On November 13, 2013, Chegg, the student hub which aims to transform the way millions of students learn by connecting them to tools and resources, made its market debut on NYSE trading under the symbol “CHGG”.
It’s cliché to point out that most overnight successes in technology actually take years of work, yet in the case of Optimizely, we have yet another example of such a phenomenon. Earlier this year, Optimizely — on a tear — finally took a large round of venture financing and further solidified its founders’ goal to build a long-term, lasting, sustainable company. While it all may appear rosy now for the company, this was the third company for the Optimizely cofounders since the pair left their jobs at Google a few years ago.
For this discussion, I sat down with with Optimizely co-founder Pete Koomen to discuss how he and his cofounder Dan Siroker left Google and started to build companies together (after Siroker’s stint with the Obama campaign in 2008 and thereafter). The duo launched an educational site to teach kids math, but felt disconnected from the target users and weren’t confident the service could grow. Later, they got into Y Combinator and, during that incubation period, dropped their initial idea (Company #2) and pivoted into what would become Optimizely. The rest, as they say, is history — for now.
What struck me most about this conversation, as it was unfolding and as I’m watching it again, is that if you listen closely, you can hear the desperation in Koomen’s voice when he talks about tasting failure during the first two companies. You can hear the stress about not having a paycheck for a year. You can hear the ambition of someone who wanted to do something on his own, and was struggling to find that one “thing.” There seem to be some tough lessons in this story. Koomen and Siroker were accomplished technical engineers, held great positions in and out of Google, and had some of the best angels in the Valley behind them — and struggled for a while until they got to a point where they were revenue-positive and could focus on building the type of company they wanted to.
Editor’s Note: Michael Abbott is a general partner at Kleiner Perkins Caufield & Byers, previously Twitter’s VP of Engineering, and a founder himself. Mike also writes a blog called uncapitalized. You can follow him on Twitter @mabb0tt.