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Table of Contents

• Some Epic Venture Misses

  • Venture is, at its core, about experimentation.

My name is Gerry Hays, Founder & CEO of Doriot® (pronounced “Doe-ree-oh”), a movement to break open the gates of venture and expand innovation and wealth beyond an elite few. Democratize Venture is my platform to explore the venture markets and share the insights, strategies, and frameworks I bring into the classroom. It’s where education meets execution—for anyone ready to play the startup game.

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Some Epic Venture Misses

Venture Capital, to a large degree, is shrouded in mystery. But peel back the layers and what you’ll find isn’t magic — it’s a group of decision-makers making bets based on gut feel, biases, and the momentum of their networks. These are the people who decide who gets a real shot at building a breakout company. And they’re often seen as the most qualified to make those calls.

But the truth is that nobody is ever truly qualified to make these calls. VCs are human, and they are prone to their own biases, fears, and insecurities. They want to be contrarian, but they don’t want to take unnecessary risk.

And as a result, they get a lot of deals wrong — and they miss out on some extraordinary opportunities.

Here are just a few of the legendary “oops” moments that still echo through startup history:

Google
Bessemer Venture Partners passed on meeting Larry Page and Sergey Brin in a garage. James Altucher said Google was “too small to matter.”

Facebook (Meta)
Battery Ventures called Facebook “the biggest fish that ever got away.” Joe Green, Zuckerberg’s roommate, missed out on a 5% stake — because his dad told him not to.

Apple
HP turned down Steve Wozniak’s Apple I design five times. Atari’s Nolan Bushnell declined to invest $50K for one-third of Apple. Ronald Wayne sold his 10% stake for $800. That stake would be worth over $200 billion today.

Airbnb
Fred Wilson of Union Square Ventures — one of the best in the game — couldn’t get past the idea of air mattresses in strangers’ living rooms. Today, Airbnb is a global hospitality platform.

Amazon
Warren Buffett admitted he “blew it.” Charlie Munger said they “sucked their thumbs” while Amazon reshaped e-commerce. Even GEICO (owned by Berkshire) was benefiting from Amazon ads — and they still passed.

Netflix
Offered to Blockbuster for $50 million. They laughed. Now, Netflix is worth over $150 billion. Blockbuster is a trivia question.

Starbucks
Shaquille O’Neal turned down the chance to open Starbucks franchises, saying he’d never seen a Black person drink coffee.

And if there’s one lesson in all of these legendary misses, it’s this:

Venture is, at its core, about experimentation.

The more experiments you’re in, the more you learn. And the more you learn, the more likely you are to spot the next opportunity — before the rest of the world does.

Because the real engine of insight — and of opportunity — isn’t prediction. It’s curiosity.

The best early investors aren’t fortune-tellers. They get into lots of tests with lots of different startups. They listen. They reflect. They stay in motion. They think of themselves as part of the experimentation process.

When you’re investing in startups and start thinking like a scientist — when every decision becomes a learning moment — you stop chasing certainty and start creating opportunity.

You won’t get it right every time. You’re not supposed to.

But if you keep experimenting, you won’t just avoid the misses — you’ll help build what comes next.

Wishing you a focused and fulfilling weekend,

– Gerry ([email protected])