From the Foothills to the Slopes: My Journey to Founding The Ski Retreat

I grew up in the California foothills, just a couple of hours from Lake Tahoe, where I started skiing at the age of two (Kirkwood was my home mountain). Lake Tahoe was my playground—each winter, I would look forward to weekends spent on the slopes, and during the summers, the lake was one of our closest “beaches.” The photo for this post is of me as a tyke sitting on the sunny Lake Tahoe shores.

Skiing was a constant in my life, and growing up so close to the mountains meant that winters were filled with trips to the slopes. But when I left for college at Cal Poly San Luis Obispo, I found myself embracing the beach lifestyle more than my mountain roots. The mountains felt far away, and my skis spent more time in storage than on the snow.

After graduating, I moved to San Francisco and began my career in tech, diving into sales and marketing roles at SaaS startups. It was exciting work, but something was missing and I didn’t even know it. The pivotal shift happened when I was working at Liftopia, a ski company based right in the heart of San Francisco. Working there reignited my passion for the mountains and, more importantly, got me thinking about entrepreneurship. The idea of running my own business was intriguing, but outside of tech, I had no clue what that might look like.

One fateful day in 2016, while browsing Heath Ceramics, I stumbled upon a beautifully designed magazine called Bossladies. It featured stories of women entrepreneurs from San Francisco, each running their own unique businesses. I bought the magazine on the spot and devoured it from cover to cover. The stories of these inspiring women and how they built their businesses lit a fire in me. Bossladies is no longer in production, but it was the spark that started my entrepreneurial journey.

From there, I dove into books like In the Company of Women, started listening to podcasts like Second Life, and immersed myself in the online communities of platforms like Create & Cultivate and The Riveter. I began following these inspiring women and realized that there was an entire ecosystem of female entrepreneurs creating impactful businesses—and I wanted in.

But what kind of business did I want to create? That was the big question. I started asking myself: What do I love? What am I good at? What excites me? As I continued working in tech, I found myself planning ski trips for coworkers and friends—sometimes mixed-gender trips, sometimes all-girls getaways. I loved every aspect of it: getting people together, coordinating the details, staying in a cozy cabin, and making lifelong memories on the mountain. It slowly dawned on me (maybe a little later than it should have) that I could actually turn this passion into a business.

I realized that what I enjoyed most wasn't just the skiing—it was the full experience of a ski trip. I love staying in the same cabin with friends, making breakfast together, chatting on the chairlift, and savoring the feeling of ripping off my helmet and goggles after a great day on the slopes. There’s something special about that post-ski glow—crazy hair, red cheeks, big smiles, and the satisfaction of having earned that end-of-day drink. And the evenings? Whether we’re cooking homemade pasta or throwing frozen pizza in the oven, it’s about gathering around the table and reflecting on the day, all while feeling completely present and at peace.

In 2017, I officially launched The Ski Retreat. My first "website" was really just a sign-up page, but I had something tangible to show as I stepped into the entrepreneurial world. I was working backward from a goal—I’d signed up for an event in Malibu in October 2017 and wanted to present myself as a legitimate business. At that event, surrounded by powerhouse women like Jeni Britton Bauer of Jeni’s Ice Cream, Shilpa Shah of Cuyana, and Natalie Kuhn of The Class, I felt both intimidated and inspired. If they could do it, why couldn’t I?

In January 2018, I hosted the first official retreat in Lake Tahoe, and it was everything I had envisioned and more. The camaraderie, laughter, and shared excitement of hitting the slopes brought the group together in ways I never imagined. That inaugural event marked the beginning of something truly special. From that day forward, The Ski Retreat has grown into a thriving community, uniting women who share a love for skiing and the mountains. The journey since then has been filled with unforgettable trips, new friendships, and the realization that I’m exactly where I’m meant to be. The rest, as they say, is history!

That’s how The Ski Retreat was born—from a deep love of skiing, a desire to connect people, and the inspiration of women entrepreneurs who dared to follow their passions.

Charlotte Lilley