Episode 9 - Lindsay and Evan DesLauriers of Bolton Valley, Vermont

Buying back the family ski hill, and leaning back into what made it great in the first place

If you could imagine the Vermont dream. What would it look like? imagine growing up with a Dad who in 2/3rds of a year built a new ski area from scratch and growing up on a ski hill that is the family business.  Imagine  after several decades  the ski area fell on hard times and the family had to sell it. But… a decade later along with your 80 year old father the kids buy back the ski area and restore it to its former glory. Throw in a mug of maple syrup and some flannel and you’ve got the makings of a Hallmark movie.

Today’s episode takes us to Vermont, where we sit down with Lindsay and Evan Deslauriers from Bolton Valley, Vermont, a family-owned resort with one of the most unique comeback stories in the industry.

From growing up on the mountain… to losing the resort… to rebuilding it as a multi-season, community-driven business—this episode is packed with lessons on resilience, authenticity, and what it really takes to create a ski experience people keep coming back to.

We get into everything from night skiing strategy and building a year-round revenue model, to building out one of the largest in-resort backcountry touring networks to why “authenticity” isn’t a marketing tactic—it’s a byproduct of culture.

If you love touring, night skiing,a good down-home, authentic ski experience or are just a sucker for a great family business story, this one is for you. Put on your best flannel, take a shot of maple syrup and let’s get it with Evan and Lindsay Deslauriers of Bolton Valley.

12 ACTIONABLE INSIGHTS

1. Lean Into Identity—Even If It’s “Less Profitable” on Paper

The Insight: Not every part of your business needs to be a profit center. Some should exist primarily to strengthen identity and demand elsewhere.

How Bolton Valley Uses ItThey openly admit backcountry is “not a real profit center… more of a passion center.” But it drives national attention, brand differentiation, and cultural credibility.

How Other Ski Areas Can Use It

• Identify 1–2 “passion pillars” (e.g., night skiing, uphill access, terrain parks, events).

• Stop evaluating them purely on direct revenue—track indirect lift ticket, pass, and brand impact.

• Double down on storytelling and PR around those pillars to amplify their marketing value.

• Use them to attract a specific tribe—not everyone.

2. Extend Hours to Match Customer Reality (Not Your Cost Model)

The Insight: Operating hours should be built around when your customer can actually ski, not when it’s most efficient to run lifts.

How Bolton Valley Uses ItThey extended night skiing to 10pm and lowered the price—counterintuitive—but saw demand surge because it aligned with real-life schedules (commuters, after-school skiers).

How Other Ski Areas Can Use It

• Map your core customer’s actual day (work end time, drive time, etc.).

• Identify friction gaps (e.g., “they only get 90 mins of skiing”).

• Extend hours or shift timing—even if margins look worse per hour.

• Pair with targeted pricing (after 5pm passes, late-start tickets).

• Measure total visits per guest, not just revenue per hour.

3. Build a Business That Works Without Real Estate Bailouts

The Insight:Many ski areas rely on real estate to survive. Bolton intentionally rebuilt a model that stands on operations alone.

How Bolton Valley Uses ItTheir “2.0” strategy focused on four-season operations (biking, weddings) and sustainable revenue—not condo development.

How Other Ski Areas Can Use It

• Stress test: “If we couldn’t build or sell real estate, would we survive?”

• Invest in year-round lift utilization (events, biking, sightseeing).

• Build recurring revenue streams (weddings, programs, camps).

• Shift leadership focus from “big wins” (development) to consistent cash flow businesses.

4. Treat Backyards Like Gold (Hyper-Local Density Wins)

The Insight:Deep local penetration beats broad destination marketing—especially for independent hills.

How Bolton Valley Uses ItThey’ve built generational loyalty through after-school programs—entire communities learned to ski there.

How Other Ski Areas Can Use It

• Partner with schools directly (transport + programs, not just discounts).

• Track “lifetime skier value” instead of one-time visits.

• Create rituals (weekly programs, race leagues, night passes).

• Measure success by: “What % of our local population skis here?”

5. Authenticity Isn’t a Strategy—It’s a Staffing Model

The Insight:You can’t market authenticity—you build it by hiring locals and keeping them long-term.

How Bolton Valley Uses ItMajority local staff, many grew up skiing there, long tenures, minimal hierarchy between ownership and staff.

How Other Ski Areas Can Use It

• Prioritize local hiring—even if it’s harder operationally.

• Create pathways for seasonal staff → long-term roles.

• Reduce corporate barriers between leadership and frontline staff.

• Let staff personalities show (less rigid brand policing).

• Measure: staff retention + % of employees who ski your hill.

6. Your Best Marketing Channel Is the One You Already Own

The Insight:Direct communication (email, passholder базы) is more valuable than chasing new audiences constantly.

How Bolton Valley Uses ItThey rely heavily on direct communication with returning guests and passholders rather than big ad spend.

How Other Ski Areas Can Use It

• Build and segment your email list aggressively (by behavior, not just demographics).

• Treat it like a product: consistent, valuable, not just promos.

• Focus on retention campaigns (return visits, upsells).

• Track: repeat visitation rate, not just new customer acquisition.

7. Don’t Kill What Makes You Special to Save Money

The Insight:Cost-cutting often targets the very thing that differentiates you.

How Bolton Valley Uses ItPrevious owners reduced night skiing hours (a core identity piece). Bolton reversed it—and performance improved.

How Other Ski Areas Can Use It

• Identify your top 2–3 differentiators.

• Protect them aggressively—even in tough years.

• If cutting costs, cut non-core experiences first.

• Ask: “If we remove this, are we just another ski hill?”

8. Price Is a Positioning Tool, Not Just Revenue Optimization

The Insight:Lowering price can increase perceived accessibility and unlock entirely new demand segments.

How Bolton Valley Uses It$29 night skiing tickets reinforce their identity as accessible, local, and community-first.

How Other Ski Areas Can Use It

• Use price strategically to define who you’re for.

• Create entry points (cheap nights, beginner bundles).

• Don’t just discount—tie pricing to specific use cases (after work, learning, locals).

• Measure: new participant growth, not just yield.

9. Let Passion Drive Product Innovation (Not Committees)

The Insight:Some of their best offerings came from internal passions—not formal strategy.

How Bolton Valley Uses It

• Backcountry → driven by Adam

• Freeride events → driven by Evan

• Biking → driven by another sibling

How Other Ski Areas Can Use It

• Identify passionate staff and give them ownership of niche ideas.

• Pilot small, don’t over-plan.

• Accept uneven ROI—some ideas will become signature experiences.

• Build a culture where ideas can come from anywhere, not just leadership.

10. Community Presence > Polished Brand

The Insight: Being visible and human beats being perfectly branded.

How Bolton Valley Uses ItOwnership is on-site, interacting with guests, part of the culture—not hidden executives.

How Other Ski Areas Can Use It

• Get leadership physically present on weekends and peak days.

• Encourage informal guest interaction (not just surveys).

• Build moments where guests “run into” leadership.

• This creates loyalty that marketing cannot replicate.

11. Stop Over-Discounting—It Quietly Kills Your Business

The Insight:Comp tickets and excessive discounts erode perceived value faster than most operators realize.

How Bolton Valley Uses ItThey’re very cautious about comps and discounting, recognizing it devalues the core product.

How Other Ski Areas Can Use It

• Audit all discounts and comps annually.

• Eliminate anything without a clear ROI.

• Replace blanket discounts with targeted offers.

• Protect your “full price” integrity—it signals quality.

12. “Big But Small” Is a Strategic Position (Not an Accident)

The Insight:There’s a powerful middle ground between mega-resorts and tiny hills—and it’s under-served.

How Bolton Valley Uses ItThey offer enough terrain and amenities for a full stay, but maintain a small, intimate feel.

How Other Ski Areas Can Use It

• Invest selectively in amenities that extend stays (lodging, food, activities).

• Avoid overbuilding scale that breaks intimacy.

• Market the contrast: “full experience without the chaos.”

• Design guest flow to minimize crowd perception (parking, lift lines, etc.).