The Pragmatic Engineer

Jean Lee, former WhatsApp engineer #19 who later became a Meta engineering manager, shares how a tiny team scaled messaging to hundreds of millions. She talks about eight native clients, Erlang, and a culture of extreme simplicity. There’s also the inside story of the Facebook acquisition, the jump into management, performance review dynamics, and why lean teams still matter in the age of AI.

Steve Yegge, veteran engineer and former Amazon and Google developer, dives into AI’s reshaping of software work. He talks about why hand coding may fade. He maps levels of AI adoption, from avoiding tools to orchestrating parallel agents. They explore Gastown, monoliths blocking agentic workflows, prototype driven product building, and the new technical debt and productivity pressure AI may create.

Boris Cherny, creator and Head of Claude Code at Anthropic and author of Programming TypeScript, joins to talk about building agentic code tooling. He describes Claude Code’s evolution, parallel agents and deterministic review patterns. They explore retrieval from large codebases, sandboxing and safety layers, and how engineering roles shift as models write more code.

Mitchell Hashimoto, co-founder of HashiCorp and creator of Terraform and Ghostty, is an influential infrastructure engineer reshaping developer tools. He discusses multi-cloud design, turning open-source into a sustainable business, building Ghostty and terminals, and how AI agents and code contributions change workflows and hiring. The conversation focuses on tooling, scaling engineering practices, and AI’s effects on open source.

Andrey Breslav, creator of Kotlin and now building CodeSpeak to combine plain-English intent with code. He discusses why Kotlin prioritized Java interoperability and null safety, the tradeoffs in designing a pragmatic JVM language, and how new languages can leverage LLMs to reduce boilerplate while keeping humans in control.

Grady Booch, pioneering software engineer and co-creator of UML, reflects on computing’s long arc. He traces three golden ages of software and why each arose from technical and human limits. He discusses AI’s role in a new era, why engineers remain essential, and which higher-level skills will matter next.

Peter Steinberger, founder of PSPDFKit and creator of Moltbot, is a prolific engineer who builds developer tools and AI agents. He discusses using LLM-driven agents to ship massive amounts of code, architecting systems so agents can handle plumbing, and designing automated tests and docs that let AI close the loop. He also covers agent orchestration, prompt-driven workflows, and rethinking engineering roles for agent-centric development.

Mai-Lan Tomsen Bukovec, VP of Data and Analytics at AWS, leads the charge on Amazon S3, one of the largest distributed systems globally. She delves into S3’s impressive scale, with 500 trillion objects and millions of servers, and the evolution of its simplicity and consistency. Mai-Lan shares insights on optimizing costs, creating robust archival solutions like Glacier, and employing formal methods for correctness. She also discusses how S3 is evolving with new data primitives like tables and vectors, shaping the future of data management.

Bryan Cantrill, co-founder and CTO of Oxide Computer and a former distinguished engineer at Sun Microsystems, dives into the evolution of servers and cloud computing. He reflects on the innovations that emerged from the Dotcom Bust, highlighting the significance of deeper technical focus. The conversation covers AWS's market impact, Kubernetes' role in cloud neutrality, and the challenges of server updates. Bryan also discusses employing AI in engineering and how Oxide preserves its culture during growth, emphasizing the importance of values and transparency.

Michelle Lim, a founding engineer at AI startup Flint and former engineer at Warp, shares her journey from top tech firms like Facebook and Slack to entrepreneurship. She discusses the unique challenges of being an early-stage engineer and the importance of a product-first mindset. Michelle explains negotiating equity, the value of asking founders for references, and the significance of tech stack choices. With insights on building autonomous websites and leveraging AI, she offers practical advice for aspiring engineers aiming to transition into founding roles.