AI Productivity
I used to think planning was the enemy of shipping. After 29 playbooks I no longer do.
For years I just shipped. Now I plan in 30 minutes, build in 30, capture in 10 — and the work compounds. Here's the loop.
Ashley KaysMay 5 / 6 min
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157 articles
For years I just shipped. Now I plan in 30 minutes, build in 30, capture in 10 — and the work compounds. Here's the loop.
Friday postmortems, pre-build pressure tests, security scans, and more. The actual prompts I use, with the small adjustments that make them deliver.
What's genuinely working in Waymaker, what still has rough edges, and what I'm betting wins anyway.
Everyone's selling AI as a magic wand. There are real gaps. Here are 9 of them, with the 7 Waymaker handles and the 2 that still need a human.
There's a protocol quietly rolling out across every major AI tool that changes what AI can actually do. It's called MCP, and once you set it up, your AI stops being a chatbot and starts being an operator.
Devin by Cognition is the most ambitious AI developer ever built—fully autonomous, capable of planning, coding, debugging, and deploying without human intervention. But once Devin ships your app, who makes sure anyone uses it? Here's why autonomous code and autonomous business are different jobs.
After 20+ years building for other people's dreams and drowning in a $500/month SaaS stack that didn't talk to itself, I snapped. This is the honest story of how Waymaker went from a 3am prototype to 54 AI agents — and why faith, stubbornness, and sleepless nights were the only ingredients that mattered.
Windsurf by Codeium is Cursor's biggest rival—Cascade agent, Supercomplete, generous free tier. But the same gap remains: an IDE builds code, not businesses. Here's why builders need a product operating system alongside their editor.
Cursor is the most exciting developer tool since VS Code itself. But an IDE's job is to help you write code faster — not to validate your market, build your pipeline, or coach you through a pivot. Here's why builders need an operating system, not just an editor.
Practical AI guide for law firms — document drafting, client intake automation, legal research, and billing optimization.
AI use cases for real estate professionals — listing descriptions, lead follow-up, market reports, and social media.
A practical guide to AI for med spas — booking automation, patient follow-ups, content creation, and more.