After leaving Square, the founder wanted to fix education and noticed schools hadn't changed much despite technology everywhere. He saw parents desperately wanted better options for their kids and built Outschool as a marketplace for learning experiences, inspired by how Uber and Airbnb disrupted their industries.
Chapters
What was the founding story for Outschool and what were the first steps that you took to start it as a marketplace?
Well, I was very interested in education when thinking about my next steps after Square and potential projects I could work on. And the reason was that I wanted to have kids, but I didn't have kids yet. And I knew if I wanted to start something again, I was gonna have kids during the starting journey. And that got me thinking, well, it'd be nice if like what I was building was gonna be relevant to my future family. So, a very personal kind of motivation to think about the space. But then I started realizing this is a really, really interesting space because it was one that wasn't hot at all from a tech perspective. It had not been transformed by technology in the same way others had, and was in fact regarded as kind of a not great venture capital proposition or startup proposition because business models selling into school systems were regarded as, yes, you can create businesses there, but they're there hadn't been breakout success, there hadn't been breakout transformation. But I looked at this more and more and I started to realize, well, hang on, there's something very interesting happening here because I personally had grown up through the internet. You know, the mobile phones were not— not everyone had mobile phones when I entered college. By the time I left college, everyone had mobile phones. Generally, people did not have computers in their rooms when I was in college. You queued up for the you know, to access your email and the computer rooms. And, but then, you know, throughout my professional career, I'd grown up with this thing called the internet. I realized that that changed significantly how I thought kids should learn and what they might need to know in the future. I started to think there's probably gonna be other people about my age thinking about having young kids today who are gonna think in the same way. And yet the school system hadn't transformed. And then I also started thinking, well, fundamentally, people really, really care about their kids. And yet there was this perceived wisdom that, oh, you know, kind of education is a good market. But if you look at the fundamental emotional drivers under it, it's like, hmm, that, that's interesting. And the thesis started to form that maybe this was a space that was on the cusp of major transformation. But it just hadn't been the right company, the right way to engage parents in, in education hadn't been developed yet. So that was one set of influences. And then the marketplace model, you know, I was so influenced by You know, how Lyft and Uber had transformed the, you know, right, with the taxi marketplace and turned it into a massively more interesting category than the taxi scene. And similarly with Airbnb and hotels. And so the thesis started to form of what if we could affect a similar transformation within education by applying a marketplace model direct to consumer? And so that was the initial conception of Outschool. Let's create a consumer marketplace for learning experiences outside of regular school.
