Ian Webster

CEO and Co-founder, Promptfoo · 1 appearance on the record.

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founderengineerexecutive@iwebst ↗LinkedIn ↗ianww.com ↗

Ian Webster is the creator and CEO of Promptfoo, an open-source AI evaluation and red-teaming platform. He previously led developer platform and LLM engineering teams at Discord, where he helped develop its AI assistant Clyde.

10statements → 4claims → 0claims resolved → 3.7/5average certainty → 2.4/5average debate potential →

4 not checkable as stated how the 4 claims stand · each chip opens the sources

2 predictions · 2 assertions · 4 opinions · 2 insights · every statement was checked. The predictions and assertions are the 4 claims: statements the public record can support or contradict. 0 are resolved, and 4 name no date, number or outcome precise enough to check. Everything else (opinions, insights, what ifs, disclosures) can never be settled by the record, so it carries no assessment.

Everything Ian Webster said on Latent Space that made the record, most notable first. Filter by type, assessment or year in the ledger →

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 Webster Oct 24, 2025 ▶ 32:20 Breaking 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 Webster Oct 24, 2025 ▶ 6:13 Breaking AI to Fix It: Ian Webster's Journey from Discord's Clyde to Promptfoo's $18M Series A
Prediction Not 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 Webster Oct 24, 2025 ▶ 14:21 Breaking 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 Webster Oct 24, 2025 ▶ 8:52 Breaking AI to Fix It: Ian Webster's Journey from Discord's Clyde to Promptfoo's $18M Series A
Prediction Not 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 Webster Oct 24, 2025 ▶ 32:54 Breaking 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 Webster Oct 24, 2025 ▶ 37:28 Breaking AI to Fix It: Ian Webster's Journey from Discord's Clyde to Promptfoo's $18M Series A
Assertion Not checkable as stated
Webster: Over 10% of Fortune 500 companies use Promptfoo
“We have a bit over 10% of the Fortune 500 that, that use PromptFu right now.”
Ian Webster Oct 24, 2025 ▶ 25:19 Breaking AI to Fix It: Ian Webster's Journey from Discord's Clyde to Promptfoo's $18M Series A
Insight
Webster: Finding enterprise AI vulnerabilities is only 20% of the challenge
“The way that I think about it is that if you're in a big company, finding the issue is only, like, 20% of the challenge. And then the rest is you have to triage it. You have to like hook it into your task tracker and your SIM and like all these other systems. …”
Ian Webster Oct 24, 2025 ▶ 26:59 Breaking AI to Fix It: Ian Webster's Journey from Discord's Clyde to Promptfoo's $18M Series A
Opinion
Webster: Big enterprises will likely require on-prem MCP tooling
“For the really big companies, something like this would probably have to be on prem, at least in my experience, just because there's, you can get caught up in security reviews and stuff like that for like quarters on, on end.”
Ian Webster Oct 24, 2025 ▶ 41:02 Breaking AI to Fix It: Ian Webster's Journey from Discord's Clyde to Promptfoo's $18M Series A
Assertion Not checkable as stated
Ian Webster: Discord's Clyde was built as a social bot, not a helpful bot
“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.”
Ian Webster Oct 24, 2025 ▶ 2:12 Breaking AI to Fix It: Ian Webster's Journey from Discord's Clyde to Promptfoo's $18M Series A

Appearances (1)

EpisodeDateSpeaking time
Breaking AI to Fix It: Ian Webster's Journey from Discord's Clyde to Promptfoo's $18M Seri Oct 24, 2025 30m
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