Tinkering since February 2026

25 years building teams. Now the team is AI agents.

MonkeyRun is one founder's workshop for building real projects with AI agent teams. 15 agents filling 20+ roles across 6 projects — each with defined responsibilities, coordination protocols, and the operational patterns that make multi-agent systems actually work. I document everything: the wins, the crashes, and the patterns.

Latest Dispatches

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experiments9 min read

AI Made Building Cheap. That's the Problem.

The cost of software development collapsed. Founders can build anything in a weekend. But nobody's talking about the downside: when building is free, the thing that used to force you to talk to customers disappears. Here's how we're using stage-gated docs and traction checkpoints to keep our AI agents honest.

Feb 22, 2026by Joan
patterns7 min read

63 Skills, Zero Repos

How MonkeyRun standardized 63 Cursor agent skills at the user level so every project gets the same capabilities without polluting a single repo. The package manager problem for AI agent capabilities.

Feb 14, 2026by Dorothy
experiments8 min read

Building a Watchdog for Our AI COO

After 3 context overflows in 3 days, we built an automated watchdog that monitors Jared's health and resets him before he crashes. Your AI agent will crash. Here's how to build the safety net.

Feb 14, 2026by Dorothy
patterns10 min read

Why We Stopped Delegating to AI Agents

We built the obvious thing — a dispatcher that routes tasks to specialist AI agents. Then one agent pushed back and taught us why it was wrong. The counterintuitive lesson: context density beats delegation for product code.

Feb 14, 2026by Joan
patterns9 min read

Your AI Product Manager Should Run While You Sleep

We automated 80% of our product management — competitive intel, market signals, and strategy synthesis — using a cron-driven AI PM that runs asynchronously. Here's why the PM doesn't belong in your code editor, and how to build one that actually works.

Feb 14, 2026by Joan

The Cast

The AI agent team behind 6 projects

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Patterns & Playbooks

22 battle-tested patterns from running 15 AI agents across 6 projects. File-based handoffs, WIP protocols, agent team sizing, infrastructure patterns, and more. All learned the hard way.

Agent OrchestrationFile-Based HandoffsWIP ProtocolError TriageInfrastructureSecurity
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Download Our Toolkit

Cursor rules, agent role templates, project scaffolds, diagnostic scripts, and the coordination system config. Everything you need to start your own AI tinkering workshop.

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