The Bigger Why Transistor (https://transistor.fm) https://feeds.transistor.fm/the-bigger-why The Bigger Why is a long-form podcast exploring meaning, growth, mindset, purpose and the decisions that shape a life and drive behavior. Hosted by Sam Weber, the show features unhurried conversations with founders, CEOs, authors, creators, artists, actors, investors and thought leaders about focus, ambition, failure, regret, triumph, philosophy, personal growth and the stories behind success, sacrifices made, lessons gleaned and wisdom embodied along the way. TBW Podcast LLC 5958a31f-ea97-59d1-abfc-0caa94b0d704 yes en Mon, 01 Jun 2026 01:00:07 -0400 Mon, 01 Jun 2026 01:03:36 -0400 https://www.thebiggerwhywithsam.com/ https://img.transistorcdn.com/XeLKSMSTajGAdvG6yogZtLPRhugpAlIuONEQf_y1FKc/rs:fill:0:0:1/w:1400/h:1400/q:60/mb:500000/aHR0cHM6Ly9pbWct/dXBsb2FkLXByb2R1/Y3Rpb24udHJhbnNp/c3Rvci5mbS9mNjEz/NmQ1NDNjYmQ5YjMx/OGEzYTc3YzA3ZjVj/NmJmZi5wbmc.jpg The Bigger Why https://www.thebiggerwhywithsam.com/ episodic Samuel Weber The Bigger Why is a long-form podcast exploring meaning, growth, mindset, purpose and the decisions that shape a life and drive behavior. Hosted by Sam Weber, the show features unhurried conversations with founders, CEOs, authors, creators, artists, actors, investors and thought leaders about focus, ambition, failure, regret, triumph, philosophy, personal growth and the stories behind success, sacrifices made, lessons gleaned and wisdom embodied along the way. The Bigger Why is a long-form podcast exploring meaning, growth, mindset, purpose and the decisions that shape a life and drive behavior. Mindset, purpose, leadership, ambition, meaning, business, goals, creativity, leadership, self improvement, spirituality, philosophy, motivation TBW Podcast LLC sam@thebiggerwhywithsam.com No No John Zeratsky on Creativity, Focus, and Building Great Companies 3 3 John Zeratsky on Creativity, Focus, and Building Great Companies full d512acbe-7411-46a0-bab5-825118f96c9b https://share.transistor.fm/s/f645faaf 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

]]> 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

]]> Mon, 01 Jun 2026 01:00:00 -0400 Samuel Weber Samuel Weber 4505 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

]]> Mindset, purpose, leadership, ambition, meaning, business, goals, creativity, leadership, self improvement, spirituality, philosophy, motivation No Jim McKelvey: Billionaire Co-Founder of Block Inc (Square) on The Innovation Stack 2 2 Jim McKelvey: Billionaire Co-Founder of Block Inc (Square) on The Innovation Stack full 01795cbb-a6cc-462c-906f-0f14016ffc2b https://www.thebiggerwhywithsam.com/catalog 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
X - https://x.com/iamsamwebber
TikTok - https://www.tiktok.com/@iamsamwebber
Instagram - 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 

]]> 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
X - https://x.com/iamsamwebber
TikTok - https://www.tiktok.com/@iamsamwebber
Instagram - 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 

]]> Fri, 27 Mar 2026 16:33:23 -0400 The Bigger Why The Bigger Why 2918 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
X - https://x.com/iamsamwebber
TikTok - https://www.tiktok.com/@iamsamwebber
Instagram - 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 

]]> Mindset, purpose, leadership, ambition, meaning, business, goals, creativity, leadership, self improvement, spirituality, philosophy, motivation No 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 1 1 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 full 402731af-4a32-482f-b478-6952b3f8a632 https://www.thebiggerwhywithsam.com/catalog 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
X - https://x.com/BiggerWhy
TikTok - https://www.tiktok.com/@samwebberartist
Instagram - 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 

]]> 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
X - https://x.com/BiggerWhy
TikTok - https://www.tiktok.com/@samwebberartist
Instagram - 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 

]]> Sun, 01 Mar 2026 19:42:20 -0500 The Bigger Why The Bigger Why 3671 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
X - https://x.com/BiggerWhy
TikTok - https://www.tiktok.com/@samwebberartist
Instagram - 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 

]]> meaning and purpose, long-form conversations, life stories, personal growth, leadership, entrepreneurship, investing, alternative investing, CEO, private equity, decision making, goal setting, resilience, fulfillment, founders, thought leaders, startups, business, No