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Outlier’s Path

Random, Special, Serendipity (RSS)

In 2005, Steve Huffman and Alexis Ohanian were building MMM (mymobilemenu), a food ordering platform similar to DoorDash, in their college dorm rooms. They didn’t find traction, so they pivoted to Reddit, the “front page of the internet.” The site faced many challenges, including the fact that Reddit was written in Lisp. Reddit merged with Aaron Swartz’s company Infogami, and Aaron rewrote Reddit in Python to improve its scalability and performance. However, Reddit remained a slog. In October 2006, Condé Nast, a division of Advance Publications, acquired Reddit for $10m to $20m.

Under Condé Nast, Reddit steadily grew, but by 2009, Steve, Alexis, and Aaron had all left. Another Steve, Steve Newhouse, Co-President of Advance Publications, believed that Reddit could be much more. Steve spun off Reddit in 2010, and the community thrived with the new independence.

By 2014, Reddit had grown to the 18th most trafficked site on the internet, despite its dated user interface, which some derided as a raw RSS feed. Yet, with so much traffic, Sam Altman believed Reddit could build a real business. He led a $50m round at $600m post-money and invited many friends, including Sequoia. The post-investment plan was simple. Hire a management team, redesign the site, and move to mobile. Figure out the business later.

Nothing is ever simple with a startup. The Reddit community revolted and became increasingly belligerent toward Reddit, the company. Reddit employees had difficulty delineating the community’s wishes and the company’s objectives. Reddit went through several CEOs before Steve Huffman returned in 2016. Steve had the moral authority of a founder to set some ground rules, yet the community still pushed back on him. Undeterred, Steve pressed forward, hired a new management team, redesigned the site, moved to mobile, and, most importantly, built the business.

Throughout these challenges, Reddit continued to grow with the internet. Today, Reddit remains the 18th most trafficked site, with over a half billion MAUs and over 70 million DAUs and content to satisfy both mainstream and niche interests across 100,000 active communities. Redditors are a “special” audience. According to Reddit’s S-1, “people who visited Reddit in the United States, 32% were not active on Facebook, 37% were not active on Instagram, 73% were not active on Snapchat, 41% were not active on TikTok, and 53% were not active on X.” With this unique audience, Reddit was able to generate over $800m in revenue in 2023 and went public last week.

The story of Reddit, Steves, and Sam is undoubtedly circuitous and quite random. Yet, on your journey, I wish you lots of random connections with special people because those ingredients often lead to serendipity.