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.

When I acquired The Onion, it was about saving the company from a failing business model and focusing on creating content that resonates with readers.

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.

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 decision to reject the offer was stressful, as many believed we should sell the company, and I realized I hadn't effectively communicated our mission to the team. Turning down Yahoo's billion dollar offer was painful because it led to a significant loss of trust within the company, resulting in many employees leaving due to a lack of belief in our vision.

The process of selling the company was very painful and arduous, especially since I had to maintain a double life and couldn't be transparent with my team during the acquisition process.

Amazon had been interested in acquiring our company for a long time, and their offer was compelling because we could remain a separate brand and business.

I turned down an acquisition offer from a clothing startup because I saw so much potential in Gobble and wanted to focus on solving a real problem in the meal kit space.

When we sold broadcast.com to Yahoo for $5.7 billion in stock, I was focused on protecting my investment from the market bubble.