We’re looking forward to introducing you to Stephan Aarstol. Check out our conversation below.
Stephan, a huge thanks to you for investing the time to share your wisdom with those who are seeking it. We think it’s so important for us to share stories with our neighbors, friends and community because knowledge multiples when we share with each other. Let’s jump in: What is something outside of work that is bringing you joy lately?
Lately I’ve been enjoying wakesurfing on Mission Bay. I keep a wake boat outside my beach club, and it’s the perfect mix of fun and relaxation—surfing at just nine miles an hour, with music playing and friends on board. It’s athletic, social, and feels like a little party on the water.
Can you briefly introduce yourself and share what makes you or your brand unique?
I’m best known for launching Tower Paddle Boards, which Mark Cuban invested in on Shark Tank back in 2012. That company went on to become San Diego’s fastest-growing company one year, and a few years later I shifted it to a five-hour workday—an experiment that led to my book The Five-Hour Workday and global media coverage.
Today my focus is on a new venture called The Cut List. It’s the internet’s most selective store and guide—featuring just three “Top Picks” in each category, chosen for quality, value, and innovation. We cover more than 1,500 product categories across 10 complete stores, including the Style & Fashion Store, Electronics Store, Kitchen Store, Patio & Garden Store, Sporting Goods Store, and Bags & Travel Store. Alongside products, we also celebrate the best of the best in all things San Diego—restaurants, bars, food, hot spots, places, and experiences. The goal is simple: help people find three great choices, fast—whether they’re shopping locally or online.
Amazing, so let’s take a moment to go back in time. What’s a moment that really shaped how you see the world?
One of the most formative experiences for me was backpacking through Australia for three months with a few college friends right before I graduated. It wasn’t just about seeing Australia—it was about being on the backpacker circuit, meeting people from all over the world, and immersing myself in different cultures and perspectives.
That trip completely shifted how I see the world. Growing up in America, it’s easy to assume everyone views life the same way, but travel shows you otherwise. Experiencing how different cultures approach work, community, and daily life was eye-opening. It taught me that true education doesn’t only come from classrooms—it comes from extended travel and real exposure to the way others live and think.
What’s something you changed your mind about after failing hard?
Over 20 years of running my own businesses, I’ve had plenty of wins and just as many failures. One lesson that really stuck came from Mark Cuban, who’s been my partner for the past 15 years. Early on, I was always focused on chasing upside—I wanted to go bigger, faster, and thought more money or a line of credit would solve everything.
Mark pushed me to think differently. He told me, “Quit worrying so much about your upside—worry about going to zero.” That shifted my mindset. Now I think in terms of building plateaus: reach a new level, then protect it before climbing higher. It’s less glamorous than going “all in,” but it’s smarter, more sustainable, and ultimately the way you build lasting success.
I’ve even carried that mindset into poker. After watching the All-In Podcast, I started playing poker tournaments in Las Vegas, including a few World Series of Poker events. Poker, like business, is a mix of skill and luck—you can’t control everything, but you can control how you manage risk. The same strategy applies: don’t blow yourself up chasing every hand, level up slowly, and make sure bad luck doesn’t knock you out of the game. I’m still a novice, but I’ve cashed in several tournaments—including finishing 19th out of over 1,200 players—which has been both fun and a great reminder that the lessons of entrepreneurship translate well to the poker table.
Sure, so let’s go deeper into your values and how you think. Whom do you admire for their character, not their power?
One person I really admire is Richard Branson. He’s built a wide range of successful businesses, but what stands out isn’t just the success—it’s the way he’s done it. For him, it doesn’t seem to be about money or power; it’s about doing interesting things, surrounding himself with interesting people, and having fun along the way.
That perspective resonates with me. At Tower Paddle Boards, we’ve had our highs—over $50 million in sales—and our near-misses with bankruptcy. Through it all, what mattered most wasn’t the money, it was the experience. I was intentional about building a great team, and together we took company trips to places like Sayulita, Tulum, Costa Rica, and even the Sundance Film Festival. Even if the business had disappeared tomorrow, those shared adventures made it all worthwhile. That, to me, is what Branson embodies: entrepreneurship as a vehicle for living a rich, adventurous life—not just chasing recognition or financial gain.
Okay, so let’s keep going with one more question that means a lot to us: If you knew you had 10 years left, what would you stop doing immediately?
This is an interesting question for me because I had a close childhood friend who was diagnosed with leukemia at age seven and told he only had a couple of years to live. He made it until 13, and I basically rode shotgun through that whole experience with him. What struck me was how he lived—fearless, present, and determined to have fun despite knowing his time was short.
That left a huge impression on me. It taught me that everyone should really live with that same urgency. I once heard a commencement speech that said you should live as if you have $5 million in the bank and five years left—and I think that’s exactly right. I try to live that way: enjoying life, striving for meaningful things, and making smart plans, but never forgetting that time is limited. If I had 10 years left, I wouldn’t actually stop anything—I’d just keep doubling down on living with urgency and appreciation every single day.
Contact Info:
- Website: https://thecutlist.com/
- Instagram: https://www.instagram.com/saarstol/
- Linkedin: https://www.linkedin.com/in/stephanaarstol/
- Facebook: https://www.facebook.com/stephan.aarstol/
