Sisters’ Side Hustle Earns $45M+ After a ‘Light Bulb Moment’

This Side Hustle Spotlight Q&A features Lauren Stephens and Kaki McGrath. With their mother, Bonnie Dudley, Stephens and McGrath co-founded the “high-performance, eco-friendly, elevated everyday-wear” brand Dudley Stephens in 2015. The digitally native brand has sold over 445,000 products to over 330,000 customers, resulting in more than $45 million in sales over the past 10 years with a 60% customer return rate, per the company.

Over the past decade, Dudley Stephens has repurposed more than seven million plastic bottles (and counting), recycled more than 2,000 pieces through its DS Renew program and donated $200,000 through DS Gives for women and children in need.

Responses have been edited for length and clarity.

^{Image Credit: Courtesy of Dudley Stephens. Kaki McGrath, left; Bonnie Dudley, center; and Lauren Stephens, right.}

What was your day job or primary occupation when you started your side hustle?
LS: Before launching Dudley, I spent my career in fashion and beauty PR, working for brands like Gucci, Calvin Klein, L’Oreal and Lancome. We started Dudley Stephens shortly after I left L’Oreal in 2015. As co-founders, the three of us — Kaki, our mom and I — had well-balanced expertise; we each brought something different to the table. Kaki spent the previous decade in loyalty marketing with Momentum Worldwide, managing their VIP experiences for American Express and was with Starwood in its global partnership marketing department then. That combination — my background in fashion and retail and Kaki’s experience in operations and loyalty marketing — proved effective.

When did you start your side hustle, and where did you find the inspiration for it?
KM: The idea arose in 2015. I was a young mom who had just moved to the Connecticut suburbs where we grew up, and Lauren was recently married and thinking about starting a family of her own.

The initial inspiration, though — that’s a credit to our mom. Our parents had relocated to coastal Rowayton and purchased a boat, which meant our mom had a new wearing occasion: pieces to wear on the boat that transitioned to docking for dinner. At the same time, Lauren and I were like every busy, modern woman, going from here to there. We realized that we, too, wanted versatile clothing that could keep up; it was a multigenerational need. That was really a lightbulb moment that we could start a company to deliver the product we all wanted together.

We pitched it as a family company to our business-minded dad, who naturally picked it all apart — but we had to show our seriousness. We were incredibly fortunate to have a small family investment to help us get our idea launched.

What were some of the first steps you took to get your side hustle off the ground?
LS: We made samples right away. We ordered fabric and designed our first style: the Cobble Hill turtleneck, which remains a top seller today. We had found our hero product, which was pivotal to our success. It instantly resonated with every woman who saw and wore it, so we made it in different colors and adapted its details and fabrics so women would keep coming back to it — and, of course, would tell all of their friends.

KM: We quickly learned that opening even the smallest of doors led to larger ones and that there was ready expertise and resources out there to help. We met our first manufacturing partner, who advised us to start small with low inventory and focus on marketing to explain who we are. So we did: We created six styles and ordered 100 of each, then told everyone we knew.

LS: Our timing was also everything. It was 2015, so we rode the relatively nascent ecommerce and influencer boom, gifting or paying small fees to influencers to help us get the word out. Our product resonated so well we found that growth happened organically; influencers just kept wearing and posting our styles.

What were some of the biggest challenges you faced while building your side hustle, and how did you navigate them?
KM: Again, one of our strategies was to start small with low inventory, so keeping up with demand was an exciting challenge to overcome. We had customers upset that we sold through so quickly, and that criticism is hard when the company is basically your baby — and you are doing all of the customer service yourself.

LS: It is no exaggeration to say we were doing it all, and on top of that, we were both pregnant! We were tagging each product, putting on the stickers. I even brought individual sleeves to the embroiderer to add our signature pineapple, then returned them to the manufacturer to finish. Since then, we’ve been lucky to build an amazing team and solidify our supply chain, but we’ve always kept that same sense of agility and ingenuity as those early days.

KM: That ability to respond and pivot when needed still serves us well. During the pandemic, we benefited from the shift toward working from home, something our product is truly made for. We were fortunate that sales tripled during those early months. However, we also lost access to our manufacturer and had to completely overhaul our supply chain. It taught us the importance of diversification!

LS: I think we’ve also learned to trust our instincts. When we started Dudley, sustainability really wasn’t important for most fashion retailers, but we always knew we wanted to build a sustainable brand. That meant choosing recycled versions of fabrics, whenever possible, from the start. Currently, 90% of the materials used to make Dudley Stephens pieces are recycled. We’re working with our production partners to make it 100%.

How long did it take you to see consistent monthly revenue? How much did the side hustle earn?
LS: We were extremely fortunate to reach profitability in 2018, at which point we were able to pay a consistent salary. That year, we became a six-figure business and began hiring full-time employees. Then, in 2019, we outsourced our fulfillment.

You’ve transformed the side hustle into a full-time business. What does growth and revenue look like now?
KM: Since 2019, we’ve tripled sales year over year. But we’re even more proud of the brand we’ve built. Our customers love our products and continue to buy them; typical returning customers have placed an average of five orders with us and own five to six Dudley pieces each. In fact, 19,000 of our customers own five or more Dudleys!

What do you enjoy most about running this business?
LS: It’s fun to work together as sisters. It’s a great partnership and so beneficial to have each other to bounce ideas off of and be in it together — through both the good and the bad.

KM: I’d also say the community we’ve created and the stories we hear of Dudley “in the wild.” We’ve had customers write in to share so many stories, from wearing our turtlenecks while undergoing treatments in the hospital to bonding with another woman wearing Dudley. It shows that our product is in people’s lives. We love helping people feel good and look good, too.

What’s your advice for others hoping to start successful full-time fashion businesses of their own?
LS: Just do it. Perfectionism is a myth; it’s never going to be perfect, and everything is a work in progress. You can always refine as you go, but you have to start somewhere.

KM: Take the challenges and learn from them. Like Lauren said, we are not perfectionists. We try to turn every negative into something positive.