The Reason Your AI Agents Keep Failing | Alex Shan, Judgment Labs

Lightspeed partner James Alcorn sits down with Alex Shan, CEO and co-founder of Judgment Labs, to discuss one of the biggest unsolved problems in enterprise AI. How do you make sure your AI agents are actually getting better over time? Alex explains how most agent teams today are stuck in a frustrating cycle. Some interactions work great, others fail in ways that are hard to explain, and fixing those failures is still a slow, manual process. Judgment Labs is building the platform that changes that, by monitoring what agents do in production, automatically surfacing where they go wrong, and letting other agents handle the fixes instead of human engineers. The conversation covers how Alex and his two co-founders, childhood friends with backgrounds in AI agent research and infrastructure, came together to build the company, why Lightspeed backed them twice with no deck, and what it looks like to work so closely with early customers that you feel more like a partner than a vendor. Alex also shares where he sees the company going, from helping developers build better agents, to giving enterprise buyers the data they need to make smarter purchasing decisions, to eventually underwriting the risk of agents operating at scale. Chapters 0:00 Putting Agent Improvement On Autopilot 2:20 What Judgment Labs Actually Does 3:09 Being A Full Lifecycle Agent Behavior Monitoring Platform 5:00 How The Co-Founders Met 7:57 The Fundraising Journey With Lightspeed 12:18 Two Core Technological Bets That Shaped The Product 15:09 The Philosophy Behind Partnering With Customers 17:28 How They Choose Their Early Customers 19:40 The 5-Year Vision For Judgment Labs 22:10 Where The Business Goes From Here 24:39 How To Get In Touch With Alex And The Team ABOUT THE INVESTMENT MEMO PODCAST The Investment Memo is a podcast interview series where founders see their original investment memo for the first time and revisit the deal that started it all. The memo becomes the spine of the episode — sparking honest conversation about early conviction, risk, growth and the relationship that formed between founder and investor. Stay In Touch: Website: www.lsvp.com X: https://x.com/lightspeedvp LinkedIn:   / lightspeed-venture-partners   Instagram:   / lightspeed   The content here does not constitute tax, legal, business or investment advice or an offer to provide such advice, should not be construed as advocating the purchase or sale of any security or investment or a recommendation of any company, and is not an offer, or solicitation of an offer, for the purchase or sale of any security or investment product. The views expressed by our guests do not necessarily represent the views of Lightspeed. For more details please see lsvp.com/legal. The Reason Your AI Agents Keep Failing | Alex Shan, Judgment Labs    • The Reason Your AI Agents Keep Failing | A...