OhHello Ep. 127: Freestar CEO Kurt Donnell on Transparent Leadership and Building Human-First Teams

Freestar CEO Kurt Donnell joins Jeremy Bloom to discuss leadership, transparency, mentorship, and building resilient remote cultures in the age of AI. Kurt shares lessons from law firms, scaling teams, navigating uncertainty, and why curiosity is the ultimate leadership trait. From hiring decisions to AI adoption, this episode is packed with practical advice for modern leaders. Takeaways Transparency builds trust during uncertainty. Curiosity is the #1 trait Kurt hires for. Great leaders show up as real humans, flaws included. AI should remove the mundane so people can do meaningful work. Delaying tough people decisions hurts the entire team. Remote culture requires intentional connection points. Work-life balance is really work-life integration. Human-in-the-loop AI creates stronger adoption and better outcomes. Leaders should focus on clarity, not panic, during disruption. Mentorship creates impact for both mentor and mentee. Chapters 00:00 Intro to Kurt Donnell and Freestar 01:40 Why mentorship matters in leadership 02:30 Early career experiences that shaped Kurt’s leadership style 04:20 From law school to ad tech and Freestar 08:00 The hardest leadership lesson: making tough people decisions 11:00 Building trust during uncertainty and pressure 13:30 The mentor who shaped Kurt’s career most 15:00 Why work-life balance doesn’t exist 19:20 Building culture in a remote-first company 22:00 The qualities Kurt looks for in future leaders 24:40 Avoiding reactive leadership during AI disruption 28:15 Using AI without losing humanity 31:20 Final leadership advice: show up as a human being