Episode 81:Brian DeDeigo: Santa Cruz, Money, And Meaning: A Santa Cruz Realtor On Community, Wealth, and Growing Up Without Losing Yourself

Episode 85: David McIntosh: What Happens When You Find Yourself In The Images You’ve Held About Life? We Are All About To Find Out.

Santa Cruz can feel like paradise and a pressure cooker at the same time, and that tension is where this conversation starts. I sit down with David McIntosh to unpack what “change” really looks like on the ground: a working class beach town shaped by Silicon Valley gravity, rising costs, and the quiet fear of being pushed out, alongside real opportunity for the people ready to adapt. David’s path to Santa Cruz is anything but linear. He grew up near Johns Hopkins in Baltimore, describes what it’s like to see hardship as a daily backdrop, and how that experience sharpens empathy. Then life takes him through Washington, DC, London, and Australia, following his wife’s career from diplomacy and government affairs into tech. Through all of it, one thread stays constant: surfing. He learned at 12 on the East Coast, obsessed over surf magazines, and carried a persistent “California dreaming” that still shows up today as the kind of stoke you can’t fake. We also get into surf industry history and why so many legacy surf brands drifted away from the core. Dave shares why he’s opening Sunny California on a storied Santa Cruz retail corner, not to “own” surf culture, but to celebrate it with a surf and moto shop, art gallery energy, and a space built around community. His north star is simple and hard to execute: make everyone leave happier than when they arrived. If you care about Santa Cruz, surf culture, California lifestyle, and what modern community-first retail can look like, you’ll get a lot out of this one. Subscribe, share it with a friend who loves the ocean, and leave a review with your take: what should a great surf shop feel like?

Episode 84: Mark Allen: The GOAT Speaks: There Is No Pressure When You’re Being Yourself-But You Might Want To Pick That Jacket Off The Couch and Hang It

Santa Cruz can make a world champion feel like “just another guy in the lineup”. That’s exactly where this conversation starts.  I sit down with Mark Allen, the GOAT and six-time Ironman World Champion, and lifelong surfer, to get under the surface of what makes this place a haven for talent and why it also has an edge that forms you over time. We talk about the strange Santa Cruz magic where titles-no matter what they are- don’t land the way they do elsewhere. How community is built through consistency, respect, and real relationships instead of status. Mark shares the story behind his biggest athletic turning point: years of leading the pack and then falling apart in Kona, and the fear he didn’t want to admit. We move to the mindset shift that finally changed everything. We go into Huichol shamanism and earth-based spirituality, how nature can become a mirror for your inner life, and why trying to perform like someone else burns energy you don’t have. One of my favorite themes is his reframe from rivalry to cooperation, using competitors as information and inspiration instead of a threat. We also get practical about daily life: stress as a motivator, the weird ways we create tension, simple disciplines that clear mental space, and what longevity looks like when you want it to be sustainable. If you’re into Ironman training, endurance mindset, performance psychology, surfing culture, or stress management, there’s a lot here to carry into your own routines. Subscribe, share this with a friend who’s stuck in comparison, and leave a review with the habit you’re working on right now.

Episode 83: Hannah Selden: The Creative Crossroads, and Making Art In Santa Cruz Without Selling Your Soul-Why Avocado Toast Speaks To The Economics of Artists

Santa Cruz loves to call itself creative, but what happens when creativity becomes a commodity and everyone feels forced to hustle? I’m sitting down with local artist and designer Hannah Selden to unpack the push and pull of making art in Santa Cruz after COVID. Hannah talks about growing up here, studying print design, and building a Santa Cruz apparel brand before stepping back to reclaim creativity that doesn’t have to fit a sales funnel. We get real about maker markets, the invisible competition that rides underneath a “hippie” vibe, and why this town can feel like the best place to belong and the hardest place to breathe at the same time. We also dig into AI in graphic design and branding: how generative tools can unlock ideas for people who don’t have technical skills, but also how “good enough” logos and instant visuals can erase paid creative work. Along the way we talk surf culture’s influence on access and status, Rockview Beach community rituals, and the difference between being nice, being kind, cooperating, and actually collaborating. If you care about the Santa Cruz creative economy, local artists, small business life, and where community goes next, this one will stick with you. Subscribe for more Santa Cruz conversations, share this with a friend who’s building something, and leave a review if you want more guests like Hannah. What part of the creative grind feels worth it to you right now?

Episode 82: James Reitano: Imposter Syndrome Pays Rent In Los Angeles, And What If The Future Depends On Who Lives 100 Feet From You

Santa Cruz can feel like paradise, a trap, and a time capsule all at once and that tension runs through our conversation with graphic designer and storyteller James Reitano. He grew up with Santa Cruz roots, found his way into the high-pressure world of Santa Cruz Skateboards (NHS), and learned early that making “cool” work isn’t the same as making work that survives a market shift. We talk candidly about imposter syndrome, creative rejection, and why the best rooms can make you feel like you don’t belong. Then we follow the path south to Los Angeles, where media culture and constant ambition can amplify isolation. James shares what it’s like to build a creative career in LA without getting swallowed by the hustle, how real friendships form when you stop chasing them, and what separation anxiety looks like when you’re alone in a giant city. If you care about mental health, men’s anxiety, and staying grounded while still pushing your craft, there’s a lot here to hold onto. We also zoom out into Santa Cruz history and the way technology changes our nervous systems. James explains how his graphic novel work tries to capture pre-1989 Santa Cruz and the cultural shift after the Loma Prieta earthquake, then we connect that sense of loss and change to today’s reality of social media, metrics, deepfakes, and AI. We end on a practical, hopeful takeaway: soft skills are the hard skills now, and the most radical thing you can do is show up for the people 100 feet around you. If this conversation hits home, subscribe for more, share it with a friend who needs it, and leave a review with your biggest takeaway.

Episode 81:Brian DeDeigo: Santa Cruz, Money, And Meaning: A Santa Cruz Realtor On Community, Wealth, and Growing Up Without Losing Yourself

Santa Cruz can feel like paradise until you look closer and realize how much pressure hides under the flip-flops. We sit down with longtime Santa Cruz realtor Brian Di Diego to talk about what it’s like to build a life in a small town where everybody knows everybody, prices keep climbing, and real estate decisions are never just “business.” The conversation starts with home: kids leaving, houses getting quiet, and the strange mix of pride and grief that shows up when family life shifts.  From there, we get honest about identity and work. Brian shares what 34 years in real estate does to your nervous system, how he had to unlearn an aggressive early-career style, and why the human element still matters even as AI and online tools keep promising to “replace” the agent. We also unpack Santa Cruz’s changing vibe as more cash buyers and out-of-area money flow in, plus what it feels like to watch friends get priced out of the community you love.  If you’re curious about the investing side, we dig into triple net lease properties, why they can reduce stress, and how 1031 exchanges help people reposition into a future retirement plan, sometimes buying a Santa Cruz home years before they move in. Then we widen the lens to legacy: nonprofits, pay-to-play sports support, the Reggie Stevens Foundation, and the quiet satisfaction of giving time and money in ways that actually change lives.  If this hit home, subscribe, share it with a friend who’s navigating work and identity, and leave a review with the biggest question you’re carrying right now.