27 - FLO PC & HOA Therapy - Ally Dickey

27 - FLO PC & HOA Therapy - Ally Dickey

This week on Ski In Sell Out, we sit down with Ally Dickie — entrepreneur, HOA operator, former consultant, mother, community builder, and unofficial therapist for modern neighborhood dysfunction. What starts as a conversation about Florida roots, consulting careers, and moving to Park City “for one winter” turns into something much deeper about identity, parenting, leadership, emotional weight, and building a life that actually feels good. We talk about: * Leaving corporate consulting behind * Starting and growing Model HOA * Motherhood vs. entrepreneurship * Why the real politics happen in HOAs * Park City community culture * Raising kids in a small town * Feeling the weight of leadership * QuickBooks as emotional support * AskKaren.com * And the tiny deck that made them stay in Park City Funny, honest, thoughtful, and extremely Park City.

26 - You Never Know Who You’re Sitting Next To in Park City

Eric Wiener’s story feels almost made up — except it’s real. Born in the Bronx, raised between cultures, working in the New York music industry during the rise of artists like Jay-Z and Britney Spears, Eric eventually left it all behind after 9/11 to become a Marine Corps Harrier pilot. In this episode we talk about: * Growing up in New York and finding community block by block * Identity, adoption, and cultural belonging * The reality of the music business and hustling in NYC * Working at Roc-A-Fella and Jive Records * Why 9/11 changed the course of his life * Becoming a Marine pilot and flying Harriers * Iraq, Afghanistan, and life on aircraft carriers * The hidden stories and people that make Park City unique * Why mountain towns and diverse communities have more in common than people think This one goes deep into identity, ambition, loyalty, reinvention, and the strange roads that eventually lead people to Park City.

25 - 'Nobody Cares' with Molly Miller

What actually makes a place feel like home? This week we sat down with Park City Councilwoman Molly Miller for one of our favorite conversations yet — covering everything from growing up as the youngest of five girls in Michigan, cleaning motel rooms in Maine at eight years old, working in news, interning at Saturday Night Live, falling in love over early Twitter, and eventually finding her way to Park City. But underneath all of it was a bigger conversation about instincts, parenting, failure, preparation, confidence, community, and what it means to build a life that feels meaningful. We talked about: * Why “nobody cares” can actually be freeing * The difference between preparation and practice * Scarcity vs. abundance in mountain towns * Raising kids who trust themselves * Why Park City still feels magical * Council, criticism, and learning in public * Moving through life transitions without fear * The people who make a community great One of the more thoughtful and human conversations we’ve had so far.

24 - Oops I Worked For A CULT - Joel Zarrow

Joel Zarrow, President & CEO of the Park City Community Foundation, joins us for one of our favorite conversations yet. We talk about growing up in California before it became “Calabasas,” turning down a job on Seinfeld, traveling through Thailand, education policy, nonprofit leadership, cult-like consulting firms, community building, and the strange emotional tension of living in a place like Park City. This episode digs into something bigger than real estate: What actually makes a town feel like a community? We talk about wealth, belonging, philanthropy, traffic, identity, affordable housing, relationships, and the reality that people are just people — whether they live in a studio apartment or a house in The Colony. Joel brings honesty, perspective, and humility to a conversation that feels incredibly relevant right now. This one’s about place. And the people trying to hold onto what makes it special.

Dry Pipeline, Full Belief!

This one is different. No guests. No script. Just Max and Lauren getting honest about what it actually feels like to build something from scratch—when the pipeline is dry, the bills are real, and the confidence gets tested daily. They talk about: * The fear that comes with betting on yourself * Why “contact roulette” might be the best lead gen strategy right now * Financial pressure vs. belief in the long game * What it really means to go all-in * And why this might be the exact moment that matters most If you’ve ever taken a leap—or are thinking about it—this episode is for you. Because this is the part no one talks about.