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

30 - Why Everyone Eventually Comes Back to Park City - Katie Wilking

Katie Wilking grew up in Park City, left for college and Washington D.C., then found herself coming home. In this episode we talk about old Main Street, Park City's early days, Mileti's, skiing as kids, commercial real estate, entrepreneurship, community, and why the people—not just the mountains—keep drawing us back. It's a conversation about growing up, leaving, returning, and appreciating a place differently with each chapter of life.

29 - What Happens When the Dream Job Ends? Jonathan Crosswhite

Jonathan Crosswhite has lived several lives. The son of an NBA player, Jonathan grew up moving from city to city before finding his way to Division I football at the University of Utah and eventually the Arizona Cardinals. In this episode, we talk about sports, ADHD, parenting, pressure, sales, real estate, and what happens when your childhood dream becomes your job. We also dive into why some athletes thrive under pressure, how great salespeople build trust, and why Jonathan's ultimate retirement plan has nothing to do with luxury homes and everything to do with coaching kids and driving a school bus. This one goes deeper than football.

28 - The 'Bumpy Road' to Powder Cats!

Bekah Stevens came to Park City thinking she’d stay for one winter. Twenty-three years later, she’s transitioning into ownership of Park City Powder Cats — one of the most unique independent ski operations in the country. In this episode of Ski In Sell Out, we talk about: * growing up in rural Vermont * moving west after college * seasonal jobs and ski town survival * why so many people stayed in Park City * how mountain towns have changed * the reality of raising a family on the Wasatch Back * entrepreneurship, burnout, gratitude, and community * what it actually takes to build a meaningful life here This one isn’t really about skiing. It’s about choosing a life — and sticking with it long enough for it to become your own. If you’ve ever wondered whether it’s still possible to build a future in a mountain town, this conversation is for you. #SkiInSellOut #ParkCity #PowderCats #MountainTown #ParkCityUtah #UtahRealEstate #SkiCulture #Entrepreneurship #WasatchBack #OutdoorLifestyle

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.