

From Tailspin to Tailwind: Curiosity, Trust, and Teamwork with Buddy Teaster
Sep 9, 2025
Buddy Teaster, CEO of Soles4Souls and author of From Tailspin to Tailwind, shares insights on purpose-driven leadership and the power of curiosity in building resilient teams. He discusses transformative leadership and how diverse experiences shape one's approach. The conversation explores Stoicism's role in adapting to change and emphasizes fostering curiosity and connections within teams, especially in a post-pandemic world. Teaster also highlights innovative partnerships that empower marginalized entrepreneurs to drive economic impact and create lasting community change.
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Career Turns Led To Purpose
- Buddy Teaster describes his winding career from theater to YPO to CEO of Soles4Souls and how it led him to nonprofit turnaround work.
- He says leading Soles4Souls has been the best thing he's ever done and recounts rescuing the organization from a tailspin.
Stoic Guardrails For Turbulent Times
- When external chaos escalates, focus on controllable levers to prevent spirals of anxiety.
- Stoic guardrails (control what you can, remember you're a small part of others' stories) help leaders respond calmly.
Protect A 10-Minute Human Ritual
- Do run a weekly all-hands with small breakout groups and two prompts: one work-related and one random personal question.
- This ten-minute ritual preserves human connection for distributed teams and staff refuse to give it up.