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Simon Eskildsen is a learning machine. 

I first interviewed him in 2020 about how he leveled up from an intern at Shopify to the company’s director of production engineering by reading and applying insights from hundreds of books.

A lot has changed over the last four years. LLMs have made it possible to contextualize information like never before—and in this episode, I sat down with Simon to talk about how this changes the way he learns.

Simon is now the cofounder and CEO of AI startup turbopuffer, which is building a search engine that makes vector search easy and affordable to run at scale.

We get into:

• How Simon’s learning rituals have evolved over time, as the cofounder of a growing startup and a new parent 

• The ways Simon has integrated ChatGPT, Claude, and Notion AI to do everything from writing legal documents to maintaining his rural cabin in Quebec 

• The custom AI commands in productivity tool Raycast that Simon uses to learn new words and cook creative dishes

• Simon’s take on how language models will reshape the future of learning, especially skills like language acquisition, for the next generation 

As we talk, we screenshare through his Anki setup, including the flashcard template he finds most useful, and try out his custom AI commands in Raycast to understand the meaning of two of my favorite obscure words, “lambent” and “eigengrau.”

This is a must-watch for note-taking aficionados and anyone who wants to supercharge their learning with AI.

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Timestamps:

1. Introduction: 00:01:06

2. How entrepreneurship and parenthood changed Simon’s learning rituals: 00:02:51

3. How Simon accelerates his learning by using LLMs to find associations: 00:12:59

4. Simon’s Anki setup and the flashcard template he swears by: 00:18:24

5. The custom AI commands that Simon uses most often: 00:26:02

6. How Simon uses LLMs for DIY home projects: 00:37:45

7. Leveraging LLMs as intuitive translators: 00:40:48

8. Simon’s take on how AI is reshaping the future of learning: 00:51:38

9. How to use Notion AI to write: 00:59:10

10. The AI tools that Simon uses to write, read, and code: 01:08:53

Links to resources mentioned in the episode: 

• Simon Eskildsen: @Sirupsen
• Simon’s startup, turbopuffer: turberpuffer.com, @turbopuffer
• My first interview with Simon in 2020: https://every.to/superorganizers/how-to-build-a-learning-machine-299655 
• The productivity tool through which Simon uses LLMs, Raycast: https://www.raycast.com/ 
• The other AI tools that Simon is experimenting with: voice-to-text tool superwhisper, copilot for developers Supermaven, code editor Cursor