Q&A with Founder & CTO of Quizlet | Remote Students

Hear how Andrew Sutherland started Quizlet at 15, and his insights on building a product and raising VC funding

Abinaya Dinesh
Nova
8 min readSep 30, 2020

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Members of the Remote Students Community had the opportunity to meet Andrew Sutherland, the founder of Quizlet, this week and ask him about his crazy founding story, how he worked on Quizlet for 10 years before raising any funding, and his tips on being a great leader. Apply here to join our community and meet our amazing lineup of guest speakers, including founders like Andrew!

Andrew Sutherland is the Founder & CTO of Quizlet! Quizlet is an education software company that serves millions of students and teachers every month. Andrew started Quizlet at 15 years old while taking a high school French class, continued working on it studying computer science at MIT, and has grown it to a successful company with more than 200 employees.

A student’s savior, bringing up grades one subject at a time.

What is the story behind Quizlet, and how has it grown to be where it is now?

The idea for Quizlet started when I was 15 and taking a French class. I had a really difficult teacher who wanted us to deeply learn French. That meant doing fun things like memorizing and reciting French poems, cooking French food, and watching French movies, but it also meant learning a ton of vocabulary and grammar. Usually, she would give us these quizlettes she made, which were little vocabulary quizzes. One day, we had to learn 111 French animals in one night, which was a crazy assignment, so I asked my dad to quiz me by saying one of them and trying to keep track of which ones I got wrong. This was not really working, and my dad would mess up a lot, so I looked to programming for the answer. Since I had done a bit of programming in the past, I had this inkling that I could make a program that would keep track of what I had already gotten right and what I needed to keep working on as I studied.

I built a tiny prototype of that, and on the next test I got a 100%, which was the first time I’d ever done that. From there, I continued working on that tiny prototype just for fun and on weekends, and gave it to some of my friends to use. Startup culture was hugely different in 2005 than it was now, so I wasn’t thinking about it being a big business or anything. But, after about 1.5 years, I opened up that prototype to the public, and teachers and students started using it and creating their own content on it.

Meanwhile, I got accepted to MIT, and after 3 years I had a hard time juggling school work, social life, and Quizlet. At that point, I felt a commitment to the ~1 million monthly users and wanted to create a reliable and stable product for them. That’s when I dropped out of MIT and started working full time on Quizlet, as well as hired my first few employees.

After that, we worked on building our consumer products, like the Android and iOS apps and making them really easy to use. In 2015, we entered the VC world and raised our first round of funding of $12 million dollars. From there, we’ve gone through two more rounds and now have 200+ employees at locations around SF, London, and Denver.

What is your advice on managing schoolwork and startup life?

The easiest answer is getting enough sleep. However, in general, I’ve come to believe that,

it’s better to do fewer things well than a lot of things, not that well.

There’s always the temptation of trying to balance a million things at once, like doing research, an internship, school work, and having a proper social life all at once. While I do think that college is a time when you are sort of indestructible, and can do it all, it is possible to make hard decisions and do fewer things even within that context. The main benefit of doing is this is to try and try to do each one better. It is a hard struggle, but the payoff of focusing on what you really care about can be great, so that you’re finally at a point where you aren’t just passing through each one and not making any useful impact.

Does Quizlet have any internship opportunities?

We’ve always had summer interns and a few outside of that, and interns have been an awesome way to build the future of Quizlet. For example, most of the people interning here have used Quizlet a lot and can teach our full-time workers how to better build the product. We also try to put them on projects where they can build what they wish existed on Quizlet. We post internship opportunities on our job site whenever they’re available, usually in the summer.

What advice do you have for a budding software engineer, hoping to flesh out a startup idea?

The advantage that I had that I didn’t even realize at the time was that I was it’s biggest user, for a long time, and that made me keenly aware of its existing shortcomings and also extremely motivated to fix them. That meant that the pace of iteration and improvement was rapid because I had high standards for myself and I wanted the product to be great. For example, if I was studying for a history test, I would realize I needed to build a feature like inline editing because I saw a typo or something that needed to be changed. And I just, like, put my books aside and add that feature, and that was it! There’s no substitute for that sort of thing; being able to use the product and see all of the ins and outs and flaws, and being that motivated to fix it.

The biggest issue I see for people trying to found a company is that they see an issue, or a gap in an industry that they want to fill, and they get really excited about fixing that issue after looking at it from an outside perspective. However, they don’t really get into the user stories and the more bottoms-up approach, where you’re experiencing the pain yourself and wishing that something existed to specifically solve that problem. To me, it’s a much better formula for starting a company to be able to really empathize and understand the issue firsthand, than do any sort of market analysis and come up with an idea through that.

Is there anything you wish you told your first-year self at MIT as a young founder?

One piece of advice I would have is to really understand best practices around investing and equity. Whether you have a co-founder or not, make sure you structure ownership, because I made the mistake if giving people ownership without enough investing or enough terms, that were pretty expensive to fix. There’s lots of resources online about the best practices for investing and sharing ownership and investing if you have a co-founder, so I’d definitely recommend looking into those.

What books, blogs, podcasts, or social media influencers do you recommend?

I read Hacker News, and I think its good to stay up to date on the startup world and software and technology. I’m also pretty interested right now in tools for thinking better thoughts. In this era of the smartphone being a very distracting device that monopolizes your attention, it can be harder to get into a state where you’re really thinking deep thoughts and connecting ideas to other ideas in a flow state. Two resources I recommend on that are Andy Matuschak’s twitter/blog and this note-taking company called Roam that has cool thoughts on that too.

What is the best and the worst thing about being a solo entrepreneur?

The best thing is that you’re self reliant, and it’s your responsibility to make your project work well and you carry the burden and the credit at the same time. The hardest thing is that you’re not going to be good at everything, and having a co-founder with complimentary skills can be incredibly enhancing and powerful.

Do you recommend trying to function just off of revenue for those first 10 years?

I think there were pros and cons to doing this. The most valuable thing that we got from it was that it engrained discipline into our company. There are a lot of companies that raise a bunch of money based on promise of user growth, and hire a bunch of people to go really fast and go from there, but they put themselves in this precarious position where they have to grow really quickly or they die. This is a super stressful position to be in, and for Quizlet, we were never really in that position. Even now, after raising our money, almost all of our expenses are paid for by revenue, and not by VC money. It means that we’ve really been in control of our company, and if there’s ever a slowdown in our business, then you can smooth that out and not be so worried about needing to lay people off, or something.

If I were to do it again, I’d still Bootstrap for a while, but I would probably start raising a few years earlier. What raising did for us was that it accelerated us and took us to the next level. We were able to move a lot faster and we were much more ambitious with thinking about going internationally and make learning better at a larger scale than we were before. If we had started two years earlier, now we would be 2 years ahead in getting on all of these things.

When making leadership decisions, do you rely mostly on facts or emotional intuition?

It’s essential to have some mix of intuition-driven and evidence-driven decisions. Because you are a founder, and you have been thinking about this product for such a long time, your thoughts about it will be deeper than it’s possible to explain logically sometimes. And so, your intuition is a really powerful thing that you really need to understand, listen to, and leverage. If you’re all evidence-driven, you’ll miss some big opportunities and maybe you won’t try some of the counterintuitive things that your gut may tell you to do, but there’s no evidence for doing so. What makes a founder special, when compared to a hired CEO or set of leaders is that they don’t have the same deep intuition about the product.

At the same time, as the company grows, there will be a lot of people who haven’t worked with you the whole time and know all of the deeper reasons as to why you make a certain decision. To be able to reason with an idea and explain it to others, you need a lot written down, and you need to make objective criteria for a specific decision. Mainly, you need to be able to explain why you’re doing certain things and have those be logical, rational behavior. If everything you do is irrational and gut-based, no one will want to work with you, so its super essential to have a good balance of both.

Join Remote Students for access to more opportunities to meet amazing founders like Andrew Sutherland! Watch the full recording here to hear Andrew’s unconventional funding process (29:20), all of the things he’s been up to since December (35:30), and his experience with mentorship while building Quizlet (42:00).

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