A Product Market Fit Show | Startup Podcast for Founders He fired all his customers. Then built a $1B startup in 2 years. | Jay Madheswaran, Co-Founder of Eve
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Feb 9, 2026 
Jay Madheswaran, founder and CEO who pivoted from VC and engineering roles to build Eve, a legal-AI unicorn. He describes firing all customers to focus on plaintiff-side legal workflows. Rapid demo wins, 40% cold-to-demo conversion, and 4-hour user sessions that signaled true demand. The conversation covers pivot pressures, go-to-market tactics, and the product discovery that sparked hypergrowth.
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NLP Sample Size Collapse Enabled New Use Cases
- Jay noticed NLP model sample-effort dropped from thousands to tens, unlocking practical extraction use cases.
- That trend convinced him AI would enable many previously impossible workflow automations.
Raised $4M During The COVID Week
- Jay raised $4M the week of COVID and struggled with legal delays like faxed forms and EINs.
- The team worked unpaid early months while founding logistics delayed payments.
Document Extraction Was The Hidden Foundation
- Jay started with high-volume document processing because CV struggled with highly variant documents.
- That extraction groundwork later became core to Eve's legal accuracy needs.