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.

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.

After the acquisition, Reddit struggled to attract the right talent and resources, leading to my departure to start Hipmunk, while Alexis pursued a career in investing.

At that time, there wasn't a clear monetization route for Reddit; we didn't have advertising or any real way to generate revenue, so we operated as a lean startup to survive with scarce resources.

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.

We chose to pursue advertising as a business model to keep Reddit free and open, aligning with our values and community expectations.

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.

After being rejected by Y Combinator with their initial idea, we were invited to join the program under the condition that we work on something else, which led to the creation of Reddit.

Many founders mistakenly believe that spending on marketing, especially through ads, will guarantee growth, but this often leads to wasted resources without learning valuable lessons.