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The Startup CEO ShowCEO coach and advisor Mark MacLeod brings you practical insights from venture backed CEOs each week. Author: Mark MacLeod
The Startup CEO Show hosted by coach and advisor Mark MacLeod, brings you veteran CEOs each week who have collectively had had billion dollar valuations, 9 figure exits, and millions in revenue each week. Subscribe to join the leading podcast produced exclusively for the CEOs of high-growth startups and the VCs who back them. This podcast offers concise, yet deep dives into specific themes within each episode, focusing on providing actionable insights for busy leaders. The format includes interviews with CEOs of VC and PE-backed tech companies, their investors, and other key industry figures, ensuring a rich and relevant listening experience for those looking to learn in short, impactful sessions. About Mark MacLeod Since 1999, I have sat at the right-hand side of the leaders of high growth technology companies as either a CFO, VC or deal maker. I served as CFO for software companies including Shopify (NYSE: SHOP) and Freshbooks. As a CFO I experienced outright failures, wildly profitable exits, and everything in between. I was a General Partner in Real Ventures, Canada's largest and most active seed stage fund. My investments there include the fund's largest cash on cash and highest IRR returns to date. Most recently, I founded SurePath Capital Partners the leading investment bank for SMB SaaS companies where we did hundreds of millions in financing and exit transactions. Language: en Genres: Business, Careers, Management Contact email: Get it Feed URL: Get it iTunes ID: Get it Trailer: |
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Jerry Colonna on the Founder’s Honest Journey
Episode 86
Monday, 16 February, 2026
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
