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Reading: The founders who cashed out on YouTube, Reddit, and Instagram—and missed out on turning into at the moment’s billionaires | Fortune
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Asolica > Blog > Business > The founders who cashed out on YouTube, Reddit, and Instagram—and missed out on turning into at the moment’s billionaires | Fortune
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The founders who cashed out on YouTube, Reddit, and Instagram—and missed out on turning into at the moment’s billionaires | Fortune

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Last updated: September 13, 2025 8:48 am
Admin
1 month ago
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The founders who cashed out on YouTube, Reddit, and Instagram—and missed out on turning into at the moment’s billionaires | Fortune
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Contents
  • YouTube: from $1.65 billion sale to $550 billion international platform
  • Reddit: From Waffle Home to eventual IPO
  • Instagram: The picture app that Fb grew by 100x
  • The founder dilemma

To promote or to not promote.

That’s the main dilemma founders all over the world face: As soon as they’ve began to get sufficiently big to draw the eye of consumers, they face the choice of whether or not to money out now, or use the praise as gas to go even greater.

Whereas it might look like a no brainer to say sure to an acquisition to the tune of tens of millions—and even billions—it may be arduous to later relaxation simple interested by how rather more you might have made independently. 

There could also be no higher latest case research than Mark Zuckerberg. In 2006, he obtained huge affords—$750 million from Viacom and $900 million from Yahoo—to purchase out Fb. However, as a 22-year-old, he was bullish that he nonetheless had loads of runway left.

“We’re focused on building the company for the long term,” Zuckerberg stated on the time. Right now, the social platform now often known as Meta is value simply over $1.9 trillion—a 2,100x enhance over twenty years. And Zuckerberg’s personal wealth has ballooned to over $260 billion, based on the Bloomberg Billionaire Index.

Years later, Fb started to make its personal acquisitions; notably providing to purchase Snapchat for $3 billion in 2013. However, Snap founder Evan Spiegel resisted, and at the moment, the picture social platform is value $12 billion.

After all, in each of those cases, the founders are actually members of the ultrawealthy and made way more by ready versus promoting out early. Nonetheless, this isn’t the fact for everybody. 

YouTube: from $1.65 billion sale to $550 billion international platform

When YouTube’s first-ever video—”Meet me on the zoo”—went dwell in 2005, nobody might have anticipated that the video platform would explode onto the web.

The expansion was so substantial that simply over a 12 months after founding, cofounders Chad Hurley, Steven Chen and Jawed Karim determined that Google’s $1.65 billion supply was too good to withstand. 

“This is great,” Hurley stated in a video posted when the sale was in fall 2006. “Two kings have gotten together. The king of search, the king of video have gotten together. We’re going to have it our way.”

Hurley, YouTube’s then-CEO, obtained shares value about $345 million by the point the Securities and Alternate Fee paperwork have been launched a couple of months later, based on The New York Instances. Chen, YouTube’s then-CTO, obtained about $326 million in shares; and Jawed Karim, who left the enterprise early to return to highschool, bought $64 million.

Whereas the sale made them financially safe for all times and cemented their standing as tech pioneers, it was only a fraction of the $550 billion that YouTube is valued at at the moment, a 333x enhance (unadjusted for inflation). For Hurley and Chen, their present slice may very well be value some $100 billion every.

Reddit: From Waffle Home to eventual IPO

After strolling out of his LSAT examination 20 minutes in and heading to a Waffle Home, Alexis Ohanian determined he wished to turn into an entrepreneur. And after assembly Steve Huffman as college students on the College of Virginia and later becoming a member of forces with Aaron Schwartz, the foundations for Reddit have been created in 2005.

Inside a 12 months and a half, the social platform exploded to over 70,000 every day distinctive guests, and consumers got here knocking. However as a substitute of holding out, the cofounders, who have been of their early 20s, couldn’t resist the $10 million supply from Conde Nast. Plus, Ohanian’s life was a bit in shambles: his girlfriend on the time was in a coma, his canine died, and his mother was recognized with terminal mind most cancers.

“As a first-time CEO fresh out of college, you’re feeling invulnerable, feeling really good about building this business,” Ohanian informed Wired final month. “And then all of these things happen. And in particular when my mom was diagnosed, it really framed mortality for me in a new way.”

Flash ahead to at the moment, Reddit is now value over $45 billion after going public earlier this 12 months. The founders may very well be sharing a pie over 4,500x the scale of the unique sale. Actually, Ohanian would even surpass his spouse, Serena Williams, together with her $350 million internet value.  

Instagram: The picture app that Fb grew by 100x

Instagram exploded on the social media stage in late 2010, with 1 million customers registering inside simply two months of its creation, and consumers quickly began expressing curiosity within the photo-sharing app.

In April 2012, Fb introduced it was buying Instagram for about $1 billion in money and inventory. It left cofounder Kevin Systrom, then 28, with about $400 million and Mike Krieger, then 25, with about $100 million; the remaining was divided between traders and Instagram’s 11 different staff.

And whereas the payday was substantial, it was not as rewarding for the cofounders as they anticipated.

“I think the biggest lesson … coming into a fair amount of money pretty quickly, was that money itself is no end. It doesn’t make you happy. It doesn’t solve health problems. It can help in those things,” Systrom stated at SXSW in 2019.

The cofounders determined to promote partly as a result of Zuckerberg allowed them to remain at Instagram; Systrom remained as CEO and Krieger CTO till 2018. Nonetheless, it additionally gave them a first-hand view into the wealth they may have made alone, with the photo-app hovering to a $100 billion valuation. Right now, it’s value about $114 billion, based on Kantar—that means every of the cofounders’ internet worths can be properly into the multi-billions.

The founder dilemma

There’s no query that in every of those circumstances, the acquisition had a constructive influence on every firm’s general success. And whereas the founders of YouTube, Reddit, or Instagram could have missed out on billions extra in wealth (Systrom, for instance, has billionaire standing at the moment), their early promote offered safety, assets, and freedom that they in any other case may need by no means obtained. 

It stays an almost not possible recreation to foretell if the startups might have scaled on par with out their new company father or mother. However finally, these examples underscore simply how the choice to promote may be one of many hardest—and most impactful—an entrepreneur could ever make.

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