Show Notes
Jay Hack co-founded CodeGen, one of the first companies building autonomous coding agents, before ClickUp acquired it and made him head of AI. In this episode of Navigators, Paul sits down with him to ask why, with models this capable, so few problems have actually been solved. Jay's answer centers on one word: siloing. He argues the biggest thing preventing companies from operationalizing agents isn't model quality, it's that sales data lives in Salesforce, chats live in Slack, and docs live somewhere else, each platform incentivized to keep your data locked in. ClickUp's bet is the opposite: put tasks, docs, and chat in one place, build a dense context graph on top of it, and let subagents pull from it cheaply and fast. He connects that same philosophy to why he's bullish on skills as memory, why curing cancer hits the same closed-loop problem as shipping software, and why an agent recently ordered him a pizza using nothing but a browser. Topics covered: 07:45 What refactors taught CodeGen about narrow use cases
10:39 The biggest problem stopping companies from operationalizing AI
11:19 Why a dense context graph beats siloed data
12:09 Evals first: building the AI stack as a context engine
15:21 Skills as memory: ClickUp's answer to compaction
24:13 What's actually stopping AI from curing cancer
26:30 Teaching an agent to order a pizza with just a browser
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