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  1. Cheeky Pint
  2. Tobi Lütke is still captivated by internet commerce, 20 years later
Tobi Lütke is still captivated by internet commerce, 20 years later

Tobi Lütke is still captivated by internet commerce, 20 years later

Cheeky Pint · Oct 6, 2025

Shopify CEO Tobi Lütke on building enduring companies by focusing on problems, shaping culture with internal software, and the future of AI in commerce.

High-Quality Products Are the True Antidote to Wasteful Consumerism

Consumerism is driven not by buying, but by buying low-quality items that fail and are discarded. The solution is creating superior, durable products that solve a user's problem permanently, eliminating the need for replacement.

Tobi Lütke is still captivated by internet commerce, 20 years later thumbnail

Tobi Lütke is still captivated by internet commerce, 20 years later

Cheeky Pint·4 months ago

Companies Are a Form of Social Technology We Rarely Try to Perfect

Companies are a technology for organizing people toward a common mission. Unlike software, they're rarely perfected because the incentive is only to be better than the competition, not to reach an absolute ideal of operational excellence.

Tobi Lütke is still captivated by internet commerce, 20 years later thumbnail

Tobi Lütke is still captivated by internet commerce, 20 years later

Cheeky Pint·4 months ago

The Best Employees Fall in Love with Problems, Not Specific Solutions

Employees attached to solutions are rigid during platform shifts. Those who love problems are adaptable and create lasting value. While they look the same in stable times, periods of change reveal their true nature.

Tobi Lütke is still captivated by internet commerce, 20 years later thumbnail

Tobi Lütke is still captivated by internet commerce, 20 years later

Cheeky Pint·4 months ago

Use Constant Reorgs to Filter For Employees Who Thrive Amidst Change

Frequent organizational change, such as reorgs, serves as a natural filter. People who are uncomfortable with flux will self-select out, leaving a team that is more adaptable and aligned with a fast-moving company's needs.

Tobi Lütke is still captivated by internet commerce, 20 years later thumbnail

Tobi Lütke is still captivated by internet commerce, 20 years later

Cheeky Pint·4 months ago

A Central Project Registry Is a Simple, Foundational Tool for Scaling

Having a centralized internal system where every project, goal, and update is tracked—like Shopify's GSD—sounds too simple to be a game-changer. However, it's a surprisingly effective foundation for organizational legibility and alignment at scale.

Tobi Lütke is still captivated by internet commerce, 20 years later thumbnail

Tobi Lütke is still captivated by internet commerce, 20 years later

Cheeky Pint·4 months ago

Build Internal Software to Shape Company Culture Faster Than Policy

Developing internal tools, like a project management system, evolves a company's environment and workflows much faster than rolling out new policies, which require extensive communication and buy-in for adoption.

Tobi Lütke is still captivated by internet commerce, 20 years later thumbnail

Tobi Lütke is still captivated by internet commerce, 20 years later

Cheeky Pint·4 months ago

Buying Enterprise Software Means Adopting the Vendor's Worldview

When a company adopts third-party software like Workday for HR, it's not just buying a tool; it's implicitly accepting that vendor's philosophy on how a process should be run, potentially limiting strategic flexibility.

Tobi Lütke is still captivated by internet commerce, 20 years later thumbnail

Tobi Lütke is still captivated by internet commerce, 20 years later

Cheeky Pint·4 months ago

Shopify Weaponized a Customer's Flash Sales to Forge a Resilient Platform

When a customer's flash sales repeatedly crashed the platform, Shopify treated the problem as a "gem"—a real-world stress test that forced them to build the high-scale infrastructure that became a core competitive advantage.

Tobi Lütke is still captivated by internet commerce, 20 years later thumbnail

Tobi Lütke is still captivated by internet commerce, 20 years later

Cheeky Pint·4 months ago

VCs Pass on Market-Creating Products by Underestimating Their Potential

VCs in 2008 rejected Shopify because the existing market of 40,000 online stores was too small. They failed to see that Shopify wasn't just serving a market; its friction-reducing product would create a much larger one.

Tobi Lütke is still captivated by internet commerce, 20 years later thumbnail

Tobi Lütke is still captivated by internet commerce, 20 years later

Cheeky Pint·4 months ago

Shopify Inverted E-commerce, Giving Small Stores Superior Tech Over Big Brands

Platforms like Shopify have enabled small businesses to have faster, higher-converting, and more technically performant online stores than many large, established brands running on clunky, homegrown legacy systems.

Tobi Lütke is still captivated by internet commerce, 20 years later thumbnail

Tobi Lütke is still captivated by internet commerce, 20 years later

Cheeky Pint·4 months ago

Truly Great Products Emerge from a Career-Long Obsession with One Problem

The world's best products, like programmer Eric Gamma's VS Code (his fourth editor), are often the result of a creator dedicating their entire career to a single problem space, achieving a level of craftsmanship impossible for newcomers.

Tobi Lütke is still captivated by internet commerce, 20 years later thumbnail

Tobi Lütke is still captivated by internet commerce, 20 years later

Cheeky Pint·4 months ago

Software Has a Two-Year Window Before Its Architecture Becomes Permanent

A mentor taught Shopify's CEO that you have about two years to get an important piece of software's architecture right. After that, it's as if "cement gets poured in the codebase," making fundamental changes nearly impossible.

Tobi Lütke is still captivated by internet commerce, 20 years later thumbnail

Tobi Lütke is still captivated by internet commerce, 20 years later

Cheeky Pint·4 months ago