Sisters' Side Hustle Makes $45M+ After 'Lightbulb 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, high-end 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, for the company.

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

Answers 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 main occupation when you started? side hustle?
LS: Before launching Dudley, I spent my career in fashion and beauty PR, working for brands such as 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 mother and I – had balanced expertise; each of us 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. This combination—my background in fashion and retail and Kaki's experience in operations and loyalty marketing—proved effective.

Related: Mom's side hustle started with a Facebook page. Now earning more than $1 million a year: 'Don't overdo it.

When did you start your side hustle and where did you find the inspiration for it?
KM: The idea was born in 2015. I was a new 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.

However, the initial inspiration – this is a credit to our mother. Our parents had moved to coastal Rowayton and bought a boat, which meant our mother had a new clothing occasion: pieces to wear on the boat that went into the mooring for dinner. At the same time, Lauren and I were like any busy, modern woman, going from here to there. We realized that we too wanted versatile clothing that could last; it was a need of many generations. This was really one moment of the bulb that we could start a company to deliver the product we all wanted together.

We pitched it as a family business to our business-minded father, who naturally picked it all up – but we had to show our seriousness. We were extremely lucky to have a small family investment to help us get our idea off the ground.

What were some of the first steps you took to get yours side hustle from the ground?
LS: We did the 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 essential to our success. It instantly resonated with every woman who saw it and wore it, so we made it in different colors and adapted its details and fabrics so that women keep coming back to it – and, of course, tell all their friends.

KM: We quickly learned that opening even the smallest doors led to bigger ones and that there were expertise and resources ready to help. We met our first manufacturing partner who advised us to start with low inventory and focus on marketing to explain who we are. Here's what we did: We created six styles and ordered 100 of each, then showed everyone we knew.

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

Related: This 20-year-old student started a side hustle with $400 — and made $150,000 over the summer

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 with low inventory, so keeping up with demand was an exciting challenge to overcome. we had CLIENTS upset that we got through so quickly and that criticism is hard when the company is basically your baby — and you're doing all the customer service yourself.

LS: It's no exaggeration to say that we were doing it all, and on top of that, we were both pregnant! We were labeling each product by putting stickers. I also brought individual sleeves to the embroiderer to add our signature pineapple, then sent them back to the manufacturer for finishing. Since then, we have been fortunate to build a great team and strengthen our own supply chainbut we have always retained the same sense of resourcefulness 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 towards working from home, something our product is really designed for. We were lucky that sales tripled during those first few 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 to most fashion retailers, but we always knew we wanted to build a sustainable brand. This meant choosing recycled versions of fabrics, whenever possible, right from the start. Currently, 90% of the materials used to make Dudley Stephens pieces are recycled. We are working with our manufacturing partners to make it 100%.

Related: This 52-year-old started a side hustle that brings people joy – and earns up to $30,000 during the wedding season: 'There was real demand'

How long did it take you to see consistent monthly income? 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 stable salary. That year, we became a six-figure business and began hiring full-time employees. Then, in 2019, we outsourced our fulfillment.

You have transformed side hustle in a full-time business. What do growth and revenue look like now?
KM: Since 2019, we have tripled sales year over year. But we are even more proud of it brand we have built. Our customers love our products and keep buying them; Typical returning customers have placed an average of five orders with us and own five to six Dudleys 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 a pleasure to work together as sisters. It's a great partnership and so helpful to have each other to bounce ideas off of and be in it together – through the good and the bad.

KM: I would also say the community we've created and the stories we hear about Dudley “in the wild.” We've had customers write in to share so many stories, from wearing collars during hospital treatment to bonding with another woman wearing Dudley. This shows that our product is in people's lives. We love helping people feel good and look good too.

Related: She started a creative side hustle that made $100,000 in 10 months – Now making up to $10 million a year: 'Find Your Niche'

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

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



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