FAM FEATURE: Amanda DoAmaral of Fiveable

How Amanda made the jump from history teacher to tech CEO with 50%+ market share

Throughout my career as a venture investor, and now the General Partner of 27V, I’ve operated under the philosophy that great ideas — and great founders — can come from anywhere. Let me tell you the story of how I first came across the indomitable Amanda DoAmaral, CEO and founder of Fiveable – on YouTube!

Back in 2019, since I hadn’t been able to make the ASU GSV Summit, I was catching up on their panels. 27V was a seedling idea at this point. I had always been passionate about education and wanted to explore the best way to have an impact. I watched this panel on teachers embracing side hustles, and heard Amanda talking about the work she was doing at Fiveable. She said she started Fiveable because she wanted to scale her own impact as a teacher beyond the limitations of the classroom, reach more students, and give teachers a way to make a more sustainable living. I was struck by her intense focus on improving outcomes for both students and teachers, so I did what I usually do when I come across interesting people – I dug deep to learn more about her story.

Unexpectedly, the first recommended video wasn’t another panel or interview but a cellphone video of Amanda at the AP World Open forum, in a heated conversation with Trevor Packer, the head of AP at College Board. She’s standing at a microphone passionately advocating for her students against the decision to omit slavery from the AP World History test. She argues that not only is it an important context to understanding the history that comes after it, but also “to show their Black and brown and Native students that their histories matter.” To raucous applause, she speaks truth to power and dismisses Packer’s (frankly pretty weak) excuses in the no-nonsense tone characteristic of great teachers.

She made quite a splash. In addition to opening up the conversation on the role of history in the classroom and the responsibilities of publishers to their students, she was quoted in the Atlantic and the Washington Post and even memed. Most importantly, she was a vocal part of the backlash that caused the College Board to roll back their plans

Founders like Amanda are the reason I wanted to build a VC firm in the first place. They don’t just have a good business idea; they are fierce champions of education, who deeply care about teachers and students. And, as any VC will tell you, this intense focus on the user is what leads to massive outcomes 🦄.

I was all-in on Amanda, and after doing a bit more research on Fiveable and seeing students sharing their content on social media unprompted, I was all-in on her company too. I cold-messaged her on LinkedIn (this cold outreach is becoming a bit of a habit – read the story of my investment in Edgi Learning) and was shocked to hear that she was struggling. Fiveable was at a do-or-die point where they didn’t have enough cash in the bank to make payroll. She wrote about her experiences on the website.

On paper, this might have looked like a bad investment, but I knew two things. The first is that nontraditional founders like Amanda — former teacher, woman of color, fundraising from outside of big tech hubs — are often written off before they have a chance to prove themselves. Her dwindling funds said more about the biases & prejudices of VC investors than they did about her product.

The second is that investing in passionate people who care deeply about their users and the impact they’re having on the world is always a risk worth taking. So much so, in fact, that I invested my own money and time in Fiveable. 

Founders who have taken non-traditional paths to starting a business are often the closest to the problem they’re solving, which enables them to build sticky products that actually work. At the same time, the VC world plays by their own set of rules. As a GP, I’ve always considered it my responsibility to support our founders in navigating that world. Amanda and I have met regularly since that initial investment for charting out the tech world together.

As I’ve gotten to know her over the past two years, I’ve seen her grow into her role as a leader not just at Fiveable, but in the EdTech space at large. Now, with Fiveable reaching 50%+ market share among AP students, the tech world is starting to see it, too. With features in TechCrunch and too many podcasts to name, Amanda is generous with her time and knowledge, holding the ladder not only for students and teachers but entrepreneurs, too. 
Of course, I wasn’t the first person to realize Amanda was a rockstar🤘. She’d always been that person to her students. It’s about time the world sees it, too!

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