By: Little Trouble
In the middle of a California heatwave, Dinah Chapman launched her first collection of kids’ apparel. It was summer, but one particular item—a hoodie—sold out almost instantly despite the sweltering weather. For Chapman, this was a promising indication that Little Trouble might become something much bigger than she had imagined.
Little Trouble, the kids’ fashion brand born from Chapman’s frustration with uninspired boys’ clothing, has since gained significant traction and become a viral sensation in many circles. What started in a garage is now a rapidly growing company, moving from a family-run fulfillment operation to a recognizable global brand. All the while, Chapman has been managing it from Bali, where she relocated with her family to be closer to manufacturers.
Building a Brand with Community at Its Core
Little Trouble didn’t grow primarily because of paid ads or aggressive marketing. Instead, it thrived on community—word-of-mouth recommendations, organic social media growth, and Chapman’s direct engagement with parents.
“The growth of Little Trouble largely depends on genuine positive reviews and word of mouth in a world saturated with brands and products at every turn,” she explains. “We continue to build upon this by consistently prioritizing quality products and authentic designs that I can connect with my community through.”
That community-driven approach is evident in everything from product development to social media strategy. Chapman frequently engages with customers, remembers small details about their lives, and makes a point to express appreciation for her team. “Send thank-you texts and Slacks—people who are working really hard and producing great work should be told!” she emphasizes. “A simple text or Slack to show appreciation or recognition goes such a long way, especially when it comes from the top.”
The Challenge of Scaling a Business from Afar
Running a high-growth brand while living on the other side of the world comes with challenges. Time zones alone create logistical headaches, but Chapman sees it as an advantage.
“Managing the business from abroad has been one of the biggest challenges I’ve faced yet because things are often easier to tackle in person,” Chapman explains. “But I knew this would be part of the deal when my family and I moved abroad, and I’m generally able to handle situations with much more patience and clarity here since the general environment tends to be far less stressful and intense than the States. I also have more time to settle any emotions that come with setbacks, giving me a chance to regroup and react in a logical state rather than an emotional one.”
Beyond Fashion: A Vision for the Future
Chapman’s vision for Little Trouble extends far beyond fashion. She sees the company potentially growing into an even bigger platform that challenges the norms of kids’ fashion and creates meaningful social impact.
“Category expansion within the baby and toddler vertical could help challenge the fast fashion, poor-quality, and disposable mainstream options that have dominated for years,” she states. “A large part of the early success Little Trouble has seen is because a new generation of parents has emerged, myself included, who want and value different things than the generations before us.”
The nonprofit Hugs for Homies is set to launch soon and will focus on direct community-based giving. Rather than donating to large, impersonal organizations, Chapman wants to create a system where funds go directly to families in need. “Hugs for Homies is a nonprofit organization I’ve been working on for well over a year and plan to launch very soon. It will have multiple community-centric giveback initiatives that are all related to motherhood, parenting, and children.”
Lessons in Leadership and Growth
“Being the founder is such a different level of responsibility than being a c-suite employee managing a team below you, which was my experience prior to starting Little Trouble,” she explains. “Now, I have the opportunity to build a team and stay fully in touch with the actual work being done on the ground.”
Her leadership philosophy, shaped by her time in corporate, centers around empowering her team, helping them develop their skills, and ensuring that everyone feels valued. “I genuinely care and invest in the development of my team’s strengths. I believe it’s much easier to be an effective leader if you understand the actual work you are expecting of your team and you invest in coaching them up and giving them the opportunity to take on big projects that require them to flex outside of their current skill set.”
Advice for Aspiring Entrepreneurs
For those looking to follow in her footsteps, especially women navigating entrepreneurship, Chapman offers a simple but powerful message: “Confidence in your skillset, instinct, and relentless drive towards your goals can create a pretty hard-to-beat combo.”
She also acknowledges the challenges that come with leadership, especially as a woman. “I’ve found that one of the most difficult things to achieve as a leader is being respected as well as liked. While not everyone thinks it’s important to be liked as the boss when you pair that with being truly respected for your skill and experience, it’s a potentially powerful path to working your way to the top.”
From a frustrated mom searching for stylish clothes to the founder of one of the most promising brands in kids’ fashion, Dinah Chapman’s journey with Little Trouble is a testament to the power of community, innovation, and fearless leadership. As the brand continues to grow, it seems clear that this is only the beginning.
Published by Drake M.
