Uploaded October 2025 | Updated September 2026, 1 week ago
Shopify founder and CEO Tobi Lütke joins John Collison to discuss the philosophies driving one of the internet’s most foundational companies. Tobi shares his perspective on why companies are a form of technology, how internal tools and "opinionated software" shape an organization's culture and accelerate its evolution, and why the best gift is finding a beautiful, unsolvable problem.
Show notes:
• [Buy] Momax: 140W Universal Travel Adapter | amazon.com/MOMAX-Universal-Technology-Worldwide-Charging-Black/dp/B0CRYPKR4H?th=1
• [Read] Benjamin Bloom: The 2 Sigma Problem | https://web.mit.edu/5.95/www/readings/bloom-two-sigma.pdf
• [Buy] Ikigai: vitamin cases | ikigaicases.com
• [Read] Kevin Kelly: 1,000 True Fans | kk.org/thetechnium/1000-true-fans
• [Read] Erich Gamma: Design Patterns | amazon.co.uk/Design-patterns-elements-reusable-object-oriented/dp/0201633612
• [Read] Charles Calomiris: Fragile by Design | amazon.co.uk/Fragile-Design-Political-Princeton-Economic/dp/0691155240
• [Listen] Business Breakdowns: Formula One | podcasts.apple.com/gb/podcast/formula-one-the-iconic-motor-sport/id1559120677?i=1000526586800
• [Watch] Netflix: Formula 1: Drive to Survive | netflix.com/title/80204890
• [Read] Mark Robichaux: Cable Cowboy | amazon.co.uk/Cable-Cowboy-Malone-Modern-Business/dp/047170637X
Full transcript on Substack: cheekypint.substack.com/p/tobi-lutke-is-still-captivated-by
Subscribe to Cheeky Pint
Spotify: open.spotify.com/show/2IHbGJJMpiFoz5YrvRfTFw
Apple Podcasts: podcasts.apple.com/us/podcast/cheeky-pint/id1821055332
Substack: cheekypint.substack.com
Key moments
00:00 Intro
07:07 How internal software shapes culture
16:32 The Shopify vision
27:49 Peak transaction capacity
34:36 Agentic commerce
49:15 Shop Pay
55:29 Stablecoins
59:20 Stripe + Shopify
1:12:23 Learning from the Coinbase board
1:17:23 Is Tobi ungovernable?
1:25:02 Entrepreneurship
1:31:50 Advice for Mark Carney
1:36:40 Motor racing
Shopify founder and CEO Tobi Lütke joins John Collison to discuss the philosophies driving one of the internet’s most foundational companies. Tobi shares his perspective on why companies are a form of technology, how internal tools and "opinionated software" shape an organization's culture and accelerate its evolution, and why the best gift is finding a beautiful, unsolvable problem.
Show notes:
• [Buy] Momax: 140W Universal Travel Adapter | amazon.com/MOMAX-Universal-Technology-Worldwide-Charging-Black/dp/B0CRYPKR4H?th=1
• [Read] Benjamin Bloom: The 2 Sigma Problem | https://web.mit.edu/5.95/www/readings/bloom-two-sigma.pdf
• [Buy] Ikigai: vitamin cases | ikigaicases.com
• [Read] Kevin Kelly: 1,000 True Fans | kk.org/thetechnium/1000-true-fans
• [Read] Erich Gamma: Design Patterns | amazon.co.uk/Design-patterns-elements-reusable-object-oriented/dp/0201633612
• [Read] Charles Calomiris: Fragile by Design | amazon.co.uk/Fragile-Design-Political-Princeton-Economic/dp/0691155240
• [Listen] Business Breakdowns: Formula One | podcasts.apple.com/gb/podcast/formula-one-the-iconic-motor-sport/id1559120677?i=1000526586800
• [Watch] Netflix: Formula 1: Drive to Survive | netflix.com/title/80204890
• [Read] Mark Robichaux: Cable Cowboy | amazon.co.uk/Cable-Cowboy-Malone-Modern-Business/dp/047170637X
Full transcript on Substack: cheekypint.substack.com/p/tobi-lutke-is-still-captivated-by
Subscribe to Cheeky Pint
Spotify: open.spotify.com/show/2IHbGJJMpiFoz5YrvRfTFw
Apple Podcasts: podcasts.apple.com/us/podcast/cheeky-pint/id1821055332
Substack: cheekypint.substack.com
Key moments
00:00 Intro
07:07 How internal software shapes culture
16:32 The Shopify vision
27:49 Peak transaction capacity
34:36 Agentic commerce
49:15 Shop Pay
55:29 Stablecoins
59:20 Stripe + Shopify
1:12:23 Learning from the Coinbase board
1:17:23 Is Tobi ungovernable?
1:25:02 Entrepreneurship
1:31:50 Advice for Mark Carney
1:36:40 Motor racing
