Kicked Off the Sailboat at 16

In this episode, I sit down with Brandon Webb — Navy SEAL, former head instructor of the Navy SEAL Sniper Course, New York Times bestselling author of twelve books, and now the author of a brand new parenting book called Puddle Jumpers, releasing May 12th.

Brandon's story starts where most men's don't — kicked off the family sailboat at 16 in the South Pacific after a blowup with his dad, finding a boat headed to Hawaii, and navigating his way into the Navy and eventually SEAL Team Three. But what makes this conversation extraordinary is watching a man who trained the most elite warriors on the planet — including some of the legends you already know — apply that same performance psychology to raising his three kids.

We dig into what performance psychology actually is, why the sniper school's failure rate dropped to nearly zero when they stopped pointing out mistakes and started painting the picture of what to do instead, and how Brandon built that same positive reinforcement framework into how he parents. We also get into the moment his daughter humbled him while he was writing Puddle Jumpers — telling him that because he was their untouchable Navy SEAL hero, she never felt like it was okay to fail.

We swap shoplifting stories, talk about the power of getting to the why before you drop the hammer, why boys between 12 and 15 are standing at a fork in the road that can go either way, and why asking better questions on a one on one trip unlocks conversations that would never happen face to face at home.

Timeline Summary

[0:00] Introduction to the Dad Edge mission and the movement to raise leaders of families and communities

[1:02] Getting kicked off a sailboat at 16 in the South Pacific — and what his dad actually taught him

[3:21] From deckhand at 13 to SEAL Team Three — and the book that made him think he could do it

[7:29] Class 215 — graduating with Mike Ritland and serving with Eric Davis

[9:20] Brandon's full background — SEAL, sniper instructor, NYT bestselling author, and now Puddle Jumpers

[11:12] Why the book is called Puddle Jumpers — the mud puddle moment that became a philosophy

[13:28] What performance psychology actually is — and why Brandon integrated it into the sniper program

[17:22] The three pillars: mental rehearsal, self-talk, and positive reinforcement versus negative reinforcement

[18:41] Why saying "stop flinching" programs failure — and what to say instead

[21:17] The sniper school failure rate dropped to near zero — and what that taught him about his own kids

[22:26] Why Brandon left the SEALs at his peak — and what the broken families around him told him about his own future

[27:23] Consequences without the belt — wall squats, push ups, and eventually the iPhone

[29:52] Owning your mistakes as a parent builds more credibility than never making them

[33:05] What made him write a parenting book — his kids impressing people at Harvard Business School

[34:19] Don't come home with a wallet full of money and a house full of strangers — the billionaire with three kids in addiction

[37:01] The 12 to 15 fork in the road — why boys in that liminal space need a present, intentional dad

[39:23] The seventh grade spiral — selling pot gummies, ordering Uber Eats to the principal's office, and what was really going on underneath

[41:27] Ask why seven times — and the teacher who publicly humiliated his son and started the whole thing

[43:42] Pull him out, take his side, change the environment — and the coach's email that said everything

[44:33] His daughter's answer when he asked what he'd done differently — and why being the untouchable SEAL hero was actually a problem

[48:42] Shoplifting, a Sonic parking lot, and the real reason his son did it — peer pressure and not knowing who his friends were

[54:11] Kids open up in cars, on bikes, on walks — never face to face

[54:41] One on one trips every year — and the two questions at dinner in New York that lasted two and a half hours

[58:40] What his daughter said in Lisbon — and why creating a home they want to come back to is one of the most underrated parenting moves

Five Key Takeaways

1. Stop pointing out mistakes and start painting the picture of what to do instead. Telling a kid what not to do programs them for failure. Tell them where to put their attention — not what to avoid.
2. Owning your mistakes as a parent isn't weakness — it's the most credible thing you can do. Your kids will model ownership and accountability because they watched you do it first.
3. Boys between 12 and 15 are at a fork in the road. If they don't feel supported during that season, you can push them in a direction that takes years to correct. Get to the why before you drop the hammer.
4. Being the untouchable hero in your kid's life can quietly teach them that failing isn't okay. Share your struggles. It gives them permission to have their own.
5. The quality of your relationship with your kids depends on the quality of the questions you ask. "How was your day" is a dead end. Ask something real — and ask it in a car, on a walk, or somewhere that takes the pressure off.

Links & Resources

• Dad Edge Business Boardroom: https://thedadedge.com/boardroom
• Puddle Jumpers by Brandon Webb — releases May 12th: Available on Amazon
• Brandon Webb's website and all socials: https://brandontylerwebb.com
• Episode Link & Resources (Episode 1473): https://thedadedge.com/1473

Closing

If there's one message from this episode that stands out, it's this: the most dangerous thing you can do as a dad is be so good at everything that your kids are afraid to fail in front of you.

Brandon Webb trained the most elite warriors in the world. He wrote twelve books. He sailed across the South Pacific at 16. And his daughter had to look him in the eye and tell him that his greatness made her feel like failure wasn't allowed.

That's the lesson. Not the SEALs. Not the snipers. The puddle jumper — the kid who jumps in the mud because he hasn't been told yet that he shouldn't.

Raise more of those.

Go out and live legendary.