Harvard in Tech Spotlight: Charlie Cheever, early Facebook engineer and co-founder of Quora and Expo
I spoke with Charlie Cheever, early engineer at Facebook, co-founder of Quora, and co-founder of Expo. Charlie shared key lessons he has learned about starting communities, online information sharing, building companies, and advice for Harvard students and founders.
Starting Quora
I asked Charlie, when starting Quora, what were sites, authors, and stories that shaped how he wanted to help people interact and exchange information online. He shared that he started by looking at what was working on the internet from 2000 to 2010: platforms like LinkedIn, YouTube, and Facebook showed that people liked to upload specific types of content like resumes, videos, and photos, respectively. The landscape was maturing with both image and text uploads, but it didn’t feel like there was a place to upload everything in your brain on topics ranging from work to TV shows to travel and living in different locations.
Blogs were an early inspiration for Quora — people wanted to write long form but didn’t know what to focus on. People were sort of “reverse blogging” — figuring out what was popular already and creating a personality to write in these areas with existing demand.
Yahoo Answers was another inspiration. They were doing 30 million uniques a month and were a way to identify what was popular. Similarly, Wikipedia was an inspiration as well — Charlie found someone in Oregon who was spending a lot of time editing Wikipedia articles and started brainstorming and working with him. More topic specific communities were coming up like Stack Overflow, but Charlie wanted to create a broader version.
The Cold Start Problem
When asked how he overcame the cold start problem, Charlie noted that he leveraged, in part, a lot of his friends in graduate school. He realized that many grad students were working on cool research, had free intellectual energy and time, and were excited to answer questions and share more about their work. Charlie would also just do research to answer random questions even ones outside of his areas of expertise (like questions on sharks). His team would also walk around wearing Quora shirts that said “PIOTS,” which stood for “put it on the site” to remind people to use Quora.
Quora had specific power users who contributed immensely — Marc Bodnick was one of them. He loved knowledge, worked in investing, and just fell in love with sharing knowledge. He would spend 12 hours a day on the site answering questions and ended up joining Quora early (he recently started a company doing knowledge sharing with crypto for rewards).
Maintaining quality and engagement
I asked Charlie how he kept the bar of quality high and continued to drive engagement over time at Quora. Charlie underscored the importance of creating a culture and reinforcing it. They dealt with spam as quickly as possible, so people didn’t see it and spiral into bad behavior. Power users became admins, and Quora created a community around them. They brought on moderators and gave them control. Machine learning was also becoming a useful flag for things that human moderators should look at.
Because Quora was a startup, they were able to scale intentionally. Moderation is easier to implement when it’s gradual. Like Amazon’s principles, Quora had 2 rules that were constantly hammered into the team: 1) make every question the best page to see if you have that question and 2) be nice, help people feel safe and don’t drive people away.
Lessons from Facebook
Charlie had been an early engineer at Facebook after a few years at Amazon. He was at Facebook when it was just a college site. He sat next to Dustin Moskovitz, who was a co-founder of Facebook. Dustin would say things like “when we have 6 billion people on Facebook…” when the company only had 1 million college student users. At first, Charlie thought it was a rather out there comment, but within a year of working at Facebook, he realized getting to 6 billion was really possible. Be at the right place with the right ambition, and you can grow a ton.
Charlie also highlighted the importance of interest. People with passion make a big difference as does the clarity of understanding that comes with it. Things could be chaotic at times, but everyone knew what had to happen.
Charlie admired Facebook’s focus on design. Facebook had a feature to show you other friends at other colleges, but it made the page look too busy, so the designers decided to sort by volume of friends you had at each college and only show the highest volume colleges.
Attention to detail for user experience was also critical — for example, if someone didn’t have photos yet, Facebook would ensure that every link would lead somewhere interesting instead of a dead end.
Founding Expo
After leaving Quora, Charlie was most interested in mobile products since mobile was rapidly growing (until ChatGPT was released, everything interesting was mobile). At Quora, it had taken them forever to build an iPhone app. Building the original version of Quora took 4 people 5 months. It was crazy that it took twice that long to build the iPhone app wrapper. Moreover, there were additional ongoing issues like keeping the Android and iPhone apps in sync.
Charlie met his Expo co-founder, James Ide, when he was graduating from college and interviewed at Quora. They stayed in touch. When Charlie had the idea for Expo, he shared it with James, and he quit his job just 36 hours later to join Charlie. In the beginning, neither of them knew how to do mobile development. They spent 1–2 years learning everything about building mobile apps. When it comes to mobile development, there are many additional considerations — for example, people fat finger their phones all the time, so unlike with desktop, you can’t have very precise buttons or small buttons.
Over the years, Expo has grown to power some of the top apps in the app store. Charlie’s goal is to have 80 to 85% of mobile apps be built with Expo. He wants to make the iPhone to Android transition smoother for developers. Web will be a 3rd platform for Expo — everyone needs a website, and you want it to be consistent with mobile. Bluesky, for example, has their entire codebase with Expo. There is an opportunity to unify everything and make Expo the obvious way to build anything. AI is changing the game in so many ways — Expo will make sure that ideas can come to life as quickly and effectively as possible. Recently, Expo launched hosting with API routes to 1) help more with distribution to get apps to the app store and 2) let one team work seamlessly across the frontend and the backend.
Advice for Harvard students and founders
Reflecting on his time at Harvard, Charlie mentions the extracurricular leadership he had. At the time, he thought many of these were wastes of time, but 6 months into working at Facebook, Charlie realized the power of having had these experiences. His work wasn’t just about technical prowess and lessons learned in class but also how to work with people and manage groups.
For aspiring founders, Charlie shares: the essence of doing something important is solving a problem for people and making something people want. Startups are in fashion now, but the fancy stuff is just trapping. The most important thing is that you build something people want and find a way to get it to them.
