March 23, 2023

I wrote about my language learning startup, Readlang, back in 2014, and then again in 2016, both times attracting attention on Hacker News, where my story of a struggling one-man startup seemed to resonate. Well, it’s now 7 years later, and a bunch has happened since, so it’s time for an update…

The Aquihire

My Readlang story caught the attention of Duolingo and I went to work there in 2016. Meeting them for the first time on their company vacation at a fancy resort in Costa Rica was a culture shock after my frugal bootstrapper lifestyle. “You’ll get used to it” said one of the other engineers, which turned out to be half right. It was a wonderful, surreal experience.

We talked about a potential Readlang sale before I joined Duolingo. But they were more excited for me to work for on other projects. It sounded like an aquihire which made me uncomfortable. So instead we agreed that I would work for them for a while and keep Readlang on the side. I spent the first 9 months working on an ill-fated chatbot (a few years too early as it turns out). After this, I decided that I had unfinished business and emailed to say that I’d be leaving to work on Readlang again. They quickly got back to me and said I could have carte-blanche to work on a completely new product around listening. I had ideas in this area already, and it seemed too cool to turn down. Get paid to hack together a new prototype that I would be in charge of? Yes please!

My idea was to launch an MVP and then leave to work on Readlang again. Within a few months we launched the first version of Duolingo Stories and the reception both internally and