#0152 – David Douglas Stone, CashStar Co-Founder & Serial Entrepreneur Behind Maine's Largest Startup Exit
In this episode of the Established Podcast, serial entrepreneur and technology innovator David Douglas Stone joins Frank Gruber, host of the podcast and Co-CEO at Established and Managing Partner at Established Ventures, for a wide-ranging conversation about entrepreneurship, recognizing transformational technology shifts, building companies in Maine, and navigating the rapidly accelerating age of artificial intelligence. David has spent more than two decades creating and building companies around emerging technologies and changing consumer behaviors. He co-founded CashStar, the Portland, Maine-based digital gifting and payments company that helped move gift cards from physical plastic into the digital era and ultimately grew to process billions of dollars in transactions. CashStar was acquired by Blackhawk Network in 2017. David later founded Forager, a technology platform designed to simplify local food procurement and connect farmers and food producers with grocers and other wholesale buyers. David shares lessons from his entrepreneurial journey, including what he learned about identifying opportunities before markets fully develop, assembling teams, raising capital, scaling technology companies, and knowing when an idea has the potential to become something much bigger. The conversation also turns to the technological shift defining this moment: artificial intelligence. David and Frank explore how AI compares with previous waves of technological disruption, where entrepreneurs may be underestimating its impact, how AI could reshape employment and customer service, and the opportunities and risks emerging as businesses increasingly replace or augment human work with intelligent systems. They also discuss what AI means for founders and investors, how to distinguish lasting innovation from hype, and whether places like Maine can capitalize on this technological transition to build the next generation of high-growth companies. Throughout the conversation, David reflects on the lessons of a career spent repeatedly betting on change and offers his perspective on entrepreneurship, innovation, resilience, and what the next generation of founders should be paying attention to now. Learn more about David Douglas Stone and his latest thinking on his website at DavidDouglasStone.com: https://daviddouglasstone.com Get Involved! Founders, investors, startup teams, entrepreneur support organizations (ESOs), and innovators, we invite you to join the Established Network, our digital hub where creativity, capital, and collaboration collide. https://established.network Watch the episode on the Established YouTube Channel at: https://soty.link/ESTYouTube Thank you for listening, and as always, please check out the Established website and subscribe to the newsletter at: www.est.us Subscribe to the Established podcast: https://theestablishedpodcast.com/ Startup of the Year helps diverse, emerging startups, founding teams, and entrepreneurs push their companies to the next level. We are a competition, a global community, and a resource. Startup of the Year is also a year-long program that searches the country for a geographically diverse set of startups from all backgrounds and pulls them together to compete for the title of Startup of the Year. Check out Startup of the Year at: www.startupofyear.com Established is a consultancy focused on helping organizations with innovation, startup, and communication strategies. It is the power behind Startup of the Year. Created by the talent responsible for building the Tech.Co brand, which was acquired by an international publishing company, we are leveraging decades of experience to help our collaborators further or create their brands and accomplish their most important goals. Check out Established at: www.established.us Connect with us on X, formerly Twitter: @EstablishedUs Connect with us on Facebook: facebook.com/established.us
