
Loading summary
Sam
Have you been dumped by a massive wave?
Kyle
Absolutely. Yeah. No, I think that that's just, that's part of it. And when you're getting into surfing bigger and bigger waves, you're not really training for big wave surfing. You're training for big wave falling.
Sam
For anybody who is not a surfer, seeing somebody get dragged out by a jet ski into a 70 foot wave, it's like 50, 50 chance you survive.
Kyle
I was learning how to kite surf. The way that kite surfing works is that the, when you pull on the kite, that's what powers it up. Put the kite up and all of a sudden I feel the wind just take it. And instead of letting go, I hold on and I get taken on the beach 20ft up and slammed down on the sand right next to this rock quarry. Snapped my right arm, like, radius ulna. I'm like, oh, like, come back up. You know, blood on my face. Have to like, wash off in the ocean. I thought that was very close to me dying, because if that kite had taken me right into the rock quarry, which I was maybe 10ft from, I probably would have died.
Sam
An entrepreneur straight out of New York City. Michael Chernow, what's cracking? So you are a lot of things. You're a podcast host, you're an author, you're a journalist, and you're a big wave surfer. And prior to the cameras rolling, I also found out that you're a birder.
Kyle
Yes. You're, you're, you're a hunter, a new birder.
Sam
So, like, if you had to, if you had to pick out what inspires you the most or what you love doing the most, like, if you could choose one thing that it would just be all you did. What do you, right now in your, in your life, what would it be?
Kyle
Writing. Writing, yeah, writing. Because writing allows me to turn the chaos of my life into stories and sort of serves as this device to make sense of how I think about things. And I find that incredibly comforting in a world of just fire hose information and chaos and me feeling like I need to make up opinions about things, but not really knowing if, like, I don't know what I think about that. Like, this is crazy. So writing allows me to sit with an idea long enough to find layers of it, and very rarely do we get to have that luxury. Like, we are informational grazers as a culture, and writing is a really good antidote to that.
Sam
Have you always been a writer? Like, did you keep a diary as a kid?
Kyle
I didn't. Yeah. Was like in love with vice journalists. Growing up, I thought that was like the coolest thing. So those guys made journalism cool to me. You know, you could go report an environmental story and make it badass like that was. I came up at a time when I had those models, but it really wasn't until I was in my early 20s. I was living this old surf shack in Santa Cruz, California with a buddy of mine who had just started a local surf magazine. And we were talking on my couch about how in Santa Cruz, it's surfing is like, it's like Texas football, you know, it's like just, you just do that thing. It's like highest status people are the ones that surf and surf big waves and like people will invest a huge amount of their life in get into getting good at this one thing. And, and we were observing that a lot of them were going to be left high and dry at 30, because you really don't learn many other skills when all you're doing is surfing twice a day. And he's like, you should pitch that as a story from a magazine. And I ended up writing a story called the End of the Ride. Is Pro Surfing a dead end Career? And I remember that experience being formative for me because it was really frightening to do. And I felt like I could only achieve that tightrope walk of showing love for my peers while also showing some concern for this career path through the precision of the written word. And that's what really got me addicted to that thing of saying exactly what you mean and thinking deeply about one subject.
Sam
Is that truth that after 30, if all you've been doing since you were a kid is surfing and you're gunning for this like pro surf status, has that been sort of, is that like brought to fruition for in most cases that after 30 it's kind of just over and then you kind of end up being left in the dust?
Kyle
Well, I think this, the smart pro surfers will recognize that they are a marketing vehicle for companies and that gives them an inside look into how marketing works. So that's one pivot that pro athletes can make. They kind of understand, well, okay, this is the game and I'm part of the game and I can transition out of it. I think a lot of them, it's easy to just expect that a paycheck will come from you going and riding good waves. And throughout the decade of what you're doing in your 20s, that's when a lot of people grow professionally. There's a great book called the Defining Decade by a woman named Meg J and she has a line in it where she said, as we age, we start to feel less like leaves and more like trees. So the throughout our 20s, I think that that's when we can learn skills that can really set us ahead, kind
Sam
of, but kind of like, I'm just thinking about that as we age, we're less like leaves and more like trees, meaning we shed less. And it's more about like, we build our core in our 20s and the trunk of our life kind of begins to take shape.
Kyle
We build throughout our 20s, into our 30s, we build our adult personalities and we build a lot of those habits that can stick with us throughout the rest of our lives. And change is possible, as I'm sure you can attest to. But I think that it gets harder. So I think that while pro surfing can be an incredible career to see the world, just recognizing which careers do have an end date and thinking ahead about what you're going to do after that is at least a worthy thing to consider while you're in it. So that was what that article was about. And since then I've written hundreds of articles. And now my first book. But that was. I felt like the only way I could bring that conversation to the community.
Sam
How was it received?
Kyle
I mean, I had moms pull me aside and be like, thanks for writing that article. That was really cool of you to do that. And yeah, and I think that I'm probably better on the page than I am here in some ways. I can leverage more of my personality on the page and be funnier and be darker. So I really enjoy playing with that aspect of my personality in the written word.
Sam
In your writing, are you hand you like pen to paper?
Kyle
I did this morning. If I'm having a hard time getting words on a page, I go pen to paper. Because one of the worst habits you can have as a writer is having your editor mind on while having your creative mind on. It's important to have both, but you don't want them at the same time. It's like putting one foot on the gas and the other on the brake at the same time. So to think through what kind of session it's going to be prior to writing can be really helpful to get words out. So for me, as a first draft is really just the shit draft. It's about putting as many words down on a page as possible. And oftentimes that's better longhand. Not always, but I like doing that. And then I will transfer it to a computer and. And then go from there.
Sam
You know, it's like, it's. We're in a very. Well, definitely an unprecedented time in history. Right. Where like, people will say, I read this book and they, they listened to the book, they didn't read the book. Right. Like, you know, I, I read, I read, blah, blah, blah. And not that there's anything wrong with audible or audiobooks, but like, you know, so for me, I have. Journaling has been something that I've loved to do. Like, I know for sure. Unfortunately, it's the one habit that I have historically been touch and go with over the years, but also the one habit that I know when I'm doing consistently, I'm just a better version of myself. And like in. Just in, in. In all ways because it, it. I typically when I journal also, I'm like when I'm on a daily journal, when I'm in a daily journal, sort of run. I'm also writing out my day, which has been very helpful for me. But I will say that because I've been so touch and go with it over the years, I'll go six months on, three, four, five, six months off. I have started audio journaling, which has been really nice because I do it when I drive to work in the morning. It's like a 20 minutes chunk of time that I'm able to actually just like talk and like get things off my chest.
Kyle
Do you use voice memos or like audio.
Sam
No, I use. I use an app called Day One.
Kyle
Okay.
Sam
And it's a, it's basically a really great audio journal that like actually will it, doesn't it? You know, like when you're talking out loud, there's like a lot of ums and it'll cut it out,
Kyle
make you sound like you want to talk.
Sam
Yeah. Like when you go look at it. Yeah.
Kyle
Yeah. I'm doing pretty well here. Yeah. That's so funny. Yeah, that's great. I, I also use audio when I'm reporting. So I think one of the big misconceptions of like, what is, what does it mean to be a writer? What is the act of writing? People think that you just sit down at your computer or you have an open journal and just like, it's going to flow out. And here's the story. If writing is hard for you, if you're having a hard time getting words on a page, it means that you're not reporting adequately. Writing is the act of taking what's out here, distilling it down and distilling it down. And professional reporters and even people who are who just want to become clearer thinkers are doing what you're doing, right? You're journaling about something that's happening in the world. And then maybe if you've got a book in you, you can take all those journals and those insights and turn them into something that is readable. Right? That's also. That's what comedians often do, right? They'll have an insight like, hey, you ever notice this is interesting about the world? And they'll say it into an audio recorder and then they'll figure out the exact words to turn it into a bit. But the reporting aspect of writing is what so many people miss. And then they, they just try and sit down and write and they're like, ah, it's not coming. I must not be a writer. I remember listening to an interview where the. The great writer Sebastian Younger, who wrote the Perfect Storm Tribe, he said, if you're having a hard time putting words on a page, it means you're not reporting adequately. I have another friend who, he's written a number of bestsellers and he's working on a book right now about wingsuiting. And he spent the last year in research mode. So he's going out on trips with wingsuiters. He's reading the books about wing suiters. He hasn't even put pen to page yet because he knows that once he does all this reporting, it's going to make the act of writing the thing so much easier.
Sam
Well, it's also like just relying on your gut, right? Like, like really smart entrepreneurs typically have a balance between gut and data, right? Like, you can't make all educated decisions or you can't really make any, like, truly educated decisions based on gut alone. There needs to be data, right? So you've got to pull the data and then be able to lay it out in front of you with your intuition and then make a decision.
Kyle
Right.
Sam
You know, and so it sounds to me like that's, that's kind of like what. Because I like the way you broke that down. I think people probably don't really. Even when people are writing a nonfiction book, I mean, a fiction book, there's probably a lot of reporting that goes on.
Kyle
Absolutely, yeah. I mean, you're still drawing from something. The writer Elizabeth Gilbert, who's written a number of bestsellers, has a system where she will, even if she's doing research for a fiction book, have a stack of index cards, and on every index card there'll be one fact. So she wrote one book called City of Girls, and it's all about this group of promiscuous girls in New York, 1920s in theater world. So there's an incredible amount of research for that story that had to be done before she fictionalized it. And she was doing research on like feeder size in New York in the 1920s. And what kind of. So she would take these index cards, write down a fact on it, take another index card, write down one fact, and then a year later, once she's done with the research, she has a huge stack of index cards she gets to pull from them and that is where then she can draw the fiction.
Sam
So like she'll randomly pull a card and then it'll inspire something for her to.
Kyle
I think that she would, she would organize them so like, okay, here's the theater cards, here's what they would wear. But I'm amazed at how many prolific writers will will consciously try and dial down the technology that they use and go analog as a productivity hack.
Sam
Interrupting this episode to share with you that Creatures of Habit finally launched our protein bar. It's called the Daily Bar. It's made with 20 grams of plant based protein, 3 grams of creatine. Yes, you heard that right. It also has 3 grams of creatine. It is incredibly tasty and clean as a whistle. All clean ingredients. Take this opportunity. Hop over to creaturesofhabit.com that's creaturesofhabit.com with a K and and use code K O H P O D20 at checkout for 20% off your first order. Back to the pod. I wanted to take a minute to thank one of our sponsors, Caraway Home. I love caraway. I've converted my whole entire kitchen to caraway. All of my cookware, all of my food storage, my cutting boards, my knives, my utensils, everything is caraway. They are third party tested and it is a clean cookware, clean kitchenware brand that I am 100% in alignment with. Mother's Day is around the corner. And flowers are awesome, roses are beautiful. We all know that to be true. But they don't last that long. And cookware does. If you are like me or if your mother is like me and cooks a lot, this would be an unbelievable gift to grant your mom. On one of the best days of the year, Mother's Day. There is an awesome Mother's Day sale if you use my code. So go to carawayhome.com churnow and you'll get 10% off. Treat your mom this year on Mother's Day and grab her an amazing cookware set. That's going to last forever. Give them the goods from Caraway. So I just want to touch on surfing for a bit because I, I think big, big wave surfing is so fascinating. Right. It's like, it's for anybody who is not a surfer, seeing somebody, you know, get dragged out by a jet ski into a 70 foot wave, it's like 50, 50 chance you survive. Right? Like, and, and for someone who knows nothing about.
Kyle
Sure, yeah, yeah, yeah. It's kind of, it's kind of like UFC where like, even if you know nothing about ufc, you can comprehend what it's like to get hit in the face. Like, I think that big wave surfing has that draw to non surfers because you're like, I don't know what's going on, but I feel it.
Sam
Like, what, have you been dumped by a massive wave?
Kyle
Absolutely. Yeah. No, I think that that's just, that's part of it. And when you're getting into surfing bigger and bigger waves, you're not really training for big wave surfing. You're training for big wave falling and whatever a big wave is. To you, there is this threshold of moving beyond your comfort zone into something that scares the shit out of you and figuring out how to manage your emotions through that experience. Where I grew up in Santa Cruz, we have one of the best, most renowned big waves in the world, called Mavericks, about an hour north, where the waves get to be 60, 70ft. You know, famously on a, on a big day at Mavericks, the Richter scale at Berkeley, which is about an hour and a half away, will register the movement of the crashing waves inland. Wow. So it's, I mean, it's very, it's, it's serious and it's, it's godlike and it's amazing. And the thing that I think is just so helpful about surfing big waves and do, and moving past what you think you can do is that it's a very transferable attitude into other aspects of life. Dealing with fear and having a more healthy relationship with it has been super helpful for me. I mean, I'm out in New York right now with my fiance. We're doing like a three month stint out here. And the two things that I've gotten really into and suck badly at are birding and the second is jiu jitsu. I've been going to jiu jitsu like five days a week and getting my ass handed to me. But the, the feeling of having like a sweaty brown belt just smother you and being like, okay, I need to think through this and not just panic is a totally transferable. Like the synapse that's happening there is the same synapse that happens that fires when you're, you know, 40ft underwater and it's black and you can't see anything. And you need to think like, okay, I'm going to be okay. I'm just going to think through this. I have enough air. Keep your arms in. You know, you don't want to blow out a rotator cuff. Okay. I'm feeling the pressure of the desire to breathe, so I feel the, the diaphragm spasm. Okay, is it time to pull an inflation vest? Is there. Was this the first wave of the set? Was it the second wave of the set? How do I, how am I doing right now? Physiologically, like having a very calm and logical conversation with yourself through that experience is the same thing that like people who are really good at jiu jitsu are having, right? You're, you're getting smothered, but you're just needing to think very calmly about what to do next.
Sam
Is there one experience from big wave surfing that stands out to you outside of riding your biggest wave?
Kyle
Yeah, I mean in terms of like a bad fall or something? Yeah. I, I remember being in Ireland with a buddy of mine and we were surfing this crazy slab out at the cliffs of Moher, which are like these famous 800 foot tall cliffs, beautiful tourist attraction. And the waves break off this boil and just turns into this massive barrel. And we were just out there alone. So part of, you know, the danger of surfing big waves is just like, okay, what kind of safety do you have? Or are you just there, the two of you? And on that day it was just the two of us. And at this particular spot, if you don't nail where you can, can come in, right, like if you. There, there's a very narrow zone of, of where you can make it out and in. You'll get swept down to this cliff where the waves are basically just breaking against this cliff at high tide and you're screwed. And we've been out there for like three hours. I got one in and as I was paddling in, a really big set came, I got flogged on the first one and my, my calf cramped. So I've, I don't know if you ever experienced calf cramp, but they're debilitating. I mean, like, you feel like you've just broken like your broken leg. Yeah. You're like, I cannot move right now. And so I remember just massaging my calf massaging my calf, there's more waves coming. And you just, you know in those moments you're thinking about your breath, right? Because you know that if you're, if you continue breathing, you continue taking deep breaths, slow, calm, deep breaths, you're not going to pass out, right? You just don't want to pass out. So as much as you can in those moments, just focus on breathing. Slow, controlled, inhale, exhale, deep breath in. Get flogged by another one. And I mean, there was like a 20 minute soup that I was in there and just looking up at this foreign land thinking, this is a very alone moment right now. And thankfully, finally the set subsided and I came in and was able to make it up the rocks. But I remember just thinking like, that was closer than I wanted it to be. But also I was able to stay calm the whole time. And that is the result of training in a bunch of other circumstances so that you don't freak out in that
Sam
moment, you know, I love that you say that. And it reminds me of, of a podcast episode that we recorded last month. Actually came out yesterday with a mentor of mine, this guy, Marcus Antebi. And he was the guy that kind of came into my life at the right time and really pulled me out of the darkness and helped me find the light. And his advice to me at this stage in my life and in my sobriety, he was like, everything boils down to the breath. Everything. Like, if you are able to switch on focus and breath specifically together, right? Like focusing on your breath in times of chaos or in times of anxiety or stress, you're able, like you are truly able to survive any and all of it. And he was so right for me. And, and that's something that I've been paying a lot of attention to over the last three years. Is this breath? Do you have breath work? Like, is breath work a part of your life?
Kyle
Oh, yeah, I love it. Getting, getting. It's, it's the best drug out there, man.
Sam
Tell me about what kind of breath you, you, you practice.
Kyle
Yeah, well, I've done various training courses where you learn how to hold your breath for a really long time. And those are contained situations where you'll either do pool breath holds, static apnea is one. Another is where you're diving down in the ocean on a line. There's a really great course that they do out at Catalina island near LA, where they'll drop a line 70ft down and you'll climb a line down with instructors. And the whole deal with holding your breath is Getting comfortable with diaphragm spasms and not immediately thinking that you're going to die right when that first diaphragm spasm occurs and recognizing that you're maybe a quarter of the way through to the point of passing out when that first one happens. So that was really, when I first got into it, was just taking these courses. Since then, one of my favorite things to do is spearfish. That was a bit more of my, my speed rather than what free divers do, which is just to like, I'm gonna go as deep as possible and try not to die. Spearfishing, you actually get to come home with a meal. And it's, it's a lot like hunting where you are in, in California. You're in kelp forests, you're looking for habitat, you're looking for structure. You dive down, you hold onto a rock, you wait for, you know, a rockfish or a lingcod to, to swim by. And that also is very much tied to the breath. Right. The longer the breath hold, the, the greater the chance you are you're going to have of, of success. So that's been really, I mean, I love activities where it doesn't feel like work, but you're getting better at a thing and maybe even come home with rockfish tacos. But yeah, the last few years, I would say spearfishing has been the primary form of, of increasing my breath capacity. And then beyond that, man, I, I feel like I tend to wake up without much energy. Like I'm just groggy and slow in the morning. And if I don't exercise or do something pretty intense, I stay groggy for the rest of the day. So often if I'm going to meditate, I will do a five minutes of breath work just to get into the meditation and wake myself up a little bit. And then I find I can do.
Sam
What kind of breath work do you do to kick it off?
Kyle
I will do like just the Wim Hof style breathing very hard for 60 counts, exhale until I need to take a big breath in. Take a big breath in and, and do that like for three rounds. But I find that, that gets, that gets the day going for me pretty well. Yeah.
Sam
Have you ever done anything like rebirthing or hydro? What's it called? Rebirthing. Breath is what I have been doing, but there's also. Oh God, I'm, I'm space.
Kyle
What is rebirthing?
Sam
So rebirthing is. It's basically an hour long sit with breath and you ease into it through just like a guided kind of meditation. And then you begin the breathing. And the breathing is about a half an hour straight of all mouth breathing in through the. Into the nose, into the mouth, but you breathe into the belly, into the chest, out through the mouth, into the belly, into the chest, out to the mouth. So it's like. And you just do that for 30 minutes. And that is hands down, bar none, without a question of a doubt, the most powerful therapy I've ever experienced in my life. The breakthroughs that you experience or that I have experienced through those breathwork sessions are just enormous. Like, you are catapulted into a new dimension when you do that. And it happens like, within the first. They call it dropping in. So I typically drop in within five to seven minutes, and it's a full somatic experience. So, like, you're. I feel my sort of core. My torso starts to feel, like, numb. My arms begin to tangle. My hands actually, like, curl in.
Kyle
Yeah, Tetany, that's called. Yeah, yeah.
Sam
There they call like, the lobster.
Kyle
Yeah, yeah, yeah.
Sam
And. And your. Your. Your. Your mind just sort of goes into these very, very, very deeply. Sort of. I feel like, for me, it's been the only way to unearth the nooks and crannies of my.
Kyle
Yeah, yeah. It takes you there pretty fast.
Sam
Fast.
Kyle
I got a funny story about that. I hadn't thought of it since you just said this, but I remember, man, maybe like seven years ago, I went down to Costa Rica to a retreat to try ayahuasca. And I'd never done ayahuasca before and was really preparing for this ceremony and wanted to. To really do it right. And the day before the ayahuasca ceremony, there was a breath work teacher at this retreat, and there was a big session, and it was. It was me and. And a bunch of. And then like, four other women who were pretty out there, like, pretty out there ladies. And I was, you know, I kind of look like a regular, you know, blonde, athletic dude. And before the session, the teacher was like, does anyone need to, you know, speak or. Or talk about any worries they have? And this one girl was like, I'm. I. This is uncomfortable for me to say, but I'm kind of afraid that, like, the guy here is going to be, like, judging me and us and like, you know, I just don't know that he's kind of from our world. And I'm like, hey, like, I get it. I mean, you're judging the way I look, but, like, I'm here for the ride, you know, Like, I hope you don't feel judged by me. Anyway. We all lay down on these mats. You know, you're in the jungle, there's like, the buzzing, you know, mosquitoes and insects outside. And within, like, 20 minutes, my hands are in that tetany form, and I'm sobbing and screaming in this fetal position. And all the girls are, like, pretty calm, not doing anything. And we, like, get to the finish. I'd never done anything like that before. And the teacher was like, all right, Kyle, like, sounds like you had a real experience there. And it's like, yeah, I don't think you need to worry about me judging you, like. And then the next night, we did ayahuasca, and it, like, didn't do anything for me. I was like, I went to Costa Rica to do that breathwork session.
Sam
You had the breath?
Kyle
Yeah, yeah. The ayahuasca was like the afterthought. So.
Sam
So funny, man. I have a very similar experience. So my first experience I did been. I had been doing in the beginning of the pandemic, I think, like a lot of people, I started doing Wim Hof breath work, right? And I would do Wim Hof with my friend every morning at 7:30. We'd. We'd hop on a zoom and we would do Wim Hof. Yeah. And we were, like, challenging each other. It was like two kind of type A guys, like, trying to hold their breath as long as they can, basically. And, like, to, like, the point of, like, you know, I'd, like, hold my breath for like, three, three and a half minutes, and I wouldn't hear John, and I'm like, is he pass out?
Kyle
Yeah.
Sam
You know, But I went to this running event in rural Georgia like, three years ago, and I get there, one of the greatest events I've ever been to in my life, quite frankly. Really cool event called Running Man. But my buddy who invited me down was like, hey, do you want to go do breath work? And I'm like, hell, yeah. Like, I'm thinking breath work, like, you know, Wim Hof or box breathing or something like that. Like, I just didn't know. Yeah, I just didn't know. And so I get there and I meet this guy, Michael Gazo, who has now become a very good friend of mine and my breath work coach and a guy who I host a men's retreat with every year. And. But I had met him for the first time, and he was like, all right, so, you know, we're gonna. We're gonna do this breath work. It was like 15, 20 people there. He's like, do you have experience with breathwork? And I'm like, yeah, yeah, yeah, look at me, bro.
Kyle
Yeah, come on.
Sam
And he's like, look at this lung
Kyle
capacity, you know, to Max, bro. It's my middle name.
Sam
He's like, what kind of breath work have you done? And I was like, oh, Wim Hof, you know, like, I'm, you know, I'm, I'm doing. He's like, okay. He's like, so this is going to be very different. He's like, I'm just going to ask you to just follow along. Just listen to my voice and close your eyes. I'm going to put a blindfold over your, your eyes and, and just, just, just follow along. And so similarly to you, yeah, I'm doing the breath and I'm going for it. Cause I'm like, I'm getting.
Kyle
Yeah, I'm gonna win. I'm gonna win. I'm gonna get first place in this.
Sam
Totally. And before I knew it, I was in this like, crazy place. But so I, I didn't. He didn't say that there was gonna be any physical component to this. Like, I had no idea. My heart is racing. I feel like I'm gon 10 minutes in, I like shoot up and I'm like, I'm dying. I gotta call the ambulance. And he runs over to me. He's like, relax. He's like, lie back down. Slow. Slow down. He's like, this is only breath. Like, this is only oxygen. You have nothing to worry about. Just, just take a breath. Literally. And then he's like, I want you to think of the people you love most. He's like, do you. Are you in a relationship? I was like, yeah, I'm married. He's like, okay. He's like, do you have kids? He's like, yeah. I was like, yeah, I have kids. And he's like, I want you to think about your wife and your children and I want you to continue breathing. And he's like, you don't have to breathe as hard as you were breathing. He's like, you could slow it down, but I want you to continue breathing. And so I did. And within two to three minutes, I fell into the most euphoric, blissful place I could say I had been to at that point in my life to date. Because what he did for me was he allowed me to see love. And I felt this unbelievable wave and warmth. If you could, if you could, if you were able to feel like full body experience what love would feel like I had that experience, like, it felt like somebody took a blanket, picked it up over me and like dropped it on me. And that blanket was love. And I just couldn't, I didn't know what to do with it, but it was, I exploded with tears because I was like, oh my God, this is what it is.
Kyle
So, so beautiful, dude.
Sam
It was just unbelievable. It was crazy. Now I've had many, many breath work experiences in that style of breath from then on that have been crazy scary.
Kyle
Yeah.
Sam
You know, just like walked me into like meeting myself as a 7 year old kid in total fear, frozen in fear, trying to like talk to that child and be like, it's okay, it's okay not being able to move that child. You know, like really wild stuff I've had in these breathwork experiences. I have no idea how we ended up on this topic.
Kyle
Yeah, no, it's, it takes, it's, it's so strange how a breathworks session will, I think similarly to a writing session, it can unearth memories that you didn't know you had. You know, a lot of people, they, you know, the act of writing is a lot like the act of improv where you don't know what's going to happen until you get on stage. And similarly with writing, you don't really. You have an idea of what's going to come. But through that session, all of a sudden you're breaking apart the history of your life and all that's in there to a degree that is very difficult to do when you're just on this surface level plane of moving forward in Costa Rica. I've never actually told this story, but during that breathwork session where I'm sobbing in the fetal position, about two years prior, I was learning how to kite surface. I was kind of like new to the sport and it was really windy day. I was, I was, you know, I was given this instructor who was like, oh, you're, you know, a surfer. Like, we can take you out, we'll give you the big kite. Day two of this thing, I'm on the beach and the way that kite surfing works, I didn't really even understand this, is that when you pull on the kite, that's what powers it up, right? So it's a super windy day and we put the kite up and all of a sudden I feel the wind just take it and instead of letting go, I hold on and I get taken on the beach 20ft up and slammed down on the sand right next to this rock quarry. Snapped my right arm, like radius Ulna, I'm like, oh, like come back up. You know, blood on my face, have to like wash off in the ocean, get taken to the hospital. I mean, and it was, I've gotten injured plenty of times before. That's really the only time that I have. I thought that was very close to me dying because if that kite had taken me right into the rock quarry, which I was maybe 10ft from, I probably would have died. And although the injury had healed, I hadn't really gone through what it was like and relive the experience until the breathwork session. And when I started breathing hard, it took me right back to being in the air on this kite. Like, like, oh my. And I, I remember just like shaking my hands out, just like shaking all this out and they're like. And then the coach was like, are you okay? Like, what's going on? I was like, I just got taken back to this near death experience that I had that I did not know. Like, I still need to work through, but clearly I did.
Sam
Wow. Yeah, that is powerful. And I think what they say with breath work, when you activate that way, that intensely, the, you release dmt.
Kyle
Yeah.
Sam
And the only time when the brain really releases DMT is right before you die. Yeah. Right. So like it's a very powerful substance and chemical. You know, like people smoke 5am Meo DMT to have these like outer body experiences. And so, you know, it's very, very interesting that the breath can do that. And so anybody that's listening to this, it would be, it's, it's, it's, it's been an incredible journey for me and it sounds like it's also been for you. I'm so, I'm, I'm. It's, it's interesting for you to have the juxtaposition of doing a breathwork session one day and then the next day doing ayahuasca. And like everybody would imagine ayahuasca would be the thing.
Kyle
Yeah, that's the sexy one.
Sam
Right. And so the ayahuasca journey was not it. Was that the only time you did it?
Kyle
No, I've done it a number of times and have had, had good trips, but that one didn't do much for me. I've done psychedelics, you know, quite a lot. I've, I've talked with a lot of the psychedelic luminaries on my podcast. I think it can be incredibly helpful for some people. And one of, I think one of the best aspects of, of what's happening in modernity right now is that More people are decoupling psychedelics from addictive substances. Like, just the broader banner of Reagan era drugs is no longer really a thing, you know, like. And I think that podcasting is largely responsible for some of those more nuanced conversations. I also love the Alan Watts quote, when you get the message, hang up the phone. And I don't really feel the need to. To get blasted into the cosmos these days. So I don't really take psychedelics that much anymore.
Sam
I love that because I feel like a lot of the figureheads that have been talking a lot about psychedelics over the last decade tend to be those that are using it often. Yeah, right. And I think, you know, me being a sober guy for a long time, but also wanting to see the benefits, the potential benefits that I've been reading so much about in terms of the science behind how psychedelics can help with trauma.
Kyle
Yeah.
Sam
And neural pathways and negative feedback cycles and things like that. You know, I see some of these, some of these people that have been really sort of talking about it a lot and I'm like, yeah, but they're like doing it all the time. Yeah. They're like, they're like going to the jungle. Like, they're lit. They like, they like move down to the jungle.
Kyle
Yeah.
Sam
You know what I mean? Like, they live in the jungle. Right. And it's like, so, you know, I.
Kyle
It can be very dangerous to attach your identity to psychedelics. The second you start to feel like you're more interesting because you take psychedelics, you're in very dangerous territory.
Sam
Problem in the world of psychedelics you've done. Have you experienced kind of all across the spectrum?
Kyle
Pretty much, man. I, you know, growing up in Santa Cruz is a very psychedelic forward town. My neighbor was actually Jim Fadiman, who wrote the Psychedelic Explorer's Guide and popularized microdosing, one of the 60s luminaries. So I had a lot of knowledge of it. And then growing up with, with friends, we would all go to Burning man and, you know, it was a very psychedelic forward place. And we all kind of grew up with this idea that any, any risks associated with psychedelics or the, you know, this is your brain on drugs ads, like that was all bullshit. And since then, I've come around to recognize that psychedelics can be abused and, and the setting in which you take them matters massively. And I've had some, some very scary and destabilizing moments where I've gotten really high on mushrooms at festivals and had to sit down. And you really hope that this is going to end. So they're something to take seriously. And, and for me, I, I think that the best way to, to take psychedelics is to go in with a really clear intention and then to also recognize that the trip isn't over until maybe a month after the experience. So to really integrate all of those new synaptic connections and guide your brain where you want it to go with new habits. I mean, there's a podcast about habit form, man. Psychedelics are very powerful to break old habits, form new habits. If you are diligent about how you are spending your days in the days and weeks after, I think that that's pretty often the miss for people. And then as a result it's like, great, I've done acid thousands of times and just becomes this thing you do for the fireworks. But ultimately you're not really improving. And, and I, you know, again, like, I think if you're signing up for, for a psychedelic trip and also being a public figure, the only advice that I can give you is to be okay never talking about it. Like, because the way in which you talk about the experience will ultimately manipulate the experience itself. Like the words you, you attach to what it was like will become the story in your mind of what it was like. And a lot of times what is unique about a psychedelic trip is that it's ineffable. Like it's. I can't actually, I don't have the words to describe what that was. And if you start talking about it immediately, especially publicly, it can flatten what the thing really was.
Sam
That's great. Yeah, great advice. What is so microdosing, Is that something that you've done?
Kyle
I have. I'm not convinced it works. Like, I'm not. I don't know, man. I mean, I feel like there's a certain point where it's just sub perceptual and you're like, is this something or is it nothing? I find that doing a morning workout is just so much more effective in terms of a mood boost than ingesting a small bit of psychedelics. And I also find that when it comes to microdosing for creativity, most of those people aren't necessarily all that creative or understand what the creative process is actually like. In my experience working professionally in advertising and now having written a book, I can say that the creative act is one of feeling like you are pushing snow up a mountain for the first hour and doubting yourself and not thinking that this is working and you're best work is behind you and it's all going to be over and then all of a sudden you break through to a good idea and the next hour is like, oh, okay, it happened. And I think that the idea of like hacking your way through creativity into this like flow state immediately is mostly just like marketing.
Sam
Do you have a morning routine?
Kyle
Yeah, I wake up and I will exercise first thing in the morning. So I will do a run. If I'm on the coast, I'll go surfing. These days I've been going to jiu jitsu at 6:30 in the morning. When I come back from that, if it's a good day, I'll throw on the Waking up app and do a 15 minute meditation. From there I will usually get into writing. I have one of those Pomodor timers, so I will crank it open for an hour. And this morning I went to a coffee shop. I didn't have the timer, but I looked at my watch and was like, okay, I'm just going to write for an hour. Wrote about birds, figured out what that story was all about. And then I will usually move from there to more like client work. You know, the stuff that actually pays the bills. So most of my days are usually like literary work in the morning, exercise literary work in the morning, midday break or, or exercise and then move on to client stuff.
Sam
I, I interviewed a guy a long time ago who really influenced me in, in regards to, I love chunking my day up. I'm. I've chunked in my calendar, but he influenced me to use the first part of my day, meaning wake time to noon, as the proactive part of my day. So not jumping into email, not jumping into anything that's going to require me to respond or react. All forward facing, right foot in front of left stuff. No stagnant or backpedaling in the first part of your day.
Kyle
Yeah.
Sam
And then you reserve the back half of your day to respond to what other people need of you.
Kyle
Yeah.
Sam
And I can't say that I've stuck to that wholeheartedly. Obviously as a founder, like I'm required to email before noon.
Kyle
Yeah.
Sam
But that thought process, that mentality, that mindset has been very, very helpful for me in the beginning of the day. And it sounds like you kind of have that too. Like you put your fitness, you put meditation, and then you put your passionate writing projects pri. Before you get into the stuff that is going to ultimately be required of you to actually like, respond.
Kyle
Yeah, yeah. I, I think that if we were here 10,000 years ago as hunter gatherers, we would be having a Conversation about how great it is to go out and hunt the animal first and bring home a kill before then, you know, prepping the meat and responding to the email version of whatever hunter gatherers did. I think it feels good and feels fortifying as a being to know that you've created something in the world. And whether that's bringing home meat or that's telling a story, look, it's material on paper. I prove that I somehow have value and exist in the world. That can be a very helpful psychological practice, I think, especially in a time when for all of AI's benefits, it can lead to nihilism very quickly. It can lead to this idea that you don't matter. So anything that you can do to counter that narrative in the morning, I'll speak everything I can do to feel like AI won't just like, wipe me off the face of the earth like a fly is very helpful for my mental health, particularly being a writer. Also, you know, I run ad campaigns for, for brands and like, you know, we'll do big, like cultural positioning campaigns, which tend to be the act of distilling a complex idea down into a really simple arrow. Whether that's like the tagline or the stunt or like the thing that's going to get everyone's attention. It's like. And if I go long form writing first, it helps me distill down into like headline writing. But if I just start headline writing, it's. I've already distilled language and it's hard to expand from that. So like I always say, like, if you're, if you run a company and you're trying to come up with a good ad campaign for, for yourself, write long form first. Just shitty first draft of like, okay, here are all the ideas. Like a crazy campaign we could do here. Or isn't it interesting that this thing is happening in culture which is sort of related to what my company is doing? And through that you might find a line that becomes a powerful piece of language that you can use as the tagline. That is the vehicle to bring that out into culture.
Sam
Your book that you just put out. One last question before you go. Let's, let's talk about that.
Kyle
Let's do it.
Sam
Tell me about the book. And, and I know that the premise is basically like interviewing your parents and not necessarily your parents, but just like the questions that one could ask their parents, basically. Am I right about that?
Kyle
Yeah, it's, it is broadly a book about how to interview your parents before they die. And beyond that, that's I would say that's this. That's the professed promise of the book. The secret motivation of the book is how to connect with people who you don't share the same worldview with.
Sam
So do you think that this could also be. I think I'm. I'm. I can't wait to go home and sit down with my kids at dinner tomorrow night and be like, all right, guys, so I've got a question for you. Or a few. Yeah, what's a memory that makes you cringe with embarrassment? Go.
Kyle
Yeah.
Sam
Yeah.
Kyle
No. Yeah. Every. Every chapter is a question so people can flip through the book at dinner time, and it can just be a great conversation starter. I've actually found, surprisingly, that a lot of people just use the book as an excuse to ask each other questions that might seem awkward to ask otherwise, but beyond, you know, just the. Okay, cool. I could interview my parents. I could come away with this audio and learn more about the stories of their lives. Questions are a bit of a lost art if you're not a podcaster, because we tend to be rewarded for having the right answers, not the right questions. You know, in school, right, you get. You don't get an A on the test for having the right question. And as a result, a lot of very smart people think that the way to come across as smart is by talking endlessly. And if there's one, you know, cultural protest that I could make, it's ask more questions. Like, if you want someone to think you're brilliant, ask them a bunch of questions about themselves. If you want someone to like you, ask them a bunch of questions about themselves. And if you turn that into a habit, your life starts to expand. You know, when I was growing up in Santa Cruz, like, a big fear of mine was that I was kind of just going to get stuck in the surf culture. Like, there was no way out of that for me. And it was a beautiful culture. I love it. I'm still part of it deeply. But I saw. I saw how often life constricts people into their subculture. And even later, they get a job and they're around the same nine people and no one else, and everything in their consciousness becomes about that thing. And we can kind of die a death of a million feelings of familiarity, like we're too familiar with this thing. And one of my favorite ways to really, like, reduce depression and just feel more amped on life is to hurl myself into a world that I have no business being in. And the only way to do that is to ask questions of people who are in that world because it turns out that if there's an expert in birding or jiu jitsu or whatever it is, like, they love being asked questions because they've spent all this time learning about that thing and now you're interested in it, right? So I, you know, I started my podcast as a way to first interview fellow big wave surfers, but then very quickly realized that I could have, you know, astrophysicists and biologists and hunters and like, all these people was just like this, this permission slip to sit down with people like you are doing right now. And my life got so much better immediately then, you know, during COVID I had my dad on the show. He's this old documentary filmmaker. He's traveled the world on, you know, shoestring budgets, and he told stories that I had never taken the time to ask. And all of a sudden, a bunch of listeners emailed in, like, you know, it's. I don't have like a massive podcast or anything, but all of a sudden you, like, you would have expected I had someone super famous on because people are like, dude, I want to interview my parents. How do I do this? Like, that was super cool. So I thought, oh, there's, like, this is really interesting. People are. Want to do this thing, but don't feel like they have the skill set to make it happen. And like, oh, my God, what if my relationship with my mom gets ruined because of this? And as you know, like, there is a craft to guiding the interview. So that's what the book kind of started as. It was like, this is how you're going to do it. And through that process, I continuously just had to make the book more and more personal because the reality is that most people have really hard relationships with their parents, and there's a ton of resentment and trauma and even just, like, misunderstanding. Like, like, he does. My dad doesn't see me, you know, my. My or my son. My. My kids have no interest in me. You know, like, these are such common feelings of pain that children and parents have. Just like, they don't. I don't see eye to eye with them. They don't care about me. They're not asking me questions. And I can. That can really hurt, you know, So I didn't want to write a book that was just like, this is going to be fun. You're going to have a fricking blast. And I mean, my story is that, like, I had a really close relationship with my mom growing up. She was like, one of My best friends. And she got really involved in some wild conspiracy theories and invested a ton of her savings in basically getting like scammed out of great sums of, of money. And me kind of like watching it and feeling like due to misinformation and like getting sucked down fucking Facebook rabbit holes. Like I was losing this person and it was really. I mean, it was fucking. It's hard for me, man. I mean, it still is hard to see what media does to people and really good people, you know, good hearted people, and how the right narrative based in falsehoods can wrap people up in a completely different universe. And then the question is like, okay, well, how do we have conversations now? Like, we believe completely different facts about the world. And I don't want my relationship with my mom to be determined based off of what we disagree on. And the interview process then became an attempt to see her in deeper and more nuanced ways. Like, who were you in the 1960s? What. What have been some of your greatest loves in life? You know, like, tell me about your relationship with your ex husbands. Like, I'm not really asked about that. Tell me about gardening. You know, my mom is, is an avid gardener and, and like famously planted more bee friendly species in her garden than anywhere else in Santa Cruz. And like, she has all these native bees in her. Her. God, I just never taken. Taken the chance to ask about that. So over the course of the year, it's really a book about like having a mom, losing her, and then using the interview process to deepen that relationship and understand her on a different level.
Sam
Is she still caught in, caught up in the conspiracy theory?
Kyle
Yeah, I mean, we have very different views about what's going on in the world. And yeah, you can read the book to get into it. I don't want to go down any rabbit holes ourselves. And maybe she's right and I'm wrong, but the bigger thing here is can we maintain relationships with people we love despite believing very different things about the world? Like, that's the question that I pose in the book. And now that I'm on the other side of it, I can say that, you know, man, ultimately what we're gonna remember about our lives and the lives of our parents are the stories. And, you know, it goes back to what I said at the beginning. Like, writing for me is a process of turning my life into stories and then using those stories as evidence for how I can act in the future, you know, and with our parents, the more stories we can craft about them that aren't just Bitter, the happier, the better time we're gonna have, man. And, and the, those are the stories that we can pass on to our own kids about who they were and what our lineage was all about. And it's just, it's just a good thing, man. And we don't know when they're gonna go. And it's just, it's a worthy thing to spend a little time doing because like psychedelics, like nothing might happen, but also a lot might happen.
Sam
What's your favorite question to ask now that you've been in this question realm?
Kyle
Yeah.
Sam
Is there any, are there any questions that stand out to you that have been just like, you have found those questions to provoke them? You know, profound answers or really interesting answers?
Kyle
Yeah, I find that one of the best. One of the things that people love talking about most are new hobbies or secret passions. And if you can start off an interview by asking them about something that they're really interested in and then use a follow up, have the fall. It's a two part thing. So you ask them about something they're really interested in, like, oh, dude, you're getting into birding. Like two. Hell yeah, I'm getting into birding. Like it's my new favorite thing. I'm like two weeks into this, I suck at it. But like passion is an all time high. Okay, well why, like, what do you make of that? Why are you into it? So this is a way of taking it from just a fact based conversation into an emotion based conversation, right? And then all of a sudden I'm like, well dude, I mean, I moved to New York and I like, I'm going to the, to McCarran park and like with my binoculars and like, I think that it is allowing me to tap into this part of myself that's like a hunter, right? Like all of a sudden I'm on like a mission and I'm just trying to look at these birds and I never would have expected that I'm getting into it, but like that part of me is now becoming satiated and all of a sudden then you're in this really rich territory of figuring out the, the peccadilloes of people, right? And that's ultimately kind of what you want with an interview with your parents. It's not about like, this is my life lesson. I'll always be a good person. Like our parents are not fortune cookies, right? Like, we want them to be specific. And the more specific of stories we can get them to tell about their lives, the more it's going to show who they really are. You know, like, my dad was a. A magician in high school, and he won his senior student body president. Like, he won the election by giving a speech in front of his school and having a dove fly out of his sleeve. And I'm like, he told that story in one of the interviews. And I'm like, that's all you need to know about who that guy is, right? Pretty cool. Pretty cool, right? So I think that the key with interviewing your parents is to go for specificity. Another thing that I think is a very easy hack to get into good storytelling is to ask your parents. Ask your parents to send prior to the interview, a bunch of photographs from their lives. And then when you sit down with them, you have the photographs and you just pass one across the table and say, tell me about this photograph. All of a sudden, that's going to give them a chance to weave a colorful story that can make for a really fun conversation.
Sam
I love that strategy. I feel like that's such a good strategy, because as you're talking, I'm thinking to myself, you know, I don't unfortunately, have the privilege. Like, I would love to interview my dad. He. He's gone. And. But I am going to interview my mom because I think that would be great. I don't know how well my mom would do in a podcast setting, so I would love to put her here, but it might be a little much for her. But, you know, asking children questions, I have found spending time with my kids, you know, they're two boys. They're 8 and 11. Like, if I'm not firing off a bunch of questions there, there's an. They could very well just sit silently, you know, and, like, not really talk much, right? And so, like, something that I am constantly thinking about. And I ask them the same questions a lot because I'm like, I'm not. I'm. I'm driving you guys to school. Like, I don't want you guys to just sit in the back quiet. Like, I want. What's your favorite color? Who's your best friend? What. What are you looking forward to in school today? Is there something that you wish you could do after school today? What happened yesterday? You know, do you have any crushes? Who's your favorite teacher? What did you learn in, you know, Egyptian studies? Like, I'm just kind of like, just, like, spitting out a bunch of questions for kids. And I, you know, I think the. The art of asking questions, it's genuinely an art. It's genuinely an art form because the goal is a story at the end of the day. Human beings have, since the beginning of
Kyle
time,
Sam
beloved moments where you're sitting around a fire listening to someone tell stories. And there's only a small handful of people that are great storytellers. But every human on the planet does appreciate a great story, right? They appreciate a great story. So, like. And that is, at the end of the day, I think this, like, what you said, when it's all said and done, what you take with you and the things that you remember are the stories. So this book, I would imagine, is there to motivate people to start thinking about how are you extrapolating these great stories from the people that you love most and even more so from the people that you don't necessarily see eye to eye with in perspective on the planet. Right. It's very, very cool, man. Yeah.
Kyle
Thank you. Thank you. No, it was really fun. It was really fun to write, and it's been.
Sam
What was the hardest part about writing the book? What was the hardest part about interviewing?
Kyle
I just don't want to hurt people's feelings. You know, like, it's. There's a real dance between being honest and. And also not wanting to be bitter and. And too angry. The nice thing about. About writing is that you can go through multiple drafts. So the first draft that I wrote of this book was very angry, and it wasn't very funny, and it seemed bitter and petulant, but I had to get that out first. And then I could weave in more love and walk more of the tightrope. But it was hard for me to get the pissed off draft out first. And I mean, I think that. That even people who. Who just journal and have no desire to publish the work have a hard time letting anger out on the page. It's just so uncouth. And, you know, in business, we're not allowed to let that part of ourselves speak. But writing from an angry place sure does get one. You. Once you let it happen. Like, God damn. No faster word count can be accumulated than the pissed off draft. So asking yourself, what. What are things that I am angry about or feel resentful about can let. Can lead to really good material eventually. And. And for me, it was hard because I was like, oh, I don't want. I don't want to hurt my mom's feelings. Like, she's still. Still my mom. But if I write this book and it's just glitzy and a marketing book and, like, I'm doing this, you know, like, all of a sudden it's not going to connect with readers who had a hard time with their parents. Right. Because they're going to think, well, that's not for me. And I think that ultimately what an audience is kind of paying you for as a writer is to say things that maybe they're not willing to say, but feel.
Sam
Hmm. Are there questions that you like to ask yourself?
Kyle
Yeah, I. I have struggled with mild depression for most of my life. Going back to just waking up and feeling low most mornings. It takes me a lot to just get into a positive mind space. Like, a lot of times I find even still that the first dozen or so thoughts that I have waking up from my bed are like, I'm not as successful as I want to be. My. I'm not as talented as. As other people who are more successful than me.
Sam
I.
Kyle
And just, like, it's just a very hard voice on myself. Like, I'm just hard on myself. Like, I. I'm not walking around thinking, like, yeah, Kyle, you're. You're killing it right now. Um, and. And it's. It's funny because then, you know, we. We do an interview like this, and you're like, you're a big wave surfer and a journalist and you have like, all these things, and it's like, I don't actually think of myself that way. And in some ways, like, the engine that has allowed me to accomplish things is the engine of, like, you fucking suck. Like, go. Like, you know, like, you're it. It can be very motivating, but it's not very fun. And a lot of the work that I've done has just been to. To figure out ways that I can be kinder to. To myself. And, and questions are. There are certain questions that I will ask myself that I find can get me out of those ruts. So, like, one is like, when am I at my best? Like, what am I doing when I'm at my best? And. And pretty quickly from there I can be like, oh, yeah, well, shoot. I have not been, like, exercising at all. And like, oh, I. Like, I haven't also been meditating at all. Like, that's so interesting. You can kind of like, track the feeling back to a certain set of habits that have either like, fallen off or. Or come back online. So, yeah, like, when am I at my best? Is one that I'll ask myself. What. What do you. What were three great things that happened today? That's one thing that I'll ask at the end of a day. And part of the reason for that is That I think it just helps me see my day as, like, oh, yeah, these are three great moments. But one thing that I've become increasingly careful of is knowing the difference between what I actually like doing versus what sounds really impressive to other people. And it's very easy to sort of promote yourself out of the work that you actually like doing, because it sounds cooler to be in a different position in culture. So that's. And I see it happen to so many people. You know, they'll be really good at, like, as. As designers, for example.
Sam
Right.
Kyle
I work with a lot of great art directors and they'll think, well, now I want to be the CMO of a company and I want to handle all of marketing. And all of a sudden they just promoted themselves out of the act of designing. Right. And now they're in 12 meetings a day and they're telling other designers how to do their jobs. Maybe they're making a little bit more money, but they're miserable. And so I'm constantly trying to navigate my career. Career to figure out, okay, like, how can I make enough money? But how can I also be actually spending a few hours a day doing the thing that I. That, like, makes me giggle. Like, makes like, dude, like, writing campaigns for brands and, like, writing long form. Like, I. I will find myself laughing alone, like, at my computer. Like, this is so cool. Like, okay, that. That's a signal to me that you should just keep. You should keep doing this as long as you can. Because it's not this idea of how other people will be perceiving you. It's like, no, you actually, you would do this if no one was watching. So I will. I really try and tune in to those questions to navigate my own career.
Sam
I feel like when you buy a journal off Amazon or you pick up a journal, you know, a lot of journals will have those prompts. Right. Something that I have uncovered. And now being a father, specifically is being a dad. Because at 6 o', clock, we typically have dinner every night together. And that was never something I did as a kid. We never had dinner together. And it was. It dawned on me that most people go through life never ever reflecting on their day. Like, never reflecting on the day ever. They don't just move forward. They just never think about what happened.
Kyle
Yeah.
Sam
During the day it's just like, that's so wild. It's crazy, right? But, but, but I would say the vast majority of human beings.
Kyle
Yeah.
Sam
Don't ever take time to just be like, you know, so at night, every night. And the Kids are not as stoked on it as they used to be when they were younger, but we have this thing called Rosebud, Thorn and Seed.
Kyle
Dude, I love it. I know about Rosebud and Thorn. This is great.
Sam
It's just like. And seed to it, which was.
Kyle
Seed is something you're excited about or.
Sam
No, seed is. Is how you've helped someone.
Kyle
Oh, that's great.
Sam
How you've helped someone today. So Rose is. Is obviously one great thing that you've done. Thorn is one great thing that sucked. Bud is something that you're stoked about coming up, like, trip. And then seed is, like, one way that you thought you were helpful for someone else.
Kyle
Oh, that's so cool.
Sam
And, you know, when starting to do that with my kids, I was like, wait a second. Like, I'm doing this with my kids because I'm just. I just want to hear about their lives. But, like, it's so. It's so great to also. For me to also say, hey, dude, like, what was something that was awesome today? What was something that you thought you could have done better today? And. And it just dawned on me. I was like, wow, man, I really have been living, like, a lot of my life. Not really reflecting on actions.
Kyle
Yeah. It can become a compass, right? Because if you think, like, wow, my. My rose for the last five days in a row was, like, birding. Like, what? Like, I was, all right, I'm gonna go birding tomorrow. I'm gonna figure out how I can carve out more time for this thing. And, man, I. It's. It's like, so much of the first part of our lives is about figuring out who we are. And then so much of the second part of our lives is figuring out how we can create a life that allows us to thrive. And, man, moving. Moving to New York, as I did two months ago, has created a bit of, like, a blank slate on what is it that Kyle actually likes to do, right? Because, like, okay, I'm not going to be surfing for a few months. You're in a totally new town that is. You're not really oriented to it. How can you maximize your happiness? And, dude, I'm a dog chasing a ball. Like, the second I found jiu jitsu and birding it, it focused my attention to be able to have these little roses in my day. I'm like, dude, I got my ass handed to me in jiu jitsu, but, like, I got in full mount one time. It was fun. And, like, these, like, narrowing life down into these, like, smaller Circles of like, little good things that happened on a day to day basis. It's just a, a cheat code for me to maintain a level of happiness and not slip into this like, broad amorphous narrative that like, you're a failure and like no one likes you. And it's just like all of this, like the storm of nihilism gets pushed a little bit further at bay from just fun little things that happened that you made time for.
Sam
You know, I think we should end with this idea that you've definitely brought to surface for me. And I would imagine once I say it for the audience, it's okay to like things that don't impress other people. You know, it's okay to feel at your best, at your best self when you don't really care about what other people think. Right. Like I. My greatest joy in the world. Most people would probably say, oh, running a business or you know, I mean, training hard is something that I love to do. People know I train hard. So like, that's true. But really my greatest, my greatest joy in life is being on vacation with my family. Hands down, 100. It is a great, is my favorite thing to do, period. Done. I would give up everything else to just be on vacation with my family all the time. I would, I love being on vacation with my family. And I would never have said that even five years ago. And now I'm like, no, no, no. Like I live to be on vacation with my family. That is what I love to do. We. I'm able to do all the hobbies that I love to do on vacation with my family. I get to spend more time with the people I love most on vacation with my family. And like, that's something. And I think what we need to start. I, I mean, the narrative is so screwed, right? Because it's. Even though I think we have gravitated further from money being the golden ticket and the North Star, like the pinnacle, I think we have less, like over the last 15 years, 20 years maybe, like, it's not all about the money anymore for people. But I do think that the narrative needs to continue to push and evolve in the direction of when are you having fun? And once you can identify when you're having fun, go harder on that. Yeah, go harder on that. Because. And the sad part about it is that technology has this false fun experience for people, myself included. I'm sure you too, to some extent. Like, there is this false fun that you have, you know, scrolling on social media account or, you know, getting hooked into a video Game and sitting in front of that for six hours.
Kyle
Yeah.
Sam
You know, so I. This conversation sparks so much thought for me. And I love having conversations with people like you that, like, you know the idea of do one thing and do it really, really well. You're not that guy. You love a bunch of things.
Kyle
Yeah.
Sam
And you figured out a way to be able to, like, implement those things into your life so that you don't have to feel the need to be like, nope, I'm gonna do this. I just can't do that anymore.
Kyle
Yeah. You know, I appreciate you saying that. I. It's okay to do things that don't impress people is such a good way to say it. And I appreciate you. You saying that about me, because I think I have a bit of insecurity that I'm a dilettante and, like, do too much. And it's like, well, if you gotta, like, what's your brand, Kyle? Like, you gotta Brett, you gotta be the brand. You know, go hard on the one thing. And I'm like, dude, birding is sick.
Sam
You know, I'll.
Kyle
Burning is sick.
Sam
I'll finish with this. I. My best friend in the world. My best friend. Childhood best friend, Godfather. My first son, he's in prison. And he is one of the most talented musicians I've ever met. And we. We've been best friends since we're 14 years old, and we partied really hard together. But the whole way through his life, he has a very, like, really talented father. He's an actor. You've definitely seen movies that he's been in. And so he's got this talent gene in his. In his family. He's a. He's a real true artist. Opened up for Bob Dylan all over the world. Been in great, amazing bands that you love music from, and has also, you know, been married and divorced and committed crimes and smoked crack on the street for five years, living on. In a tent, and now is in prison. And I was on the phone with him last night for over an hour, and he's doing the best I've heard him do in years. Thank God he's in prison, you know, but we were having this really interesting conversation where he was basically saying, I've lived the most incredible experience. I've experienced every aspect so far that I could think of that would make a. That would make a great story to tell. And he's like, you know, the fact that I'm still alive and this guy, I'm sitting with this guy, he's in prison. You know, he's in prison. He's been in prison for a bit. He doesn't know when he's getting out exactly, but he's like, I just can't wait to tell my story. You know, Like, I really, I've lived, like, really incredible story, and I don't regret any of it. And I'm sitting in prison here talking about it. Like, I'm not saying go to prison and smoke crack on the street, but I am saying that, like, life, the story of life, is ultimately what we end up leaving with. Right. And ultimately what people. Our legacy is. Right? Like, people tell our stories when we're gone. And if we do it really well, our strength when we leave doesn't go with us. Someone else picks it up and uses it to become stronger. Right. Like, that's kind of the way I think about it. We build this muscle of experience in life, and then if you've done a good job of that, when you pass on that strength now gets passed off to somebody to then ultimately use to strengthen themselves and the others around them.
Kyle
Yeah.
Sam
And so I love the fact that you're a true storyteller. And I'm stoked to read this book. And I can't thank you enough for popping on the show, man.
Kyle
This was so great.
Sam
It really was.
Kyle
I loved this conversation.
Sam
It really was.
Kyle
I fucking love you, man. Dude, let's go mushrooms.
Sam
Let's go birding.
Kyle
Let's go take some mushrooms and go birding. This is going to be the best. I.
Sam
Where can people get the book?
Kyle
Amazon. Yeah, one last question before you go on Amazon, and I hope you enjoy it. You know, it's a memoir meets manual. There's a very clear how to list at the end, and the rest of it, you will get taken on a wild and unexpected ride.
Sam
Awesome, dude. Where can people follow along your journey?
Kyle
Substack.
Sam
Okay.
Kyle
Yeah, yeah, just go to substack and type my name in. I do a newsletter and the podcast is there as well. Yeah.
Sam
Friends, family, and all of the above. What a fun, fun conversation that was. Ping ponging all across the board. We talked about a lot of different things, but all of it really just, like, had my juices flowing and I was, like, sitting on the edge of my seat waiting to ask the next question, which, oh, I always know is a sign of just, like, great content that you guys are going to love and listen to and be excited about. So for me, I was truly stoked on this one and I can't wait to listen back on this podcast. I, you know, when I'M sitting here and hosting a podcast, I get to experience, like, the, the, the. The tangible component of being a podcast host. But then when I get to listen back to these podcasts and I listen to them all, not only to hone my skills, but to also, like, be able to, like, actually step outside and get the, get the information, I. It just like this one I know is gonna, is gonna put a big old smile on my face. So if you feel the same way I do right now, do me a favor and share the podcast. Friends, family, social media, wherever you want to share it, share it. That is how we grow this thing. A five star rating and review would be incredible, and I say that every episode, but I really, really mean it. If you've listened this far and you've been listening to this podcast and you have not given us a five star review and written a short little five star rating and written a short little review, now would be the time. It means a lot. It really does. It actually does help us grow and get in front of more people, which is ultimately my goal here. And yeah, Kyle's the man. And you got to pick up his book. I can't wait to read it. One last question before you go. I love you guys. I appreciate you guys for being on this journey with me. Until the next one, y'. All. Peace. Sam.
Kreatures Of Habit Podcast
Host: Michael Chernow
Episode: Interview Your Parents Before It’s Too Late | Kyle Thiermann
Date: May 6, 2026
In this episode, Michael Chernow sits down with journalist, author, and big wave surfer Kyle Thiermann to explore the importance of interviewing your parents before it’s too late—a theme at the heart of Kyle's new book, One Last Question Before You Go. The wide-ranging conversation touches on the value of asking great questions, the craft of storytelling, habits that improve well-being, breathwork and resilience, and how to connect across generational or ideological gaps. Kyle shares insights from his own life, surfing career, and deeply personal experiences, while Michael reflects on family, personal growth, and living authentically.
Finding Clarity Through Writing
Reporting as the Foundation of Writing
Lessons from Big Wave Surfing
Staying Calm in Crisis
Breathwork Practices
Breathwork & Emotional Healing
Psychedelics in Modern Life
Microdosing Skepticism
Day Structure for Productivity
Habits That Build Wellbeing
Questions for Self & Others
Premise and Deeper Purpose
Questioning as Connection
Dealing with Difficult Relationships
The Power and Pain of Being Honest
Doing What You Love, Not What Impresses
Legacy and Story
This episode is a must-listen for anyone interested in living more deliberately, reconnecting with family, and building their life on stories that matter.