Kail talks to Abhishek “Shake” Chatterjee, who gained infamy on the latest season of Love is Blind. Shake talks about his big move to Florida and his recent career change. He also addresses some of the rumors about him and tries to clear up some of the comments he made on the show. What was he thinking during the reunion? Does he have any regrets on what he ... Show More
Nov 21
Turning Setbacks Into Startups with Debo Williams
<p>Delaware-born linebacker Debo Williams joins Kail this week to talk honest, unfiltered life after football, chasing the NFL dream, and becoming a 23-year-old tech entrepreneur. From growing up in Smyrna, grinding his way from an under-recruited high school athlete to the Unive ... Show More
1h 4m
Nov 14
Breaking Cycles in Real Time with The Dude Dads
<p>In today's episode Kail sits down with the Dude Dads for a candid, funny, and unexpectedly tender catch-up that hits everything from joining the “dead dads club,” visiting her estranged father before he passed, and what closure actually feels like. Tom and Jerry open up about ... Show More
1h 13m
Nov 7
Beyond My Super Sweet 16 with Jazmin Knighton
<p>This week Kail sits down with Jazmin Knighton from MTV’s My Super Sweet 16 for a raw, 20-years-later conversation that goes way beyond the glitz and the glam. Jazmin opens up about being adopted as a teen , reconnecting with biological family, how reality TV edited her voice, ... Show More
59m 6s
Jan 2023
Deconstructing Memes (with Penn Badgley)
Penn Badgley is warm, kind, and incredibly thoughtful – fortunately, the exact opposite of his character in the Netflix series “You.” As someone who’s been acting since he was a child, Penn shares his views on Hollywood and what it means to be an actor. He also talks about why he ... Show More
34m 36s
Nov 2023
One of My Faves: Starting a TikTok Trend (with Moses Storm)
This week, we're revisiting my interview with Moses Storm. Moses Storm has led a crazy life. The comedian and actor tells me about growing up in his family’s “failed” cult, living in a bus with his five siblings, and eventually meeting his hero Conan O’Brien on a rooftop that sme ... Show More
37m 59s
Jul 2023
Grape Therapy: Is Love Wirth It?
<p>It’s American model Wirth Campbell’s first podcast ever and we promise it won’t let you down. Gym owner, TV personality, and Kaitlyn’s very close friend Wirth is finally joining the pod to talk about, among many other things, the most recent episode of Charity’s Bachelorette s ... Show More
51m 1s
Oct 2022
Sketch(ing) Comedy (with Kevin Nealon)
I grew up watching Kevin Nealon on SNL, and now he’s on my podcast. Are you joking??? Along with being an incredible comedian, Kevin tells me about his lifelong passion for drawing. His new book “I Exaggerate: My Brushes with Fame” features stories about celebrities he’s met, acc ... Show More
37m 47s
Jun 2023
Owning Your Onstage Flops (with Nimesh Patel)
Nimesh Patel is a standup comedian, former SNL writer, producer and on top of all of that, he has a freaking finance degree from NYU. Nimesh tells me the story behind his hilarious new special called “Lucky Lefty”, where he muses on his testicular cancer diagnosis and cure. It wa ... Show More
30m 7s