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From 40 Rejections to $100M Raised

Fundraising
March 30, 2025
Edo Liberty explains how Pinecone overcame VC rejection to raise $100M and become essential to AI apps.
Topics discussed in the episode:
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What does it feel like to be right when others didn't believe you?
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How to adapt your product for future scalability?
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Why is aligning with your family crucial when starting a startup?
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Should you leave a high-paying job to start a startup?
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How to manage explosive growth during a market shift?
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Why simplifying your marketing message can boost adoption?
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How can talking to users help find product-market fit?
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How can simplifying your pitch help secure funding?

What does it feel like to be right when others didn't believe you?

Being proven right when others doubt you is validating.

"I remember meeting an investor... that had rejected me in my seed... In the meeting, he said... I now understand that what you were pitching that you were gonna do, you actually did... I said, isn't that how it usually works?"

• Persistence leads to success despite doubt. • Achievements can change skeptics' views. • Continue focusing on your vision.

How to adapt your product for future scalability?

Anticipating future scalability needs is vital in product development.

"We started seeing... what scale the workloads... look like... We basically redesigned the whole DB... We had to rebuild the entire system."

• Plan for future scaling from the start. • Be willing to make strategic changes. • Investing in redesign can yield long-term benefits.

Why is aligning with your family crucial when starting a startup?

Aligning with your family is essential when embarking on the startup journey.

"She said, what's the worst that can happen?... Go do it. It's what, that's your calling... Let's do it."

• Ensure your family supports your decision. • Communicate openly about risks and expectations. • Plan finances together to handle uncertainties.

Should you leave a high-paying job to start a startup?

Leaving a well-paying job to start a startup is a tough decision requiring careful thought.

"I had a pretty fun and exciting job at AWS... There's something really nice about like a nice lump of cash landing in your bank account every month."

• Weigh the risks and rewards of leaving stability. • Assess your passion and belief in your idea. • Prepare for financial and lifestyle changes.

How to manage explosive growth during a market shift?

Rapid market shifts can cause explosive growth; effective management is critical.

"We started getting thousands of signups a day... we just couldn't meet the demand. It was insane. We started spending insane amounts of money on the free tier."

• Be prepared to scale infrastructure rapidly. • Monitor costs closely during sudden growth. • Focus on maintaining service stability.

Why simplifying your marketing message can boost adoption?

Simplifying your marketing message makes your product more accessible and boosts adoption.

"Here's the API. Here's how much it's gonna cost you. If you like it, great. If you don't like it, go to hell... It went from essentially nothing to something that looks like adoption."

• Keep your message simple and focus on essentials. • Cut unnecessary details from your marketing. • Clear communication attracts customers.

How can talking to users help find product-market fit?

Engaging directly with users can reveal insights that lead to product-market fit.

"We went to the people who use our system... and we just went to them and we asked them, what do you call this thing? ... 'We just call it a vector database.'"

• Talk to your users to understand their perspective. • Use customer feedback to shape your product positioning. • Align your product naming with user terminology.

How can simplifying your pitch help secure funding?

Simplifying your pitch can help secure funding when investors don't grasp your complex product.

"I'm going to just rewrite the whole thing... and I went to the call and said, hey, forget everything that I told you, we're just building a different kind of database. That's it."

• Simplify your pitch to its core essence. • Present your idea in a way that investors can easily understand. • Focus on the main value proposition.