A Product Market Fit Show | Startup Podcast for Founders

He got rejected by 40 VCs & had 6 months of runway—2 years later, he raised $100M from a16z. | Edo Liberty, Founder of Pinecone

Mar 17, 2025

Edo Liberty, founder of Pinecone and former AWS AI services leader, shares his entrepreneurial journey filled with challenges. He faced 40 rejections from VCs while launching his innovative vector database startup. However, a strategic pitch pivot enabled him to secure a $10M seed round, transforming Pinecone into a vital resource for AI applications when ChatGPT hit the scene. Liberty emphasizes the importance of market timing and practical solutions, providing invaluable insights for early-stage founders navigating the startup landscape.

01:02:14

Episode guests

Edo Liberty

AI Summary

AI Chapters

Episode notes

Podcast summary created with Snipd AI

Quick takeaways

Edo Liberty's transformation from facing 40 VC rejections to securing a $10M round illustrates the importance of perseverance and adaptability in fundraising.

Clarity in product communication was pivotal for Pinecone's success, emphasizing that understanding customer needs can drive significant adoption.

The timing of product launches, particularly in the AI space, shows that external market factors play a crucial role in startup success.

Deep dives

Founders' Control and Market Realities

Founders often misjudge the actual control they have over their companies and the market. They might think they can dictate how things work without considering customer input, but in reality, understanding customer needs is crucial. At the same time, founders may overestimate how much they can influence market trends and timings. The recent boom in AI technologies like ChatGPT shows that sometimes external factors shape business success more than individual efforts.

Intro

2min

Leaving Stability for Passion

6min

From Physics to AI: A Journey Through Machine Learning

23min

From Rejection to Success: The Turning Point in Fundraising

3min

Navigating Fundraising Challenges in Tech Startups

11min

From Struggles to Success: A Founder's Journey

14min

Navigating the Startup Landscape: Control and Market Influence

3min

Edo Liberty left a high-paying job at AWS—where he was building AI at the highest level—to start Pinecone, a company no one understood. He pitched 40+ VCs, got rejected by every single one, and nearly ran out of money. Then, he flipped the pitch, raised $10M, and built one of the most important infrastructure companies in AI.

Then ChatGPT dropped.

Suddenly, Pinecone was the must-have database for AI apps, with thousands of developers signing up daily. The company exploded, leading to a $100M round led by Andreessen Horowitz and a 10x revenue surge.

If you’re an early-stage founder, this episode is a must-listen.

Why you should listen:

•How he went from from 40 VC Rejections to a $10M Seed Round

• Why he quit a High-Paying Job at AWS to start a Startup

• The game-changing shift that made VCs finally “get it”

•What really happened inside Pinecone when AI took off

•Why most founders misunderstand market timing and what to do about it

Keywords
AI, Machine Learning, Startups, Entrepreneurship, Vector Databases, Fundraising, SageMaker, AWS, Technology, Innovation, Pinecone, vector database, seed funding, ChatGPT, startup growth, business model, AI, infrastructure, early stage founders

Timestamps
(00:00:00) Intro
(00:07:50) Edo's Story
(00:12:27) The Early Days of Machine Learning
(00:32:23) Seed Funding
(00:42:09) Unsustainable Scaling
(00:53:41) Told You So
(00:59:24) A Piece of Advice

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