The Knowledge Project

Shopify founder and CEO Tobi Lütke joins Shane Parrish to discuss AI agents, better decision-making, and the future of work. He explains how he uses an AI council to examine his hardest decisions and why taste, judgment, and responsibility become more valuable as AI becomes more capable.

They go inside Shopify’s work with River, an AI colleague with memory, personality, and permission to challenge the CEO. They explore how to choose between several good options, why the best long-term decisions often lack immediate feedback, and why building something that lasts requires pruning and rebuilding.

Tobi also shares how he cultivates intuition, the affirmations he uses to change his own behavior, and why his kids must add “yet” when they say they can’t do something.

Enjoy!

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Chapters:

(00:00) Introduction

(3:46) The Case for Skeuomorphism

(5:16) How Bing's Chatbot "Sydney" Inspired Shopify's AI

(7:18) River: Shopify's Internal AI

(8:55) How to Encourage Osmosis Learning

(10:52) AI Dreaming and Self-Reflection

(11:53) How to Use AI for Strategic Decision Making

(14:11) The One Thing AI Cannot Do

(16:04) What AI is Making Worse at Shopify

(19:46) Predictions: Where AI is Headed Next

(21:55) The Future of AI-Powered Software

(24:40) Will CEOs Be Replaced with AI?

(27:54) Can Superintelligence Be Controlled?

(31:13) Critical Skills in AI Age

(34:22) Why Complex Solutions are Usually Wrong

(36:33) Conditions Needed for True Intuition

(38:02) The Optimal Path Doesn't Have Instant Feedback

(44:51) How Affirmations Can Shift Your Behavior

(50:44) The Inobvious Thing Hurting Companies

(52:37) Relationship Between Beauty and Creation

(56:23) How SpaceX Moves Forward By Subtraction

(1:00:24) Why Companies Need Refounding Events

(1:01:50) Use Books as Cheat Codes

(1:02:39) Three Books That Change Your Thinking

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Follow Tobi:

X: https://x.com/tobi

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*Note:* ‍Shane and guests may hold positions in assets discussed in this episode. This podcast is not investment advice, and is intended for informational and entertainment purposes only. Nothing in this conversation should be considered investment advice, financial guidance, or a recommendation to buy or sell any security. Always do your own due diligence or consult with a qualified financial advisor before making investment decisions.
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We all know the Steve Jobs who came back in the late 1990s and saved Apple from becoming a footnote. And we've all heard the story of how, in 1985, he was pushed out of the company he'd created.

What we don't know is what happened in between.

Geoffrey Cain spent years reconstructing the decade Jobs spent outside Apple. NeXT spent years losing money. His co-founders left. His investors lost faith. His fortune nearly disappeared. At one point, he was a weekend away from shutting the company down.

Somewhere in those failures, Jobs learned how to become the leader Apple would eventually need.

This is Steve Jobs before he became Steve Jobs.

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Chapters:

(0:51) Why Steve Jobs Was Pushed Out of Apple

(3:04) Steve Jobs' Failed Coup Attempt to Oust CEO

(4:33) The Failure of Macintosh II

(8:27) Starting NeXT Computers

(9:34) The Story Behind NeXT's Iconic Logo

(11:38) A Perfect Cube: The Impossible Design of NeXTcube

(13:50) What Movies Get Wrong About Steve Jobs

(14:02) The Ultimate Trait Steve Jobs Looked For in Hiring

(14:59) Decision Making By Intellectual Combat

(16:40) Steve Jobs' Reality Distortion Field

(17:25) The Flaw that Almost Destroyed Steve Jobs

(21:25) How NeXT Software Changed Computing Forever

(24:44) Steve Jobs' Self-Sabotages at NeXT

(25:02) Ross Perot and Steve Jobs

(28:48) How Pixar Saved Steve Jobs from Bankruptcy

(29:19) The Realization Steve Jobs Had at Rock Bottom

(31:49) The Last Ditch Effort to Save NeXT Computers

(38:55) Steve Jobs Gets His Revenge

(43:09) Larry Ellison's Friendship with Steve Jobs

(45:05) How Steve Jobs Brought Out the Best in His Employees

(48:08) The Lessons Steve Jobs Learned From Failure

(50:08) Bill Gates and Steve Jobs Rivalry

(51:44) The Funniest Steve Jobs/Bill Gates Moment

(53:43) Steve Jobs Takes Over As Apple CEO

(57:08) How Meeting Laurene Changed Everything

(59:01) Rapid Fire Questions

(59:21) How Steve Jobs Inspired His Team

(1:00:31) Steve Jobs Medical Treatment

(1:01:42) What We Can Learn from Steve Jobs

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Follow Geoffrey Cain:

X: https://x.com/geoffrey_cain

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David Baszucki is the co-founder and CEO of Roblox, a platform built around a simple idea: give people the tools and incentives to create together.

In this short conversation we discuss how a health decision saved his son's life and how it changed how he eats, why bureaucracy compounds unless you actively destroy it, monitoring your mind before making decisions, and why the best products often improve by removing complexity.

It's time to listen and learn.

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Chapters:

(0:00) How Keto Can Help Treat Bipolar Symptoms

(2:38) Connection Between Physical and Mental Health

(3:58) Current Metabolic Routine

(4:40) How Your Metabolic State Affects Decision Making

(5:48) The Signs of a Great Product

(6:32) Bureaucracy is the Enemy of Progress (ALT: Why You Need to Destroy Bureaucracy)

(7:20) Giving Feedback that Actually Motivates

(7:50) The Key to Feedback is Tone

(8:44) The Email You Should Never Send

(9:53) Patterns in Bad Decision Making

(10:38) Principles of Good Decision Making

(11:19) Mental Models for Problem Solving

(11:56) The Gaming World Said the Avatar Was a Disaster. He Didn't Listen. (ALT: Why the Gaming World Hated the First Avatar)

(12:58) When Instinct and Data Disagree

(14:12) Roblox's Magic Decision Making Quadrant

(14:38) Inner Monologue of the Best CEOs

(15:36) Manufacturing Threats to Achieve Alpha

(16:08) Mistakes in Roblox History

(18:30) Biggest Generated Universe in World

(19:33) Roblox Community's Pushback on New Avatars

(20:20) Capital Allocation Strategy

(22:28) Building Incentives on Early Roblox

(24:31) Early Disagreements on API

(26:18) How Erik Cassel Supercharged Roblox

(27:05) The Economic Model that Almost Ruined Roblox

(31:43) How Robux Works

(32:22) Robux as Future Digital Currency

(33:34) What True Focus Looks Like

(35:14) How Roblox Uses AI

(36:11) Age Ban and Verification Policy

(38:29) Is Age Verification Slowing Growth at Roblox?

(38:56) Positioning and Optionality for Long Term Growth

(39:43) The Future of Immersive Gaming

(42:51) Reaction to Ready Player One

(43:48) Advice For To a 16-Year-Old Wanting to Start a Company

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Follow David:

X: https://x.com/DavidBaszucki

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Thank you to the sponsors for this episode:

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NOTE: This episode discusses health and medical topics for informational purposes only. Shane and his guest are not medical professionals, and nothing in this conversation should be considered medical advice. Please do your own research and consult a qualified healthcare professional before making decisions about your health.

NOTE: Shane and guests may hold positions in assets discussed in this episode. This podcast is not investment advice and is intended for informational and entertainment purposes only. Nothing in this conversation should be considered investment advice, financial guidance, or a recommendation to buy or sell any security. Always do your own due diligence or consult with a qualified financial advisor before making investment decisions.
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This summer, I’m revisiting one of my favorite episodes. If you haven’t heard it, now is the time. If you have, it’s a classic and worth listening to again.

Brad Jacobs has built eight billion-dollar companies, completed more than 500 acquisitions, and created extraordinary returns for shareholders over four decades. Few people understand how great businesses are built better than he does.

This conversation is about the principles behind that success. Brad explains how he spots trends before they become obvious, why psychology matters as much as strategy, and how he thinks about acquisitions, hiring, capital allocation, decision-making, and building organizations that consistently outperform.

He also shares lessons from therapy, meditation, and decades of leadership that changed how he manages people and makes decisions.

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Chapters:

00:00 - Finding Every Opportunity to Make Money

02:03 - The Singularity & The Future of AI

04:14 - How to Think Rationally

05:40 - The Meta-Trend Driving the Future

07:50 - His Research Process

10:21 - How to Ask Better Questions

16:26 - Rearranging Your Brain for Success
20:55 - What Music & Math Teach Us About Business

30:59 - The Asymmetry of Leverage, Debt & Optionality

35:07 - The Psychology of Contrarian Bets

40:41 - Where True Confidence Comes From

50:19 - The Hidden Cost of Negative Feedback

56:12 - Core Lessons on Money & Wealth

58:11 - The M&A Playbook: How to Build an Empire

01:07:50 - The Exact Questions to Read Anyone Instantly

01:11:10 - The Reality of Board Meetings

01:16:55 - Frameworks for High-Stakes Decision-Making

01:23:35 - The Brutal Truth About Capital Markets

01:25:40 - Avoid Hiring This Type of Person

01:31:16 - Traits of the World’s Best Capital Allocators

01:33:53 - The Biggest Lesson of the Past Year

01:37:20 - Redefining Personal Success

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*Note:* ‍Shane and guests may hold positions in assets discussed in this episode. This podcast is not investment advice and is intended for informational and entertainment purposes only. Nothing in this conversation should be considered investment advice, financial guidance, or a recommendation to buy or sell any security. Always do your own due diligence or consult with a qualified financial advisor before making investment decisions. -----

Follow Brad Jacobs:

LinkedIn: https://www.linkedin.com/in/bradjacobsqxo/

QXO: https://www.qxo.com/

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Newsletter: The Brain Food newsletter delivers actionable insights and thoughtful ideas every Sunday. It takes 5 minutes to read, and it’s completely free. Learn more and sign up at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠fs.blog/newsletter⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

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Insta: ⁠https://www.instagram.com/farnamstreet/⁠

LinkedIn: ⁠https://www.linkedin.com/in/shane-parrish-050a2183/⁠

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Thank you to the sponsors for this episode:

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+Matic: the robot vacuum that does it all—grab yourself a year of free bags here. http://maticrobots.com/shaneparrish

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John D. Rockefeller became the richest man the world had ever known by thinking differently about business, competition, and family.

This episode isn’t just the story of Standard Oil. It’s about the principles that built one of history’s greatest business empires and what they can teach us today.

Along the way, you’ll see the rise of Standard Oil, the public backlash that made Rockefeller America’s most hated businessman, the breakup of his company, and the philanthropic legacy that continues to shape the world today.

Enjoy!

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Chapters:

(00:00) The Making of John D. Rockefeller

(04:56) The Search for Belonging

(07:33) Business Lessons From his Mother

(10:54) The Unlikely Lessons he Learned from His Father

(15:09) When Rockefeller Decided to Get Rich

(17:50) The Relentless Job Search

(21:21) Learning How to Run a Business

(29:49) The Power of a Good Reputation

(34:57) The American Oil Boom

(36:34) Rockefeller's Biggest Early Bet

(43:28) Rockefeller and Henry Flagler

(46:21) The One-Drop Difference

(49:22) Building Standard Oil’s Partnership

(53:06) How Rockefeller Used Leverage

(56:43) From Competition to Cooperation

(01:00:43) Why America Turned on Rockefeller

(01:08:54) The Cleveland Massacre

(01:17:41) Rockefeller’s Private Family Life

(01:25:45) Rockefeller and the Panic of 1873

(01:29:39) A Private Life, A Public Empire

(01:32:50) Standard Oil’s Pipeline War

(01:38:40) Creating the Standard Oil Trust

(01:42:37) The Fortress on Broadway

(01:48:07) The Backlash Against Standard Oil

(01:54:33) Ida Tarbell Takes On Rockefeller

(02:02:00) Rockefeller’s Failed Media Strategy

(02:14:31) How Standard Oil Stayed One Step Ahead

(02:16:06) Breaking Up Standard Oil Made Him Richer

(02:19:40) Why Rockefeller Gave It All Away

(02:26:28) The Weight of the Rockefeller Name

(02:28:52) Rockefeller's Hardest Goodbye

(02:34:22) Why Rockefeller Gave Away Dimes

(02:38:46) The Richest Man Couldn't Buy Time

(02:41:41) John D. Rockefeller’s Legacy

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Newsletter: The Brain Food newsletter delivers actionable insights and thoughtful ideas every Sunday. It takes 5 minutes to read, and it’s completely free. Learn more and sign up at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠fs.blog/newsletter⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

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LinkedIn: ⁠https://www.linkedin.com/in/shane-parrish-050a2183/⁠

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Thank you to the sponsors for this episode:

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