Louis Knight-Webb - Can AI Understand Legacy?

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BASELINE: How Innovation Really Happens

Baseline Podcast

64 episodes

1 day ago

An independent media platform uncovering how AI and technology are transforming business, creativity, and society. Through in-depth conversations with founders, investors, enterprise leaders, and policymakers, BASELINE reveals the people, decisions, and ideas driving the next era of innovation. From startup breakthroughs to large-scale AI adoption, BASELINE cuts through hype to deliver clarity and insight that leaders can act on today. Contact: info@baselinepodcast.com

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Louis Knight-Webb - Can AI Understand Legacy? - BASELINE049

BASELINE: How Innovation Really Happens

56 minutes 50 seconds

3 months ago

Louis Knight-Webb - Can AI Understand Legacy? - BASELINE049

Louis Knight-Webb combines technical brilliance with rare composure.As co-founder of bloop.ai and a Y Combinator S21 alum, Louis is building AI tools that don’t just touch legacy systems - they understand them. From mainframes to COBOL, his team is using generative models to translate decades-old infrastructure into clear, maintainable modern code.In this BASELINE episode, Louis breaks down:

– Why mainframes still power trillions in daily transactions

– How AI can turn legacy code into natural language

– The real blockers in enterprise modernisation (and how to overcome them)

– Why modernisation is about translation, not disruption

EPISODE CHAPTERS:

00:00 – Intro: Why legacy still matters

01:00 – Mainframes, batch jobs, and modern AI

03:00 – Louis on Y Combinator and the founder mindset

08:30 – What bloop actually does

14:00 – AI vs enterprise systems: reality check

21:00 – Turning COBOL into natural language

28:00 – Real-time systems, Kafka, and the death of the calendar

35:00 – Technical debt, team knowledge, and scaling modernisation

43:00 – Future-looking: language models, trust, and quantum

51:00 – Final reflections: calm innovation and quiet disruption