Kai wrote for Seinfeld alum Wayne Knight's upcoming sketch project and has opened for touring comics such as Doug Stanhope, Dave Attell, Sam Morril, Judy Gold, and Gary Gulman. The New York Times Comedy Critic Jason Zinoman described him as a "smart, elite college, comedy nerd."

Kai's short documentary film received an official screening at the Chan Zuckerberg Initiative Center (Mark Zuckerberg's Nonprofit), where he was a featured speaker, and is set to be screened at Google, where he will also be a speaker.

Kai's podcast features Oscar Nominated Filmmaker Jed Rothstein, New York Times Comedy Critic Jason Zinoman, and Bestselling Author Esther Wojcicki (who invented Google Docs and is the mother of the CEOs of 23&Me and YouTube).

The podcast theme song was composed/performed by Grammy-Winning Musician Greer Baxter and the podcast cover art was illustrated by Time Magazine's Person of the Year Illustrator Jason Seiler, who were both also guests.