GrowthCurve Episode 17: Duke & Winston

Can’t Knock the Hustle

June 3, 2019

An interview with Seun Olubodun, founder of Duke & Winston, is reviving his lifestyle apparel company with hopes to grow the business and become a national brand.

GrowthCurve Episode 17: Duke & Winston

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Regarded as a self-proclaimed hustler, Seun Olubodon followed his passions and entrepreneurial spirit to create a lifestyle apparel brand called Duke & Winston. Named after his English bulldog Duke and former British Prime Minister Winston Churchill, Olubodon developed a t-shirt displaying his pup in a top hat, which culminated into his signature brand logo. Inspired by other clothing brands like Johnny Cupcakes, Olubodon leveraged grassroots marketing to elevate his local Philadelphia venture into an emblem that garnered national recognition.

In this episode, Olubodon opened up to me about his journey, and talked very candidly about not only the highs and lows of Duke & Winston, but also the toll the past decade has taken on his mental state and overall well-being. Hearing Seun’s story made me take a step back and reflect on the challenges that we all face as entrepreneurs. With that said, I thought I would change the approach of this week’s recap to discuss the juxtapositions that we often see in startup culture and use Seun’s journey to guide the conversation. The topics we explored are the paradox of leadership traits, the difference between the image and reality of your business, and ultimately, the turbulence an entrepreneur encounters between successes and failures.


Seun Olubodon


Seun designed a cool logo with his English bulldog that he started selling out of his van in Northern Liberties. Through successful partnerships, press coverage and event marketing, Seun opened a store in Center City Philadelphia. While Seun had to shut the store doors a few years ago to focus on his mental health, he is now ready to relaunch his brand using key learnings from his past to drive his new business plan.


Seun also runs an Instagram account @TisARoughLife that provides motivational quotes and images for aspiring entrepreneurs that is based on Seun’s business experience.

Relaunch of Duke & Winston

Seun is planning to sell t-shirts, hats and so much more. Instead of having a store presence, Seun plans to create an e-commerce hub to sell his products and reach a larger audience. Due to his prior success, Seun also seeks to leverage partnerships with wholesalers and other collaborators.

Leadership: Visionary versus Operator

Visionary. Self-Starter. Influencer.

Building a national lifestyle brand demands that these character traits are exhibited in its founder, and Seun Olubodon demonstrated these leadership qualities in his startup apparel company. While having a true vision for your brand is important, there is also a real need for an analytical mind to operate and scale a business. In hindsight, Seun would tell you that he should have employed someone who knew the business fundamentals to complement his creative mindset, yet, this is always easier said than done when reflecting on your business venture.

To me, Seun’s story reveals the common paradox of the divided brain. In our anatomy, we try to connect our left and right side of the brain to make decisions, but whether or not that decision is deemed logical or emotional is dependent upon our genetic makeup. As entrepreneurs or leaders within our organization, we also must find a delicate balance of business acuity (left side) and creativity (right side) in order to make and then act on strategic decisions that will benefit the company. Having a visionary founder is crucial, but there is also a dire need for an operator that can think long-term and execute the less-glorified functions of a business.

In this example, Seun’s unconventional business model proved grassroots marketing effective, yet exposed a real need for operational excellence. Seun was well-connected within communities to garner significant press coverage, create successful collaborations with strategic brand partners and execute events in high-traffic areas. But, being laser-focused on his vision, Seun did not heed outside counsel and struggled to get out of the monotony of maintaining his business in order to scale his business effectively. Seun was a true visionary, but employing someone that focused on the strategy and finances of the business would have been a real asset for Duke & Winston.

Business: Image versus Reality

Uncovering Seun’s journey illustrates the juxtaposition of the portrayed image of your business and the reality. It is so easy to convince others and even ourselves that everything is going great, yet there are issues that we may minimize to give us a confidence boost about the actual performance of the company. There were many times in Seun’s story that you would think as an outsider that the business was booming, but in reality, they were struggling to make ends meet. Because, often times, even though you are bringing in hundreds of thousands of dollars in a year, you might not be generating significant profits.

As you follow Duke & Winston’s journey, you would think that the company was making forward progress, and rightfully so. The company started with Seun selling t-shirts out of his van at local events and ended with him opening a store on 18th and Chestnut in Philadelphia. His designs were being sold at Urban Outfitters, and more than forty other wholesalers as well as generating national press in publications like Travel & Leisure.

While that upward trajectory is substantial, the company was struggling financially with rising rents, stolen merchandise and a lack of an e-commerce presence. The grand opening of the stores, parties and press are often glamorized in culture and seem like forward growth, but in actuality, can deter from the nuts and bolts of the business. We had a similar experience in the beginning years of Brolik, and ultimately had to rethink our strategy to grow the business.

“I thought that the more you hustle, the more success. I hadn’t had any major failure at that point. There were a ton of fires, but I put them out.”

– Seun Olubodon, Duke & Winston

Personal: Successes versus Failures

In our discussion, Seun stated that he assumed 100% responsibility for his business and it was difficult for him to delegate tasks to his team. In fact, it was even difficult for Seun to bring on partners or investors because it would cause him to lose control of his business. This is challenging for anyone starting a business because we become so consumed by the project, and in this case, Seun not building a team around him that complemented his strengths caused some significant issues within his business.

We have become obsessed with this gogogo mentality in today’s culture, and Seun would be the first to tell you that he would constantly put out fires in his 20-hour workdays, but there was nothing critical that needed to be addressed. Until it did. Seun found early success, which he was able to turn into a storefront in a prime location, which should have been the moment the business skyrocketed. But, it was this moment that represents one of the darkest times in Seun’s life. That non-stop mentality led to the collapse of Duke & Winston, and ultimately, Seun Olubodon.

Seun decided to close Duke & Winston to focus on his mental health and wellness. As we saw in the last episode with NeuroFlow, it is important to introduce behaviors that address our mental ailments as well as the physical ones. But, after much self-reflection and time away from the business, Seun started @TisARoughLife on Instagram as a platform to inspire budding young entrepreneurs by sharing motivational quotes and images from his own personal experience.

While Seun Olubodon might have experienced a low moment both personally and professionally, like many of us have, it is not the end of him. He is continuing to manage his Instagram account and has plans to revive the Duke & Winston brand. And, I know, I personally am excited to see what Seun does next as he navigates this next phase of his life.

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Jason Brewer

GrowthCurve is hosted by Jason Brewer. As CEO of Brolik, Jason has spent 15 years of his career working directly with business owners, helping them navigate through growth phases and difficult challenges. Jason is an experienced business advisor and passionate storyteller, and brings these talents together in each episode of GrowthCurve.