Jerry Colonna on the Founder’s Honest Journey

Join a community of ambitious CEOs who are looking to build market-leading companies without sacrificing health and happiness. Check out: https://limitless.ceo What if the fastest way to scale your startup is to stop pretending you’re “crushing it”? In this episode of The Startup CEO Show, I sit down with Jerry Colonna, legendary CEO coach, former VC, and author of Reboot, for a raw conversation about the founder’s inner journey: the anxiety, the bravado, the “should,” and the quiet suffering that often hides behind high growth. Jerry challenges the startup ecosystem’s obsession with spinning a story and reframes “vulnerability” as something simpler and harder: honesty. We unpack why founders feel pressured to perform, how hustle culture disconnects leaders from clarity and compassion, and why building a company is often a personal development journey disguised as a business. We also explore meditation, purpose, equanimity, and why poetry can cut through the monkey mind when nothing else will. If you’re a founder, CEO, or investor who wants to build something big without burning out, this is one of those conversations that sticks with you. Connect with me: My website: https://limitless.ceo/ Linkedin:https://www.linkedin.com/in/themarkmacleod/ Instagram: https://www.instagram.com/markmacleodcoach/ Subscribe for more founder-level conversations. Jerry Colonna - Reboot.io | LinkedIn https://www.linkedin.com/in/jerry-colonna-reboot/ Subscribe to Mark MacLeod for The Startup CEO Show Podcast, actionable insights, coaching, and strategy for CEOS. https://www.youtube.com/@MarkMacLeod-CEOCoach?sub_confirmation=1