When Jordan Kivelstadt, E04, arrived at Tufts University, he was certain he wanted to become a surgeon. He had been interested in medicine since he was 13, worked on ambulances starting at 15, and pursued a pre-med engineering degree with every intention of attending medical school. What he hadn't anticipated was that a few entrepreneurship classes would lead him down an entirely different career path and entirely change his life trajectory.
Today, Jordan has founded five companies across industries ranging from event production to wine and hospitality. He currently serves as CEO of Trellis Management, a diversified hospitality group based in Sonoma, California, and has remained involved with the Derby Entrepreneurship Center as a board member over the years.
Jordan was among the first few students to complete Tufts' Entrepreneurship minor, then known as the Entrepreneurial Leadership Studies program. In 2004, he graduated alongside just two other students in the program.
Coming from a family of entrepreneurs, Jordan had been experimenting with business ideas since high school. When Tufts introduced ELS 101, an introductory course focused on entrepreneurship and business planning, he was immediately interested. Taught by Pamela Goldberg, who was the inaugural Director for the entrepreneurship program at Tufts, the course gave Jordan an opportunity to explore his interest in building businesses alongside his engineering studies.
"I loved her. She was incredible," Jordan recalled of Goldberg. "I loved the class."
Although he continued pursuing medicine through much of college, his entrepreneurship courses gradually changed how he thought about his future.
"The entrepreneurship classes really opened my eyes to the fun and the joy of creating businesses and taking ideas and making them a reality," Jordan shared.
This interest soon extended beyond the classroom. During college, Jordan partnered with a friend who had started a small DJ business called Groove Boston. Together, they identified an opportunity to transform ordinary college events into large-scale productions.
Their business offered colleges high-quality events at a fraction of the cost of booking major musical acts.
"I'm not a good DJ. In fact, I'm a terrible DJ, but I'm a pretty good business guy," Jordan joked.
By their senior year, the pair had won Tufts' business plan competition. The company continued growing after graduation, eventually becoming what Jordan described as one of New England's largest collegiate event production companies.
Despite this early success, Jordan did not immediately pursue entrepreneurship full-time. He accepted a consulting position in the pharmaceutical and biotechnology industry which combined his interest in healthcare with the business skills he had developed at Tufts.
After spending a couple of years in consulting, however, Jordan began to reconsider what he wanted from his career.
"I want to do something tangible," he remembered thinking.
He left consulting, returned to his home state of California, and spent a summer exploring his options. A conversation with a family friend introduced him to the possibility of working in winemaking. In 2006, he took a three-month harvest internship and discovered an entirely new interest.
"I just fell in love with the industry, with the product, with the business," Jordan said.
Over the next few years, he gained winemaking experience in California, Australia, and Argentina. As he became more familiar with the industry, he noticed an opportunity to address the environmental costs and inefficiencies of traditional wine packaging.
Jordan began questioning why wine needed to be sold in heavy glass bottles, with corks and labels that would eventually be discarded. Inspired by the popularity of draft beer, he asked himself a simple question: "Why can't we have draft wine?"
That question became the foundation of Free Flow Wines, a company Jordan co-founded in 2009 to bring high-quality wine to restaurants and hotels through reusable kegs.
Over the following decade, Free Flow Wines grew from a garage operation into a company with 120 employees and production facilities in California and New Jersey. The business raised approximately $20 million in combined debt and equity financing and expanded its wine-on-tap model to roughly 10,000 hotels and restaurants nationwide, according to Jordan.
Beyond its commercial success, the company also helped reduce packaging waste in the wine industry, an environmental impact that had motivated Jordan from the beginning.
Free Flow Wines was sold in 2017, and Jordan stepped down as CEO in 2019. He has since continued building businesses in the hospitality industry. Today, through Trellis Management, he oversees a restaurant, a winery, and a travel and experiences business that brings visitors together around food and wine in Sonoma.
Looking back on his journey, Jordan believes one of the most valuable lessons from his entrepreneurship education was that entrepreneurial skills extend far beyond starting a company.
"Having an entrepreneurial mindset does not mean you have to become an entrepreneur," he explained.
He emphasized that creativity, critical thinking, and adaptability are equally valuable for those pursuing careers within established organizations, whether as employees, managers, or executives.
Jordan also encourages students to broaden their understanding of what entrepreneurship looks like. While successful entrepreneurs are often associated with high-growth technology startups, he believes entrepreneurship includes a much wider range of ventures.
"If you decided to move back to your hometown and open an ice cream shop on the corner, you're still an entrepreneur," he said.
For Jordan, who once envisioned an entirely different future in medicine, entrepreneurship has ultimately been less about following a predetermined career path and more about remaining open to creating something new.
"It's really a mindset and a framework more than a job," he said.
Jordan continues to stay connected with Tufts and the Derby Entrepreneurship Center; most recently, he hosted the Tufts Entrepreneurial Network (TEN), 'Bos of the Last Decade (BOLD), and the Derby Center in Sonoma, California at Kivelstadt Cellars. [pictured above]
Jordan is also a member of the Derby Entrepreneurship Center Board of Advisors.