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Kylen and Kenda

She's trying to help him build that life. He's trying to help her understand why his whole generation is stuck.

On now

The show

Kylen is 33. He lives in a shed on his dad's property, gets most of his news from YouTube, plays video games until 3am, and somehow still wants a wife, a family, a house, and a completely different life.

Kenda is a Gen X mom of three, entrepreneur, mentor, and apparently qualified to give life advice.

Kylen and Kenda is an unfiltered conversation about the generational divide, masculinity, money, dating, and the manosphere, and why so many people know the life they want but can't figure out how to build it.

Sometimes they agree. Often they don't. No scripts, no life-coach voice, and neither of them is sure it's working.

Meet the hosts: Kylen and Kenda.

We say a lot of numbers on air. Check our numbers, episode by episode.

Kylen crouched in the studio holding a microphone, eyebrows up — Kylen, in the studio

Kenda playfully putting Kylen in a headlock — mentorship, roughly

Latest episodes

Episode 14 · October 23, 2026 · 51 min
Ep. 14: AI Insider: No One Really Knows What Our Actual p(Doom) Is
Kenda's friends who have nothing to do with tech keep asking her the same thing about AI. Should they be worried?
Episode 13 · October 16, 2026 · 50 min
Ep. 13: How to Build Grit When Everything in You Wants to Quit
Kenda signed them up for Running Man after a little too much to drink one night in May. She was scrolling Instagram, and she didn't check the dates or where it was. It turned out to be a festival in Rome, Georgia,...
Episode 12 · October 9, 2026 · 24 min
Ep. 12: Is Looksmaxxing Culture Maxing the Joy Out of Life?
Kenda has been researching maxxing. Looksmaxxing, aura farming, solomaxxing, sleepmaxxing, pheromone maxxing, side quest maxxing. Kylen is supposed to be the one who's in the know. He knows very little of it.
Episode 11 · October 2, 2026 · 38 min
Ep. 11: The "One Artist's Lyrics Raises Your Kid" Showdown
Somebody in the comments told Kenda to give up on Kylen. It is Kylen's favorite comment, and he agrees with the guy.
Episode 10 · September 25, 2026 · 60 min
Ep. 10: Growing Up Poor and Still Feeling Broke After Making Money
Kylen picked the topic and went first, which meant Kenda had to go second.
Episode 9 · September 18, 2026 · 47 min
Ep. 9: Success Is Not Winning (And He Coaches For A Living)
Kylen brought his best friend in. Jake Landel is the head coach of the men's indoor volleyball team at UC Santa Cruz, he has been coaching for close to two decades, and he is the person Kylen calls when he has doubt...