WaniKani
I probably started work on WaniKani by the end of 2011. We launched it and got paying learners started to sign up around mid-2012.
Currently, I'm doing most of the product design. In the beginning, I did most of that. Then in the middle bunch of years, I let other people get involved. Turns out it was too much product-design-by-committee. Now I'm back to doing most of it again. And, it's been really fun to get back into it. I think I hold myself to a much higher standard in terms of what I'd define as learning (if it's not transfer or leading to transfer, it's not learning). That leaves a lot of room on the product side of things. A lot of change that will make a big difference in people's studies, I think.
I can't talk too much about it here, now, but I'm excited for what we're working on.