“Being a father is probably one of the toughest and most rewarding jobs I’ve ever had. A lot of the principles I used to teach snipers apply to kids: dealing with negativity, replacing negative self-talk, learning that well-meaning adults can say terrible things — and you don’t have to take that on as baggage.” — Brandon Webb

Brandon Webb defines himself as an author, entrepreneur, Navy SEAL sniper, and father. But not in that order. The first three he leveraged into a series of bestselling books about the art of sniping. The fourth — the art of being a loving father — he dodged and ducked for years.

But fatherhood might be Webb’s real calling. People regularly pulled him aside after meeting his grown children to ask him about his “secret” for being an effective dad. His kids were making eye contact, they were asking good questions rather than staring at their phones. Most astonishingly, they seemed happy.

Webb’s new book, Puddle Jumpers: Simple and Proven Ways to Raise Confident and Joyful Kids, reveals his secret of parenting. It applies the positive performance psychology Webb learned as a Navy SEAL sniper instructor — how to redirect negative self-talk, how to deal with well-meaning adults who say damaging things, how to build mental toughness without destroying connection — to the work of raising children. It outlines his parenting philosophy of both high expectations and high support. Think of Puddle Jumpers as simultaneously the manual for tiger and the bunny parenting.

Brandon Webb’s ultimate calling in life is as a parent. Father, author, entrepreneur and Navy SEAL sniper. In that order.

Five Takeaways

• The Sniper Instructor as Parenting Coach: Webb was running the Navy SEAL sniper program at 27 years old. The psychology they taught there — positive self-talk, replacing negative internal narratives, dealing with adversity without being broken by it — is what he applied to parenting. The connection is not as strange as it sounds: both sniping and parenting require performing under pressure, dealing with failure without catastrophising, and building confidence that is genuine rather than brittle. The difference is that the stakes in parenting last a lifetime.

• High Expectations, High Support: Webb’s alternative to the false choice between permissive parenting and authoritarian discipline. Permissive parenting replaces preparation with protection. Authoritarian discipline breaks connection. Puddle Jumper Parenting holds both simultaneously: clear expectations and emotional safety. Kids need to know what’s required of them. They also need to know they won’t be abandoned when they fail. Webb’s word for children raised this way: puddle jumpers — kids who leap into life’s messy moments with full-hearted abandon, not because they’re fearless but because they trust themselves to recover.

• The Credit Card Lesson: Don’t Bail Them Out: Webb’s son Jackson managed a self-storage facility through college and ended up with a $25,000 ownership payout as a sophomore at St Andrews. He spent it like a drunken sailor on shore leave, got a credit card, ran up $12,000 in debt at predatory interest rates, and called his father for help. Webb’s response: you remember that conversation we had? Figure it out. He let his son suffer. Jackson’s girlfriend hated Webb for two years. At the end, Jackson paid off the debt with a new business and told his father it was one of the best lessons he’d ever been taught. It would have been easy to bail him out. The suffering was the lesson.

• Purpose and the War Veteran: Viktor Frankl’s Lesson: How does a combat veteran come home intact? Webb’s answer: purpose. His Afghanistan deployment had clear moral logic — the propaganda posters in the caves, the training camps, the towers. That clarity carried him through. Iraq was different. Soldiers who went to Iraq with no understanding of why they were there — and whose friends in 2010 were saying we have no idea what we’re doing here — came home broken. Viktor Frankl’s Man’s Search for Meaning: purpose is the thing that makes endurance possible. Without it, violence that cannot be assigned rational meaning produces serious mental illness.

• Teach Kids About Money: The American Economy Preys on Them: Webb has strong opinions: America’s economy is largely fuelled by consumer debt. Credit card companies prey on college students because they know the parents will bail them out. Kids need to understand the system before the system takes advantage of them. His prescription: teach them age-appropriate financial literacy early. The Acorns Early app gamifies financial learning for children. The deal he struck with all his kids in college: I pay for school, you have a roof and food, but if you want to socialise, get a job. The lesson is not just about money. It’s about agency.

About the Guest

Brandon Webb is a combat-decorated Navy SEAL sniper, multiple New York Times bestselling author, Harvard Business School alumnus, and father of three. He is the author of Puddle Jumpers: Simple and Proven Ways to Raise Confident and Joyful Kids (Authors Equity/Simon & Schuster, May 12, 2026), The Red Circle, The Killing School, and The Making of a Navy SEAL. He divides his time between Portugal and New York City.

References:

• Puddle Jumpers: Simple and Proven Ways to Raise Confident and Joyful Kids by Brandon Webb (Authors Equity/Simon & Schuster, May 12, 2026).

• Viktor Frankl, Man’s Search for Meaning — Webb cites it as one of his favourite books, and the source of his thinking on purpose and combat trauma.

• Episode 2888: Helen Benedict on The Soldier’s House — directly referenced in the interview; Webb’s purpose-in-war argument is the complement to Benedict’s moral injury argument.

About Keen On America

Nobody asks more awkward questions than the Anglo-American writer and filmmaker Andrew Keen. In Keen On America, Andrew brings his pointed Transatlantic wit to making sense of the United States — hosting daily interviews about the history and future of this now venerable Republic. With nearly 2,900 episodes since the show launched on TechCrunch in 2010, Keen On America is the most prolific intellectual interview show in the history of podcasting.