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  1. A Product Market Fit Show | Startup Podcast for Founders
  2. He fired all his customers. Then built a $1B startup in 2 years. | Jay Madheswaran, Co-Founder of Eve
He fired all his customers. Then built a $1B startup in 2 years. | Jay Madheswaran, Co-Founder of Eve

He fired all his customers. Then built a $1B startup in 2 years. | Jay Madheswaran, Co-Founder of Eve

A Product Market Fit Show | Startup Podcast for Founders · Feb 9, 2026

Eve co-founder Jay Madheswaran shares how he fired all his customers and pivoted to AI, building a $1B legal tech startup in just 2 years.

Users Exploiting a Bug to Onboard Their Whole Team Is a Strong PMF Signal

Eve knew they had product-market fit when customers found a bug that let them bypass invite restrictions. Users onboarded their entire firms months ahead of schedule, demonstrating an urgent, unmet need for the product.

He fired all his customers. Then built a $1B startup in 2 years. | Jay Madheswaran, Co-Founder of Eve thumbnail

He fired all his customers. Then built a $1B startup in 2 years. | Jay Madheswaran, Co-Founder of Eve

A Product Market Fit Show | Startup Podcast for Founders·10 days ago

Frame Pivot Discovery as "Roadmap Brainstorming" with Top Clients

To explore a pivot without alarming existing customers, Eve's founders framed discovery calls as "product roadmap brainstorming." This allowed them to validate new, high-value problems with their best clients without disrupting current operations or revealing their pivot intentions.

He fired all his customers. Then built a $1B startup in 2 years. | Jay Madheswaran, Co-Founder of Eve thumbnail

He fired all his customers. Then built a $1B startup in 2 years. | Jay Madheswaran, Co-Founder of Eve

A Product Market Fit Show | Startup Podcast for Founders·10 days ago

Test Product-Market Fit By Announcing a Shutdown and Seeing Who Protests

Eve discovered the true product-market fit for their old product only when they announced its shutdown. The most passionate customers protested vehemently, revealing the product's actual value and core user base, a high-stakes but effective test.

He fired all his customers. Then built a $1B startup in 2 years. | Jay Madheswaran, Co-Founder of Eve thumbnail

He fired all his customers. Then built a $1B startup in 2 years. | Jay Madheswaran, Co-Founder of Eve

A Product Market Fit Show | Startup Podcast for Founders·10 days ago

Tap Niche B2B Communities Where Local Competitors Collaborate Nationally

Eve discovered that plaintiff law firms, while competitive locally, actively share strategies with non-local peers. By delighting early adopters, they organically gained access to this national referral network, turning a fragmented market into a powerful go-to-market channel.

He fired all his customers. Then built a $1B startup in 2 years. | Jay Madheswaran, Co-Founder of Eve thumbnail

He fired all his customers. Then built a $1B startup in 2 years. | Jay Madheswaran, Co-Founder of Eve

A Product Market Fit Show | Startup Podcast for Founders·10 days ago

A 40% Cold Outreach-to-Demo Rate Signals Extreme Market Urgency

Eve's new legal AI product saw a 40% conversion rate from cold outreach to demo requests, compared to 1% for their old product. This massive quantitative jump was an undeniable signal of a burning market need and strong product-market fit.

He fired all his customers. Then built a $1B startup in 2 years. | Jay Madheswaran, Co-Founder of Eve thumbnail

He fired all his customers. Then built a $1B startup in 2 years. | Jay Madheswaran, Co-Founder of Eve

A Product Market Fit Show | Startup Podcast for Founders·10 days ago

Eve Pivoted From a $3M Business Because Its $6K ACV Was Economically Unfeasible

Despite having a working product and millions in revenue, the team realized their low average contract value (ACV) of $6K would prevent them from scaling to hundreds of millions. This economic reality forced them to pivot and find a new, higher-value vertical.

He fired all his customers. Then built a $1B startup in 2 years. | Jay Madheswaran, Co-Founder of Eve thumbnail

He fired all his customers. Then built a $1B startup in 2 years. | Jay Madheswaran, Co-Founder of Eve

A Product Market Fit Show | Startup Podcast for Founders·10 days ago

Live Demos in Service-Based Industries Can Achieve 90% Pilot Conversion Rates

In the legal industry, where clients buy human services, Eve's live software demo was a revelation. Showing the product solve a real problem on the spot, rather than just talking about it, blew potential customers' minds and led to a 90% demo-to-pilot conversion rate.

He fired all his customers. Then built a $1B startup in 2 years. | Jay Madheswaran, Co-Founder of Eve thumbnail

He fired all his customers. Then built a $1B startup in 2 years. | Jay Madheswaran, Co-Founder of Eve

A Product Market Fit Show | Startup Podcast for Founders·10 days ago

A VC's Conviction in AI Became Too Strong to Just Invest, Forcing a Return to Founding

Jay Madheswaran transitioned from VC at Lightspeed back to founder because his conviction in AI's potential was too high to express through investing alone. He felt a compelling need to build directly in the space while he still had the "operational chops."

He fired all his customers. Then built a $1B startup in 2 years. | Jay Madheswaran, Co-Founder of Eve thumbnail

He fired all his customers. Then built a $1B startup in 2 years. | Jay Madheswaran, Co-Founder of Eve

A Product Market Fit Show | Startup Podcast for Founders·10 days ago

Plaintiff Law Firms Were a Better AI Target Than Big Law Due to Repeatable Workflows

Eve found Big Law wanted bespoke AI projects with marginal gains. In contrast, plaintiff firms had highly repeatable workflows where AI could drive massive efficiency, perfectly aligning with their contingency-fee business model, making them a far better target market.

He fired all his customers. Then built a $1B startup in 2 years. | Jay Madheswaran, Co-Founder of Eve thumbnail

He fired all his customers. Then built a $1B startup in 2 years. | Jay Madheswaran, Co-Founder of Eve

A Product Market Fit Show | Startup Podcast for Founders·10 days ago