Charlotte Lilley: Turning Weekend Ski Trips Into The Retreat Co

Charlotte Lilley is the founder of The Retreat Co, a Lake Tahoe company that runs women's ski, camp and work retreats across the American West. She started it in 2018 as a one-weekend-a-year side hustle while working in Silicon Valley, then left a 15-year tech career in 2024 to run it full-time. Today the company hosts more than a thousand women a year, and Lilley is restoring a 90-acre property of her own to give those retreats a permanent home. This is the story of how organizing ski trips for coworkers turned into a business built on community, confidence and the outdoors.

Table of Contents

• From a Side Hustle to a Full-Time Founder
• What The Retreat Co Actually Sells
• Why Women Show Up Alone
• The Business Behind the Weekend
• Serene Ravine and What Comes Next
• Lessons for Women Founders
• Frequently Asked Questions
• Conclusion

From a Side Hustle to a Full-Time Founder

Lilley grew up in the Sierra foothills of California and was on skis as a toddler, taught by her father at Kirkwood and Palisades. After Cal Poly San Luis Obispo she moved to San Francisco and fell into the startup world, spending more than 15 years in sales and marketing at companies including Box, Liftopia, WeWork and Coupa. Every one of those teams was male-dominated, she told SFGATE in July 2026: often one woman in a room of twenty, watching a male culture of informal deals and sponsorship happen in front of her.

Her escape valve was planning ski trips. She booked big houses, organised the driving, cooked the dinners — first for friends, then for colleagues at every company she joined. In 2018 she launched The Ski Retreat with a single women's trip, and for six years it stayed a weekend project: limited bandwidth meant one or two retreats a year alongside a full-time job. She moved to Lake Tahoe in 2023 and left tech for good in 2024, with a bad boss as the final straw. What was The Ski Retreat was renamed The Retreat Co, and the side hustle became the whole business.

The demand was hiding in plain sight. In the 2024/25 U.S. ski season women made up only 38% of all skier visits, according to the National Ski Areas Association — but more than 62% of beginner skier visits. Lilley's instinct that women wanted in, and wanted company once they got there, was backed by the industry's own numbers.

What The Retreat Co Actually Sells

The company runs three pillars of retreats plus community events: Ski Retreats in winter, Camp Retreats in summer and Work Retreats for corporate teams, with virtual sessions bridging the off-season. Destinations include Lake Tahoe, Sun Valley, Jackson Hole, Breckenridge, and Stowe and Sugarbush in Vermont. Weekends run three to four days and mix the anchor activity — skiing, hiking, paddling — with yoga, art classes, a survival-skills workshop, open-fire cooking, private chef meals and fireside conversations with female founders. The company motto is "Can't sit still," and the itinerary reflects it: rest is scheduled, but so is everything else.

Guests book first-come, first-served, which produces an unusually mixed room. "Whoever signs up goes: teachers, stay-at-home moms, tech people, lawyers, previous CEOs, artists, the full gamut," Lilley said. Everything except flights is handled before arrival, so guests do not pack a camp stove or play logistics coordinator — a deliberate design choice for an audience that does enough organising at home.

Why Women Show Up Alone

The defining feature of The Retreat Co is that almost nobody arrives with a friend. According to Lilley, 99% of attendees come solo, and a large share tell her the same sentence: they have no other women to ski with. The loneliness is the product's real market gap, and it is also why the weekends work. Women arrive as strangers, and the combination of nature, shared first-timers' nerves and dinners without an existing social hierarchy makes connection fast. "Women arrive as strangers and by the end of the weekend you'd think they've known each other for years," she has said.

The results are measured. The company's post-retreat survey found 100% of attendees said they felt inspired, empowered or personally motivated by their retreat, based on 47 responses. The wider outdoor market is moving in the same direction: the Outdoor Industry Association's 2025 Outdoor Participation Trends Report recorded a record 53.4% participation rate among American women, with 183.2 million Americans getting outside at all — the highest participation rate ever measured. The Retreat Co sits exactly where growth, gender and spending meet.

Confidence transfer is the recurring testimony. A guest in her early seventies worried she would be the oldest and slowest at a Sun Valley trip, then led her group down the mountain by day two. Another guest told SFGATE that the experience gave her confidence travelling solo and meeting strangers. Lilley's point is that the mountain is only the setting: what women take home is evidence that they can do hard, unfamiliar things.

The Business Behind the Weekend

Behind the campfires is a solo operator running an unusually lean company. Lilley is the marketer, the accountant, the sales lead, the customer service team and the CEO; she answers the calls, runs social media and pitches press. Profits go back into the business, and the transition years were cushioned by savings and her husband's salary — an honest picture of what leaving a tech income actually costs.

Her calendar follows the seasons. Summer is destination scouting, house bookings and vendor research; autumn is launch season, when bookings open and promotion peaks; winter and spring are execution, when she is hosting instead of selling. She credits her startup years for the operating habits: wear many hats, test ideas instead of debating them, and treat every pitch as an experiment. Brand partnerships came from that same approach — cold emails to companies she already loved, including Coalition Snow, Flylow, Spiritless, Siblings Candles and Wild Rye, turned into welcome bags, activations and guest speakers rather than banner ads.

The media footprint grew from the same consistency. The Retreat Co has been featured in Outside Magazine, Forbes (as one of six experts on solo female travel), Thrive Global, the Tahoe Daily Tribune, SFGATE, Moonshine Ink and Wild Rye, plus a long list of podcasts. For a one-person company, that coverage is the cheapest customer acquisition channel available — and it compounds every season.

Serene Ravine and What Comes Next

The next chapter is land. Lilley bought 90 acres in the Sierra Nevada between Truckee and Nevada City and named it Serene Ravine — previously a marijuana farm — and is restoring it to host camp retreats, weddings, glamping, long-table dinners and a flower farm. Owning the venue changes the economics: no rented houses, no capacity ceiling, and a physical place that the community can return to year after year.

Roadmap items beyond the property include more destinations, more co-hosts (the company already works with community builders such as The Ski Moms' Nicole Feliciano), and virtual retreats and workshops for women who cannot commit to a full weekend away. The strategic logic is a year-round ecosystem rather than a seasonal trip: connection should not happen only once a year.

Lessons for Women Founders

Three lessons stand out. First, start before you are ready and let the side hustle prove the demand — Lilley ran six retreats a year around a full-time job before betting on it. Second, sell the transformation, not the activity: the ski trip is the container, confidence and friendship are what guests actually pay for and talk about. Third, build community as an asset. Her stated belief is that "community is built, not found," and it shows up in return guests, partner referrals and press that arrives without a publicist.

Founders in adjacent markets can borrow the same playbook — the demand for curated, women-first experiences shows up well beyond skiing, from wellness to creative businesses. Whatever the niche, the sequence is the same: solve your own access problem, run it small, measure how people feel afterwards, then scale the format rather than the overhead. For more on that trade-off, see our guide to integrating wellness into your daily entrepreneurial routine and Cydnee DeToy's story of leaving a C-suite role to build a coaching business.

Frequently Asked Questions

Conclusion

Charlotte Lilley's business began as the answer to her own problem: a woman in male-dominated rooms who wanted other women on the mountain. Eight years later, The Retreat Co turns that answer into a company of retreats, partnerships and a 90-acre home base, built without venture funding and largely by one person. The lesson for founders is not about skiing. It is that a side hustle started before you feel ready, measured by how people feel when they leave, can become a durable business — as long as you keep showing up for the community that showed up first.

Sources

• The Retreat Co — Our Story (company history, values, post-retreat survey of 47 attendees)
• The Retreat Co — Press (features in Outside, Forbes, SFGATE, Tahoe Daily Tribune and more)
• Las Vegas Sun / SFGATE — "The recovering tech leader who is empowering women in Lake Tahoe" (July 11, 2026): 1,000+ women hosted, 90-acre Serene Ravine, five-plus ski trips
• Wild Rye — Meet the Founder: Charlotte Lilley of The Retreat Co (99% of attendees come solo)
• IdeaMensch — Charlotte Lilley, Founder of The Retreat Co (career, daily routine, operating principles)
• National Ski Areas Association — Downhill Snowsports Participant Profile 2024/25 (women: 38% of visits, 62%+ of beginner visits)
• Outdoor Industry Association & Outdoor Foundation — 2025 Outdoor Participation Trends Report (record 53.4% female participation; 183.2M participants)
• SKI Magazine — NSAA 2025-26 Kottke End of Season Study (64% male, 36% female participants)
• CanvasRebel — Meet Charlotte Lilley (tech career, brand partnerships, media features)