Caterina Fake knows a thing or two about taking risks -- and finding success. She's had a hand in some of the most innovative internet ventures of the last decade. She co-founded pioneering image-sharing service Flickr (under Yahoo's umbrella since 2005) and recommendation and mapping platform Hunch with Chris Dixon, which sold to eBay in 2011. And as a founding partner of seed-stage venture capital firm Founder Collective, she has supported ventures like Buzzfeed, Uber, Cloudera and Etsy -- she's also Etsy's Chairwoman of the Board. And she isn't slowing down anytime soon.
Fake is now the founder and CEO of Findery. This latest venture which officially launched last month (after two years in beta) is all about discovering and engaging in what's unexpected all around you. The app lets users leave Notes and create Notemaps about travel destinations, regular haunts, favorite subjects and everything in between -- a little local color and community in a digital world.
We caught up with Fake to talk about diving in head first, learning from the past, the value of failure and what you can count on in human nature.
Q: Knowing what you know now, what would you have done differentlywhen you were first starting up?
A: As entrepreneurs, we're all making thing up as we go along, each new thing has its own challenges and different way of being run. There will be surprises, things you didn't expect and issues you thought you would never have to deal with. Esther Dyson told me this, she was an early investor in Flickr, and she actually has this as her e-mail sign-off: Always make new mistakes. So that’s the motto that I try to live by, don’t make the same mistakes twice.
Q: What do you think would have happened if you had had this knowledge then?
A: Going back in time to the early days of Flickr, sometimes we hired because we needed to fill a chair.
We needed a back-end engineer, but we didn't have the person with the right skills, so that person ended up building the wrong systems for us and put us back about year. I should have gone and waited another six months to hire the right person. You don't realize how painful it has to have the wrong person. I'm a big believer in that the team is everything.
So when I was starting out with Findery, I took a longer time than I would have liked. I knew that I had to wait for the right people and I was much better at trusting my instincts the third time around. Having the right team together and hiring people that are smarter than you is key. It's important to really work at recruiting, sometimes even over the building the product. Having done this three times, I've had had the opportunity to really learn from my mistakes. Being a serial entrepreneur means you can be the person you wished you had been the first time around.
Q: How did you learn this lesson?
A: With Findery, this is a new thing I've never done before -- Findery is mobile. I've worked with social networks and user generated content, and I'm now bringing that knowledge over into a new field and doing things that are completely out of my comfort zone.
Research shows that when people have had a successful company, they tend to become more cautious, don't want to take more risks. But that's an anti-entrepreneurial way of thinking. You have to go out and try new things. Technology moves so fast and what was true a year ago is no longer true today, so it's important to judiciously take advantage of the advantages you've already got, while simultaneously approaching things with a beginner's mind. Its constant disruption, so you have to stay on your toes.
Q: Besides invent a time machine, how might they realize these sorts of helpful pearls of wisdom sooner?
A: Being open and observant of people and the world around you is really important. People have the same desires and needs online as they do offline. The way that people are stays constant. You can change the format, make it easier for them to communicate or use photos instead of words but human necessities never change.
Q: What are you glad you didn't know then that you know now?
A: Not knowing what you're getting into can be a great advantage. Being an entrepreneur is so glamorized in the media. You see the winner's circle, see them ringing the IPO bell, but they don't show the people who lost their shirts or went into debt. If you knew how dreadful some of those days are -- at first, we didn't have enough money to build Flickr. And there's not getting paid for a year, living on cooked noodles, lying awake at night knowing you had a terrible day, lost a key employee, or a person you wanted to join your board thinks your product is crap. Blissful ignorance can be a huge advantage -- entrepreneurism is not necessarily for pessimists.
Q: Best advice for aspiring entrepreneurs?
A: Really understand people, their needs and how society works. Start building something immediately. Don't wait for the magic co-founder to join you, just start. Recently I had a friend write me a note. She just started a business and said 'thank you for that conversation we had.' She had been trying to decide whether to go into an entrepreneurial MBA program or not and I said, 'why would you go into a grad program, why don't you just start a company? You learn how to build companies by building them.' If you want to start a business, it's easier now more than ever. It might fail, and God knows I have a lot of failures under my belt. But the one thing that doesn't work out puts you one step closer to your goal.
-This interview was edited for clarity and brevity.