Character AI

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.

Outlasting Noam Shazeer, Crowdsourcing Chai AI w/ 1.4m DAU — with William Beauchamp, Chai Research

Jan 26, 2025 · 1:13:33

William Beauchamp, founder-CEO of Chai AI, explains how he pivoted from algorithmic trading to build a character chatbot platform before Character.ai, growing to 1.4M DAU and $22M+ revenue by crowdsourcing model improvements through Chaiverse. Starting with GPT-J in 2021, he found product-market fit with a therapist bot and shifted to user-generated content, letting users define prompts, images, and names. Competing against well-funded rivals like Character AI and Talkie, Chai ships over 100 LLMs weekly via its developer platform, spending $10M on compute in 2024 and tripling it. Beauchamp argues AI follows an S-curve, not scaling laws, and focuses on inference optimization using rejection sampling and reward models to serve better responses. He prioritizes 'insanely great' products over technology-driven features, noting that audio and image features failed to move metrics, while a data flywheel and aggressive user acquisition drove rapid growth.