Podcast Summary: Cheeky Pint – Tobi Lütke is Still Captivated by Internet Commerce, 20 Years Later

Podcast: Cheeky Pint
Host: Patrick Collison (Stripe cofounder)
Guest: Tobias (Tobi) Lütke (Founder & CEO, Shopify)
Date: October 6, 2025

Overview

In this wide-ranging and entertaining discussion over a pint, Stripe’s Patrick Collison sits down with Shopify CEO and founder Tobias Lütke. They explore the enduring appeal of internet commerce, what it means to build and scale world-class software, the philosophy of company-building, the power of internal tools, and why Tobi still finds e-commerce fascinating two decades in. The conversation is rich with insights on entrepreneurship, software craftsmanship, agency, capitalism's best and worst elements, and even Canadian economic policy—with plenty of humor and personal anecdotes.

Key Discussion Points & Insights

1. The Joy of Unsovable Problems and Company-Building

• Tobi on passion for problems: "The best gift in life is finding a beautiful problem that you can never solve. And even if you accidentally solve it, if you're so unfortunate to solve it, hopefully it has plenty of enlightened problem children." (00:00)
• Falling in love with problems vs. solutions: Tobi prefers working with "people who fall in love with problems," as opposed to falling in love with solutions. (00:32, 79:06)
• Companies as technology: Tobi views companies themselves as an underappreciated technology, vehicles for social acceptance, and collective mission-pursuit. They “adopt the complexity” of the real world to make things simple for users. (01:16–03:47)

2. Scaling Shopify: Software, Reviews, and Internal Tooling

• Sheer scale: Shopify’s core backend is 20 million lines of code, with the Typescript admin interface adding another ~10 million—making it possibly the largest Ruby and Typescript application globally. (01:16)
• Navigating complexity: Thousands of projects run at Shopify at any moment; they rely on a systematic internal product operations team and a central project-tracking system.
• GSD (“Getting Shit Done”): Shopify’s internal system for project tracking, documentation, and product reviews. Teams use it to report progress, surface learnings, and gather feedback, giving leadership real-time visibility into the “actual state of the business.” (07:27–10:07)
  • "Let's get the actual state of a business into a legible internal system by which you can reason about where is every project, what are the deadlines, what has changed." (07:27)
  • Shopify’s software culture: When off-the-shelf products don’t fit, they build their own—even to a fault (cf. internal Geocities-like site app!). (11:13–12:34)
• Software worldview warning: "Softwares have a worldview. So you're adopting Workday's worldview when it comes to your HR, which may or may not be what you want to do." (Patrick, 13:07; Tobi, 13:14)
• The role of environments: Tobi believes changing the company’s environment—often via tooling—is the most effective lever, more so than policies or incentives. (14:19–16:28)
  • "If people are really insightful, they talk about culture as well. But it's the environment that's even more powerful than all those things." (15:00)

3. Software Craftsmanship, Taste, and Scaling Complexity

• Quantifiables vs. unquantifiables: Business optimization often chases what’s easily measurable, but many vital aspects—quality, taste—aren’t quantifiable. (06:29–07:04)
• Cycles of tech improvement: From Taylorism’s time-and-motion studies to the Toyota lean system, but the next leaps "won't come from just optimizing quantifiables." (05:08–06:29)
• Maintaining taste: Product search and recommendation, especially, require taste and deep product knowledge, which most search experts don’t possess. (41:38–44:59)
  • "The fundamental thing is there is a generic bias in search and a text is king. ... Product search ... really should be seen as its own completely different domain." (41:53)

4. Inversion of Market Power: Small vs. Large Merchants

• Small businesses have better tech: The internet, and particularly Shopify, has flipped the traditional dynamic—smaller retailers now have superior e-commerce platforms to many legacy giants. (19:47–21:24)
  • "We're living in an inverted world where the very large retailers are worse off in their ecommerce experience." (Patrick, 19:47)
  • Tobi: "My fundamental belief is like people should use amazing software that really, really like is like perfectly fit to the problem they have.” (21:50)
• Shopify’s mission: Focus on making entrepreneurship simpler, not just on a particular market segment. Many top customers began as tiny shops and scaled up. (22:19–23:59)

5. Building for Spikes: Drops, Scalability, and Technical Challenges

• Drops culture: High-traffic "drop" events (e.g., Supreme, Kylie Jenner lip kits) pushed Shopify’s and Stripe’s platform scalability—and culture—forward dramatically. (28:50–31:55)
  • “Every single time it went on sale, it took Shopify down. ... We realized obviously, shopify down is the worst possible thing.” (Tobi, 28:50)
• Technical bottlenecks: Scaling transactionality (e.g., inventory and payment flows) is fundamentally hard due to lock contention, a core challenge since the Oracle database wars. (31:58–34:18)

6. Agentic Commerce, AI Shopping, and Product Discovery

• Emergence of AI-assisted commerce: Patrick describes a frictionless “agentic commerce” experience—researching and buying a product via ChatGPT, with fully integrated checkout. (35:04)
  • “Filling out web forms is not a value add activity for people.” (Patrick, 35:04)
• Shopify’s role: Focusing on infrastructure so agents and LLMs can effectively connect to Shopify stores and catalog data. (35:45)
• Personalization and meritocracy: AI stands to make product recommendations based on true merit/fit, benefiting both well-crafted products and indie brands. (39:33–40:47)
  • “The thing that solves consumerism is quality products which you want to keep using.” (Tobi, 39:33)
• Weakness of current e-commerce search: Existing search is still “stuck on keywords”; Tobi admits Shopify hasn’t solved this well—yet. (41:38–43:12)

7. The Power of Personalized, Direct Advertising

• Instagram + Shopify = new retail engine: Personalized, targeted advertising on Meta platforms is the main growth channel for Shopify merchants, enabling discovery and scaling of niche products. (53:03–55:15)
  • “The Meta Shopify loop has created more businesses than any government policy in history.” (Tobi, 53:03)
  • “It’s the first time you can advertise niche products… niche products actually doing better.” (Patrick & Tobi, 53:54–55:15)

8. Stablecoins & Fintech Infrastructure

• Shopify is bullish on stablecoins: Rolling out stablecoin pay-ins across the platform, enabling merchants to accept new payment types without additional complexity. (55:28–58:56)
  • “I'm obviously just like you, a huge fan of the concept of stablecoins...I think the most important thing to happen there is we need to expand what can be purchased with stablecoins.” (Tobi, 55:50)

9. Stripe & Shopify: A Model Partnership

• Long-standing, productive collaboration: Despite tech’s common partnership dysfunctions, Stripe and Shopify have grown “many, many times” together without “prisoner’s dilemma” breakdowns. (59:22–61:56)
  • “I think a lot about main quest and sidequest… I have such good, I guess founder market fit with commerce.” (Tobi, 60:05)
• Focusing deeply vs. diversifying: Comparing this to Nvidia’s relentless vertical focus, versus the Silicon Valley trope of lateral expansion. (62:32–63:39)
  • “More founders should be willing to follow their nose of what's just a good product.” (Patrick, 66:43)

10. Entrepreneurship, On-Ramps, and Building Culture

• Entrepreneurial origin stories: Many founders start with a core habit of spotting and acting on opportunities, often from early “side hustles.” (85:00–87:58)
  • “The commonality behind entrepreneurs is that very early in life somehow something happened that told them that the world is dynamic and it changes.” (Tobi, 86:29)
• Shopify and education: Mentions Shopify’s role in entrepreneurship clubs, and broader educational philosophies (e.g., mastery, “everything’s interesting”, “I’m not good at it yet”). (90:03–91:28)

11. Canadian Policy and the Future

• Advice for Mark Carney (potential Canadian PM): Tobi calls for Canada to embrace economic growth, resource development, and depoliticize implementation, focusing on global competitiveness and collaborating with the US. (91:54–96:39)

12. Personal Passions: Racing, Hobbies, and Continuous Improvement

• Motor-racing as craft and competition with self: Tobi finds resonance between his day job and endurance racing, pursuing “the difference between that lap time and the theoretical possible lap time [as] the exact report card of all your inadequacies as a driver.” (96:50–99:41)
• Everything is interesting: From discovering new hobbies to appreciating Formula 1’s evolution into an entertainment juggernaut—Tobi’s curiosity mantra pervades.

Notable Quotes & Memorable Moments

• "The best gift in life is finding a beautiful problem that you can never solve." – Tobi (00:00, 61:39)
• "Softwares have a worldview. So you're adopting Workday's worldview when it comes to your HR, which may or may not be what you want to do." – Patrick (13:07)
• "If people are really insightful, they talk about culture as well. But it's the environment that's even more powerful than all those things." – Tobi (15:00)
• "We're living in an inverted world where the very large retailers are worse off in their ecommerce experience." – Patrick (19:47)
• "Drops culture": “Every single time it went on sale, it took Shopify down. ... We realized obviously shopify down is the worst possible thing.” – Tobi (28:50)
• "Filling out web forms is not a value add activity for people." – Patrick (35:04)
• “The Meta Shopify loop has created more businesses than any government policy in history.” – Tobi (53:03)
• “Everything's interesting. This is a sentence you will hear a lot in our household.” – Tobi (90:52)
• "You kind of have to fall in love with a problem to want to look at it from so many sides." – Tobi (25:16)
• “If you build things that are of value, then people will figure that out. ... [People] deserve economic value. It comes to them. It's the best parts of capitalism all rolled up for everyone to inspect and review.” – Tobi (67:51)
• “Great entrepreneurs are ungovernable and it's the problems often arise when people somehow manage to figure out how to [govern them].” – Tobi (75:52)

Episode Structure & Timestamps

| Segment | Topic | Time | |---------|-----------------------------------------------------|-------------| | 0:00 | The joy of unsolvable problems; company-building | 0:00–3:47 | | 3:47 | Hard-to-measure R&D; software review rituals | 3:47–9:35 | | 9:35 | The value of GSD/internal build culture | 9:35–13:14 | | 13:14 | Software as ideology; impact of internal tooling | 13:14–16:33 | | 16:33 | Shopify’s vision for merchants | 16:33–21:24 | | 21:24 | Small stores outpacing big brands | 21:24–25:16 | | 25:16 | Complexities of software scaling | 25:16–28:50 | | 28:50 | Surviving the "drop" era; Supreme / Kylie Jenner | 28:50–34:18 | | 34:18 | Agentic commerce and product personalization | 34:18–44:59 | | 44:59 | The challenge of product search | 44:59–47:12 | | 47:12 | Recent favorite products; Shopify’s Shop Pay | 47:12–53:03 | | 53:03 | Instagram, personalized ads, and e-commerce growth | 53:03–55:15 | | 55:15 | Stablecoins and payment innovation | 55:15–58:56 | | 58:56 | The Stripe-Shopify partnership | 58:56–63:39 | | 63:39 | On deep focus vs. diversification | 63:39–67:51 | | 67:51 | Entrepreneurship, authentic stories, value creation | 67:51–70:41 | | 70:41 | Pure capitalism vs. rent extraction | 70:41–72:05 | | 72:05 | On joining Coinbase’s board, learning from others | 72:05–77:04 | | 77:04 | Org design, functional structure, adaptability | 77:04–81:31 | | 81:31 | Programming culture & lowering barriers | 81:31–85:00 | | 85:00 | On-ramps to entrepreneurship/Shopify in schools | 85:00–87:58 | | 87:58 | Early hobby projects, building for yourself | 87:58–90:03 | | 90:03 | Parenting, learning, and educational philosophy | 90:03–91:46 | | 91:46 | Canadian policy/economic advice for Mark Carney | 91:46–96:39 | | 96:39 | Racing as personal craft and pursuit | 96:39–101:27 | | 101:27 | F1, Netflix & the entertainment business | 101:27–end |

Tone:
Candid, intellectual, curious, irreverent, with substantial humor and mutual respect.

This episode offers a masterclass in thoughtful company-building, engineering culture, the future of commerce, and never losing curiosity—ideal for founders, engineers, and anyone fascinated by how digital tools shape our world.