Founders Who Sold Out on YouTube, Reddit, and Instagram Now Regret Their Timing

The Founders Who Cashed Out on YouTube, Reddit, and Instagram—and Missed Out on Becoming Today's Billionaires In a tale of what-ifs and could-haves, the stories of YouTube's Chad Hurley and Steve Chen, Reddit's Steve Huffman and Alexis Ohanian, and Instagram's Kevin Systrom and Mike Krieger serve as cautionary tales for entrepreneurs who have cashed out on their startups. These founders sold their companies at a fraction of what they are worth today, leaving them to ponder the "what ifs" of staying independent. According to reports, YouTube's Hurley and Chen sold the video-sharing platform to Google in 2006 for $1.65 billion, a sum that has grown more than 333 times since then. Reddit's Huffman and Ohanian sold their social news site to Condé Nast Publications in 2006 for an estimated $20 million, while Instagram's Systrom and Krieger sold the photo-sharing app to Facebook in 2012 for $1 billion. "I think we were just naive about how big it could get," said Huffman, Reddit's co-founder. "We thought we had a good shot at being one of the top 10 websites, but we didn't think it would be one of the top three." The decision to sell out is often driven by financial considerations, with founders weighing the pros and cons of staying independent versus taking a big payday. However, as the stories of these founders illustrate, selling out can come with long-term regrets. Mark Zuckerberg, Facebook's co-founder and CEO, is often cited as an example of what could have been. In 2006, he received massive offers from Viacom and Yahoo to buy out Facebook, but chose to reject them, believing that the company still had plenty of room for growth. "We were a small team at the time, and we didn't think we needed any more money," Zuckerberg said in an interview with Fortune. "We thought we could just keep going on our own." However, not all founders are as fortunate as Zuckerberg. The stories of Hurley, Chen, Huffman, Ohanian, Systrom, and Krieger serve as a reminder that the decision to sell out can have far-reaching consequences. "It's a tough decision, but it's also a personal one," said venture capitalist Fred Wilson, who has invested in numerous startups over the years. "Founders need to think about what they want to achieve with their company and whether selling out is the right choice for them." Today, these founders are left to wonder what could have been if they had stayed independent. While some have gone on to start new ventures, others have spoken publicly about their regrets. "I wish we had taken a little more risk," said Chen, YouTube's co-founder. "We were so focused on making sure the company was successful that we didn't think about the long-term implications of selling out." As the tech industry continues to evolve, the stories of these founders serve as a reminder of the importance of staying true to one's vision and taking calculated risks. Background and Context The decision to sell out is often driven by financial considerations, with founders weighing the pros and cons of staying independent versus taking a big payday. However, as the stories of these founders illustrate, selling out can come with long-term regrets. Additional Perspectives "I think it's a mistake for founders to sell out too early," said venture capitalist Marc Andreessen, who has invested in numerous startups over the years. "They need to think about what they want to achieve with their company and whether selling out is the right choice for them." Current Status and Next Developments Today, these founders are left to wonder what could have been if they had stayed independent. While some have gone on to start new ventures, others have spoken publicly about their regrets. As the tech industry continues to evolve, the stories of these founders serve as a reminder of the importance of staying true to one's vision and taking calculated risks. *Reporting by Fortune.*