I tried to start a language learning app that would use product placement within lessons to make it free. The idea was to have VR style real world lessons such as how to order a beer - "I'd like a Heineken please".
I took it pretty far. My cofounder had a Phd in Computational Linguistics, we had professors from U of M as advisors, I got us into an accelerator, we built a working prototype, and I had several big ad companies interested.
The problem was that Duolingo came out at the exact time. Then due to our concept being immersive / media heavy, it required a lot of funding to build a v1. Ultimately, investors didn't think we'd be able to compete with Duolingo and we couldn't raise the funding.
I started the company almost 10 years ago now.
Facebook page: https://www.facebook.com/SavvyLanguages/