The Story of Sequoia Capital's $6.4 Billion 'Revenge' on Mark Zuckerberg How the top venture capital firm had the last laugh -- all the way to the bank.

By Nicholas Carlson

This story originally appeared on Business Insider

He's become a successful CEO and a generous person, but ten years ago, Facebook CEO Mark Zuckerberg used to have something of an attitude.

For example, he used to carry a business card that read, "I'm CEO...Bitch."

Once, back then, Zuckerberg played a pretty nasty prank on top venture capital firm Sequoia Capital.

It was 2004, and Zuckerberg still wasn't convinced that he wanted to run Facebook forever. He thought maybe another startup idea of his, called Wirehog, would be a bigger success.

So he was out talking to venture capitalists about raising money.

Sequoia Capital reached out to him.

Zuckerberg had no intention of considering an investment from Sequoia. That's because Zuckerberg had hired, and become friends with, Napster co-founder Sean Parker. Sequoia had invested in Parker's startup Plaxo, and it hadn't gone well. There was bad blood.

But even though there was no way Zuckerberg was going to take Sequoia money, he took the meeting anyway. He had a prank in mind.

There were three elements to it:

First, Zuckerberg showed up intentionally late to the 8 a.m. meeting.

Second, he showed up late wearing ... pajamas.

Third, Zuckerberg walked to the front of the room and presented a PowerPoint deck titled "The Top Ten Reasons You Should Not Invest."

In the style of David Letterman, he began to tick his way down the list.

Some of those reasons:

  • "We have no revenue."
  • "We will probably get sued by the music industry."
  • "We showed up at your office late in our pajamas."
  • "Because Sean Parker is involved."
  • "We're only here because [a Sequoia partner] told us to come."

Obviously, Sequoia did not invest in Wirehog.

It never invested in Facebook either.

Even by 2010, Zuckerberg felt bad about the prank. He told David Kirkpatrick, author of "The Facebook Effect," "I assume we really offended them and now I feel really bad about that."

Yesterday, Zuckerberg made amends.

Yesterday, Facebook announced that it would acquire messaging startup WhatsApp for $19 billion.

Guess who was WhatsApp's sole venture investor -- according to Forbes, owner of about 40% of the company?

Sequoia Capital.

The firm Mark Zuckerberg pranked when he was a kid will make about $6.4 billion dollars on the deal.

Thanks to CityNotes CEO Dan Frommer for reminding me of the Sequoia prank, and to David Kirkpatrick for telling the story of the prank so well in "The Facebook Effect."

Want to be an BIZ Experiences Leadership Network contributor? Apply now to join.

Business Solutions

Stop Duct-Taping Your Tech Stack Together: This All-in-One Tool Is Hundreds of Dollars Off

Sellful combines the best parts of 25+ SaaS tools and lets you take the credit.

Business Ideas

70 Small Business Ideas to Start in 2025

We put together a list of the best, most profitable small business ideas for BIZ Experiencess to pursue in 2025.

Business Culture

4 Easy Ways to Build a Team-First Culture — and How It Makes Your Business Better

How creating a collaborative culture preps your business for prosperity.

Science & Technology

OpenAI's Latest Move Is a Game Changer — Here's How Smart Solopreneurs Are Turning It Into Profit

OpenAI's latest AI tool acts like a full-time assistant, helping solopreneurs save time, find leads and grow their business without hiring.

Starting a Business

I Built a $20 Million Company by Age 22 While Still in College. Here's How I Did It and What I Learned Along the Way.

Wealth-building in your early twenties isn't about playing it safe; it's about exploiting the one time in life when having nothing to lose gives you everything to gain.

Business Solutions

Tell Your Story and Share Your Strategies with the $49 Youbooks Tool

Use AI to craft full-length non-fiction books that can help build your brand.