Navy SEAL Dad Reveals How to Raise Confident Kids After Divorce | Brandon Webb
The James Altucher ShowMay 21, 2026
1400
00:59:3254.51 MB

Navy SEAL Dad Reveals How to Raise Confident Kids After Divorce | Brandon Webb

James talks with former Navy SEAL and bestselling author Brandon Webb about parenting, divorce, discipline, confidence, and raising resilient kids. Brandon shares practical lessons from co-parenting, military training, and fatherhood—and why kids need love, limits, failure, and real responsibility to grow.

A Note from James:

Today on the show, I have a very special guest and a good friend of mine, Brandon Webb.

Brandon has been on the show many times before. He’s a former Navy SEAL, and he also ran the Navy SEAL sniper school that trained some of the best snipers in the world, including the sniper the movie American Sniper was based on. He’s written a ton of books about the military, leadership, confidence, mental toughness, and even military thrillers. A few weeks ago, we talked about what was going on in Iran, and I encourage you to go back and listen to that episode too.

His new book is Puddle Jumpers: Simple and Proven Ways to Raise Confident & Joyful Kids. This is not your typical parenting book. It’s not filled with abstract academic theory. I hate those books. This is written by a dad who has been through war, divorce, rebuilding businesses, and raising three kids as a committed co-parent after he and his ex-wife split.

And I know his kids. From my perspective, he’s done a great job.

As a father myself, I was really interested in this book. And even beyond parenting, it was useful for thinking about the kind of discipline I need to apply to myself. I’ve been divorced. I’ve had failed businesses. It’s hard navigating those life traumas while also trying to be a good father. Brandon has lived that, and he writes about it honestly.

So let’s get into it. My friend, the one and only Brandon Webb. Welcome back to the show.


Episode Description:

James talks with former Navy SEAL, bestselling author, entrepreneur, and father of three Brandon Webb about parenting, co-parenting, discipline, confidence, failure, and what it actually takes to raise resilient kids.

Brandon’s new book, Puddle Jumpers, is not a parenting book written from an ivory tower. It comes from lived experience: war, divorce, rebuilding after business failure, co-parenting across households, and trying to raise kids who can handle real life. His central point is simple but difficult: kids need love, support, boundaries, and enough ordinary stress to develop confidence.

The conversation is practical and personal. Brandon explains why successful co-parenting requires putting the kids ahead of old resentments, why parents should ask better questions, why punishment without understanding the “why” can backfire, and why kids need to experience failure instead of being protected from every hard moment.

What makes this episode useful is that the advice works beyond parenting. The same ideas—take responsibility, ask better questions, tolerate discomfort, celebrate small wins, and learn from failure—apply to adults too.


What You’ll Learn:

  • Why Brandon wrote a parenting book after years of writing about the military, leadership, and mental toughness.
  • How he and his ex-wife built a healthy co-parenting relationship after divorce.
  • Why “happy mom, happy kids” became one of his guiding principles.
  • How everyday stressors—ordering food, asking for an autograph, taking the subway—build real confidence in kids.
  • Why parents should praise effort, risk-taking, and resilience rather than simply telling kids they are smart.
  • How to discipline with love by getting to the “why” behind bad behavior.
  • Why sometimes the best parenting move is not advocating for your kid.
  • How to help kids find purpose by exposing them to lots of people, places, skills, and experiences.


Timestamped Chapters:

  • [02:00] Brandon on parent-to-parent advice versus academic theory
  • [03:02] A Note from James: Brandon Webb returns
  • [04:42] From Navy SEAL books to a parenting book
  • [05:27] Why Brandon never expected to write about parenting
  • [06:14] Friends asking Brandon for parenting advice
  • [07:25] Why he saw a gap in parenting books
  • [08:12] Applying SEAL mental management tools to parenting
  • [09:01] Co-parenting after divorce
  • [09:29] Brandon’s ex-wife and kids joining the audiobook
  • [09:47] Publishing with Authors Equity
  • [11:07] Why co-parenting often breaks down
  • [11:48] How the family court system can create conflict
  • [13:22] The therapist who helped Brandon and Gretchen divorce well
  • [15:29] “Happy mom, happy kids”
  • [16:31] Responding when plans change after divorce
  • [17:35] What the kids remember about healthy co-parenting
  • [18:24] Why each chapter could be its own book
  • [19:41] Building confidence and celebrating small wins
  • [21:00] The power of ordinary stress
  • [21:53] Asking for an autograph and building courage
  • [23:33] Why kids need “wind” to grow stronger roots
  • [24:47] The New York subway story and trusting kids
  • [25:31] Failure, responsibility, and protecting kids too much
  • [26:35] Praising effort versus praising intelligence
  • [28:26] Brandon’s daughter failing her belt test
  • [30:19] Why painful moments can become gifts
  • [30:53] What Brandon wishes he had done better as a father
  • [31:51] Three questions Brandon asked his kids
  • [32:36] Why parents need to ask better questions
  • [33:22] One-on-one trips with each child
  • [34:00] Questions that led to a four-hour dinner conversation
  • [38:25] Discipline, emotional reactions, and over-punishment
  • [39:43] Getting to the “why” behind behavior
  • [42:00] The pizza delivery suspension story
  • [43:25] Changing the environment when a kid is struggling
  • [44:26] Discipline checklist and making kids feel heard
  • [44:49] When parents over-advocate
  • [45:10] Getting kicked off the basketball team
  • [46:00] The talented jerk problem
  • [46:38] What changed when Brandon took the coach’s feedback seriously
  • [48:24] Accountability, consequences, and adult life
  • [49:00] Helping kids find purpose
  • [49:39] Travel, culture, and exposing kids to new experiences
  • [50:14] Supporting a child’s talent when it shows up
  • [51:17] What to do when your kid chooses a path you don’t love
  • [52:33] Becoming an advisor as kids grow up
  • [53:14] Why mentors matter
  • [53:32] Purpose changes over time
  • [56:23] Creating a “forever family”
  • [57:26] Brandon reads a letter from his daughter
  • [59:23] Why the lessons apply to adults too
  • [01:00:07] Closing thoughts on Puddle Jumpers


Additional Resources


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[00:00:00] Today on The James Altucher Show There's a lot of academic material, but not a lot of kind of parent-to-parent advice. And I reference a ton of academic studies in the book, which are, I think, super valuable and have their place. But it's like, if you and I want to go climb Mount Everest, we're not going to go to a professor and ask him what's the best way to climb a mountain.

[00:00:24] We're like, OK, let's go ask Conrad Acker, the guy that actually climbed and summited the mountain, for his advice. Because he's been there, got the scar tissue to tell about it. He survived. But we got through it all. And I'm here as a divorced dad who rebuilt his life after the Navy. Lost the business, built one back, went through divorce, raised kids as a divorced co-parent. And I'm proof that you don't have to be living in the same house. Their mom and I did a pretty damn good job.

[00:00:57] This isn't your average business podcast, and he's not your average host. This is The James Altucher Show. Today on the show, we have a very special guest, a good friend of mine. He's been on the show many times before. Not only as a former Navy SEAL, but he also ran the Navy SEAL school to train snipers,

[00:01:26] including the sniper that the movie American Sniper was about. He's written a ton of books about all this stuff. Plus, he's even written military thrillers. He's written books on leadership, competence, mental toughness. Of course, we're talking about Brandon Webb. We've talked to him a few weeks ago about what was going on in Iran. I encourage you to go back and listen to that podcast. His new book, Puddle Jumpers, Powerful Mental Techniques from a Navy SEAL Performance Coach and Father of Three.

[00:01:55] This is not your typical parenting book. It's not filled with academic theory or abstract advice. I really hate those books. It's written by a dad who's literally been in the trenches through war, divorce, rebuilding businesses, and raising three kids as a committed co-parent, even after he and his ex-wife split. And it's really impressive what he's done. And I know his kids. And I can tell you from my perspective, he's done a great job. As a father myself, I was very interested in his book.

[00:02:23] And even just for learning what kind of self-discipline I need to apply to myself, even though I'm not a kid, it was very useful for that. And of course, I've been divorced. I've had bailed businesses. It's hard navigating all those life traumas, I'll call them, when you're also a father and you want to do the best for your kids. And you have to be disciplined in yourself to do that. So let's get into it, my friend, the one and only Brandon Webb. Welcome back to the show.

[00:02:59] Brandon, you've written a lot of bestselling books. You've written about being a Navy SEAL. You wrote about the sniper school you started in the SEALs, where the American sniper himself had trained. You've written about confidence with helping our good friend Kamal learn to swim. And that kind of blossomed into a book on confidence. And you've written, of course, all these military murder mysteries. And now, sweetly, a book on parenting.

[00:03:28] Which, by the way, I know one of your kids. I know your son very well. And we've all played chess together. And I could tell you're a really great parent. I was happy to see your book and then read your book. It's great. And what got you into doing that book? That's a good question. And I'd never in a million years thought I would write a book on parenting. Coming after COVID, you and I had similar experience. We both moved away from New York.

[00:03:55] And I was in Lisbon and thinking, what's my next book? You know, I like to write. And I was becoming, you know, I started writing. I wrote a few books with John Mann, who's an amazing writer. But I was becoming a stronger writer on my own. And I'm like, hey, what's my next solo book project? And I started thinking about it.

[00:04:17] And then I became overwhelmed with requests for advice from my peer group of friends. Even Kamal, who's not a parent. Kamal has been around my kids since they were young and grown up. And he knows my oldest, as you do, very well. And he's like, you have great kids. You should really write a book on parenting because your kids are like happy. And they can make eye contact and have a conversation.

[00:04:47] They're not on their phones all the time. I'm still learning about the eye contact part. Maybe you can show me. Yeah. And it was just overwhelming. Because I think my peer group has much younger children. Like I had kids young in the military. My ex was 19. I was 22. We were kids having kids. But now that I'm the age I'm at, all my friends have kids. Some in diapers. They're all like under 12 years old.

[00:05:16] They would meet my older kids. Because I'm good about bringing my kids around my network. And they would meet them and inevitably ask me for advice over and over and over. And that's when it dawned on me, okay, I think maybe I have something to contribute in the parenting space. And I was shocked when I was doing the research on Amazon how little is out there.

[00:05:41] There's a lot of academic material, but not a lot of kind of parent-to-parent advice. And I reference a ton of academic studies in the book, which are, I think, super valuable and have their place. But it's like, if you and I want to go climb Mount Everest, we're not going to go to a professor and ask him what's the best way to climb a mountain. We're like, okay, let's go ask Conrad Acker, the guy that actually climbed and summited the mountain, for his advice. Because he's been there, got the scar tissue to tell about it.

[00:06:11] He survived. And that was my philosophy with this book, was my experience share as a parent. You know, we have kids. We don't get a manual with the, an owner's manual with the kid, right? We just kind of wing it. And I think one of the things that I had as an advantage as a dad was I had all this training and experience teaching mental management to snipers, which applies to parenting. It applies to anyone can use these tools.

[00:06:41] And I think that was an advantage that helped me. I mean, there's plenty of things that their mom and I encountered along the way, as I'm sure you did. The sex, drugs, alcohol, all of the above. But we got through it all. And I'm here as a divorced dad who rebuilt his life after the Navy, lost a business, built one back, went through a divorce, raised kids as a divorced co-parent. And I'm proof that you can, you don't have to be living in the same house.

[00:07:11] Their mom and I did a pretty damn good job. And she wrote the intro for the book. Yeah, she not only wrote the intro, we have a whole 30-minute bonus content section on audio about how we decided to be co-parents and put all our differences aside in the divorce and focus on being really positive influences and co-parents raising our kids. So we have a whole conversation about that. My kids are on the audio book.

[00:07:37] You know, there was a story, plenty of stories that were, you know, they were telling it from their side. So I think the audio is going to be a, it's an amazing, amazing book. Because you can hear the kids themselves and speak themselves. But that's how I decided to write the parenting book. I did it with a new publishing company. You know, I told you about Authors' Equity, which James Clear, the Tomic Habits author, is a co-founder. I think maybe even Tim Ferriss invested in Authors' Equity.

[00:08:06] But it is, because you and I have strong opinions about publishing and how it can seem a little antiquated. But Authors' Equity, they nailed it. It's a 70% profit share to the author. There's no advances. But they only do 30 books a year. They focus on quality. And it's the best publishing experience I've ever had. It's really great. Yeah, so I highly recommend these guys. Really know what they're doing.

[00:08:33] And you have the same level of influence as if you're self-publishing, right? You're going to get the title you want. You're going to get the cover you want. And if they push back, it's going to be a data-driven kind of decision, which we did often. But yeah, that's how I decided to write the book. They have distribution deals to get you in bookstores? Yeah, they have a distribution deal with Simon & Schuster. So that's the big thing too, right? When you self-publish, you don't have that distribution network.

[00:09:02] And they have all the distribution airport, big box stores. So it's been a good experience so far. That's great. You know, it's very interesting that your ex-wife wrote the intro. Why is it the case, and this is just a small question that I want to get into the parenting, but why is it the case that some parents don't successfully co-parent? Like, shouldn't they always have the focus on the kids, obviously? Because the kids are so impressionable. They're the ones who need the help the most.

[00:09:30] But people still bring their anger into co-parenting situation. Yeah, I think, you know, and also I was listening to an old, I love Milton Friedman. He's one of my favorite economists. And I was listening to some of his old talks that he gave. And he was talking about how the government set up a system that creates, you know, the intent is right. And he was talking about the welfare system. But what it actually does is encourage poor people to stay poor and have more kids and

[00:09:58] get more benefits from the welfare system. It's actually a terrible incentive. And I feel like the family court system in America is set up to create a fight. And then when the divorced parents are fighting, in a certain case is this, right? If the mom gets greater than 50% of custody in most states, that means more money for her. So her lawyer is going to be fighting for more custody. And I think a lot of fathers get triggered. I did.

[00:10:27] When I like, I don't want to go. I'm not a 40% dad. I want to be 50-50. So I feel like the family legal system in America is a disaster and creates this mess. But to your point, parents should put aside their bullshit and get along. But it's, I think it was Thayer wrote, misbehaving, right? He was the first economist to really push behavioral economics. Because the previous version of economics theory was taught as if everyone should behave rationally.

[00:10:57] And we know that the world we live in isn't that way. And so parents behave irrational. They weaponize the kids. The kids are smart. They're trying to use their leverage. And if mom and dad aren't united, they're trying to use mom and dad against each other to get their way. Because that's, you know, that's them trying to outsmart the system. But thankfully, I think what really anchored Gretchen and I through our divorce,

[00:11:27] number one, we were in therapy with amazing psychologists. And not somebody that had went to, you know, national university online. Nothing against national university. But I've been through counseling sessions with somebody that doesn't have a PhD on the end of their name. And it is very, very different level of help. And we were in with this PhD out of La Jolla, Dr. Baker. It was incredible.

[00:11:56] And she said, look, you know, you guys, we decided in therapy to divorce. And she says, I'm going to show you how to do this so your kids will develop into happy young adults. She's like, I had so many clients that did not take my advice. And now they're dealing with adult kids who are nightmares. She's like, if you want a peaceful adult life and have a good relationship with your adult kids, follow my advice.

[00:12:24] If you want the opposite, go ahead. She's like, I've seen how that story ends over and over. And I think Gretchen and I had been through a lot of trauma. Like I had my oldest who I use pseudonyms in the book. So in the book, he's Jackson. Jackson was born when I was in Afghanistan right after 9-11 attacks. You know, so she was like having a baby at home while I was at war, home by herself.

[00:12:50] And we just been through a lot and done, you know, the same terrible things that people do. And, you know, in relationships, the one thing that aligned us was listening to this Dr. Baker say, if you do this, your kids are going to be happy, well-adjusted. And you guys, you don't have to be best friends. But if you commit to being good co-parents, you're going to reap the rewards.

[00:13:17] And so we love the kids so much that we're like, okay, let's do that. And we listened to her and we saw like it was hard. Divorce is hard. Even though we had a relatively good divorce, it's still tough. You get emotionally triggered. I remember I had a solo session with the doctor and she says, because I was really upset that she wanted to move the kids four or five counties away. And I'm like, she can't do that. It's against the law.

[00:13:44] And she was like, Brandon, happy mom, happy kids. Do you want your kids to be happy? And I was like, of course. She's like, well, she needs to get stable. She wants to move to her family's ranch. And it's a stable environment. That's what she needs to kind of get her peace of mind back. And I said, got it. And when I, so that was my default mode. Every time I got emotionally triggered, I'm like, happy mom, happy kids.

[00:14:11] And I was just like, and there were several times that I would get really upset about maybe some decisions that she was making almost in a unilateral sense. Like she met her new husband. And I had orientated my whole life around her living on her family's property in Paso Rovo's. And then she's like, she met her husband now, Bob. And she's like, hey, we're moving to Oregon. And I'm like, well, I just reorganized my whole life around this.

[00:14:40] Now, it took me two seconds to get out of my own way. But I was like upset about it at first. But then I remembered happy mom, happy kids. And I said, okay, let me think of all the positives of this situation. They can afford a good house. They can, the school system is better. Actually, it triggered my move to New York. I was like, there's a very easy nonstop between Portland and New York. So I said, okay, I'll just make the best of it.

[00:15:04] But that's what kind of caused us to get, to make sure that we played nice together. And in the beginning, it was tough. You know, our parents take sides like many do. But once our own family saw the example we were setting, they started to get along. They've taken vacations together since. I'm talking my parents and her parents. Wow. Crazy. Yeah, yeah, crazy. I was invited for the first four or five years.

[00:15:34] I could come up and stay at their guest house in Paso Roblo. So Gretchen would go on the weekend and get a break. I would live on the property and even go to her home and stay with the kids. And we would have our own adventures. And it became a real positive environment. And the kids still talk about it. They're like, yeah, it was so nice. Because they know they have friends in school who are divorced. And their parents can't be in the same room as each other.

[00:16:01] And they're like, dad, you cooked Thanksgiving dinner for mom, our new sisters, and our stepdad, Bob. Twice I cooked his holiday dinner. I'm almost going to say that's over the top. But that's still very mature and impressive of you. No, but that's really good advice to kind of step back and always kind of focus on that happy mom, you know, happy kids philosophy. Take a quick break. If you like this episode, I'd really, really appreciate it. It means so much to me.

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[00:19:00] And you know, the book is great and there's so many stories, both external stories and your own stories about parenting. You know, what I like about your book, and this is more of a writing thing, but just for a second, is I always think most books are like expanded articles. Like somebody wrote an article for, I don't know, the Atlantic Magazine, a publisher liked it, and said, can you make this 300 pages instead of 12 pages? And then the books are sort of mediocre.

[00:19:28] And I always try to do the opposite with my own books, which is basically to actually keep, you know, make it seem like every article or every chapter could potentially be expanded into a book rather than, which is the opposite of what most of these bad books do. And I feel like your book is similar. Like every chapter could be its own book, like Creating the Forever Family or Disciplining with Love. Like Discipline is a book on its own, but that's just a chapter.

[00:19:56] Or Raising Kids with Purpose, that could be a book on its own. And so I kind of just want to go back and forth and ask specific questions I had while reading the book. And for me, Cultivating Mental Strength, Building Confidence, these are two different chapters, Raising Kids with a Purpose, Building Confidence somehow, that chapter really hit me because I feel that's an area where I sometimes lack. And a lot of the techniques and suggestions I sort of learned as an adult.

[00:20:24] But there's one part that's been hard for me since I was a kid, and it's been hard for me as a parent, and it's been hard for me as an older adult, which is your last idea of building confidence is celebrating those successes, even small successes. I don't know how to do that. Yeah, no, that's, I don't know where I got it. I think it was maybe through YPO or the EO when I joined it, but it was remembering to celebrate, to celebrate even the small, small things.

[00:20:53] And I always tried to make that. And again, we're humans, we're incentive-driven creatures. And I wanted to, you know, show the kids, like, look, this is, when they had a success, and I knew that it's something they worked very hard at, we would celebrate even if it was a nice dinner, or something like that. But I always made sure to kind of celebrate those small things. Because I believe that creates a really good incentive system for them to want to, you know,

[00:21:23] go on to the next challenge. But the most important thing, I think, that I talk about in the book is the normal, everyday things that parents stop their kids from doing, whether it's they're overprotective, or it's maybe more convenient for them to make them school lunch, or just check out at Starbucks on their own.

[00:21:45] But when you let a kid do that, and the data backs this up, I checked a lot of my, what I thought I was doing right against a lot of studies. And even though I got a lot of things wrong, there were a lot of things I did right. And this was one of them. Letting my kids experience the everyday ordinary, which seems to us trivial, but as a kid, you know, going to Starbucks to buy their own coffee and check out and having to interact with the barista,

[00:22:15] it could be very stressful for, you know, an eight-year-old kid. I remember I tell a story when Tyler was, I think, around nine or ten, and I had flown to Portland to take the kids to see my dad up in Idaho. So we were flying to Spokane, and we're in the Portland airport, and Tyler's like, Dad, he points over across the food court. That's my favorite Timbers player, and the Timbers are the Major League Soccer team in Portland. And he was like, Dad, can you get me an autograph?

[00:22:45] Can you go ask for an autograph? And I was like, buddy, you've got to learn how to ask yourself. Like, you can do it. Just go over there and ask him. Like, he wanted a picture or something. How old was he? 19? He was like nine or ten. And his sister started chiming in, because they knew where this was going. And my whole, my triple dog dare to the kids was, do it for Dad. And I was like, come on, buddy, do it for Dad. That was like, if I laid that down, they knew it was like the triple dog dare,

[00:23:15] you know, from that, what was that movie with Ralphie, the Christmas movie, Christmas Story. And so his sister started, like, come on, buddy, you can do it. So eventually he worked himself up and went over and asked, because he was the shyest of the two older siblings. And next thing you know, their cell phones are out. They're taking selfies. They went above and beyond to make this kid happy. And he comes back with the autograph and a big smile on his face. That was a breakthrough moment for him.

[00:23:44] Because then he wasn't so shy to kind of do things on his own. And it would have been easy for me as his dad to just go ask for the autograph, right? But that, I knew that this was going to be, you know, a lesson for him and help his confidence. And I talk about the, this Mars biosphere experiment they did in the 90s in Arizona, where they're seeing what it was like to colonize on Mars. And they were growing trees in this dome.

[00:24:11] The trees would grow to a certain height and just fall over. And the scientists were like, how, why is this happening? How come the trees are falling over? Because the trees needed the stress of wind that they weren't getting inside the shelter dome to grow strong roots. And the kids are the same. Like, they need these tiny little stressors to grow up into confident, resilient kids. And if parents, if you rob them of that, you always go ask for the autograph yourself.

[00:24:39] You're doing everything for these kids, protect, overprotecting them. You end up with kids who are in college that are just like shocked at how the real world works. And they're not prepared for adulthood. And, you know, I think that puts them at risk. So, you know, the ordinary magic is, I talk about in the book, is super important that we let the kids experience this stuff. And the last story I'll finish with, when I wrote the book, I sent the kids three questions.

[00:25:07] And one of the three questions was, what's one thing that you remember about me as your father that really stuck with you? And Jackson, my oldest, says, he's like, it was when I came to New York, you had got me a summer internship. He was 16, about to turn 17. He's like, you gave me an MTA card and told me how to get to work and let me do it on myself. He's like, I knew that none of my friend's parents would do that for them.

[00:25:34] Jackson's telling me this as a 24-year-old tech company founder, that that was like a super pivotal point in his life that he felt like, wow, my dad believes in me. My dad trusts me. I'm responsible. I can do this. Like that made a huge impact on him. And to me, I forgot that long ago. But it shows you how powerful these little ordinary moments can be in the development of a child. You know, related to that, and you talk about this in the book, is the role of failure.

[00:26:03] So A, how to learn from failures, but B, also how to accept responsibility for failures. And I think a lot of parents, myself included, they don't want their kids to ever experience failure because we've experienced it. And by the way, it's very unpleasant and you never want your kids to have to think alone at night. I always picture my kids just crying by themselves at night in their bedrooms. And I don't want them to experience that. And so you try to protect your kids from failure.

[00:26:31] Like, you know, I'll give a kind of abstract example. This is not about chess, but I'll ask you. Like, when they were younger, did you let your kids win? Or did you crush them? Not just chess, like anything. Like, did you try to protect them from failure is really the question? Or did you kind of do anything you can so that they experience success? And what's good or bad in this? The answer is sort of unclear.

[00:26:59] Well, I think the data says, and I talk about a study they did in Stanford where they had two sets of kids. One set was encouraged to fail and try. And they were praised for their ability to kind of like take on a challenge. And even though if it didn't go well, they were encouraged. Like, wow, you did a great job at that. Let's try over again, right?

[00:27:27] So that was that set of kids. And the other set of kids were just praised constantly. Like, wow, you're so good. You're so smart. And as the challenges ramped up, the kids that were praised just for being smart stopped taking risks. They didn't want to be seen as dumb. Because they're like, wow, I'm being told I'm smart. I'm being praised for being this like smart kid. So I don't want to make a mistake. I'm afraid to kind of take on this challenge where these kids were just like excelling.

[00:27:56] Because they'd been praised differently. Praised for failing and trying over again. As opposed to just the kind of, which goes to this kind of culture that was really, I think, a millennial trend at the time was everybody gets a trophy. Everyone is special. Well, life doesn't work that way, you know, outside of that system. And so I think, you know, for me,

[00:28:22] I knew the value of failing and how it was a learning lesson. I tell tons of stories. And yeah, as a parent, you don't want to have your kids suffer or cry. And the first time I remember, and, you know, I have two boys and a girl, was when my daughter was testing for her purple belt. And her brother, her older brother, I drove up to Paso Robles for the tests. They did the whole, you know, we're in the dojo. Every time I think of that,

[00:28:51] I think of that movie Foot Fist Way. I don't know. It's hilarious. It's with Danny McBride. It's a hilarious movie. He's like this overzealous Taekwondo teacher, right? But it's a good, put it on your list to watch. Yeah, that's a good one. Danny McBride. If you watch Napoleon Dynamite, it's kind of the Rex Kondo guy, right? Okay, yeah. Remember Rex Kondo? Grab my wrist. Yeah, the wrist. But anyway, they're doing their tests.

[00:29:21] All the students are there. The parents are in the back. They do their whole thing. And then afterwards, students sit down. They get called one by one. They have to stand up. And I remember her brother stands up, bows to the sensei. And he's like, okay, you did this right. This is stuff you need to work on. But you did a good enough job. Here's your belt. Can't even get the belt. And then when it came down to my daughter, same thing. She stood up very stoically. And he gave the same critique. You know, this is in front of a room full of parents and their peers.

[00:29:49] And he's like, yeah, you didn't do a good enough job. You're not going to get your belt today. And she sat back down, stoic face. I told her mom, like, let me take her home separately so I can talk with her. We got to the car. She broke down in tears. My brother got his belt. And I didn't get, I'm not good enough. She just lost it. And you feel so bad. You know, I wanted to cry with her. But I knew that this would be a great learning experience for her because I knew she was going to retest

[00:30:19] in two, three weeks. And I told her, I was like, look, this is the way life is. You know, you're going to test and you're going to earn it. And you're going to feel very good about it because you'll have known that you earned it. It wasn't just handed to you. You know, and then a couple weeks later, I got a text from her mom with a big smile on her face and she's holding the belt in her hand. It's nice. These are the things that are gifts for our children. As much as we, it's hard to discipline sometimes and see your kids suffer.

[00:30:48] But you also realize, hopefully realize, that this is something that they need and will make them a better person. And again, the one thing I wish I had have done better, and I didn't realize this until I was writing the book, because one of the three questions I asked all the kids before I started writing was, what do you wish I had done better as your father? And my daughter, Madison, she said, Dad, you were my hero.

[00:31:17] You were always setting a great example. But I wish you had have shared with me about your own struggles and your own failures, because I would have felt safer to kind of struggle and fail. Like it wouldn't have been this bad thing. I would have taken more risk probably. And she was telling me this as a 21-year-old. And I'm like, wow. Wow, I wish I had have done that. Because my thing was, I need to be an exemplary dad

[00:31:46] when I have them, because I didn't have them full time. I need to be on full dad mode, no cell phone. And I did that. But the one thing I wish I had have done, in hindsight, was share more stories about my own personal challenges and overcoming them. Because it would have obviously made an impact on my daughter. So what are the three questions? So it's like, what do you remember from your childhood about me as a parent? It's what could I have done better?

[00:32:15] What's the other question? Yeah, the other one was to define my parenting style in one sentence. Like that was the three questions. And to your point, first, I don't think people are good at asking questions, right? You and I had 20 minutes catch up, and we had an honest catch up about what's happening in our life. Or most people say, oh, how are you? How's your day? My day is good. You know, that's bullshit. You know, it's like, no, actually, my freaking back is killing me.

[00:32:43] My freaking, my great grandmother just broke her hip. You know, like, that's the real stuff. But we don't, we don't get to that. And I think as parents, we need to ask better questions. If you ask your kid how their day was, it's a bullshit question, and you're going to get a bullshit answer. Rather say, if today in school was a movie, what would it be called and why? Like, that's going to get a very interesting answer as opposed to like, and so, you know,

[00:33:12] and I always try and be a good question asker. When another thing I did with the kids was, and the agreement that their mom and I had, because she had them for most of the time, they had one stable house, I would get them on all the big vacations, and I could take them on a one-on-one trip every year, because I found that getting them alone, like one-on-one with me, they behave very differently than when they're in like the sibling pack, you know, the wild pack. Yeah.

[00:33:42] And I still do that to this day. So I asked my youngest, he's a freshman at University of Oregon, and I said, hey, what do you want to do this year? He's like, Wemby, who's a super tall basketball player for the Spurs, he's like, Wemby's playing the Brooklyn Nets, like let's go to New York and do like a dad-son trip. So we went, we saw Wemby, we saw New York Rangers hockey game, and I took him to dinner, and I was like, okay, I want to have, I want to check in with him, because he's a freshman in college, you know, I just want to see, you know, how it's going.

[00:34:12] So I was like, I need to ask, you know, a couple good questions. So I did my research, I'm like, okay, I think I even asked Claude, I'm like, what's some good questions? So I asked him two questions that lasted four hours of dinner conversation. It was, first one was like, what's something that you're, you're feeling a lot of pressure on that your mom and I may not notice? And what's something that you're, that's happening to you at school right now, that things that you were doing that maybe you realize

[00:34:40] aren't serving your best interest, like you're kind of wasting your time doing? Those are the two questions. And the first, the answer to the first one blew me away because he says, dad, a lot of my friends' parents, even my girlfriend's parents, they put a lot of pressure on me because of your identity as a SEAL. They're always asking me, oh, are you going to be a SEAL like your dad? What are you going to do? He's like, I get a lot of pressure from these adults. And so we had a whole conversation about his future

[00:35:10] and how all his mom and I want for him is for him to be happy and find his thing. And then I had a conversation. I was like, don't let these adults who are putting their own bullshit insecurities on you as a 19-year-old, you know, it's like, don't, you got to realize, like, we're all dealing with things, you know, adults all have different things and anxieties and pressures and lost dreams. So don't let them, like, put their own baggage on you.

[00:35:39] And then the other answer to the question, he said that he felt he was getting peer pressured into going to parties at college and he's like, dad, I don't even like to drink and I feel like I'm, my roommate's peer pressuring me to go out every night and it's like, I just don't like it. So we had a whole conversation about peer pressure and being a leader and standing up for yourself. But that was four hours of conversation at dinner.

[00:36:08] I'm like, that's why you got to ask good questions as a parent. It's so important because it's so easy to slip into the pattern of like, hey, how was school? When really, it's like they're just going to, they're not going to lift their eyes from the screen, they're just going to say, good. And there's no content. But kind of, like the way you put it, like if today's was a, if you could, if you could, say what movie today's day of school was, what would it be? Like that makes them, they have to at least listen up for a second to think about it.

[00:36:48] Also, I think the chapter I really enjoyed writing was on discipline because I think a lot of, again, back to the question asking, a lot of parents and it's something we made a mistake, you know, Gretchen and I as co-parents, we made plenty of mistakes and a common one was we would over punish. Because when you realize when your kid does something, it either, it's in, it's in putting their future in jeopardy

[00:37:17] or maybe putting their, them in physical danger, you have this emotional reaction. And as parents, especially as the way I was disciplined, I remember my mom would like have my rap sheet out when my dad came home after like having a few beers with the guys in the construction site. And then I would just get hauled upstairs and get a leather belt to my bare ass. And nobody asked me like, why are you behaving like this? Like, what's the cause of this behavior?

[00:37:48] No one asked me that, you know? Would you have been able to answer? Would you have known why you were behaving like that? Yeah, I think I would have got to a point of it. Because the point is what really surfaced for me was when our youngest was having, he was struggling in middle school as a seventh grader. He was getting D's and F's, hanging out with a bad friend group. I know his older brother who was very active, both him and his older sibling, they get along great and they're always looking out for each other.

[00:38:17] But his older brother called me, he's like, dad, you know, he's getting in, he's doing some things that he probably shouldn't be doing and making money certain ways. And I'm like, I kind of read between the lines, like, oh, he's freaking selling drugs. So, so this was him as a seventh grader, right? And a seventh grader, his, his older siblings in high school, all their sibling friends knew who this young kid was, Tyler, because he was like the cool middle school kid selling him pot gummies at recess

[00:38:46] to all the high schoolers, right? Oh my gosh. It's like crazy. So, anyway, his mom's calling me once a week when I'm in York, you got to take this kid, he's, I don't know what to do with him. I was researching military schools. Then he gets suspended. She calls me, hey, he got suspended from school, we need to freaking drop the hammer on him and discipline. So parents have this emotional reaction and they go right into the punishment. And I remember, because this, the same therapist that helped us

[00:39:16] with our divorce, we had used a few times to look kind of like for conflict resolution with her and I, but also like we had questions about tricky situations with the kids and this is one of them. So I said, look, let me, let's call Dr. Baker and I'll set up a call and the three of us can get on. So we had this whole chat with the psychologist and she says, look, he's acting out for some reason. Like your job is to, for one, boys going through

[00:39:44] that developmental stage from 12 to 15. She's like, hormones, all sorts of things. This is such a risky time and if you, if you don't make him feel supported, you could push him away and lose him forever. And I was like, wow, that's crazy. So she said, you need to get to the why of the behavior. So I flew to Portland. He's suspended, right? He had lots of time off and I spent two weeks with him and I got to the why

[00:40:13] and it turns out and the reason he got suspended, it was a culmination of bad behavior but he had ordered pizza on, on Uber Eats to the classroom like Spicoli and Fast Sight at Richmond High and the teacher freaking outraged, right? So she, teachers eating the pizzas and then she's like, you can't do this. You know, you never, you can't send pizza to class. The next day he tried to work around and this had him all sent to the principal's office that got him suspended and so

[00:40:43] I found out that he's like, dad, you know why I'm acting out because I can't stand my homeroom teacher. She has embarrassed me over and over in front of my classmates and turns out like what she said was some terrible stuff and he's like, I think I'm trying to show her that I'm in control, not her and I was like, wow, that's pretty self-aware. Yeah, but it took us a while to get there and what, one of the things this teacher said in Oregon who is a

[00:41:12] white woman, she screamed at him one day in front of his classmates and said he was a victim of white privilege among a lot of other terrible things and I'm like, how could you say that to a 12-year-old kid in front of his classmates? So we went to the principal, turns out this teacher had had, you know, 20 complaints against her and he was like, there's nothing we can do, we're short-handed, we don't have enough teachers so his mom and I decided take him out of the environment.

[00:41:42] So sometimes you have to change the environment because environment is very important. We pulled him out of school, we told him, look, we're taking your side here, we're trusting in you and we got your back, we're taking you out of school and this is the plan, we're going to go on independent studies for the rest of 7th grade, 8th grade and then you start high school with a clean slate. The relief on his face when we told him we had his back, it was like nothing I'd ever experienced and I was like, whoa, this is going to be

[00:42:12] very good for him. All of a sudden his grades shot up to B average, COVID happened his 8th grade year so all his friends were on homeschool anyway and then he started high school with a clean slate and carried a 3 point plus average all through high school and it's the kid that was failing out and ended up getting in with a much better friend group and still like wasn't perfect. He got, this is another story I talk about in the book but first, let me finish

[00:42:41] on the discipline side. So the getting to the why of the behavior is so important. Making your kids feel heard and supporting them, huge and most parents don't do that. They go right to the punishment. They want to just sentence, you know, bang the gavel and sentence them without getting to the kind of core issue of the behavior. So that's why I made a checklist for the discipline in puddle jumpers. The other thing I think parents do is they have a tendency

[00:43:11] to over-advocate for the kids. So now he's in high school. He had a growth spurt. He went from like 5'5 to 6'3 and he's a basketball player. So gets recruited to the basketball team two weeks later. Coach sends his mom an email. Hey, I'm kicking your son off the team. He's unfocused. He's a distraction to other players. His ego, blah, blah, blah. Just the rap sheet went on. I was like, oh, wow. You know, the first reaction is, okay, F that coach.

[00:43:40] My kid is the best player on the team. I'm going to go and get him back on the team. So his mom and I talked. I was like, well, let's use this as a learning. Like we took the feedback seriously, which I think a lot of parents don't do. They just want to protect the kid and get the kid back on the team. I told his mom, I was like, this is going to be, I know how much he wants to be on that basketball team, especially on game day and suit up with all his buddies. Like this is going to be a good learning experience for him. He needs this

[00:44:10] because he was a little cocky and man, that chip got knocked right off his shoulder. I again, I flew to Oregon. I had a lot of conversations with him about dealing with my own experience with what I call talented jerk. You know, these people that are extremely talented, they know they're talented, but they can't work in a team because their ego gets in the way and they're freaking nightmares to work with. I see it in the author space, the musician space. It's like, you know, people got to want to work with you.

[00:44:40] They got to want to like to work with you. And so, next year, he makes the team as a sophomore. Coach writes us another letter. It was like, thanking us for taking the feedback. And he's like, I don't know what you guys did, but he's a totally different player. He's a great team player. He's a good leader. He listens. And it was like, that's what he needed. And parents need to realize also, sometimes you got to not advocate for your kid

[00:45:09] when they need to learn a lesson like this. Because I, as someone who was coached youth sports, I was a little league coach for two years. Parents are the worst. I have this, I still remember this couple. She was a doctor and he was a private equity guy in San Diego. They show up to the game, always late. And then, first thing, they start laying it on me. Why isn't my kid playing in the infield? Why is he in the outfield? And, I'm just like, okay, if you guys were here for the first three innings,

[00:45:38] your kid was in shortstop. He's one of the best players on the team. But the parents are the worst. So anyway, I just remind, yeah, I remind parents in the book, you know, let your kids, you know, take, take the consequences for their actions and you see it in that crazy documentary about Charlie Sheen. He's saying this as like a 60-year-old man now today. He's like, I wish my parents,

[00:46:07] my professional peers had have held me accountable for my actions. He's like, I got away with everything because I was Charlie Sheen. I was the cool guy. The cops would let me go, you know, after him pranking the other actor. They were on a flight to San Francisco and got the PA system and said the plane was going to crash to all the passengers. But he's like, we landed, the cops were there and they found out it was Charlie Sheen and Nick Cage and they just let us go. He's like, I never had any consequences for my bad behavior and he's like, I wish somebody

[00:46:37] had held me accountable. Maybe I wouldn't have had wasted the first, you know, 55 years of my life. You know, this is such good advice not only for parents and kids but just in life. Like if somebody, if anybody in your environment does bad behavior, you know, that's a broad umbrella but they need to have consequences or if you're misinterpreting it, then they'll show you your consequences. Like this all needs to be, to happen. You can't let people walk all over you for instance. Yeah. And allowing this advice

[00:47:06] applies really to adults and, you know, taking responsibility and asking the why when there is bad behavior. But the other thing I wanted to ask is, like, and this is for adults and kids but also for parents helping kids, you have a chapter on finding your purpose. How do you help kids? It's such a hard thing for adults but even for kids. Like how do you help kids find a purpose or a passion? My philosophy with that was

[00:47:36] how do I expose them to as many different things as possible? Experiences, culture, which was travel. I made sure they were very well traveled as kids and thankfully their mom was a big supporter of that. She'd let me take them, you know, my oldest was in Africa when he was 12. My mom took him on a trip there. So to see, like, poverty up close and different cultures I think is super important. But, I remember I would put them in these like

[00:48:05] multidisciplinary camps when I would take them for the summer. It was a camp in San Diego where they did drama, art, they did sailing, all these different things. And I remember that was the summer my daughter was maybe seven or eight years old and the art teacher came up to me when I picked them up at camp and she's like, hey, your daughter has a talent. She's like, I've been teaching art for years, like she's got something and you should support that. And so I had a conversation with her. I was like, hey,

[00:48:35] would you want to take private classes? I heard you got this compliment from the teacher and she's like, yeah, Dan, that would be amazing. So, you know, anytime I found something that kind of like lit up their eyes, I'm like, okay, I'm going to support this. And, you know, with my oldest, it was computers and chess. You know, I taught him the basics of chess and then when he lived with me in his first semester in college because of COVID, he taught me chess. He was like, yeah, dad, let me teach you

[00:49:05] some openings. It's funny, the parent becomes a student. That must be when I was giving him lessons, like four years ago. Yeah, yeah, exactly. But yeah, the main thing is to expose them to as many different things as you can and when you see what gets them excited is lean in and support that and sometimes you may not be happy with it. I was talking to, I was on a parent panel the other day and a parent asked, he's like, my son is turning 17,

[00:49:34] he really wants to go in the military and his mom and I keep trying to talk him out of it and he says he doesn't feel supported, how do I deal with this? I was like, well first, of course he doesn't feel supported because you're not supporting him. I was like, regardless of whether you think it's a good idea or not, he has latched on to this mission of joining the military. He has clearly something that he's really excited about and you guys are trying

[00:50:04] to talk him out of it. It's one thing to kind of facilitate a conversation. This is especially, I think, appropriate to parents with kids in high school because your kids, especially as like sophomore or junior, they realize they're adults and they're realizing they're getting to 18 and you can write their own notes to get out of class. They're becoming adults and you need to start treating them as adults as a parent, not grasping onto this dictator-like

[00:50:34] scenario when they were younger where you could pretty much, whatever you said as parents goes. No, they're going to be pushing for their own independence and parents need to come to grips with that and shift their parenting style to more of an advisory role. That's why I'm so grateful to have people like you in my kids' lives and Kamal and my other friends and they say, hey, can you, I know that my oldest, because I don't have the same background in computer science as he does,

[00:51:04] isn't going to listen to me about this thing. Even though, like, fundamentally, I think I'm right. I'm like, no, can you talk to James about this or Rusty, one of his mentors who built a billion-dollar software company called MarketScan, which evaluates trade-in value on automobiles, like, bootstrapped it to, you know, billion-dollar exit. I was like, go ask Rusty what he thinks, because I know they're going to have a conversation and he's going to take it differently as if it's his dad, right?

[00:51:34] So I think that's, as the kids get older, like, you've got to realize you're more an advisor and you need to kind of help them and I think getting them mentors is huge or surrounding them with a network that can help them figure things out is huge. But that was my philosophy and the one thing I did have a conversation with them as they were transitioning out of high school was, look, purpose is going to change. Like, I wanted to be an astronaut, then it was a fighter pilot, then it was a SEAL, I was like,

[00:52:03] then I was a SEAL and I left and I'm like, okay, who the hell am I now? Like, your purpose will change throughout your life and that's okay. I think even more so these days with the technology changing so fast. But, you know, purpose is an important one and I told this parent who asked me that question, I was like, you need to support him. I was like, I don't care if your wife, you and your wife don't think it's a good idea, that's what he wants. Just be supportive and then he'll be more open to kind of your feedback knowing that you support him

[00:52:33] and then maybe he'll figure it out on his own that he doesn't want to do this or he'll listen to you now that you've backed off. You know, it's a really good point. I think there's really, two really great insights here. One is people find their passion when they're exposed to lots of things. Like, that's just the reality. The other thing is they're going to change passions and purposes a lot. Like, I've had like 10 different careers since I graduated college. So, you know, and I know you have also. So, it's really important to realize that

[00:53:03] and being supportive doesn't necessarily mean they're in favor of it, but just that they're there to talk to them about it and to be, you know, to receive. Yeah. No, exactly. And it was like the noticeable shift in mood when I supported Tyler when he found out his mom and I weren't going to just drop the hammer on him for being suspended. We actually took his side, listened to him and supported him

[00:53:32] and he was, I could see the weight drop from his shoulders. Like, he was a different kid and it was like a huge moment and that's when I'm like, wow, we're supporting him and he recognizes that. It's such a powerful thing. That's why I was, when I listened to his dad trying, you know, he's just trying everything he could to talk his kid out of the military. I was like, yeah, but you're not. And he says, we're not supporting him. I was like, well, no shit, you're not, because you're not. I was like, you don't have to be happy about it. I'm not happy with

[00:54:02] a lot of decisions my kids make, but I'm like, and I can have, and they respect me enough now as adults. I have this adult kind of relationship with them, but they know I always got their back and I always, I always support them. I may not be happy with it, but I'm not going to, you know, scream and throw a tantrum. You know, I feel like when I was even doing press for the book, I did that Wall Street Journal article and I offered up my kids. My kids were actually in the same Airbnb

[00:54:31] on a ski trip and Pamela who interviewed me through Wall Street Journal as a mom and, because I just know, like, you've met my oldest, Jackson, and the kids just speak for themselves, right? So, recently, I host my daughter and her friend, she's in grad school, both of them were roommates in undergrad and went on to the Royal College of Art to do their masters and she's like, Dad, we want to come, you know, enjoy our Lisbon time and I talk about this in the end of the book about the forever family,

[00:55:01] like creating an environment and traditions to keep your kids kind of coming back when they're, when they're adults, which is a very fulfilling thing, I can tell you as a parent with older kids. So, I hosted them and I always go out of my way when she comes, you know, I'm like, mani-pedis, you know, nice dinners, whatever it is, like I bought her and her friend and I had bought them dipty candles and like little welcome packages and we had an amazing two weeks together

[00:55:31] and then I was, I went into the guest room and I was kind of like cleaning up a little bit and I found this letter she had left on the bed and she wrote me, it was the back of a postcard but I'll read it because this is like, to me, mission accomplished as a parent and this is, I wish and hope other parents can have this relationship with their grown kids because my daughter is now 22, she's getting ready to get her masters in June

[00:56:00] and start her career path but she wrote me this note and I'll read it for the audience. It says, dad, in parentheses, says, friend, master matcha maker, because I was making a matcha every morning, like hand crushing strawberries to make their little strawberry matcha. She says, dad, friend, master matcha maker, yoga buddy, et cetera, et cetera. You've created a home in Lisbon and how lucky am I that you've been making homes and places all around the world my whole life. Jealous,

[00:56:30] you get to live out the New York experience soon. You always go above and beyond to support me. The older I get, the more I see and appreciate it. Thank you for helping me live out my dreams in London. I'm so happy and passionate about what I do and study and I owe the privilege to you. Thank you for always welcoming my friends and treating them like family. You've taught me to find good people. Love you so much and thanks for letting us hang. You're the coolest.

[00:56:59] Love, Madison. But that's what she wrote me recently before I came on the New York trip. But to me, I'm like, I've read that letter probably 50 times. But that's like mission accomplished, right? Like, the best I want as a father is just for my kids to feel supported and for them to be living their own life, not the life that their mom and I wish for them. No, live the life that they want to live and make them feel supported. And,

[00:57:29] you know, when I read a letter like that, I'm like, okay, I feel good about being a dad even though I made plenty of mistakes. Well, you know, again, I've been a dad, a stepdad. Of course, we've all been kids. But even as an adult, the advice in your book is so valuable because these lessons can be learned anytime. You don't have to be 10 years old. You could be 50 years old and still learn a lot of these lessons. And it's valuable on every side of the equation. And so, I think this was a really strong book. You have such a variety of experiences.

[00:57:59] You're really a wise person and I value our friendship and getting to know you. And again, reading this book put into perspective a lot of stuff I'm going through as a parent even right now and my kids are mostly older. So, I can't recommend it highly enough. Puddle Jumpers, Powerful Mental Techniques from Navy Seal Performance Coach and Father of Three. Of course, that person is Brandon Webb. Just really impressed with the book. It's a lot of stuff to think about and you've been given a lot of great context

[00:58:29] in this podcast above and beyond the book. So, I really appreciate it. And thanks once again, Brandon, for coming on the show. Yeah, no, thanks for having me and I also appreciate the friendship and the chess coaching. Yeah, always happy to do that. I know I've been busy lately, but we'll get back to that. Yeah, let's do it.

[00:59:00] At first, I didn't think it was real. I woke up to this blinding light and I was transported to another place. Pluto TV! Then I heard a voice. Come with me if you want to live. There were thousands of movies and shows and they were all free. The truth is ours. It's just so beautiful. On Pluto TV, free streaming of Terminator 2, Fringe, Arrow, The 100 and The X-Files may cause excitement, loss of sleep and sudden belief in extraterrestrials. No credit cards or alien encounters necessary. Pluto TV. Stream now, pay never.

[00:59:31] To be continued... ... ...