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LET IT OUT

Fear Calcifying, Not Aging ft. Smiling Strange

LET IT OUT

Katie Dalebout

Health, Well Being, Fashion & Beauty, True Crime, Mental Health, Arts, Wellness, Self-help, Self-care, Love, Personal Growth, Katie Dalebout, Health & Fitness, Society & Culture

4.8831 Ratings

🗓️ 25 April 2026

⏱️ 81 minutes

🧾️ Download transcript

Summary

This week I spoke with Kyle (Smiling Strange) about generations, the internet then vs. now, and how we discover music as we grow up. We talk about his process of making videos while walking around his neighborhood, why authenticity cuts through the algorithm, and how culture is shifting faster than we can keep up. It’s an eclectic conversation that moves from music to the internet to creativity to philosophy (and even economics), and it left me with a lot to ponder.

Transcript

Click on a timestamp to play from that location

0:00.0

I don't mind being older. I don't even mind the fact that my back hurts and my knees

0:09.8

kind of hurt and stuff like that. Like, I don't mind go to bed early because it's whatever. That's fine.

0:14.7

I would mind if I got to the point where I calcified so much that I wasn't open to new, beautiful, true things or something like that. That's the thing that I feel like young people don't have to do that because it's all new. But like as you get older, you do have to fight against like, you know, I'm thinking like, man, I didn't like reggae when I was 22. Maybe 22 year old me was wrong. Let's give it another shot.

0:38.3

And trying to listen to it like a new person that doesn't have all this other baggage.

0:42.1

It's impossible to do, but you've got to try because the second you stop trying, it all calcifies

0:47.3

real fast. And that's what I'm really trying to avoid.

0:52.0

Okay. Hi. Hello, how's it going?

0:55.8

I hope you're doing well.

0:57.7

It's good to talk to you.

1:01.1

I'm back with another episode of this podcast.

1:05.3

So this week I spoke to Smiling Strange, also known as Kyle.

1:10.2

You probably know makes these videos where he's walking and talking,

1:13.6

and they are really conversational,

1:16.6

and it felt like this week we were on a long walk together, talking.

1:23.6

And we cover a lot of ground on this walk.

1:28.2

He's a musician, and a lot of his videos are about music.

1:31.8

And he also co-hosts this podcast that I listen to a bunch of episodes of,

1:36.9

and he has a great co-host, and they're really fun to listen to.

1:42.4

And he's really an interesting guy who's super smart and fun to talk to

1:48.2

which you'll hear in a second yeah we really get into a you know a lot of areas here we talk about

1:54.3

music discovery and developing taste and not calcifying and know, the taste musically and otherwise from when we

2:03.3

were younger and generational shifts, millennials, Gen Z, Gen Alpha, and some differences.

...

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