Community Involvement for Year-Round Sales Success

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When you think about boosting your sales, you might jump straight to the holiday season. But what if your business could thrive year-round? Engaging your community may help contribute to a steady stream of customers and sustained growth.

Dayyan Armstrong, co-founder of Sailing Collective, an experiential travel company, builds deep local connections in New York and worldwide to enhance clients' experiences. Princeton, New Jersey-based Loren Feldman, founder of 21 Hats, an online community for small-business owners, witnesses the profound impact of peer-to-peer learning and support within his network. And Patricia Silva, owner of Rock Rock Hair, finds that year-round connections within New York City's seasonal Rockaway Beach community are key to her salon's success. By weaving their businesses into local, remote, and even international networks, these entrepreneurs prove that businesses can foster customer loyalty and sustain growth through lasting relationships.

Strengthening Business Through Local and Global Connections

Dayyan Armstrong, co-founder of the Sailing Collective, cultivates deep local connections in New York City and globally. Hosting an annual holiday party and maintaining a strong online presence through their website, newsletter, and social media, the company fosters a sense of connection even among those who have yet to embark on a Sailing Collective adventure. "All of this relationship-building helps them to feel part of the community," he says.

In spring 2025, Armstrong and team will launch their upcoming book aboard a historic sailing vessel in NYC – an event likely to draw passionate mariners while also promoting their new offering. Reflecting on their first book, Sailing the Seas, released during the pandemic, Armstrong says, "It was an exciting way for people to still be able to interact with travel, even if just through a book. Seeing and reading about a remote cove sparks imagination for those yet to visit, and nostalgia for those who have."

“Many businesses mistakenly prioritize promoting their own products or services. But that's not what compels someone to join and tell all their friends.”  —Loren Feldman, founder, 21 Hats 

The Sailing Collective crew also engages deeply with people on the islands they explore. "Over the years, we've become friends with local farmers, fishermen, and other residents. During a Croatia voyage, we befriended the lighthouse keeper on the island of Vis," says Armstrong. "He invited the Sailing Collective travelers and crew for a home cooked-meal – inside the lighthouse! On Jost Van Dyke, we connected with a local janitor whose family ran a waterfront breakfast shack. As our friendship grew, they began cooking dinners for our charters, nearly doubling their income during the sailing season." These connections enhance the travel experience and encourage Sailing Collective clients to bond over shared experiences, even if their trips are years apart.

The company also invites other entrepreneurs and creatives to lead retreats on their trips. "Strategic partnerships, like our collaboration with artist-in-residence Windy Chien, can lead to quick sell-outs," Armstrong says of the fiber artist best known for her work The Year of Knots. "While a typical group charter might take months to fill, our voyage with Windy sold out in five days. Launching new residencies focused on wellness, arts, or coaching offers genuine cross-promotion of sales and diversifies our reach."

The Power of Shared Experiences

Feldman's 21 Hats community thrives on shared experiences. The daily newsletter and weekly podcast feature real talk from active entrepreneurs, fostering a continuous sense of belonging and growth. Feldman selects podcast guests willing to be transparent and vulnerable. "I look for people who are open about the tough times, as well as their successes," he says. Drawing on decades of experience covering entrepreneurs for top business publications, Feldman knows they most value peer-to-peer insights, especially from those who faced similar hurdles.

Feldman also cautions against a common pitfall: focusing too heavily on sales and marketing within communities. “Many businesses mistakenly prioritize promoting their own products or services,” he says. “But that's not what compels someone to join and tell all their friends.” 21 Hats' live events prioritize genuine connections, and they’re all about participant interaction, he says. No speakers, just meaningful discussions initiated by the attendees, about their current challenges. Feldman describes 21 Hats' approach to events as unique: "To kick off the event, everyone throws out topics they'd like to discuss with the group. We vote on them and prioritize the most popular. It's a chance to program your own conference."

Feldman's in-person events have provided valuable insights into customer preferences, and this clarity guides his content strategy. While he hasn't directly linked these efforts to increased sales or signups, audience engagement and community-building boost advocacy for the brand, he says. "I'm trying to reach an audience that has no time to waste. The best way for me to break through that is for one entrepreneur to share with another why the 21 Hats newsletter and the podcast are worth the time." 

Building Bonds Through Events and Social Media

Patricia Silva, the Brazilian-born owner of Rock Rock Hair in Rockaway Beach, New York, illustrates the profound impact of community engagement. "Before I came to Rockaway, I never felt true community. It started with surfing here, just being in the water and meeting people," she says. She credits this close-knit community as essential for her personal and professional development.

Silva's commitment to community engagement extends beyond her salon business. She bonded with Monice Small, owner of GoodForm fitness studio – a business in the historic building also housing Silva's salon – after attending Small's workout classes. Soon after, they collaborated to open Vazio, a light-filled event space in the same building where they were already growing their companies.

They created Vazio as a venue for people to gather, especially important during their beach town's quiet off-season. Hosting art shows and diverse events, Vazio attracted local artists and residents, nurturing community bonds and boosting visibility for Silva's salon and Small's studio. Although Vazio has since closed, its impact on the community remains significant.

Silva leverages both offline and online engagement to grow her brand. "My Instagram branding has really helped to create the salon's identity and expand my client base," she says. Her upcoming venture, Little Cuts, which will offer online classes for kids' haircuts by parents, aims to apply these community-building principles on a national scale.

Through their strategies and stories, Feldman, Armstrong, and Silva demonstrate that the heart of community engagement lies in dialogue, shared discovery, and genuine connection. These elements are essential for small-business owners, helping to enable them to sustain growth and navigate the challenges of entrepreneurship year-round.

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