• Captain Douglas Stein

  • Yacht Broker

At 65, Captain Doug has found his true calling as a charter yacht captain on the waters of Lake Michigan. His journey to this point has been full of twists, turns, and unexpected adventures. After a lifetime of work across the globe, he chose to pursue a passion that had been with him since childhood: boating.

Doug’s story began far from the water. He spent over 25 years in the restaurant industry, opening and managing restaurants across the U.S., Asia, Australia, and Africa for well-known brands like Houlihan’s, Spaghetti Warehouse, and Planet Hollywood. Although he wasn’t supposed to return to the U.S., life had other plans. Twenty-two years ago, Doug moved to Chicago to care for his father, leaving behind his international life and career. Little did he know that Chicago would become his permanent home.

While caring for his family, Doug shifted gears and launched Mad Style, a fashion brand that grew from his basement into a global business. His company made the Inc. 5000 list of fastest-growing companies for four years in a row and collaborated with prominent retailers worldwide. However, as the retail industry faced challenges in 2019, he sold the business.

Then came COVID-19. Doug leveraged his experience in sourcing products from Asia to pivot into the PPE industry, where he quickly became a recognized authority, particularly in exposing fraud in the nitrile gloves market. His work was featured in multiple media outlets, including CNN, and he consulted on high-profile fraud cases. While this was rewarding, at 62, Doug knew it was time to focus on something closer to his heart—something that would allow him to enjoy life rather than simply chase business success.

That’s when Doug became a yacht captain—a passion he had nurtured since childhood summers spent on his dad’s boat. Now, he shares that love for boating with others, creating unforgettable experiences for clients on Chicago’s beautiful lakefront. In just three short seasons, Doug has become one of the city’s most highly reviewed and sought-after captains, dedicating himself to making every trip amazing and memorable.

For anyone looking to sell their boat in Chicago, Captain Doug is the perfect choice. As a dedicated captain with intimate knowledge of the Chicago boating community, he now proudly works with Knot 10 Yacht Sales. With his expertise, passion for boating, and strong connections, Doug is the only logical choice to help find the right buyer for your boat.