#183 - Ian Boswell, Professional Cyclist


In this episode I sit down with Ian Boswell—former WorldTour pro, now gravel racer, Wahoo leader, husband, father, and Vermont farmhouse fixer. We trace his journey from racing the Tour de France with Team Sky to building a life surrounded by family, gardens, and 250-year-old plaster walls.Ian and I dive into what it means to shift identity when sport no longer defines you, how leadership looks different inside the peloton versus at home, and why self-reliance (yes, even fixing hydraulic hoses) matters. We talk about community, faith, mortality, and the legacy of his friend Sule Kangangi, whose vision for East African cycling lives on through Team Amani.What stood out most for me was Ian’s answer to my last question: the message he wants to leave his daughters when they turn ten. His words—about showing up fully and going all in—are a reminder I think all of us can take to heart.Ian’s IG: https://www.instagram.com/ian_boswell/ SQ Socks: ⁠https://stupidquestions.show/pages/sq-merch⁠ SQ Newsletter: ⁠https://stupidquestions.show/pages/newsletter-signup⁠