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 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.

With my return, we redesigned the site, moved Reddit onto mobile, and focused on building a sustainable business model.

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.

In 2006, major tech companies like Google and Yahoo began expressing interest in acquiring Reddit, highlighting its growing presence in the online space.

Returning to Reddit in 2015 was the hardest decision I've ever made, as I had to leave Hipmunk, but I felt a strong responsibility to help the company I co-founded. Reddit is more important to the world than many realize, and it would be a shame if it didn't live up to its potential.

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.