This Side Hustle Q&A features Lauren Stephens and Kaki McGrath. Stephens and McGrath, along with their mother Bonnie Dudley, founded the brand of “high-quality, eco-friendly and high-quality casual clothing” Dudley Stephens in 2015. The digitally native brand has sold over 445,000 products to over 330,000 customers, resulting in over $45 million in sales over the last 10 years with a customer return rate of 60% per company.
Over the last decade, Dudley Stephens has reused over seven million plastic bottles (and counting), recycled over 2,000 through DS Renew and donated $200,000 through DS Gives to women and children in need.
Responses have been edited for length and clarity.
Photo credit: Courtesy of Dudley Stephens. Kaki McGrath, left; Bonnie Dudley, center; and Lauren Stephens, right.
What was your day job or most important occupation when you began working on the side?
LS: Before founding Dudley, I used to be in fashion and beauty PR, working for brands comparable to Gucci, Calvin Klein, L’Oreal and Lancome. We founded Dudley Stephens shortly after I left L’Oreal in 2015. As co-founders, the three of us – Kaki, our mother and I – had a well-balanced expertise; each of us brought something different to the table. Kaki spent the previous decade in loyalty marketing at Momentum Worldwide, managing their VIP experiences for American Express, and then worked at Starwood in global online marketing. This combination – my experience in fashion and retail and Kaka’s experience in operations and loyalty marketing – proved effective.
When did you begin your side business and where did you discover the inspiration for it?
KM: The idea was born in 2015. I used to be a young mom who had just moved to the Connecticut suburbs where we grew up, and Lauren had recently gotten married and was pondering about starting a family of her own.
However, the initial inspiration comes from our mother. Our parents had moved to coastal Rowayton and bought a boat, which meant our mother had a recent clothing option: clothes to wear on the boat that may dock for dinner. At the same time, Lauren and I were like any other busy, modern woman, traveling from here to there. We realized that we, too, needed versatile clothing that might sustain; it was a multi-generational need. It was truly a breakthrough moment where we were capable of start a company that may work together to deliver the product all of us dreamed of.
We proposed this company as a family business to our business dad, who naturally took all of it apart, but we had to indicate our seriousness. We were incredibly lucky to have a small family investment that helped us bring our idea to life.
What were the first steps you took to interrupt away from the game?
LS: We made samples instantly. We ordered the fabric and designed our first style: the Cobble Hill turtleneck, which stays a bestseller to this present day. We found our hero product, which was crucial to our success. It immediately appealed to every woman who saw and wore it, so we created it in different colours and customized its details and materials to maintain women coming back to it – and, after all, telling all their friends about it.
KM: We quickly learned that opening even the smallest door leads to larger ones and that there is ready knowledge and resources to assist. We met our first manufacturing partner who advised us to start out small, with low inventory and focus on marketing to elucidate who we were. That’s what we did: we created six styles and ordered 100 of each, then told everyone we knew.
LS: Our time was also of the essence. It was 2015, so we navigated the relatively nascent e-commerce and influencer boom by giving influencers gifts or paying small fees to assist us spread the word. Our product was so successful that we found that the growth happened organically; influencers simply wore and posted our styles.
What were the biggest challenges you faced in building your side team and how did you overcome them?
KM: Again, one of our strategies was to start out small with low inventory, so maintaining with demand was an exciting challenge to beat. Customers were upset that we sold products so quickly, and that criticism is difficult when the company is essentially your baby – and you do all the customer support yourself.
LS: It would not be an exaggeration to say that we did all this, and on top of that, we were each pregnant! We tagged each product and put stickers on it. I even brought the individual sleeves to the embroidery machine so as to add our signature pineapple and then returned them to the manufacturer for ending. Since then, we have been fortunate to build an incredible team and strengthen our supply chain, but we have all the time maintained the same sense of agility and ingenuity as we began.
KM: This ability to react and pivot when mandatory continues to serve us well. During the pandemic, we benefited from the shift to working from home, which is what our product was really designed for. We were lucky that sales tripled in the first months. However, we also lost access to our manufacturer and needed to completely rebuild our supply chain. This taught us how essential diversification is!
LS: I think we have also learned to trust our instincts. When we began Dudley, sustainability wasn’t really essential to most fashion retailers, but we all the time knew we desired to build a sustainable brand. This meant selecting recycled versions of materials from the start every time possible. Currently, 90% of the materials used to supply Dudley Stephens clothes are recycled. We work with our manufacturing partners to attain 100%.
How long did it take for you to attain stable monthly income? How much did the side hustle earn?
LS: We were very fortunate to attain profitability in 2018 and were then capable of pay a regular salary. That same 12 months, we became a six-figure company and began hiring full-time employees. Then, in 2019, we outsourced the project.
You turned your side hustle into a full-time business. What does growth and revenue appear to be today?
KM: Since 2019, we have tripled our sales 12 months over 12 months. But we are much more happy with the brand we have built. Our customers love our products and proceed to purchase them; typical returning customers place an average of 5 orders with us and each have five to 6 Dudleys. 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 working together as sisters. It’s a great partnership and very useful when we are able to exchange ideas and be in it together – for higher or for worse.
KM: I might also talk about the community we have created and the stories we hear about Dudley “in the wild.” Customers have written to us with plenty of stories, from wearing our turtlenecks while undergoing hospital treatment to bonding with one other woman wearing Dudley. This shows that our product is present in people’s lives. We love helping people feel good and look good.
What is your advice for others who want to start out their very own successful full-time fashion business?
LS: Just do it. Perfectionism is a myth; It won’t ever be perfect and every little thing is a work in progress. You can all the time improve your style, but you have to start out somewhere.
KM: Take on challenges and learn from them. As Lauren said, we are not perfectionists. We attempt to turn every negativity into something positive.
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