About Kyle

Kyle Thiermann is a professional big-wave surfer, journalist, and creative director whose career bridges storytelling, advertising, and adventure. He’s written for Men’s Health, Surfer, and Outside Magazine, and helped shape campaigns for brands like Patagonia, Yeti, and Mudwater, with his ads and viral spots reaching over 100 million people. Kyle is also the author of One Last Question Before You Go: Why You Should Interview Your Parents Now, a deeply personal exploration of family, curiosity, and conversation. In this episode, Justin and Kyle dive into the fear that drives creativity, the lessons of surfing six-story waves, and how to use curiosity and courage to build a more meaningful creative life.

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Ah-ha! Justin’s Takeaways

Deadlines create gravity: Surrounding yourself with people you respect and setting clear deadlines are two of the most powerful tools for getting things done—it is the engine of creative work, which turn ambition into action and ensure you finish what you start.

Proximity is an accelerant: Kyle’s learned, both in the ocean and in his creative career, that the fastest way to improve is to surround yourself with people already doing the thing you’re learning. Mentorship and shared goals create a rhythm of steady progress that’s hard to find alone.

Better questions equal better understanding: We’re trained to have answers, but not to ask better questions and that’s where understanding truly lives. Whether you’re exploring a design challenge or rebuilding a relationship curiosity has the power to turn conversation into insight. Kyle’s book about interviewing his parents is a masterclass in curiosity.

Show Notes

“The power of deadlines and more specifically, the fear of disappointing people I respect has driven my career.” (00:04:55)

We start by talking about the writing group where Kyle and I met, guided by New York Times best-selling author Neil Strauss. Together we dig into how essential structure and accountability are for any creative project including the value of mentors, peers, and most of all, deadlines. If you’ve listened to this podcast before, you’ve heard me say it: deadlines are magic. They turn vague ambition into finished work.

“Find the people that are doing the thing and hang out with them as much as possible.” (00:15:58)

Kyle connects his life as a big-wave surfer to his creative process, showing that fear and mastery follow the same pattern. Whether you’re paddling into six-story waves or starting a new creative career, the fastest way to grow is to surround yourself with people already doing what you aspire to do. Mentorship, proximity, and shared accountability accelerate progress more than any course or tutorial ever could.

“Copywriting is much more like stand-up comedy, where you’re trying to take an idea and distill it down to its most essential form that’s going to get someone’s attention and connect them to this thing that you are selling.” (00:34:49)

Kyle compares copywriting to stand-up comedy and it’s a perfect analogy. Both rely on timing, clarity, and emotion. Every word has to earn its place. For designers, writers, and storytellers, the lesson is simple: your job isn’t to explain, it’s to distill. When you can make someone feel something in a single line, you’ve revealed its essence, making it easier for your audience to understand, and therefore, to buy.

“We’re taught to have the right answers, but never taught to have the right questions.” (00:51:56)

Kyle wrote a book about interviewing his partents. His book grew out of realizing that curiosity—especially toward the people closest to us—is a learned skill. We train for answers, but not for questions, and that leaves entire parts of our relationships unexplored. As Kyle discovered, interviewing is about transforming judgment into curiosity. Asking better questions of our parents, our collaborators, or ourselves is how we rediscover the people we thought we already knew.

* Kyle’s Upcoming Book: https://geni.us/onelastqbeforeyougo

* Kyle’s Website: https://www.kylethiermann.com/

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