Jim McKelvey: Billionaire Co-Founder of Block Inc (Square) on The Innovation Stack

John Zeratsky on Creativity, Focus, and Building Great Companies

What is truly worth our attention? In this episode of The Bigger Why, I sit down with John Zeratsky—venture capitalist, entrepreneur, designer, and co-author of the bestselling books Sprint, Make Time, and Click. John is the co-founder of Character Capital, an early-stage venture firm that backs ambitious founders building at the frontier of software and AI. Before that, he helped create the Google Ventures Sprint process, which has been used by hundreds of startups to solve critical business and product challenges. Our conversation goes far beyond productivity. We explore creativity, focus, venture capital, artificial intelligence, decision-making, founder psychology, and why boredom may be one of the most underrated ingredients for great thinking. We also discuss how to identify what truly matters, how founders make better decisions under uncertainty, what AI will and won't change, and why human experiences may become even more valuable in the years ahead. Whether you're building a company, pursuing a creative project, or simply trying to spend your time more intentionally, this conversation offers practical wisdom for navigating an increasingly distracted world. Topics include: • Creativity and innovation • Making time for what matters • Building great companies • Venture capital and startup investing • AI and the future of work • Decision-making under uncertainty • Focus and attention • The value of boredom • Character Capital and founder evaluation • Living intentionally Connect with John: https://www.character.vc Subscribe to The Bigger Why for conversations with leaders, creators, investors, and thinkers exploring ambition, meaning, purpose, and the ideas that shape our lives. 00:00 Introduction 03:10 John's journey from Google to venture capital 08:15 What Character Capital looks for in founders 14:45 How great investors make decisions under uncertainty 22:30 The venture capital scorecard and cognitive biases 31:40 AI, software, and the future of work 44:50 What AI is unlikely to replace 52:15 Why human experiences become more valuable in an AI world 58:40 What young people should learn in an age of AI 1:07:20 Creativity, intelligence, and original thinking 1:15:45 How large companies lose their edge 1:24:10 The origins of Make Time 1:33:30 Productivity, focus, and attention management 1:42:20 The power of boredom and long periods of thinking 1:49:15 Walking, creativity, and generating ideas 1:54:50 The Foundation Sprint and validating big ideas 2:03:40 Building companies and building a meaningful life 2:10:30 John's advice for navigating uncertainty 2:14:00 Closing reflections

Jim McKelvey: Billionaire Co-Founder of Block Inc (Square) on The Innovation Stack

Jim McKelvey co-founded Square with Jack Dorsey and built a billion dollar company. Then Amazon came after them. They survived. In this episode Jim breaks down the Innovation Stack — the strategy that made Square uncopyable even by the world’s most powerful company. This conversation will change how you think about building something that lasts. About the Show The Bigger Why is a long-form interview podcast hosted by Sam Weber, exploring meaning, purpose, strategy, and the stories behind enduring success—across investing, business, creativity, and life. Connect with The Bigger Why on Socials YouTube - https://www.youtube.com/@TheBiggerWhy [https://www.youtube.com/@TheBiggerWhy] X - https://x.com/iamsamwebber [https://x.com/iamsamwebber] TikTok - https://www.tiktok.com/@iamsamwebber [https://www.tiktok.com/@iamsamwebber] Instagram - https://www.instagram.com/iamsamwebber/ [https://www.instagram.com/iamsamwebber/] LinkedIn - https://www.linkedin.com/in/samuel-weber-esq-6b11a248/?utm_source=share_via&utm_content=profile&utm_medium=member_ios [https://www.linkedin.com/in/samuel-weber-esq-6b11a248/?utm_source=share_via&utm_content=profile&utm_medium=member_ios]

Christopher Alan Zook: Founder of CAZ Investments and Co-Author of The Holy Grail of Investing with Tony Robbins on the Future of Alternative Investments

Christopher Zook — Author of The Holy Grail of Investing (with Tony Robbins) — joins The Bigger Why to explore the future of alternative investing, enduring advantage, and long-term value creation. Zook is one of the world’s leading thinkers on strategy and growth, best known for his work on enduring companies and his collaboration with Tony Robbins on The Holy Grail of Investing. In this conversation, we go deep on how alternative investing is evolving, what separates enduring businesses from the rest, and how investors and founders should think about the next decade of capital. Topics we cover: -The future of alternative investing -What creates enduring advantage over decades -Lessons from The Holy Grail of Investing -Strategy, focus, and long-term decision-making -Why most growth strategies fail—and what actually works -Lesson from Tony Robbins -Lessons from his Childhood -Asset classes such as GP Stakes, private credit, private equity, venture capital, defense investing, sports investing and other niche asset classes 🎧 Listen to the full audio episode: https://thebiggerwhywithsam.com 📩 Subscribe for long-form conversations on meaning, strategy, and the human side of success: https://thebiggerwhywithsam.com About the Show The Bigger Why is a long-form interview podcast hosted by Sam Weber, exploring meaning, purpose, strategy, and the stories behind enduring success—across investing, business, creativity, and life. Connect with The Bigger Why on Socials YouTube - https://www.youtube.com/@TheBiggerWhy [https://www.youtube.com/@TheBiggerWhy] X - https://x.com/BiggerWhy [https://x.com/BiggerWhy] TikTok - https://www.tiktok.com/@samwebberartist [https://www.tiktok.com/@samwebberartist] Instagram - https://www.instagram.com/thebiggerwhy/ [https://www.instagram.com/thebiggerwhy/] LinkedIn - https://www.linkedin.com/in/samuel-weber-esq-6b11a248/?utm_source=share_via&utm_content=profile&utm_medium=member_ios [https://www.linkedin.com/in/samuel-weber-esq-6b11a248/?utm_source=share_via&utm_content=profile&utm_medium=member_ios]