Metin Seven’s review published on Letterboxd:
Win It All felt really authentic. It's like Jake Johnson and just about everyone else in the film plays himself / herself.
The plot is slightly predictable, but that's OK. It's a sympathetic story. There were times that the continuous waffling of Jake Johnson's charming loser character annoyed me a little though. But despite the minor overacting of Jake Johnson every now and then, Win It All has an enjoyable, refreshing film style. I liked it.