"DDD has to continually think about its relevance."

Irving Levin's journey with Digital Divide Data began with a bike trip to Vietnam and a side visit to Siem Reap, shortly after the Vietnamese departed from Cambodia. He and his wife returned to Oregon struck by the country's brokenness but unbroken spirit. Through a chance connection—a friend whose son knew Jeremy Hockenstein at Harvard—Levin met the co-founder at Grand Central Station, made a small donation, and got pulled into the work. Over 20 years, he moved from advisor to board member to chairman, finally retiring from the board recently. He watched DDD evolve from a bootstrapped operation with no money, no management, and terrible internet connectivity into a competitive business. "We were a very young, raw, undermanaged operation," he says. The transformation came through better management, more sophisticated clients like Google and Microsoft, and expansion into Kenya, where a more educated workforce helped DDD compete for advanced work like self-driving car data annotation.

Levin saw plenty of failures along the way. The Liberty Source venture serving military spouses never found its footing; the Battambang office couldn't be sustained. His favorite successes were the data entry operators who became managers and senior leaders, people he watched build careers from the ground up. But he's concerned about DDD's future relevance. Cambodia's needs have changed dramatically since Hockenstein arrived 26 years ago, and technology increasingly demands fewer people, not more. "DDD has to continually think about its relevance," he says, pointing to fundamental tensions: How do you serve both the mission of training youth and the business reality of competing in sophisticated markets? Should DDD expand to places like India with deeper talent pools, and what would that mean for the original countries? These aren't existential questions yet, but they're the strategic ones the board must grapple with.