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Human In the Loop · EP 06

Anthropic Killed the AI-for-SMB Playbook

Podcast Episode45 minMay 18, 2026
PodcastAIIndustry
In this episode

On May 13, 2026, Anthropic shipped Claude for Small Business: 15 ready-to-run agentic workflows wired into QuickBooks, PayPal, HubSpot, Canva, DocuSign, Google Workspace, and Microsoft 365, plus a 10-city US training tour. Three months ago on Episode 1, we asked if there was a real founder business in selling AI to small businesses. This week we watched a frontier lab ship it themselves in 90 days.

If you were six weeks into building that company, what do you do Monday morning? That's the cold open. From there, Oscar and Matt filter the week's AI noise — Thinking Machines' Interaction Models, Sierra's $950M round, the Trump admin's reversal on AI oversight, Cloudflare's "AI did it" layoffs — debate the tools they actually adopted, and close with two hot takes you won't hear anywhere else.

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