companies include fundraising platform Kickstarter and art community 20×200. “There’s a very common theme if you look at the investments that I do,” she says. “Those are all things that have some aspect of user-generated content, creativity, self-expression – there’s something very human about all of those companies, the things that they create. That has been the type of company that I am very much drawn to.”

She says that while the founders of her portfolio companies are very different, they all have the same passion for community. “The founders themselves are all very different. They have the same intuition about products, about how to create and build communities, how to sustain communities, how to create contributory systems,” she says. “Kickstarter is growing like wildfire, and the reason for that they’ve really found an amazing way of putting people together in a very human way. They’re really good at highlighting certain projects and matching creators and their funders. I see the same thing happening with 20×200, where they have created a great audience full of artists, in the art world which is actually a very difficult world to penetrate.” She says that while the companies’ products and services differ, they have a lot in common: great products, great communities, community-building, self-expression, creativity, and something very human.

Fake has said she believes entrepreneurs flourish under apprenticeship, and says angel investors are often great teachers. “A lot of the time the people that are doing angel investing, it’s very common for them to be entrepreneurs themselves. I am an angel investor and I have very close relationships with many of the people – I interact with them very frequently. Often you can find good mentors in the angel community.” She says that mentorship doesn’t have to be one-on-one though, and says online resources can be the best source of knowledge for new entrepreneurs. “You can learn from other people’s experiences, they write about them all the time and publish all kinds of articles and blog posts,” she says. “There’s amazing information out there about entrepreneurship, which didn’t exist when I was starting out in the early 2000s. I don’t necessarily think you need a single person to be your mentor, you can learn from everybody. The best way to do it is to just engage in the conversation. Participate, be in the community.”

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