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It started after a trip to Maine during my son's first year of college. We attended his high school basketball coach's wedding and noticed that most of his teammates were wearing bow ties. We thought it was a trend, but we discovered something much bigger.
My son and I started playing around with the idea of starting an online bow tie business. Roland liked the idea of being his own boss, of being an entrepreneur. I liked the idea of building something for the family. I loved the idea of naming it after my father and my son, who share a name. I also liked the idea of having something to keep us connected while he was away at school.Roland was the creative force. I was responsible for operations and logistics. He was away at college, but we made it work. We were excited to build a legacy together.After studying the Amazon private-label business and learning about online traffic and keywords, we quickly mastered the process. It came at a great time. Roland had transferred from a junior college to a private four-year HBCU. It was an exciting move, but also very expensive, with tuition, fees, and room and board.At first, we thought we would be selling to young, swaggy college students and professors. Then someone asked if we could make one for her pig. Another person asked for a smaller size for a woman. We began looking at our data to learn who was actually buying. Our customer base was broad and far from what we expected.The business was doing well, and the money was going toward college expenses and being reinvested in growth. We explored different designs and complementary accessories, such as socks and pins. But the bestseller remained our bow ties. The winning formula was volume.Roland began looking into fashion week and selling in retail. He toyed with the idea of writing a book and creating a style guide. Social media was growing, and opportunities seemed plentiful.The breaking point came when Walmart approached us to sell on Walmart.com. Roland wanted to build a couture brand and sell on the runways of Fashion Week. I believed in the volume of a mass audience. We could not close that gap.I wanted him to be the face of the brand. He wanted to stay behind the scenes. I wanted to highlight one celebrity. He wanted to highlight another. Our differences were slowing us down. My son and I got on conference calls and disagreed in front of other people. It was awkward and uncomfortable.He wanted more control of the money, but I wanted to prioritize tuition and business growth. Soon he was saying left, and I was saying right. The arguments got tedious, and we reached an impasse. The conversations were tense. Holidays were not fun. Everything became a potential powder keg for us and anyone nearby.On the surface, it seemed like we disagreed about money and strategy, but below the surface was a mother who needed additional income to provide the college experience I wanted for him, and a son who was learning to flex his business skills and his adult independence. It was not just money for either of us. It was identity.I had to check myself, especially after watching "Succession" on HBO. Was I becoming Logan Roy, the controlling parent who made his children feel unworthy? I also thought about "Soul Food," which had aired years earlier. That show is about family bonds under strain and the terrifying realization that money, pride, and seemingly reasonable solutions can still tear apart what matters most.Roland was trying to build an independent life while being shaped by family dynamics and expectations. The thing we had built to bring us closer was starting to tear us apart. So, while the business was profitable, I had to ask whether it was actually successful.Some people asked why one of us could not simply run the business without the other. We contemplated that. But the deeper reality was about what the business had come to mean between us. Neither of us had the appetite to untangle it. It was easier to walk away.We can have fun now: at family dinners, on holidays, and on vacations. We now have priceless memories as mother and son, not co-founders.
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