Episode 32 · Oct 4, 2026 · A Healthy Conversation

Entrepreneurship, AI, and Maine's economy

with David Douglas Stone

About this episode

David Douglas Stone built CashStar in Portland against long odds, turning the plastic gift card into a digital payments platform used by major national retailers and sold to Blackhawk Network in 2017. Co-hosts Dr. Lisa Belisle and Dr. Jeff Barkin talk with Stone about what drew him to build in Maine, where he saw a workforce of dedicated, down-to-earth people as a genuine competitive advantage over better-capitalized markets. Stone describes how the company evolved from an early vision of internet-based money transfers into a gift card platform that could handle personalized, on-demand transactions at scale, eventually setting a record sales volume in a single promotion with a national daily-deal partner. The conversation covers what Maine's startup ecosystem still needs: meaningful exits, sectoral focus, and anchor companies in payments, life sciences and food that can attract out-of-state capital and talent.

Stone and the co-hosts turn to Maine's food economy, which Stone describes as a largely underrecognized industry spanning aquaculture, agriculture and specialty food production. He argues that the sector would benefit from the same discipline he prescribes for tech: focused investment, more conferences, and stronger connections between small producers and the distribution networks that could get their goods to market. Barkin raises food insecurity as a pressing concern, noting that cuts to federal nutrition assistance will push more Maine households into hardship, and Stone points to food waste in the supply chain, particularly surplus harvests that never reach consumers or those in need, as a place where innovation could make a real difference.

The final segment takes up artificial intelligence, where Stone has written and spoken publicly about the risks of deploying increasingly capable systems without adequate oversight. He draws a parallel to historical technological disruption, noting that earlier automation hit physical labor hardest while AI is positioned to displace white-collar and knowledge workers on a much broader scale. Stone, Belisle and Barkin discuss the gap between AI's genuine utility in fields like medicine and the absence of regulatory structures comparable to those governing drugs or financial markets. Stone calls for mandatory pre-release testing, meaningful accountability for developers and executives, and greater engagement from consumers and legislators, while acknowledging that the pace of development has outrun the political will to act.

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Mentioned in this episode

Also mentioned: CEI · Good Shepherd Food Bank · Maine Organic Farmers and Gardeners Association · Maine Tech Week · Maine Technology Institute · Roux Institute · WEX

Also on Bountiful Path: The Last Layer (Jun 28, 2026)

From this episode

“AI is so different because of this ability to keep improving, keep improving, keep improving while it's trying to solve a problem. And if it can't solve the problem, it'll go around it and try to solve it anyways. It has independence on its own and that is a scary thing.”

David Douglas Stone

“Maine has an incredible workforce of really down-to-earth, dedicated people. In fact, Starbucks was our client and they told us we were the best vendor they ever had in their entire history.”

David Douglas Stone

“We should have teams of challengers that test these things rigorously in a laboratory, like developing a new drug or a new virus or something that contain it and test the hell out of it in all kinds of scenarios before it's released. That would be the first thing. I would also penalize any CEO or CTO that lets this happen.”

David Douglas Stone

“I think if you take the human out of the tech rather than take the tech out of the human, I think that's where you really have to think about it.”

David Douglas Stone

“I always say if you want to be an entrepreneur or a good one, you have to be a little delusional, right?”

David Douglas Stone

“We need exits. We need more conferences. We need our expertise and frankly, we need the state and these various institutions to pull together.”

Listen on A Healthy Conversation · Sundays 11am and 9pm · WGAN AM 560 / FM 98.5