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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