Simon Taylor | How He Went From Writing 20,000 Jokes for Jay Leno to Making His Own Show

Andrew sits down with comedian and writer Simon Taylor, who became a writer for The Tonight Show with Jay Leno at 24 and later became the first Australian comedian to perform stand-up on The Tonight Show Starring Jimmy Fallon — earning a rare invitation to join Fallon on the couch. Simon opens up about still battling imposter syndrome despite the résumé, the supportive rejection that pushed him to finally make his own show, and the discipline that came from writing thousands of jokes on Twitter before he ever met Leno.

They also dig into the ethics of the unregulated podcasting world, whether audiences actually want authenticity or just a convincing performance of it, and what it's like releasing a satire about podcast culture just as real headlines start mirroring the show almost exactly. It's a candid, funny look at collaboration, rejection and building something of your own.