The Kylen and Kenda Show

Saint Kay Media
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  • Comedy Interviews

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.

Episodes

  1. 3d ago

    The Algorithm Finally Picked Someone Good (And He Logged Off)

    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 — the 16-year-old son of Kenda's best friend, a junior lifeguard who pulled another kid out of heavy surf. It went viral enough that the White House commented on it. He missed most of that, because he is not on social media. "That wasn't even the hardest save I had that day." Plus family dinners, whether children are tyrannical or just looking for the edges, and a first date that ended in a cold-sore panic attack. 0:00 Social media has become the Home Shopping Network 0:37 The experiment: a full digital detox, starting tonight 4:37 Reading Digital Minimalism together 5:45 It is not just the kids, look at us 6:21 The dinner party and the 16-year-old who never put her phone down 8:30 The rooftop in Marrakesh nobody looked at 11:11 Saying the uncomfortable thing out loud 13:13 Dad the channel clicker, and second screens while gaming 14:32 14,600 hours a year against the 10,000 it takes to master anything 16:54 The son studying in Spain, and what changed 21:21 Ryder pulled another kid out of the waves 23:15 On that job you cannot be on your phone 23:56 Junior lifeguards, and pushing through the fever 25:31 He has no social media, so he missed his own story 27:47 Ninety days on a boat and what it might teach 29:14 Family dinners as the actual intervention 31:22 Parenting, boundaries, and whether children are tyrannical 34:50 The viral clip of the dad and the crying kids 37:44 The date, the cold sore and the panic attack 41:53 "I am reformed" 43:10 Two weeks without a phone 49:50 Everybody is just selling you something The Kylen and Kenda Show.

  2. Jul 31

    A Therapist Called Out My Personality as a Strategy

    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 stops listening, and says so out loud. The turn comes when he brags about jokingly threatening to fight his boss's mother, and adds that she laughed. She is sitting right there. She did not laugh. CHAPTERS0:00 Getting set up1:10 Meet Ann Whittington, psychotherapist of 35 years1:56 "You need tools" / "What boundaries?"3:05 Do bad tattoos count?4:03 Every single red flag there is6:45 It doesn't sound like play, it sounds like strategy7:37 Humour as a defence mechanism11:22 Rearranging the furniture15:14 Playing devil's advocate19:12 Are you arguing or are you learning?19:55 Am I attacking you?20:22 "I'm a very spastic person"22:35 Knowing when you're triggered29:49 Still the scared little child33:47 "I feel like I'm checking out"34:15 Talking at someone instead of with them40:25 Defence mechanisms are your talents42:52 The boss's mom story44:25 "I don't have boundaries. I have yours."46:12 Don't send the comedian out every time48:45 Six foot six, and read as a threat49:41 The six-foot-six elf59:22 Forgiveness is a natural flower of understanding The Kylen and Kenda Show — a mentor and a mentee, arguing their way toward something useful.

  3. Jul 24

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

    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 benefits from a broken economy, boomers vs "lazy bones," and whether the doom is real or just your algorithm marketing you an apocalypse. Kenda answers with agency — the MBA she got with no bachelor's, "if you don't ask, they can't say no" — and Kylen keeps naming the darkness until she's in tears. Then he flips the mentorship on its head with the line the whole episode was building to: the only thing you can see in absolute darkness is light. Chapters:0:00 Cold open: suit roast + trailer teasers2:37 The 401k confession5:04 401k 101: compounding, 59½, penalties8:16 Credit cards, APR, and the organ-selling riff10:35 Kylen's counter-philosophy: bet on yourself12:10 Kenda's priorities lecture: diversify, then decide16:24 Survival mode: the fridge situation21:00 Victimhood vs. stomaching the bullshit24:54 The cost of becoming anything: nursing, debt, $1,000 crutches28:27 Who benefits from a broken system32:17 Generational blame: 'their eyeballs work'35:53 Vitamins vs. the virus: complacency and radical transparency40:13 The manosphere experiment & chicken-or-egg43:25 Apocalyptic, or amplified?46:14 Power, choices, and showing up50:45 Kenda's tears & the ref is like the weather55:53 'Be realistic' is a trap59:47 MBA without a bachelor's: 'watch me'1:04:41 Personal vs. societal: the Camino gift1:08:52 'Show me how it affects you' + Mandela's light1:14:45 Finale: light in absolute darkness 🎙 The Kylen and Kenda Show

  4. Jul 16

    Should a Grown Adult Still Blame Their Parents?

    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 real episode. Kylen uses comedy the way some people use a security blanket, and this week he says it out loud: 'I'm like a mix between a golden retriever and a clown' — every charming, loud, look-at-me thing he does traced straight back to a lonely kid who just didn't want to get sent home. We also get the origin story for all of it: the week young Kylen was dead certain his Nintendo was haunted, right up until Dad explained it wasn't a ghost — it was a divorce and an airborne pan of marinara sauce. Somewhere in there we cross-examine a 10-year-old's 'you suck,' relitigate an apostrophe Kylen swears he'll remember until he dies, argue about whether pain is the only teacher that ever actually works, and debate whether comedy just got too smart for its own good. It's the usual: two people using jokes to sneak up on the truth, then getting caught in the act. Come for the mentor battle, stay for the accidental honesty. The Kylen and Kenda Show is a mentor and a mentee figuring out ego, insecurity, and connection one conversation at a time. New episode every week. Chapters:0:00 Cold open: take your vitamins3:19 'Do you want me to mentor you?'3:50 Cross-examining a 10-year-old's 'you suck'8:10 The bimbo incident (and the case for fear)14:32 'I remember the apostrophe'20:07 The haunted Nintendo25:22 Why pain is the only teacher40:40 Golden retriever and a clown42:51 In defense of the Neanderthal47:19 Has comedy gotten too smart?54:01 The mentor battle: rock, paper, scissors 🎙 The Kylen and Kenda Show

  5. Jul 9

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

    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 as easily tip into a riot. From there it goes where it always goes on this show. Kylen reframes the phone debate ('what have you designed your phone to be a vector of?'), we make the case for feeling small but not insignificant, and then dating gets serious: Kenda opens up about the emotionally abusive relationship she was in at 19 with a man ten years older — and the deliberate restraint of her therapist mom, who stayed quiet so she could stay close. Kylen owns his side too: the cigarettes, the leather-jacket logic, the bully-baiting — all the same move of trying to prove a value he didn't feel. We land on the question Kenda asks everyone she loves: do you want to be right, or do you want to get along? Plus a hotboxed Police concert, a bathroom-stall nacho story we apologize for in advance, and Kylen's confession that he can read people perfectly — and has been using it all wrong. The Kylen and Kenda Show is a mentor and a mentee figuring out ego, insecurity, and connection one conversation at a time. New episode every week. Chapters: 0:00 — Cold open 1:02 — Back from a week of World Cup crowds 3:35 — Collective effervescence: why crowds feel magical 9:18 — What have you designed your phone to be a vector of? 19:25 — Small but not insignificant 24:52 — Dating, values alignment, and red flags 31:30 — Laughter as the marriage repair tool 42:17 — Why proving your worth pushes people away 49:55 — Where insecurity originates 58:19 — Do you want to be right or get along? 1:01:29 — A confession about reading people

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

  6. Jul 2

    The Podcast About Why Your Generation Feels Alone

    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 an infection that started in his teeth and was creeping toward his brain. Edgy, funny, and unfiltered — this is the conversation that launched the show. This is the origin episode. Kylen and Kenda lay out the whole reason they're doing this: a phone-addicted, lonely generation that's struggling with technology, late partnerships, hard-to-find jobs, and a quiet inability to connect. Their mission is simple and stubborn — get people back to real community, real dialogue, and the social skills nobody seems to teach anymore. Along the way they get into the near-death tooth story (eight childbirths' worth of pain, apparently), why fighting is wrong but so much fun, and the difference between curiosity and confrontation. You'll also hear the honest mentor/mentee tension underneath all the jokes. Kenda's line says it all: "I don't have to mentor you... you are not an easy person, and every day I choose it." They dig into red flags versus "the ick," what's actually worth suffering through in a relationship, and why teaching kids real psychology matters before they learn the wrong kind. So pull up a chair, you little voyeur. New episodes drop here — hit subscribe and come build something better than another night alone with your phone. Chapters: 0:00 Cold open — "I live in a shed. Peter Pan complex." 1:23 Who Kenda is + her hope: community without phones 4:01 Self-aware but still an infant (road rage, control) 8:42 The fight code & mental toughness 13:54 Kylen almost died from a toothache 20:14 Why "show me the research" really means trust 30:00 Why this generation feels so alone 35:21 Real red flags vs. the "ick" 43:24 Wrap — the origin story 🎙 The Kylen and Kenda Show

    The Podcast About Why Your Generation Feels Alone
  • 6 Episodes

About

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.

Information

  • Creator
    Saint Kay Media
  • Years Active
    2026
  • Episodes
    6
  • Rating
    Explicit
  • Copyright
    © Copyright 2026 Saint Kay Media
  • Show Website
    The Kylen and Kenda Show