“The interesting thing about Clyde was that it wasn't really meant to be a, necessarily a helpful bot, but instead more of a social bot, like a bot that would just like be in your channel and, you know, help people interact and that kind of thing.”
quote is from the automated transcript, cleaned for reading:
filler sounds and stutters are removed, nothing is rephrased. names can be misheard
(the analysis reads context, assessments check outside sources). how →
More from Ian Webster
Opinion
Webster: AI guardrails are a commodity and easy to build
“Building a business on guardrails really scares me because there are so many incumbents that can come in and eat your lunch. And it's like, It's not actually that hard to build a guardrail. I don't know if I'm gonna make people angry by saying that maybe some …”
Ian WebsterOct 24, 2025▶ 32:20Breaking AI to Fix It: Ian Webster's Journey from Discord's Clyde to Promptfoo's $18M Series A
Opinion
Webster: AI evaluation tools are table-stakes commodities facing a feature-parity bloodbath
“I think evals are our table stakes. I think that they're a commodity and everyone should be doing them. And yes, there are companies that are doing great in the eval space, but To me, it just seemed like a bloodbath, you know, like we would just be, had a grea…”
Ian WebsterOct 24, 2025▶ 6:13Breaking AI to Fix It: Ian Webster's Journey from Discord's Clyde to Promptfoo's $18M Series A
PredictionNot checkable as stated
Webster: Meaningful AI red teaming will require internal tracing and observability
“I think especially where, where things are headed, like with more complex rags and agents and so forth, you're going to have to have some type of observability or like internal tracing in order to have, to do meaningful automated red teaming.”
Ian WebsterOct 24, 2025▶ 14:21Breaking AI to Fix It: Ian Webster's Journey from Discord's Clyde to Promptfoo's $18M Series A
Insight
Webster: Enterprises do not want AI models to be maximally helpful
“OpenAI Anthropic, everyone else, they're all building models that are like maximally helpful. And in Actually, most cases in a corporate environment, you don't want that to be maximum. You don't want the model to be like helpful in every way possible.”
Ian WebsterOct 24, 2025▶ 8:52Breaking AI to Fix It: Ian Webster's Journey from Discord's Clyde to Promptfoo's $18M Series A
PredictionNot checkable as stated
Webster: The future of AI security is in CI/CD, not runtime
“So the future is really, like, not in runtime, but Earlier in the software development lifecycle, ideally in CICD or before that.”
Ian WebsterOct 24, 2025▶ 32:54Breaking AI to Fix It: Ian Webster's Journey from Discord's Clyde to Promptfoo's $18M Series A
Opinion
Webster: Most corporate MCP implementations are just glorified API wrappers
“The way that a lot of corporates are implementing MCP is just like a glorified API wrapper, not, not like super innovative just kind of checking the box.”
Ian WebsterOct 24, 2025▶ 37:28Breaking AI to Fix It: Ian Webster's Journey from Discord's Clyde to Promptfoo's $18M Series A
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