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AI & I

Every's Dan Shipper on how AI gets used in real workflows

Deep reads here4 / 132 episodes
Cadence~1 every 7.0 days
Latest2026-10-14
Official transcriptincluded
TopicsAI & Tech
PriorityT2
33:46
AI & I 1007

Most personal AI agents get abandoned; the shared company agent keeps getting stronger

At Every, most personal agents were voluntarily abandoned by employees because ordinary people cannot sustain the maintenance burden. Only company-level agents that receive continuous investment grow stronger with use, eventually becoming external products.

7 Points 7 Quotes AI agentOrganizational design
47:58
AI & I 0902

AI writing's moat isn't the model, it's the proprietary data you feed it

Every writer Katie spent two years turning ChatGPT from a career coach during a layoff into a one-person content company and a compounding editor; the core method isn't prompts, it's using proprietary experience to cover the "last mile" the model can't reach.

9 Points 6 Quotes AI writingcontext engineering
1:07:06
AI & I 0826

AI Isn't a Personal Tool — It's an Organizational Change Leaders Must Model Themselves

AI is not a personal tool; it is an organizational change that leaders have to demonstrate personally. At Walleye, everyone uses AI every day and every meeting gets recorded, building a first-mover advantage out of operating leverage and a data lake.

8 Points 6 Quotes Organizational changeHedge funds
1:22:08
AI & I 0819

An AI Companion at $4M a Year: No Scripted Plot, Just Memory and Improvisation

Tolon, the AI companion from Portola, threw out scripted plots and character sheets: memory is the character sheet, generation is improvisation, and the product is now at $4M in annualized revenue. This "improv actor" methodology and its mixed-model strategy are a second product path alongside ChatGPT.

8 Points 4 Quotes AI CompanionsImprov Narrative