Show notes
EPISODE SUMMARYI love conversations that get underneath success and ask: What's actually driving it?I was introduced to Keegan Walden through our mutual friend Cameron Bodenstadt, who predicted we'd hit it off. He was right. What followed was a fascinating conversation about the psychology behind ambition, achievement, and the patterns that can make us successful — until they become the very things holding us back.We go all the way back to childhood to unpack how our early fears, defenses, identity wounds, and need to be seen can quietly shape the way we lead, build, perform, and burn out. And we explore the question many high achievers eventually face: What happens when achievement stops being enough?WHAT WE TALKED ABOUTHow Keegan went from psychology to building a venture-backed companyThe childhood experiences that shaped his ambition and need to be seenBuilding Torch, raising nearly $100 million, and eventually selling the companyWhy the patterns that make us successful can eventually hold us backHow childhood defenses quietly shape leadership and decision-makingThe Enneagram, founder psychology, and the "dark triad" of personality traitsWhy AI may make great coaching and human development even more valuableWhat therapy can uncover when you feel stuck despite being successfulWhy more achievement doesn't necessarily resolve insecurityWho are you when achievement is no longer enough?TIMESTAMPS0:00 Intro and welcome 1:37 Keegan's upbringing as the only child of a single mom 3:01 Growing up attuned to his mom's emotions 4:22 Childhood safety, uncertainty, and growing up in a rough neighborhood 7:04 Survival skills, daydreaming, and trying on different identities 11:24 The desire to be seen and the Yale story 15:55 Keegan's unexpected path into psychology 18:17 Feeling stuck and finally choosing the psychology path 23:10 Building a private practice and wanting something bigger 25:47 The text that led to co-founding Torch 26:46 Scaling Torch and raising venture capital 27:52 Selling Torch and how AI changed the business 34:08 Why coaching matters more than ever 36:27 Studying and writing about founder psychology 40:16 The hero's journey of entrepreneurship 43:34 How childhood defenses show up in founders 45:26 Idealization, startup culture, and the Enneagram 47:22 Core founder fears and the "status founder" 50:39 The dark triad and its risks in leadership 55:01 What to do when you feel stuck or unmotivated 57:27 Where to find KeeganLINKS & RESOURCESFollow Keegan's work at: keeganwalden.substack.comConnect with Keegan on LinkedIn: linkedin.com/in/keegan-walden-ph-d-672ab9101Subscribe & Share: If you enjoyed this episode, please subscribe, rate, and review — and share it with someone who needs to hear this!
