From SEAL Sniper to Puddle Jumper: Brandon Webb on How to Raise Confident and Joyful Kids

00:00:31 Andrew Keen: Hello, everybody. My guest today is four things. Well, actually more than four things, but he focuses, in terms of his own self-identity, on four things. He's an author. He's an entrepreneur. He's a Navy SEAL, and he's a father. As an entrepreneur, he seems to have leveraged his experience as a Navy SEAL into a series of best-selling books. Brandon Webb will be familiar to you for all sorts of books, like The Red Circle: My Life in the Navy SEAL Sniper Corps, The Killing School: Inside the World's Deadliest Sniper Program, and The Making of a Navy SEAL: My Story of Surviving the Toughest Challenge and Training the Best. Brandon is in the business, in some ways, of giving us advice. And his latest book, which is out this week, Puddle Jumpers: Simple and Proven Ways to Raise Confident and Joyful Kids, is not Brandon speaking as a Navy SEAL but as a father — his fourth identity. Brandon is joining us from the Upper West Side in New York City. He mostly lives in Portugal, but he's in New York this week promoting the book, which, as I said, is out. Brandon, congratulations on the new book. Is that how you order your identity, or is it just the luck of the draw? Do you start with the A and end with the F? Author, entrepreneur, Navy SEAL, and father. Or is it impossible to actually create a hierarchy out of those four things?

00:02:09 Brandon Webb: I mean, I identify with those four things, and it just depends on the situation. But, yeah, I would say this — I talk about it in Puddle Jumpers — being a father is probably one of the toughest and most rewarding jobs I've ever had. Never set out to write a parenting book. It was just a byproduct of having kids very young, then becoming a co-parent and a divorced father. And my peer group, who had kids much later than I did, would meet my grown kids, and always, to a T, afterwards they'd come up to me and say, look, I don't know what you did, but your kids are amazing. They're not on their phones. They make eye contact. They ask good questions. They seem happy. Please tell me and my wife — what's your secret? And it just happened enough over the past, I would say, seven, eight years that I thought, okay, maybe I have something to offer in the parenting space, because I did recognize a lot of the psychological training that we learned as a sniper instructor cadre when I was running the sniper program at, I think, 27 years old. We had learned this method of positive performance psychology, and I said, well, it can apply to kids. When I left the Navy — and I largely left because of my kids, I wanted to spend more time with them — I realized that a lot of these principles I used to teach snipers apply to kids: teaching them how to deal with negativity, how to push negative self-talk out and replace it with positive self-talk, how to identify when adults, maybe well-meaning adults, say very negative things, and that they don't have to take that on as baggage. And whether it's a counselor, kids' friends, parents, a teacher, or a coach — they can say some really terrible things and have an impact on a kid's trajectory. So teaching the kids very young how to deal with that stuff was something I really focused on as a father. And I think their mom and I did a good job. We were very present and ended up with great kids. We've had the same troubles a lot of families face — with drugs, alcohol, sex. But this is my experience as a parent, and I came out the other side. I'll send you a note — my daughter recently, when she visited me before I came to New York, just told me how supportive I'd been of her and how grateful she is to be living life on her own terms. And to me, that's the best thing you can ask for as a parent.

00:05:14 Andrew Keen: Yeah. And you write about that — about getting a handwritten postcard from your daughter that taught you about twenty years of parenting. I know that's on your blog, but it's also part of the book. Brandon, let's step back a little bit and try and historicize this. Maybe you can compare your experience as a parent to your experience of being parented. I assume — well, of course, everybody has parents. How well did you know your parents? Are they still around? What kind of parenting did they do? And in a way, is this a generational crisis? Is your generation — all these people who came to you after meeting your kids, with unhappy kids — coming to you and saying, what's the secret? What's gone wrong in parenting these days? Or is the problem the kids, this anxious generation, or is the problem the parents? Or is the problem both of them, or perhaps neither?

00:06:11 Brandon Webb: Look, I would say — well, let's answer the first part of your question. So my parents are still alive. I have a great relationship with my mother. My father and I have a very complicated relationship. It's not perfect. We're still working through some things.

00:06:31 Andrew Keen: What kind, do you think?

00:06:33 Brandon Webb: Well, I'll tell you. My father was very strict. His father threw him out of the house at 17 because he wouldn't cut his hair. My grandfather was a strict disciplinarian. When I was disciplined, I got the leather belt. I lied — I can remember getting caught in a lie at seven, eight years old and getting a bar of soap shoved in my mouth.

00:06:58 Andrew Keen: Where did you grow up? Which part of the country?

00:07:02 Brandon Webb: Yeah. So my father's Canadian, my mom's American. My parents met when my father was running a landscaping business in Malibu — picked my mom and her girlfriend up hitchhiking, fell in love, moved her from Malibu to interior British Columbia, Canada. Had me and my sister. So I lived in Canada until the first grade, and my father had lost his construction business. And my parents had this dream to sail around the world, so they said, screw it — we lost the business, let's buy a sailboat and pursue this dream. So we moved, you know, a year and a half later, to Washington state, but we found a boat in Vancouver. They moved the family on a boat. We sailed from Vancouver ultimately down to Ventura, California, and I lived on a boat for five years. So I'd say my parents were very adventurous that way. I appreciate them. They had a lot of trust in my sister and I to do things on our own. Living on a boat — sometimes, you know, before they got the bus to actually show up to the marina, we'd have to ride our bike to school almost an hour to get to school. So there are these little things I talk about in Puddle Jumpers that stack up over time and build confidence. I think — to get to your other point of your question — well, let me finish that point. So my father and I had a falling out when I was 16. We were on our second family sailing trip, and I'd grown up working on boats as a 13-year-old. I worked on a scuba diving boat out of Ventura, California. It was an amazing experience as a young kid. I became a competent deckhand. I was a rescue diver. I would drive the boat at two in the morning — the captain would trust me to take a one-hour shift. So I grew up on this boat and had all this boating experience. Now, on the second big trip my father and family had taken us on, we were to sail from Ventura, California down to Mexico, from Acapulco over to the South Pacific, and eventually we were ending up in New Zealand. I made it to Tahiti. My dad and I had this huge argument, and he says, son, time to get off the boat. So I was 16 when I left home. My mom was a mess — she's crying, my sister's crying. And I found a boat, a catamaran sailing to Hawaii that needed help. So I jumped on this catamaran.

00:09:38 Andrew Keen: I bet he didn't quite put it like that — 'son, time to get off the boat.' Did he? What language did he use?

00:09:44 Brandon Webb: Well, I don't remember the exact language, but typically it was arguing over some type of seamanship — what to do on the boat. We had a huge fight. It almost got physical, and he kind of calmed down. But he says, look, I know you're independent. I know that you didn't necessarily want to come on this trip in the first place. I think, if you feel strongly and this isn't working out between us, that maybe you find a way back to California. I'd finished my junior year early on independent studies. I ended up calling — on a landline — my old boss who owned the scuba boat out of Ventura, and said, hey Bill, can I get my job back? And he's like, yeah, you can live on the boat. So, yeah, it was a heated argument, but it ended up being a family discussion. We resolved it, but it was very clear that my father wanted me — it was time to go.

00:10:49 Andrew Keen: Yeah. I mean, you were more than a puddle jumper — you were an ocean jumper.

00:10:54 Brandon Webb: Right. Yeah, exactly.

00:10:56 Andrew Keen: So the rest is history. You went off, you became independent, you became a Navy SEAL — and as I said, the rest is history. So what were the positive and negative lessons you learned from your parents in terms of parenting? Because — I mean, it's a truism, but it's no less true that we all learn the lessons of how to and how not to parent from our parents.

00:11:25 Brandon Webb: Yeah. When I think of my parents, the two things that come to mind on the negative and the positive — on the negative side, I knew I did not want to discipline my kids the same way my father did to me, because a lot of times, there was no — it was just a reaction to behavior. And I talk about this in Puddle Jumpers — it's so important to get to the why of the behavior and understand why is this kid acting this way, rather than just jump into the discipline situation. Right? My dad — if I screwed something up, I don't ever remember him asking me, why the hell did you do that? Like, what was the motivation behind that? It was, nope, get up to your room, drop your pants, and you're going to get the leather belt. And it created this fear-based relationship. And as I was getting older, I was rebelling against that. I think that eventually pitted me against my father physically, to where it got to a point — when I was 16, on the sailing boat in Tahiti — where it just came to a head.

00:12:41 Andrew Keen: You never had a physical fight with your father? You never —

00:12:44 Brandon Webb: No. But almost — almost, in Tahiti. It almost got there. I think that's what scared all of us. My mother talks about it.

00:12:55 Andrew Keen: And presumably — I mean, you're still a big guy, but at 16, you could look after yourself, so your father wasn't guaranteed to beat you.

00:13:05 Brandon Webb: Yeah. So that would be the one thing — I remember when Gretchen and I had our first son, we were both on the same page: we did not want to punish or discipline our kids the same way our parents did to us. And on the positive side, my parents were hippies. They were from that generation in the sixties where it was, like, peace, love, and let your kids run around barefoot and free. Thankfully we were in environments where that worked out okay for us. That's not — I wouldn't want my kids running around New York City.

00:13:46 Andrew Keen: Although, it doesn't sound like typical hippie behavior. I mean, he was beating you with a belt. He was telling you what to do. He was throwing you off the boat and forcing you to find your own way back from Tahiti. That's not classic sixties hippie behavior.

00:14:01 Brandon Webb: Maybe not, but they were very much into that hippie lifestyle for sure, at the time. But, yeah, my dad was very strict. My mom not as much. What I did appreciate about my parents was that they were very liberal with letting my sister and I explore and do things. They let me take this job, which I wanted as a 13-year-old, on this dive boat. Let me get scuba certified, and I was going and working as a 13-year-old. My weekends — when not spent with my friends, I was on the scuba boat, diving these crazy locations off the Channel Islands. And I appreciate, being a parent, that they let your kids explore and do things on their own — because I also talk about this in the book, how important it is.

00:14:55 Andrew Keen: Coming to the second question — I'm sorry to throw so many questions at you — the historical element. You know, I obviously can't speak on behalf of your family or your parents. But it seems the big difference between that generation — and I'm in a relatively similar generation to yours, and our generation as parents, and you and I have similar-age kids — is that we take parenting a lot more seriously. Doesn't mean we're better parents — some people might argue we're worse, in a way. But what happened, Brandon? And it's not that your parents, my parents' generation, were necessarily bad parents — but parenting wasn't the thing in itself. When they wrote down their four identities, I'm guessing most of them wouldn't put father or mother in the top four. Parenting just kind of came naturally. They let the kids do whatever they liked, often. Sometimes they disciplined them. What has happened? Why is our generation so obsessed with parenting, for better or worse?

00:15:58 Brandon Webb: I think a lot of parents, especially in America, are feeling lost. We talk about — when you and I grew up, it was more of a village. I remember the teacher at school had a big wooden paddle. You knew if you stepped out of line that that teacher was going to handle business and that your parents were okay with that. It was more of this village of support, where family lived close by usually, and you had this support system. Now that's gone. We've, for better or worse, kind of sterilized that. Imagine a world today where a teacher punishes a kid at school — the parents would be outraged. So I think it's a combination: this evolution of kind of whitewashing the village, so to speak, where we as a society have taken away a lot of that from the teachers and the coaches, and so it's all falling on the parents now. And now add to that, we're in this super-connected digital world where — I talk about this in Puddle Jumpers — eventually, you can only manage technology so much, and your kids are going to become 100 times more proficient at dealing with family IT stuff than you or your spouse will ever be. So my kids, and it sounds like yours as well, are one of the first generations to grow up totally connected to the Internet. They don't remember anything else. My youngest, I remember him asking me, dad, what the hell is a CD? I was like, that wasn't too long ago — we were putting those CDs in the car to listen to music. So I think that's a big issue, to answer your question — we've lost that village. And so parents today — I see so many, whether it's my business school alumni group or, you know, after losing my first business I ended up having a successful second business and grew it to a size where I could join business groups like Entrepreneurs' Organization and YPO, which is Young Presidents' Organization. And I started meeting these very successful parents of much younger children who are desperate for feedback. They're like, I don't know what to do. I think a lot of successful parents today, they try and just outsource everything, and that does not work. They get a tutor and a private coach for the kids' sporting event, they have the nanny — and then they show up and read a bedtime story at night and think that that's parenting. And it's not the case. And then they wonder why their kids are off the rails, and whether that's drugs and alcohol, or they just don't have a relationship with their parents. I read somewhere recently that there's been so many kids growing up — like Gen Z kids — that they don't have a relationship with their parents. They're ghosting their parents.

00:19:25 Andrew Keen: Or talking to them. I mean, there's a whole new literature movement around naturally — formally or informally — divorcing your parents.

00:19:37 Brandon Webb: Which I cannot fathom, because I have a truly great friendship and relationship with my now-adult kids, and I just can't imagine it the other way. And, to keep it real, right? My father was very unhappy with me writing my first book, The Red Circle, because I talked about my experience as a young man and what it was like for me to be on the other side of getting kicked out of the house at 16. He's very upset about that.

00:20:13 Andrew Keen: Yeah. And that was The Red Circle: My Life in the Navy SEAL Sniper Corps and How I Trained America's Deadliest Marksmen.

00:20:20 Brandon Webb: Yeah. You know, we were —

00:20:23 Andrew Keen: I hope you gave him a good spanking, Brandon. He sounds like he loves you. Although it's funny that you and he both failed in your first businesses. You both seem to be quite entrepreneurial and emotional. So you probably have a lot more in common with your father than either of you would acknowledge.

00:20:43 Brandon Webb: Yeah. And I get it. My father comes from a very different generation. The problem that my dad and I have — and I'll put on my psychologist hat here — it seems like his problem is he's struggling with the idea that I had a totally different experience than he did, and he often defaults to his experience as the truth. And you and I both know we can experience things very differently. The same event, we could experience very differently than the other person. But I've really tried over the years to rebuild this relationship with my father, which is super complicated.

00:21:36 Andrew Keen: Yeah. Well, one of the other interesting things — and I've seen this with family members — is the way in which siblings have entirely different experiences and then develop entirely different narratives. Is your sister's version of your childhood, and of your father and mother, the same as yours?

00:21:56 Brandon Webb: I think so. I would say so. My sister and I talk about it. We talk about our father. Both my sister and I have a great relationship with our mother.

00:22:11 Andrew Keen: Are they still together, your parents?

00:22:13 Brandon Webb: No. They divorced after twenty years, and I was already out of the house. But my sister experienced that. And, to go a layer deeper — there were things that my father did in the divorce, when I was already in the Navy, that I could have been very upset about. He didn't necessarily pay what he should have paid to support my sister. My mom put my sister through school all on her own, working two jobs, eventually started a successful company on her own. But as I got older as a father, I realized that I am not perfect and I've made mistakes. Five years ago, I wrote my father a letter and gave it to him at Christmas, and just said, look, I think I've been too hard on you. I've reached the age where I've realized that we're all imperfect humans. We make mistakes. And I don't want to focus on the bad things — I want to focus on these great memories I have of you as my father — and I listed those. He was in tears. I thought we were in a really good place. But last summer, some media company excerpted a story from The Red Circle, and he thought I'd given this fresh interview, and it just reopened this wound. And he wrote me an 18-page letter of grievances going back to when I was a teenager. I was reading this letter, and at first I was really upset, angry. And then I became embarrassed that a father would write this and say these kinds of things, because it was not nice things he was saying — in some cases, pretty nasty. And I was like, wow. I'm so grateful that I have a really positive relationship with my children. I consider them friends, and I would be terrified of any parent writing the letter my father wrote me. So, anyway, that's me keeping it real.

00:24:23 Andrew Keen: You talked a little bit about violence. Your career was in the violence business. You became a Navy SEAL sniper. Is there a role for violence or intimidation in creating confident children?

00:24:45 Brandon Webb: Oh, I think people would be surprised to hear me say this, but I've always tried to lead, as a dad, with love and compassion. I wrote a checklist — I'm big on checklists, because I'm a pilot, and in the military we use checklists to save lives, so you don't miss anything. So I wrote a whole checklist on discipline, because I think parents tend to react with strong emotions. Maybe they have a bad day and they're carrying that into the discipline process. So it's, hey, check your emotions at the door, recognize whether you're in an emotional state or not before having this conversation with your kid, and really get to the why of the behavior. Because in many cases where my ex, Gretchen, and I would initially want to discipline for some behavior issue, we ended up supporting — especially our youngest, who probably had the most difficult time in school — taking his side, supporting him.

00:25:48 Andrew Keen: He's currently 19, right?

00:25:50 Brandon Webb: Yeah. When he was in seventh grade, he had a really terrible homeroom teacher. We had no idea this relationship had gotten so bad, but he ended up getting suspended from school. I flew out there to visit him, and I got to the point where I was like, why are you acting out like this? And he's like, dad, this teacher said some really terrible things about me and embarrassed me in front of the class. He says, I think I was just acting out, trying to show her that she's not in control of me. And we went to the principal and said, look, this is what our son says — how could a teacher say this stuff? And one of the things she'd said to him — and she's a white woman herself — she said to a 12-year-old boy, you're a terrible kid, you're a victim of white privilege. And I was shocked that somebody could say that to a 12-year-old boy in front of the whole class. So the principal said, look, we've had multiple complaints, we're shorthanded, I know the situation. So we pulled him out of school, put him on independent studies. He went from D's and F's to B's and A's, started high school with a fresh slate. And ultimately, what could have been a situation where we could have just dropped the hammer and disciplined him for getting suspended from school — instead we took time and were very thoughtful about what was driving this kind of behavior, and realized we have to change the environment. We have to pull him out, get him in a different friend group, get him away from this teacher and this adversarial relationship. I mean, I don't know if you remember, but I can think of a few great teachers and a few bad ones. I had a terrible guidance counselor in high school. He was — now he's a politician and mentor, go figure — but I still remember this guy. Such a jerk.

00:27:48 Andrew Keen: You've moved around a bit. You've moved to Portugal. In fact, you've done some YouTube videos on moving your kids to Portugal. A couple of your kids are in Europe, and at college in the UK. Do you think, Brandon, in terms of developing as a parent these puddle jumpers — kids who are confident and joyful, willing to jump puddles, get themselves a bit dirty — do you think that moving around a lot as a family is a good or a bad thing? I'm kind of ambivalent on that one. I'm not entirely sure. Maybe you can do it a bit too much. But certainly, do you think it can be dangerous to just stay in the same community, in the same village? We live in a global village, so maybe move around a bit, see different cultures, different cities, different languages.

00:28:37 Brandon Webb: Well, to be clear — when we divorced, Gretchen and I created a plan, and we were lucky enough to divorce with a very good psychologist, this woman, Dr. Baker.

00:28:51 Andrew Keen: Why did you get divorced? It sounds like you're very close.

00:28:55 Brandon Webb: Well, we married very young. She was 19, I was 22. And like a lot of young love, you're not even mature enough yourself to realize what you want out of life. And as we were getting older, we figured out that we wanted different things. I still like to travel; she didn't like to travel. She wanted a more stable, nine-to-five kind of partner. And so that was the main reason. So it was a mature decision, but, thankfully, what unified us in the divorce was that we both wanted what was best for the kids. In her case, she wanted to go stay with her family — they had a very nice property in Northern California. So we decided the kids would have one home, with her. I would get them on the major holidays, I would come visit them for any big events, birthdays, school events.

00:29:51 Andrew Keen: How old were they when this happened?

00:29:54 Brandon Webb: They were seven, five, and three. So very young.

00:30:00 Andrew Keen: Really young.

00:30:02 Brandon Webb: But they had a stable household. They lived in Paso Robles for years and then moved to Oregon. So they only had two moves after the divorce. I like the idea of having a stable household and not bouncing kids back and forth between houses. I have friends who are divorced, and I can't imagine how unstable that would be for a kid — having two homes, back and forth. A lot of parents don't get along in the divorce, and they weaponize the kids, which makes it even worse. But my kids had a very stable household. What I did, in my role as their father, was — to your point — how do I give my kids these experiences so they can see different cultures, different foods, different languages, different perspectives? I think that's super important for kids. So I was very purposeful in taking them on trips, and I would do one-on-one trips with the kids. Also, my mother was a very active grandmother. She said, I'm not getting younger, I want to take your kids on a big trip each. So she took my oldest to Africa when he was 12. He saw poverty up close. I think these are great experiences for children — but also, it's important to have a stable house. I'm glad, actually, because I remember getting judged when I was in New York. They're like, what do you mean you don't see your kids every week? I was like, look, we just created a system that works for us, and it worked. The kids felt loved and supported. They saw that I was getting along with my ex's family and vice versa, because that's a big problem when you're forced —

00:32:02 Andrew Keen: A blog piece I read last month — fifteen minutes of unfiltered presence beats a weekend of half-hearted parenting — so I take your point. You also — you've written in your blog of the art of raising leaders. You have a photo of your son graduating from St Andrews University in Scotland, one of the top universities. And the book is about how to raise confident kids. But not everyone, Brandon, can grow up to become Brandon Webb. Not everyone can get into the SEALs. Not everyone can be a successful entrepreneur or writer. Is one of the things about being a parent preparing your kids for failure without undermining that confidence, and making them recognize that they're not always going to get everything they want?

00:32:56 Brandon Webb: Yeah, it's a great point you bring up. I was very intentional, when I was raising the kids when they were very young, on showing up and trying to always set a good example and be this exemplary leader. Where I failed — and I talk about this in the book — I remember, starting to write the book, I sent my kids a few questions to get feedback. And one of them was, what's one thing you wish I had done differently as a father? And my daughter, who was 21 at the time, she says, look, you were this hero to us, and I remember you were always present and I appreciate that. But the one thing I wish you'd done as my father is be a little bit more vulnerable and tell me some stories of how you failed. Because, she said, had I heard those things, I would have felt safer knowing that it was okay to screw up. My two oldest were very driven, very —

00:34:03 Andrew Keen: Yeah. At least she didn't escalate it into an 18-page letter.

00:34:07 Brandon Webb: Yeah, exactly. Not angry, though. And I was like, wow — what a thing to hear. And I wish I had done things differently. So the cool thing about this book is my kids are a big part of it. They're all on the audiobook. Their mom wrote the foreword. She's on the audiobook.

00:34:27 Andrew Keen: Were you ambivalent about — I mean, for people watching, there's a photo of Brandon with three delightful kids in Lisbon at a restaurant. Were you in any way ambivalent about exposing your kids to all this? I mean, who knows what their lives will be like, and sometimes this stuff can come back to bite you. You note how your father is still pissed with you about The Red Circle.

00:34:51 Brandon Webb: Yeah. During the process, I shared everything with them and their mom. Sometimes we made decisions together on what to keep in, what to keep out. To your point about the pressure — I think this is something I talk about in the book. Parents need to become better question-askers. I think adults could just be better at asking better questions. I took my 19-year-old, Tyler — every year I take him on a one-on-one trip. I said, where do you want to go this year? He's like, dad, let's meet in New York. He's a big basketball and sports fan. So we went and saw Wemby play the Brooklyn Nets, and spent seven days together in New York. And one of the things — I took him to a nice dinner, and I had prepared two questions. The two questions were: what's something you're feeling a lot of pressure about right now that your mom and I don't realize? And: what's something you're spending a lot of your time on that you realize is not serving you well? These two questions lasted almost four hours of conversation at dinner. To your point, the first question I asked about the pressure, he says, dad, you have no idea the amount of pressure my friends — even his girlfriend's parents — put on me because of who you are as a Navy SEAL. He said, everyone is like, are you going to be a Navy SEAL like your dad? And he says, I feel a lot of pressure about this. And so he and I were able to have this long discussion about how the only thing I want for him is for him to be happy, find what he's excited about, and do that. Because, to me — and his mom feels the same way — that's the best thing as a parent: to have your kids excited about something they're doing, and support them in that. And also telling him that that thing will change, maybe. I've changed my purpose several times. But I do think purpose is a big conversation worth having with the kids and helping them find that purpose. Because even yesterday, I was on a parenting Q&A, and a father was asking me, my 17-year-old wants to join the military — how do I talk him out of it? And he said, my son doesn't feel supported by me and his mom. And I was like, of course he doesn't feel supported, because you're not supporting him. You're trying to talk him out of the thing he really wants to do, and he needs your permission to sign up at 17. I said, whether or not you like the fact that he wants to join the military, there's a lot of positives that could come out of that journey. If my kid did that — I wouldn't want my kids to join the military, but if they did, I would support them, because that's what a good parent should do: be supportive, be there, especially when the kids get older into the later teen years. You can't be a dictator. You're going to push your kids away, and you're not going to have a relationship with your adult kids if you do that, in my opinion. So, yeah, you've got to be supportive.

00:38:17 Andrew Keen: Brandon, what do you make, then — we've talked a lot about parenting — what about, I mean, your kids look delightful, as you know. Like all kids, they're not always delightful, but they look a lovely group. What do you make of this generation? Jonathan Haidt has called them the anxious generation. A lot of that's bound up, of course, in social media and their supposed addiction to smartphones, although our generation seems equally addicted. Is there something uniquely anxious about our kids' generation, these teenagers and 20-somethings? Is it a consequence of economic instability, too much Internet? It's hard to know what's really happening, and whether every generation worried about their kids.

00:39:05 Brandon Webb: Yeah. To your point, every generation has its challenges. My kids, for sure, being totally Gen Z, plugged in. I wrote an article on the Substack about just how to translate Gen Z talk, because they have a whole system of language that we don't know about. We're definitely dealing with — you have these social media companies whose whole job is to grab your attention, and they really prey on these young kids. That's why in China, China limits TikTok.

00:39:47 Andrew Keen: I mean, are the Australians right to ban social media for young people?

00:39:51 Brandon Webb: Me as a parent, I look at that and I kind of laugh to myself, because any kid will figure out how to get connected. They're so smart, so much more technologically advanced. And if you try and take it away at home, they're going to go to the friend's house and get it. So I think the true focus, as parents, is to be present and raise your kids to make good decisions. Because when my oldest was 16, he deleted all his social media. Still to this day, at 24, he has no social media. I asked him — Jackson, what's behind this? He's like, I don't want to be too stressed. There's too much pressure. These kids are on it. He's like, I just deleted it. I'm like, man, what a great thing to hear a 16-year-old say, and what a healthy thing to do. And it's the same with his younger brother and sister. I feel like their mom and I have done a good job raising them to make good decisions. And that's the best thing you can do as a parent — not worry about these thousands of variables that could go wrong. Focus on raising confident kids who can make good decisions, and then hopefully you've done your job well enough that they come to you to seek counsel. That's a big thing when the kids are in their late teens, mid-to-late high school age. You have to recognize that your role as a parent is shifting more to one of a guidance counselor. They're old enough, and they realize at a certain point they're going to make their own decisions. And I think parents have to kind of let go, and hopefully you've done your job well enough that the kids are going to be good decision-makers. And then you realize also that sometimes they're not always going to get it right — but letting them — I don't know how many times my oldest has come back to me and said, damn, dad, you were right about that. Should have listened to you. But I know he's got to make these mistakes himself to arrive at that, and at least he comes back to me and shares it with me.

00:42:05 Andrew Keen: Yeah, and that's usually the reverse with my kids — I usually go to my kids and say, yeah, you were right about that. You've got a very nice piece in the Wall Street Journal last week, front page, and actually, interestingly enough, next to it was a Wall Street Journal piece — I'm reading the headline — 'The great $110 trillion wealth transfer won't happen anytime soon. Americans 55 and up control most wealth.' What's your advice when it comes to money and our generation, since we control this — not necessarily just you and I, Brandon, but collectively we have $110 trillion which we're going to pass down. There's a lot of press about how kids these days can't afford to buy their own places, can't afford to get on even the lowest level of the ladder, can't have families because they can't afford to have kids — which may or may not be true. I'm not sure how much money you really need to have kids. But do you think parents should rethink how they pass on their wealth? Is that part of being a good parent these days?

00:43:14 Brandon Webb: I think the part of being a good parent that a lot of parents tend to skip over is just teaching your kids about money. Especially — I have strong opinions about America and our economy. Especially now that I've had a chance to live in Portugal almost three years and experience what a good tax deployment looks like, when you can actually take the tax revenue and put it into health care and education. At a basic level, kids in Europe, if they have decent grades, can go to school free and not be saddled with this mountain of student debt. A trip to the emergency room is not also going to bankrupt the family like it would in America. So I think we have big problems in the United States that need to be fixed. But the main thing is, it starts at home. I wanted to make sure my kids understood that having a credit card is a tool, but not to be taken lightly, because the interest rates are predatory. These kids at colleges — these credit card companies prey on them, because they know the parents putting them through college are probably going to be there to bail them out if they get over their head in any credit card debt. Which happened to my oldest, after we'd had a long conversation about the risks. He had managed an investment for me. I made the same deal with all my kids in college: I'm going to pay for their school, they have a roof over their head, they're not going to go hungry. But if they want to socialize, they need to get a job on their own, or they can help me in this real estate investment I made — I own a self-storage facility. So Jackson managed the self-storage facility, soup to nuts, all through college. We sold a facility, and he had some ownership in it. So he ended up getting a $25,000 check as a sophomore, I believe, at St Andrews. He reinvested some and then spent the rest like a drunken sailor on shore leave. And then he said, dad, I want to get a credit card. I want to build my credit. And I was like, son, let's have a conversation. We had this talk about the dangers, and I said, well, just pay it off every month. Six months later, he calls me. He's like, dad, I'm in trouble. I owe $12,000 on my credit card. I have no way to pay it back, and the interest rates are eating me alive. And I was like, you remember that conversation we had six months ago? He's like, yeah, dad. I was like, so why are you calling me? He's like, your problem — figure it out. And I let him suffer. He spent two years as a friend — his girlfriend hated me. But last year, he paid it off, and he's like, dad, that was one of the best lessons you taught me. He's like, I lost sleep over this, but I paid it off, with this new business. And he's like, I will never make that mistake again. So these are the kinds of lessons. It would have been easy for me to bail him out, but I knew that going through that pain was an important lesson for him, and he came out the other side how I thought he would. But there's plenty — I learned a lot writing this book. One of the things I learned: they have this resource called Acorns Early. It's an app you can get on the kids' phones, and it gamifies learning about finance, to the point where I think it prepares our children — back to being good decision-makers — to realize what they're getting into. Because when they leave home and go to college, or out on their own, inevitably, they're in the system. Right? And the American economy is largely fueled by consumer debt. And I want my kids to understand how that system works, so the system doesn't take advantage of them.

00:47:21 Andrew Keen: Well, it's all in Puddle Jumpers — powerful mental techniques from a Navy SEAL performance coach and father of three. Finally, the book is out this week. I'm sure it'll be a bestseller, like many of your other books. I wonder — we had a show a couple of weeks ago with the journalist Helen Benedict, who wrote a novel about American soldiers overseas. She's done a number of books and articles on American soldiers in Afghanistan and Iraq. She argues that Iraq turned some American soldiers, not all, into monsters. Maybe it was a structural consequence of the war. How has being a parent, Brandon, helped you address and perhaps slay some of the ghosts, the dragons, that you must have had to face as someone who has been in war as a Navy SEAL?

00:48:20 Brandon Webb: My personal experience — I've thought long and hard about this, because I've had many friends and people I know from my community who have gone down a very dark road. You're put into these situations. For me, I went to Afghanistan right after the terrorist attacks of 9/11. The mission was very clear: just go to Afghanistan, destroy the training camps, and kill the bad guys. And when I was over there, I saw the propaganda posters in the caves of the planes crashing into the towers. It was very real. To me, my deployment was very purpose-filled. We did terrible things — that you do in war — but I came back from that. And I had my oldest when I was there. When I came back in 2002, Jackson was five months old. First time I'd seen him or held him. But I think it has to do with purpose, because when I transitioned to an instructor, part of my reason for giving up my military career was, one, I wanted to spend more time with my kids. I saw what guys that had stayed twenty, thirty years had — no relationship with their children. Their marriages were a mess. Not everyone, but the majority. I didn't want that life. And I also saw that foreign policy was kind of off the rails in America. I'm like, why are we in Iraq? Doesn't make sense. Why are we still in Afghanistan? And I had friends who were over in Afghanistan in 2010, and they're like, we have no idea what we're doing here. So I think if a service member is put in that situation — in a warfare-like environment — and they have no idea what the hell they're doing there, that's what gets to what you just referenced, what that previous author, that woman, said: I think you're going to end up creating monsters in that situation, because people are doing things and witnessing things, and they can't assign rational purpose to them. That's when they have serious mental issues. One of my favorite books is Man's Search for Meaning, Viktor Frankl's book about his Holocaust experience. When I look at the generation that fought World War II, it's very clear — you have this evil of Hitler and everything that he stood for in Germany at that time. Even in World War II, the casualties were immense. It was a very violent war. But the veterans coming off of that felt like, okay, we won. Good overcame evil. All these terrible things we did, there was a purpose behind it. Now I can go live my life. And there's a ton of veterans coming out of World War II in America that went on to build huge businesses and become successful. I think they dealt with it a lot better psychologically than, say, Vietnam War veterans, which is proving my point, right? There was no purpose to the Vietnam War. People knew that. They come home. And my Afghanistan, my version, was the same as Vietnam — we just got a better homecoming. It was, like, all this support. But for me, personally, I think I've been able to deal with the demons because I remember a very clear purpose behind my combat deployment. Iraq — I can understand why these veterans are coming back going, what the hell was I doing there? And so, me personally, I'm very anti-war.

00:52:11 Andrew Keen: Yeah, and I'm sure this would extend — it's probably a conversation for another show — would probably extend to Iran. Well, it's a fascinating conversation. Brandon, you've been a good sport to deal with my nosy questions about your relations with your father and your kids — although it's somewhat confessional. This new book, Puddle Jumpers: Simple and Proven Ways to Raise Confident and Joyful Kids. I'm sure you're going to get lots of notes, Brandon, from kids asking you to adopt them. Are you open to new kids?

00:52:47 Brandon Webb: I am. I'm single, looking for a partner, but I do really enjoy being a father. As much as it's nice to have them out of the house, with the right partner, I would do it all over again.

00:52:59 Andrew Keen: Well, there you have it. Any unattached ladies who want to start a new family — Brandon Webb, the author of Puddle Jumpers, is open to it. Congratulations, Brandon, on the new book, and that was a wonderful conversation. Thank you so much.

00:53:12 Brandon Webb: Thank you, Andrew. Enjoyed it.