The archive · 47 essays · 12 talks · since 2015
Everything worth saying twice.
Eleven years of writing on conversational AI, the pragmatics of shipping ML, and why most "AI transformations" are just CRUD apps with extra steps.
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2026
04 pieces · so far2025
11 pieces Dec 11 The 10,000-hour chatbot Essay 14 min → Nov 04 Retrieval is not a product Essay 9 min → Oct 22 On leaving, staying, and building in public Interview 24 min → Sep 08 Open source and the enterprise long tail Essay 16 min → Aug 17 Prompt caching is a compiler, not a feature Notebook 8 min → Jul 03 Why "agentic" is doing too much work Essay 11 min → May 29 The boring case for open-weights models Talk 28 min → Apr 12 Shipping against a moving model Essay 10 min → Mar 18 A cheap trick for deterministic tool-calls Notebook 5 min → Feb 14 Ten years of Rasa, told badly Interview 36 min → Jan 07 What I was wrong about in 2024 Essay 7 min →
2024
09 pieces Dec 19 The dialog manager comes back around Essay 13 min → Oct 30 Finetuning is for when you've run out of better ideas Essay 11 min → Sep 12 Four failure modes of LLM products Talk 22 min → Jul 24 Cheap guardrails that actually work Notebook 7 min → Jun 06 On being specifically useful Essay 9 min → Apr 15 The second-system problem in AI product work Essay 12 min → Feb 28 On open source, Berlin, and boring wins Interview 28 min → Feb 01 Why your copilot isn't a copilot Essay 8 min → Jan 18 Structured output, five ways, ranked Notebook 6 min →
2023
08 pieces Nov 22 The ChatGPT moment, six months in Essay 15 min → Sep 08 Why intents still matter (sorry) Essay 10 min → Jun 14 Conversational AI, 2013–2023: a trajectory Talk 34 min → Apr 02 The end of the classifier era Essay 9 min → Feb 19 Three prompts, one product Notebook 5 min → Jan 09 What LLMs are actually good at Essay 14 min →
2015–2022
15 pieces · the old guard 2022 A decade of conversational interfaces, in ten mistakes Essay 16 min → 2021 Against single-turn benchmarks Essay 11 min → 2019 Rasa Open Source 2.0 — what changed and why Essay 13 min → 2017 Supervised dialogue learning from scratch Essay 18 min → 2015 How I ended up building a chatbot company Essay 8 min →