Condé Nast acquired Reddit for $10 million, presenting a crucial decision for the founders: to sell to an established media company or gamble on Reddit's potential as part of the internet's future.

The acquisition by Condé Nast in 2006 was a crucible moment for Reddit, providing liquidity but also revealing the differing priorities of team members after the acquisition.

Reddit was founded in 2005 by college roommates Steve Huffman and Alexis Ohanian, initially as a mobile food ordering app idea, but it evolved into a platform for sharing and discussing topics.

In 2011, Condé Nast spun Reddit out into an independent company again, which is rare in my experience, allowing us to fundraise and bring in new talent like CEO Yishan Wong.

By the time of the acquisition discussions, I was working 16-hour days, balancing my responsibilities at Reddit with my graduate studies, which was a challenging period for me. When I received an offer to sell Reddit for $10 million, I realized I could make life-changing money in just a year of work, which was more than my parents would earn in their entire lives.

The success of funded companies like Dropbox and Reddit added legitimacy to Y Combinator, leading to increased media attention and respect from investors.

After turning down Yahoo's offer, we decided to focus on connecting more people, which ultimately led to significant growth.

At the time of Yahoo's offer, Facebook had 10 million users, and it wasn't clear that we would succeed beyond that point, leading to intense discussions within the company about whether to sell or continue building.

In 2006, YouTube's board faced a crucial decision on whether to sell the company or continue independently, ultimately leaning towards an acquisition due to overwhelming legal pressures.