Shopify is known to obsessively collect and focus on data to make its decisions, and this philosophy seems to extend to the CEO as well.
In a recent appearance on the Acquired podcast, Shopify CEO Tobi Lutke revealed a remarkable personal data collection habit that has been running continuously for over a decade and a half. The German-Canadian entrepreneur, who built Shopify from a snowboard equipment store into a $100+ billion e-commerce empire, disclosed that he has been systematically logging every keystroke and taking screenshots of his computer screen every 10 minutes since the company’s early days.
The Digital Archive
Lutke explained his unusual documentation system in detail: “I have run a keyboard logger and sort of what is the active window and take a screenshot of a window of my machine every 10 minutes and archive this for going on 15 years now. It’s something I’ve always been running and it just for my own purposes.”
When pressed about the scope of this digital archive, Lutke confirmed he possesses “a archive of your daily digital activity of the last 15 years. Yes.” The podcast hosts’ amazement was palpable, with one exclaiming “Oh, holy crap. Wow” and calling it “what a gift. Nobody has that.”
Lutke himself acknowledged the unexpected value of this practice: “I would never imagined this ends up being as valuable as it is. “It’s like how Toby became Toby, how Shopify became Shopify,” the hosts said. “It’s basically that,” Lutke agreed.
Weekend Projects and AI Analysis
The Shopify founder revealed that analyzing this vast trove of personal data has become a regular weekend activity. “A lot of my weekend projects are actually just running through all of this and putting it together because of course it’s dispersed keyboards with lots of noise in it. Different formats over time. And every once in a while I use Vim, at which point there’s a lot of what’s in the keyboard buffer is complete nonsense.”
However, Lutke has found modern AI tools instrumental in making sense of the chaotic data: “The nice thing is, with enough AI tools, you can turn this into pretty clean timelines, right? Without you having to write a script that’s like, okay, every time I’m hitting queue that disregard. And of course a format change a million times and there has missing bits and pieces.”
Building a Comprehensive Personal Database
Beyond keystrokes and screenshots, Lutke has been integrating additional data sources to create a more complete picture. “Then I have my calendar, which I’m now adding to it over the times. And a lot of emails, headers of who I converse with and so on.” When asked if he maintains this in a repository, Lutke confirmed the system allows him to query AI models with instructions like “Hey, I need you to make something like Toby, just look at this. And then do it like this.”
Lutke emphasized his preference for future-proof storage formats: “The actual format was I just always turned it into text files… it’s the best format to move world because it lasts forever.” He noted that he has “been working on doing more and more work on just analyzing it and cleaning it and adding more things because the value of this is getting incredibly high.”
The Implications of Radical Self-Documentation
Lutke’s extreme approach to personal data collection reflects a broader trend among tech leaders who view comprehensive data analysis as fundamental to understanding patterns and making better decisions. His 15-year digital archive essentially creates a complete map of his professional evolution and decision-making processes during Shopify’s transformation from startup to global platform.
This level of self-documentation goes far beyond typical productivity tracking or time management tools. It represents what could be called “life logging” on an unprecedented scale for a major CEO. The practice aligns with Shopify’s data-driven culture, where the company famously uses extensive analytics to understand merchant behavior and platform performance — Shopify collects so much data that they had begun showing employees the dollar cost of every meeting to encourage them to avoid pointless meetings. With AI tools now making it feasible to analyze such massive personal datasets, Lutke’s archive could provide unique insights into entrepreneurial decision-making patterns, the evolution of leadership thinking, and the day-to-day reality of scaling a technology company. And like the hosts said, this isn’t just personal productivity data—it’s “how Toby became Toby, how Shopify became Shopify.”