Here's an interview from the FailCon archives way back in 2009.
Diane:What was Kiko's biggest failure? And biggest success?
Justin:Biggest failure: Focus. My cofounder, Emmett Shear, and I were constantly thinking of ideas for new products that weren't remotely related to web calendars and building prototypes of them, only to lose focus a few weeks later and try something else. Creativity is important, especially in entrepreneurship, but it would have been better had we focused it on solving one problem. It probably didn't help that neither of us used or liked to use a calendar at the time.
Biggest success. While I think it was pretty nifty that the first version of Kiko was one of the first AJAX enabled web applications, I think our biggest success was how much Emmett and I learned over the 14 months we were working on it. Specifically, how to raise money, hire first employees and recruit talent, operate a web site, and other basic skills that most tech entrepreneurs probably take for granted. When we started Kiko, we were just out of undergrad, and really didn't know anything about the industry or startups at all. Perhaps it's a bit telling how green we were that our biggest success was essentially learning about failing so that we could go on to Justin.tv.
Diane:How did you avoid making those same mistakes at Justin.tv?
Justin:With Justin.tv we focus on our mission of making live video part of the every day web experience. Fortunately, that covers a lot of different products and ideas, and that keeps working on one thing interesting. It has actually been quite a long road to get our focus, and it wasn't a mistake we entirely avoided repeating. I'd love to say we set out to be the world's largest live video site, but the truth is that we began Justin.tv with an entirely different idea (trying to entertain the starving masses with our own reality show), and stumbled upon what people have demonstrated they really want (a site for users to broadcast and interact around live video content). However, we are now happily organized around creating live video products that serve tens of millions of users every month.
Diane:What has been your biggest success to date? And why was it a success?
Justin:I think our biggest success thus far was recruiting the original founding team. Michael Seibel (our CEO) and Emmett Shear (our CTO) were friends from college, and Kylve Vogt (our VP Engineering) dropped out of school at MIT to join JTV. We've all grown into our roles over the three years we've been at it, and starting the company with three technical founders went a long ways in informing out company culture to be analytical and experiment with lots of different things. We've also recruited great talent thus far, and I think a lot of our success to date is due to getting really great initial hires.
Diane:What has been your biggest failure to date? And why was it a failure?
Justin:Not giving our employees enough independence. Being entrepreneurs we've definitely got an urge to just do things ourselves when we see something that needs to be done. Unfortunately, that process doesn't scale, and eventually you have to rely on other people. The advantage of this, however, is that you can hire people who are smarter than you and better at doing the job than you are. About six months ago we had meetings with the founders and small groups of employees and asked "What would make you able to be more productive at Justin.tv? What do you like and dislike?" We were surprised to learn that team members mostly wanted more responsibility, even if it came at the cost of them having to be on call when the systems broke or work longer hours. After those meetings, we went back to the table and tried to incorporate the feedback we'd gotten in order to shift more responsibility away from the founders. We didn't get it perfect the first time, and we are constantly trying to iterate ourselves organizationally. Overall, we've found out that smart people want independence in their jobs, the ability to make their own decisions and decide what is important, and after some hard lessons I think we've created a place that can deliver that to our talent.
Diane:Do you have any advice for other entrepreneurs in the social web space?
Justin:If you are just starting a new business, my advice is to solve a problem that provides a lot of utility to a specific group of people. If you're in the social space, like Justin.tv, and trying to get massive adoption, I think it's very important to consider how your product provides utility to a large base of people. This may seem very obvious, but I think a lot of companies (and we've made this mistake ourselves at times) will find something that provides some utility to a narrow group of people and mistakenly expect that the product universally applies and will go mainstream. Even if you're growing really well today, you should always consider whether the product is positioned to grow to the milestone after next.
