From Geek Squad to MongoDB Advocate

In this episode of HTML All The Things, Mike sits down with Jesse Hall, Staff Developer Advocate at MongoDB and creator of the popular codeSTACKr platform. Jesse shares his journey from working at Geek Squad to becoming a self-taught developer, educator, and now an advocate at one of the biggest players in the database space.

They discuss the principles that make technical concepts “click” for beginners, how to help teams move from relational-first thinking to designing flexible MongoDB schemas, and the pitfalls to avoid when working with document databases. The conversation also dives into MongoDB’s role in the AI landscape, including Jesse’s “AI in Two Lines” approach and what it really takes to go from toy chatbots to robust agentic systems.

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Show Notes

Interview Questions

Who is Jesse Hall?

How did you go from Geek Squad tech to self-taught developer, educator, and now a Senior/Staff Dev Advocate at MongoDB?
You’ve done some fantastic work with your codeSTACKr platform on teaching developers complex concepts, what principles make a technical concept “click” for beginners?

MongoDB

What’s the fastest way to help a relational-first team unlearn table-centric thinking and design great document schemas?
Tactics to keep schemas flexible without creating “everything bagel” documents (validation, versioning, polymorphism).

MongoDB + AI

Can you describe how MongoDB is participating in the AI landscape right now?
What does a solid RAG baseline look like on Atlas today (chunking, metadata, Vector Search), and
- what mistakes derail teams early?
In your “AI in Two Lines” talk, what did you mean by “two lines,” and what’s the real roadmap from toy chatbots to robust agentic systems?

Jesse's Links

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From Geek Squad to MongoDB Advocate | w/ Jesse Hall

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