Many successful businesses have launched from humble beginnings. Take, for example, Tuckernuck, the apparel boutique that’s made waves for its chic yet timeless pieces, like the viral Jackie dress that’s been commonly spotted on Capitol Hill and all over TikTok. Though now a multimillion-dollar e-commerce and brick-and-mortar brand, the spark of Tuckernuck came in 2012 with just a garage, a camera, and a clear vision.
During CO—’s Small Business Day 2025, Barbara Thau, Editorial Director of Features, sat down with Jocelyn Gailliot, Co-Founder and CEO of Tuckernuck, for an inside look at how the company has scaled profitably, built a fiercely loyal customer base, and stayed nimble in the face of economic headwinds.
Building a profitable brand with customer connection
From the beginning of Tuckernuck, Gailliot and her co-founders prioritized two things: customer connection and profitability. With this mindset, the team prioritized “inspirational” content — styling advice, travel guides, and high-quality photographs — to encourage customers to not only visit, but stick around.
“We didn’t think of it as … [just] selling product,” Gailliot shared. “What we wanted to do was form an emotional connection with our customer, and we wanted to invest more than other brands online in providing a service for [them].”
For small businesses looking to adopt a similar approach, Gailliot emphasized that this content doesn’t need to be overthought or overly polished. Rather, she encouraged business owners to simply start by creating, experimenting, and testing out different content.
“In those early days, we would just get out in front of [my parents’] garage and get my dad to take a picture of us,” she said. “It doesn’t need to be professional models … it really can just be anyone on your team, your family. But content is king; it still is on these distribution channels, and we’re always trying to evolve with it and keep up with it.”
[Read more: How to Create Small Business Content to Generate Leads Online and Thrive]
What we wanted to do was form an emotional connection with our customer, and we wanted to invest more than other brands online in providing a service for [them].Jocelyn Gailliot, Co-Founder and CEO, Tuckernuck
Retention over acquisition: The strategy behind 65% repeat customers
Tuckernuck’s connection-first, content-driven approach has also shaped the brand’s customer acquisition and retention strategy — one that’s led to a 65% repeat customer rate, far above the average for e-commerce retailers.
For the initial sale, rather than focusing on deeply-discounted loss leaders, Tuckernuck prioritizes items that are genuinely representative of their brand and their customers’ lifestyles.
“We acquire customers with a dress that we love that’s a certain price point,” Gailliot explained. “From there, we think about what that customer would want to buy once we’ve built that trust.”
In service of this, Tuckernuck sells both third-party and private-label products, building out their private-label offerings based on any “white space” in terms of price points or design. The e-commerce retailer has also expanded into brick-and-mortar, with a flagship store in Washington, D.C., and plans for a New York City location in spring 2025.
“The way people want to shop these days is … a very omnichannel experience,” Gailliot said, noting that the e-commerce store is ideal for broad discovery, while the brick-and-mortar store offers a curated, high-touch experience.
Gailliot admits Tuckernuck’s business model is more complicated than others. However, the brand’s range of products, price points, and ways of shopping continue to encourage repeat business at “every point in [a customer’s] life.”
“Most customers say that we’re their life hack, and I couldn’t think of a better description than that,” she added.
[Read more: 5 B2B Customer Loyalty Strategies for Thriving Businesses]
Adapting to tariffs and a shifting global supply chain
Tariffs are a major concern for today’s small businesses, especially those that partner with global suppliers. Tuckernuck, which operates as both an aggregator and a private label, has seen this impact firsthand.
“A lot of our third-party brands that are much smaller … don’t necessarily have the margin or ability to move as fluidly, so they’re taking seasons off,” explained Gailliot.
To navigate these challenges, Tuckernuck has implemented a multi-pronged approach. In addition to repricing items where necessary, Gailliot’s team has focused on diversifying their suppliers and warehousing strategy as much as possible.
“We have found a lot of amazing factories in other countries,” Gailliot said. “To accelerate it and have to do it quickly has been stressful, but I think we’ve come out stronger as a result.”
[Read more: Tariffs on Imports Rocking Small Businesses as They Scramble to Adapt]
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