I also feel bad that he has seemingly tied up so much of himself into this. Although the technical interviews at Google kind of require this prep, at the end of the day interpersonal skills and other factors contribute to the final decision as well. It's possible someone interviewing him will find this distasteful. It's also possible someone might just not like him. It's impossible to know exactly what will happen, I just hope he's somewhat psychologically prepared to not be offered a job.