20 years ago, a Facebook profile was optional—nice to have but certainly not a Must. Today, for most Westchester small businesses, a social media presence is as essential as a phone number, and considerably more complicated. The question is no longer whether to show up online; it’s how to do so in a way that actually moves the needle, without consuming every spare hour of your day or turning you into someone you’re not.
“We try to just be authentic to what we’re actually doing day to day.”
—SAMANTHA BENSON, SAMMY + NAT
To find out what’s actually working, we talked to six Westchester businesses getting it right: a fourth-generation hot dog institution, a grocery chain with a cult following, a chocolate shop that went viral before it even opened, a fashion brand threading the needle between local boutique and national brand, a legendary music venue, and one of the country’s most-followed dermatologists. Their follower counts range from around 29,000 to over a million. Their strategies are different. But the lessons they’ve learned rhyme in ways that should matter to any local business owner still trying to really figure this out.
Just start. Seriously.
If there’s one thing every person in this story agrees on, it’s this: The biggest mistake is waiting.
“Facebook proves to be our best social strategy in actually getting people to the shows.”
—JESSE HERMAN, MARKETING COORDINATOR AT THE CAPITOL THEATRE
One way to think about timing and social media posting is the way legendary late-night producer Lorne Michaels has reportedly described the process of preparing for any episode of “Saturday Night Live.” Specifically, that the show goes on at 11:30. Not because it’s ready, not because everyone is completely happy with it, but because 11:30 is when the show starts. Waiting for perfect is how you end up with nothing.
Gene-Christian Baca runs Walter’s Hot Dogs, the Mamaroneck-based institution his great-grandfather founded in 1919, now with 32,000 Instagram followers. He learned the hard way that waiting for the perfect post is a trap. “I spent way too much time trying to make everything look polished and perfect and overthinking every post,” he says. “The content typically performs best when it’s the most real and in the moment, about what’s actually happening.”
Film-and-television-producer-turned-shop-owner Kate Bolger, who built a 50,000+ Instagram following for her Sleepy Hollow candy boutique, The Village Confectionery, before it even opened, cosigns that advice. “Just press post. We live in a world with so much judgment, but you’re never going to know unless you put yourself out there,” she points out. “And who’s considering you cringe? Someone who’s never done anything in their life.”
“We live in a world with so much judgment, but you’re never going to know unless you put yourself out there.”
—KATE BOLGER, OWNER, THE VILLAGE CONFECTIONARY
Chappaqua dermatologist Dr. Whitney Bowe, who has 216,000 Instagram followers and 1.1 million on TikTok, puts it simply: “When I started on social media, I had no idea what I was doing from a technical perspective. I just showed up and relied on my knowledge and experience. If you show up as you are and genuinely try to put out content that will improve people’s lives, that’s a great place to start.”
Authenticity is an actual strategy, not a buzzword.
For Bolger, the decision to lead on social media with radical personal openness was months in the making. She played around with formats, studied what worked on other accounts, talked to friends and family, and soul-searched before landing on the only thing that felt true. “The only way that this was going to work was authenticity. My personal authenticity,” she recalls. Her first post, which she was convinced was “too weird,” reached nearly 2,000 people within the hour. “I looked at my phone and I was like, ‘Wait, how have almost 2,000 people seen this? I don’t know that many people in my life.’”
Annika Ziels, the marketing director behind DeCicco & Sons’ 62,000-follower Instagram account, discovered the same thing the hard way. “The most frustrating thing is when I spend hours filming, editing, and meticulously planning a reel that barely reaches our audience. Then I’ll post a five-minute clip of something raw and spontaneous that goes viral.” Her takeaway: “Our community often values authenticity and real-time store updates over high-production polish.” The proof came when a store manager called to tell her a customer had come in asking for the ingredients from one of her reels, and they were already sold out of everything. “It’s not always about every post being a viral hit,” she says. “It’s about those consistent, smaller stories that customers connect with.”
Samantha Benson, who runs the Rye and Ridgefield, Connecticut-based children’s clothing store Sammy + Nat (29,000 Instagram followers), keeps the same principle top of mind. “We try to just be authentic to what we’re actually doing day to day and post that,” she says. “Luckily, that seems to be interesting to people.”
Consistency beats perfection every time.
Baca spent years in the trap that most new social media creators fall into: obsessing over the just-right audio, the perfect caption, the best special effects. “Consistency is more important than perfection,” he points out. “If I knew that early on, it would have made a world of difference.”
Ziels echoes this sentiment. “None of this is linear, but finding some sort of consistency in content helps. Celebrate the little wins and learn from the mistakes.”
“The content typically performs best when it’s the most real and in the moment.”
—GENE-CHRISTIAN BACA, WALTER’S HOT DOGS
Know which platform is actually working for you.
Not all platforms are created equal, and the one with the most growth isn’t necessarily the one driving revenue. For Baca, Facebook served longtime loyal customers and local reach for years before Instagram took over as the engine for growth and national discovery. Now Reels drives the most engagement and has helped Walter’s expand its retail presence beyond Westchester. “Different platforms serve different audiences,” he says. “You don’t have to be everywhere equally.”
Jesse Herman, marketing coordinator at The Capitol Theatre in Port Chester, learned this distinction the hard way. Despite Instagram growing faster and reaching a younger audience, Facebook remains the venue’s most effective platform for actually selling tickets, largely because of its events feature and its presence in local community groups. “Facebook proves to be our best social strategy in actually getting people to the shows,” he notes.
His most surprising lesson, though, is about the limits of virality altogether. When a scheduled Ashanti show wasn’t selling, the team got the R&B artist, who has over 8 million Instagram followers, to post a video shoutout. It got tens of thousands of likes and hundreds of comments, yet ticket sales barely moved. “Even with seemingly infinite exposure, a show still has to be appealing to the fans in terms of price and location for a viral social post to move the needle.” In other words, reach without relevance is just noise.
For Dr. Bowe, Instagram feels most like home, but TikTok is where her Skin Cycling Method went mega-viral and expanded her reach exponentially. “I love the creativity, rawness, and spontaneity of TikTok,” she says. Ziels, meanwhile, keeps her focus squarely on Instagram. “It’s the most fun to run, too.”
“It’s not always about every post being a viral hit.”
—ANNIKA ZIELS, MARKETING DIRECTOR, DECICCO & SONS
Write up a content strategy, even it’s just a loose one.
For her social media planning purposes, Bolger thinks intentionally about filling three buckets each week: Monday posts explore what she calls confectionery philosophy: the cultural meaning of sweets, the psychology of gifting, the idea of savoring small moments. Wednesdays are for character-driven storytelling with a scripted wink. Fridays offer business updates about the shop itself. “There’s actually a brand strategy behind all of that,” she says. Each post serves a purpose beyond filling the feed.
Ziels plans a week or two in advance and reviews the calendar with her team every Monday, incorporating input from department directors on what’s new, seasonal, and trending. Herman, by contrast, operates almost entirely in real time at The Capitol Theatre: no rigid content calendar, just moment-to-moment posting that keeps the feed fresh and flexible enough to accommodate last-minute artist requests. “This allows us to be more current on trends,” he says.
Dr. Bowe batch-preps her content, filming roughly two hours every other week, and relies on her team at Dr. Whitney Bowe Beauty to build out the calendar and manage brand account responses. But she personally responds to every comment on her founder channels. The division is deliberate: systems for scale, personal touch where it counts most. “I never just put content out there into the void,” she says. “I think about my community with every post I create. What is she thinking about? What are her concerns?”
Keep content management in-house if at all possible.
Nearly every source in this story tried outsourcing at some point. Nearly everyone came back to running it themselves or insisting on tight control if they hired support. Baca worked with outside agencies over the years but kept returning to managing it himself. “Outside help can be great for structure and ideas, but sometimes it’s hard to replicate the voice and feel of Walter’s, in terms of the history, the personality, everything behind the brand.” Herman makes the same call at The Cap: “When we do the content ourselves, we’re able to capture a more authentic aesthetic and truly nail the brand voice we want to give off.”
Bolger has brought in a producing partner to help with brainstorming and editing—“so I’m not up until midnight every night”—but keeps creative control firmly in her own hands, sometimes with an early-stage AI assist. “I take an idea I have and push it to see where else it could go,” she says. “And then once I have the nugget, I’m off and running.”
Followers and community are not the same thing.
This distinction came up, unprompted, in almost every interview. “Followers are a number; community is a conversation,” says Ziels. “You see it when followers start answering each other’s questions in the comments or sharing our posts with their local town groups.” For Baca, the signal is even simpler: “When people are commenting, sharing their own photos, tagging us, telling their own stories about Walter’s, that feels like a real community. Anyone can have followers. You can pay for them.”
Bolger frames it through the lens of the digitized world we live in now. “In the world of AI, I want people to know me and to know that I’m a real human,” she explains. “I infuse myself into my social media content so that people can connect with me and know there’s a real heart behind The Village Confectionery.”
Once again, this all comes down to starting.
The best advice for any Westchester business owner still sitting on the sidelines comes down to this rec from Ziels: “Just start documenting what you already do day to day. You don’t need to hop on a viral trend. Just show the passion and heart behind your business. Your customers are already on these platforms looking for you. The only way to lose is to not be there to meet them.”
Related: Turning Social Media Into a Career: Where to Study in Westchester County
