Clyde

Breaking AI to Fix It: Ian Webster's Journey from Discord's Clyde to Promptfoo's $18M Series A

Oct 24, 2025 · 43:17

Ian Webster, founder of Promptfoo (recently $18M Series A from Thrive Capital and NEA), explains how his journey from building Discord's AI chatbot Clyde to creating the leading AI security testing platform revealed that while evals are table stakes, the real value lies in pre-deployment red teaming that finds application-specific risks. Webster argues that traditional guardrails are insufficient—'you can't fix stupid'—and that Promptfoo uses AI-versus-AI techniques to generate tailored attacks for each app's business context. Over 10% of Fortune 500 companies now use Promptfoo, and he discusses the evolving challenges of MCP security (mostly 'glorified API wrappers') and the need for IDE plugins and code-aware discovery to keep up with increasingly complex agents running 30-minute tasks. The episode also covers why security sales in AI is uniquely hard, how open source builds trust in a space full of 'snake oil,' and why the future of AI security must shift from runtime protection to earlier testing in CI/CD.

Claude Code: Anthropic's CLI Agent

May 7, 2025 · 1:16:22

In this episode, Boris Cherny and Cat Wu from Anthropic discuss Claude Code, a CLI-based coding agent they describe as a Unix utility rather than a polished product, emphasizing raw model access and simplicity. The tool started as Boris's personal experiment, then spread internally after engineers used it daily, with Anthropic's product principle of 'do the simple thing first' guiding features like memory via markdown files and context compaction by asking Claude to summarize. They ship updates including web fetch, auto-accept, and thinking via chain of thought, and note that 80% of Claude Code's code is written by Claude Code itself. Average spend is $6/day per user versus $20/month for Cursor, and Boris reports a personal 2x productivity gain, with some engineers seeing 10x. The team is growing and investigating open-sourcing the tool, while continuing to build for the terminal as a raw, composable utility for power users.