Why your CEO mentality is wrong (with investor Byron Deeter) | Masters of Scale

Byron Deeter has spent two decades at the epicenter of tech as an investor with Bessemer Venture Partners. He talks with Masters of Scale host Jeff Berman about his advice for both founders and investors in this moment of AI transformation, why CEOs need to think more like athletes, and more. Chapters: 00:00 Introducing Byron Deeter 01:30 The accidental cloud bet that nine out of ten VCs rejected 05:00 Surviving the dot-com crash by raising early 09:30 Selling to IBM and the hardest year of his career 15:00 How the best investors leverage time with trust and curiosity 20:00 The Century Fund and the discipline of a clean anti-portfolio 23:00 The Cloud Wave One miss and the Anthropic conviction 27:45 Why sleep-deprived CEOs are the same as driving drunk 30:15 Founder mental health and the relationships that compound 33:30 Capitalizing through the cycle and the one-person billion-dollar company 📫 THE MASTERS OF SCALE NEWSLETTER 35,000+ read our free weekly newsletter packed with insights from the world’s most iconic business leaders. Sign up: https://hubs.la/Q01RPQH-0 🎧 LISTEN TO THE PODCAST Apple Podcasts: https://mastersofscale.com/ApplePodcasts Spotify: https://mastersofscale.com/Spotify 💻 LEARN MORE Our website: https://mastersofscale.com 🚀 JOIN OUR COMMUNITY LinkedIn:   / 11096326   Facebook:   / mastersofscale   Instagram:   / mastersofscale   X/Twitter:   / mastersofscale   TikTok:   / mastersofscale   💡ABOUT US On Masters of Scale, iconic business leaders share lessons and strategies that have helped them grow the world's most fascinating companies. Founders, CEOs, and dynamic innovators (from companies like Uber, Airbnb, Apple, and Disney) join candid conversations about their triumphs and challenges with a set of luminary hosts, including founding host Reid Hoffman — LinkedIn co-founder and Greylock partner. From navigating early prototypes to expanding brands globally, Masters of Scale provides priceless insights to help anyone grow their dream enterprise. #mastersofscale #leadership #leadershiplessons #entrepreneurship #entrepreneur #tech #technology #ai #artificialintelligence #artificialintelligencetechnology #futureoftech #startup #startupfounders #startupinvesting #venturecapital #investors #investing #anthropic #founders #foundersstory