Episode 29: Connecting with Chris George

Meet Chris George, Co-Founder and CEO of SubSummit, the largest meetup for subscription, membership, and loyalty brands. A serial entrepreneur, Chris has launched seven companies and successfully exited three, including the popular subscription brand Gentleman's Box. Chris founded SubSummit to bring together founders, operators, and innovators building recurring-revenue businesses across eCommerce, SaaS, and retail. Under his leadership, SubSummit has grown into the largest event dedicated to the subscription industry, bringing together hundreds of brands, technology partners, and thought leaders each year. Chris is passionate about helping entrepreneurs grow profitable businesses and regularly mentors emerging brands, invests in startups, and shares practical insights on acquisition, retention, and scaling subscription models. Explore Chris's journey from identifying a gap in the men's subscription market to launching Gentleman's Box in 2014, founding SubSummit in 2016 with zero event experience, and ultimately building and exiting both. His passion for connecting people and creating value drives everything he builds — including his next venture, an academy designed to equip the next generation of college graduates with the communication skills and career readiness they need to succeed. IN THIS EPISODE, WE TALK ABOUT: The power of purpose over profit, "When I stopped focusing on revenue and focused on bringing people together, that's when we made a million dollars in year three." The discipline required to build something great, "Being an entrepreneur is a very lonely journey. You have to be 100% okay with missing things." Why legacy matters more than wealth, "The real legacy isn't what you had or what you bought. The real legacy is how many different people have you helped."