The Kylen and Kenda Show

15 Episodes
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By: 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.

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Andrew Tate and the Four Controls Every Cult Uses
Andrew Tate and the Four Controls Every Cult Uses episode artwork
Today at 12:00 AM

Kenda came into this one with a stack of research and a question. How does anyone end up in a cult?

Her answer starts with Steven Hassan's BITE model, four basic things that all cults have. Behavior, information, thought and emotion. They try to control all of it. She says the people who join are not who you would expect. They are not troubled or unintelligent. They are intelligent people who are searching for connection and something to improve.

Kylen brings Andrew Tate. He admits he first took him for a guy who cracked the...


Ep. 14: AI Insider: No One Really Knows What Our Actual p(Doom) Is
Ep. 14: AI Insider: No One Really Knows What Our Actual p(Doom) Is episode artwork
#14
10/23/2026

Kenda's friends who have nothing to do with tech keep asking her the same thing about AI. Should they be worried?

So the show brought in a guest who works in AI. He stayed off camera and nobody says his name. Kylen started calling him Jimbo, for his own safety.

Jimbo thinks of AI as an exoskeleton. It amplifies what you already do, the smart things and the stupid ones. Kenda built a new website with it in about 16 hours. Kylen wanted to know if he also gets the Master Chief armor.

They...


Ep. 13: How to Build Grit When Everything in You Wants to Quit
Ep. 13: How to Build Grit When Everything in You Wants to Quit episode artwork
#13
10/16/2026

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, the same week as a podcast convention in New York. She said she'd make it work.

It was 95 degrees and humid inside their tent. Kenda ran the half marathon in dark blue socks and got blisters, and the timing machine missed three of her laps. Kylen was the cameraman. When he got hot, he went...


Ep. 12: Is Looksmaxxing Culture Maxing the Joy Out of Life?
Ep. 12: Is Looksmaxxing Culture Maxing the Joy Out of Life? episode artwork
#12
10/09/2026

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.

He does know that maxxing started in Dungeons and Dragons, and that looksmaxxing involves a guy with a hammer. He knows aura farming starts with cool guys not looking at explosions. And his little brother, a gym rat who can deadlift 500, once told him it's not B.O., it's musk. Kenda would like everyone to remember that hygiene is important.

Then Kenda admits...


Ep. 11: The "One Artist's Lyrics Raises Your Kid" Showdown
Ep. 11: The "One Artist's Lyrics Raises Your Kid" Showdown episode artwork
#11
10/02/2026

Somebody in the comments told Kenda to give up on Kylen. It is Kylen's favorite comment, and he agrees with the guy.

From there they get onto what people owe each other. Kenda has a friend in her fifties with no spouse, no kids and a life full of joy, and she is resentful anyway. That takes them through taxes, maternity leave and why it takes everybody to make a society run. Kylen thinks nobody is teaching people how any of it works.

Then Kenda brings up something Kylen said the other day about liking...


Ep. 10: Growing Up Poor and Still Feeling Broke After Making Money
Ep. 10: Growing Up Poor and Still Feeling Broke After Making Money episode artwork
#10
09/25/2026

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...


Ep. 9: Success Is Not Winning (And He Coaches For A Living)
Ep. 9: Success Is Not Winning (And He Coaches For A Living) episode artwork
#9
09/18/2026

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 rather than the point...


Ep. 8: He Was Ranked Number One In The Country And Living In A Toyota
Ep. 8: He Was Ranked Number One In The Country And Living In A Toyota episode artwork
#8
09/11/2026

β€œNo 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 β€” they called it the fart tube β€” and woke at 6am to compete with other homeless people for bathroom rights before going out to compete for real.

It cost him the re...


Ep. 7: Rick Rubin Says Everything Is Creative (Even This, Apparently)
Ep. 7: Rick Rubin Says Everything Is Creative (Even This, Apparently) episode artwork
#7
09/01/2026

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. Kenda thinks perseverance is a muscle, and that most people quit...


Ep. 6: The Algorithm Finally Picked Someone Good (And He Logged Off)
Ep. 6: The Algorithm Finally Picked Someone Good (And He Logged Off) episode artwork
#6
08/27/2026

Kylen and Kenda put themselves on a full digital detox β€” no video games, no social media, bed by ten β€” 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 β€” the 16-year-old son of Kenda's best f...


Ep. 5: A Therapist Called Out My Personality as a Strategy
Ep. 5: A Therapist Called Out My Personality as a Strategy episode artwork
#5
07/31/2026

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 her long enough that she...


Ep. 4: Social Media Almost Made Me Cash Out a 401k I Don't Have
Ep. 4: Social Media Almost Made Me Cash Out a 401k I Don't Have episode artwork
#4
07/24/2026

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 β€” what a 401k actually does, compounding, the 59Β½ rule, APR β€” 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 benefits from a broken economy, boomers vs "lazy bones," and whether the doom is real or just your algorithm marketing you a...


Ep. 3: Should a Grown Adult Still Blame Their Parents?
Ep. 3: Should a Grown Adult Still Blame Their Parents? episode artwork
#3
07/16/2026

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 β€” rock, paper, scissors, winner takes the title. 'I'm the mentor now. You'll learn.'

Underneath the bit is the real episode. Kylen uses comedy the way some people use a security blanket, and this we...


Ep. 2: If You Need to Prove Yourself in Every Room, Listen to This
Ep. 2: If You Need to Prove Yourself in Every Room, Listen to This episode artwork
#2
07/09/2026

Kenda's back from a week of chasing the World Cup with her family β€” three matches, three stadiums β€” 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 as easily tip into a riot.

From there it goes wher...


Ep. 1: The Podcast About Why Your Generation Feels Alone
Ep. 1: The Podcast About Why Your Generation Feels Alone episode artwork
#1
07/02/2026

Welcome to The Kylen and Kenda Show β€” 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 an infection that started in his teeth and was creeping toward hi...