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.

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.

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.

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.

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.

One mistake during the acquisition was assuming that advertising would transfer easily to Reddit, which was a very different product compared to others like style.com.

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.

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

I found Y Combinator because I was on Reddit during graduate school, where I discovered Paul Graham's essays that inspired me to pursue starting a company, despite the prevailing belief that the web was over after the dot-com crash.