What does it truly mean to be human in an age of artificial intelligence? David DeWolf, founder of KnownWell, offers a refreshingly nuanced perspective on how AI should enhance our humanity rather than diminish it.
Having built and sold a 2,500-person digital products company before founding KnownWell in 2023, DeWolf observed a critical gap in how businesses were approaching AI. While many focused solely on advancing the technology or boosting personal productivity, few were addressing how AI would transform business leadership, organizational structure, and human relationships.
DeWolf's solution tackles what he calls the "professional services paradox" – the phenomenon where the very human elements that drive growth (relationships and specialized knowledge) traditionally undermine scalability. By analyzing natural information flows between service providers and clients, KnownWell creates objective relationship health metrics for businesses that previously relied on subjective assessments. The results are remarkable: companies using the platform see a 50-60% reduction in at-risk clients within six months.
Beyond the technological innovation, DeWolf shares profound insights about purpose-driven leadership, challenging the conventional notion of work-life balance. "I am a single human being," he explains, advocating for integration rather than separation between professional and personal identities. For aspiring entrepreneurs, he emphasizes the importance of "humble confidence" – the seemingly contradictory combination of unwavering determination and genuine openness to learning that characterizes successful founders.
Whether you're a business leader navigating the AI revolution, an educator wondering how to prepare students for this new landscape, or an entrepreneur seeking to build something meaningful, DeWolf's conversation offers valuable wisdom about maintaining our essential humanity while embracing technological advancement.

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