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

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

• Puddle Jumpers: Simple and Proven Ways to Raise Confident & Joyful Kids
• Brandon Webb’s official website
• SOFREP, the military and foreign policy news site Brandon runs
• Puddle Jumpers Parenting, Brandon’s Substack on raising joyful, resilient kids
• Wall Street Journal interview with Brandon Webb about Puddle Jumpers

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