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PODCAST

The Kylen and Kenda Show

Saint Kay Media

Kylen is 33. He lives in a shed on his dad"s property, gets his news from YouTube, and plays video games until 3am. He also wants a family, a home, and a life that looks nothing like the one he"s living. I"m trying to help him build it. He"s trying to help his mentor, Kenda, understand why his whole generation is stuck. Neither of us is sure it"s working.

comedy comedy interviews

All Episodes

01:00:28

Growing Up Poor and Still Feeling Broke After Making...

The Kylen and Kenda Show ·

2026/09/25

Kylen picked the topic and went first, which meant Kenda had to go second.His example is small and he refuses to let it be small. He stays up for one more hour of a day he is enjoying, and he pays for it with the whole of the next one. Not a little sleep. A lot of him.Hers is six nights in Paris and Champagne for her sister-in-law’s 40th, and she spent most of it anxious in beautiful rooms. Kenda grew up in a VW van on the beach, on welfare, then in an apartment with a rug she can still describe

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47:06

Success Is Not Winning (And He Coaches For A Living)

The Kylen and Kenda Show ·

2026/09/18

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 or emotional anguish. Kenda had been bracing for the worst.What she got instead is an hour about what a coach is actually building. Jake's answer to "what is the one thing you would put in a kid" is not a skill: it is redefining success so winning is the byproduct

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25:42

He Was Ranked Number One In The Country And Living In...

The Kylen and Kenda Show ·

2026/09/11

“No one’s looked at you and your problems and thought, I could make a show out of this. I thought I could make a show because I am a problem.”That is how Kylen opens, and then he tells the whole thing. Number-one rated amateur volleyball player in the US. Took the government money during COVID, souped up the back of a Toyota, lived in it — they called it the fart tube — and woke at 6am to compete with other homeless people for bathroom rights before going out to compete

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27:55

Rick Rubin Says Everything Is Creative (Even This,...

The Kylen and Kenda Show ·

2026/09/01

Kylen has had cold sores since he was born. The only salve that ever really worked got discontinued, so Kenda went looking for it, talked her way through about twenty people until somebody finally said yes, and is now pressing him a batch herself. Along the way: gigartina and why nothing else will do, the suspicion that the things which actually work are the first ones to quietly disappear, and The Creative Act, which Kenda has been reading and Kylen needs explained to him. Then the real argument

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53:28

The Algorithm Finally Picked Someone Good (And He...

The Kylen and Kenda Show ·

2026/08/27

Kylen and Kenda put themselves on a full digital detox — no video games, no social media, bed by ten — and agree to read Digital Minimalism while they do it. Then they spend the episode working out why it is so hard, and who it is actually for. Along the way: the dinner party where a 16-year-old never put her phone down, a rooftop in Marrakesh that nobody looked at, and the arithmetic on what eight and a half hours a day adds up to against the 10,000 hours it takes to master anything. And Ryder —

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01:16:37

A Therapist Called Out My Personality as a Strategy

The Kylen and Kenda Show ·

2026/07/31

Kylen sits down with a psychotherapist of thirty-five years. She is also Kenda's mother, which means the person taking him apart has known his boss since he started.He agreed to it half asleep. Within ten minutes she has ruled on his tattoos, Kenda has called him every red flag there is, and he has explained that being six foot six makes it hard to hide. It gets sharper from there. He describes his playfulness and she tells him it does not sound like play, it sounds like strategy. He talks at

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01:20:33

Social Media Almost Made Me Cash Out a 401k I Don't Have

The Kylen and Kenda Show ·

2026/07/24

Kylen nearly cashed out his 401k over a market-crash panic his feed served him. He does not have a 401k. Kenda turns the confession into the financial-literacy class school never taught — what a 401k actually does, compounding, the 59½ rule, APR — while Kylen argues the other side: he's too busy surviving to flourish, the system wasn't built for his generation, and betting on yourself beats feeding someone else's dream.It escalates: student debt as indentured servitude, who actually

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45:29

Should a Grown Adult Still Blame Their Parents?

The Kylen and Kenda Show ·

2026/07/16

This week we finally settle the fight that's been running since episode one: which one of us is actually the mentor? Kylen spends the pre-show lecturing Kenda about finishing her vitamins; Kenda spends the whole episode quietly proving she never needed the lecture. It builds, it escalates, and it ends the only mature way two grown adults can end a standoff like this — rock, paper, scissors, winner takes the title. 'I'm the mentor now. You'll learn.'Underneath the bit is the

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01:07:34

If You Need to Prove Yourself in Every Room — Listen...

The Kylen and Kenda Show ·

2026/07/09

Kenda's back from a week of chasing the World Cup with her family — three matches, three stadiums — and she came home with a question: why did a crowd of total strangers feel so kind? Australians buying drinks for rival fans, people photographing each other's families, not one political argument. Turns out sociologists named the feeling back in 1912: collective effervescence. We dig into why awe shrinks the ego, why nobody at a match has to argue their values, and why the same crowd energy can just

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46:03

The Podcast About Why Your Generation Feels Alone

The Kylen and Kenda Show ·

2026/07/02

Welcome to The Kylen and Kenda Show — a podcast about why your generation feels alone, and what it actually takes to grow up. Kenda is the mentor: a tall, no-nonsense woman (daughter of a psychologist) who manages and mentors a whole bunch of young men and tries to help them become better versions of themselves. Kylen is her project: self-described as living in a shed, with a Peter Pan complex, half his friends dead, a guy who gets in fights, hates favorite-color questions, and once nearly died from

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