Company: Fiveable

Founder and CEO: Amanda DoAmaral

Year founded: 2018

Fiveable is a startup supported by Northwestern Mutual Cream City Venture Capital.

After five years of teaching high school history, Amanda DoAmaral left the classroom without a clear idea of what she wanted to do next. So when some of her former students reached out asking for help preparing for their advanced placement classes, she was happy to oblige. She started livestreaming teaching sessions, and before she knew it, her audience grew to 2,500 kids. That sparked her decision to turn her project into a business.

DoAmaral ended up founding Fiveable, a social learning community that provides live review sessions, interactive study guides and competitive trivia games aimed at helping both students and teachers prep for AP exams. Fiveable takes its name from the highest score you can get on an AP exam, and when DoAmaral was teaching AP classes, her students were passing the tests with scores that were 2 points higher than the national average. She wanted to help students across the country do the same, while adding an online community aspect to their learning.

Below, DoAmaral explains how she made the leap from teacher to CEO, the surprising way the pandemic has impacted her business and how she embraces disruption as an entrepreneur.

How did you prepare for your transition from teacher to entrepreneur?

I did a lot of online research into startups on YouTube and read different blogs and entrepreneurs’ Twitter feeds. I actually met the members of my early team on Reddit. I was encouraged to find there was a lot of overlap between teaching and running a business. You have to be data-focused, and really creative and nimble about fixing any problems that arise. Both roles also force you to consider where you’re going, and then you reverse plan into that. So this direction made a lot of sense for me because I knew I had more experience dealing with this specific problem than other entrepreneurs who were working on the same thing.

Which entrepreneurs inspire you?

I follow a lot of tech company founders on Twitter, such as Backstage Capital’s Arlan Hamilton and Austen Allred, cofounder and CEO of Lambda School. They change the way we think about the world. Many of them were initially written off or told their idea was crazy, but then they went out and raised a lot of money and built very successful businesses. I admire people who are clearly going against the grain because they know what they are doing is right.

How has the coronavirus impacted your business?

It has actually accelerated our plans. People in edtech have been thinking about innovation for a long time, but the problem in the education space is that it always moves very slowly. Change is difficult because the institutions are entrenched and don’t adopt technology very quickly.

But COVID-19 shoved almost all of education into the 21st century overnight. In some ways, it was shocking to see how many schools were not ready for remote learning and how much that impacted students and teachers. There are certainly a lot of growing pains and inequities right now that we need to address, but it’s definitely pushing all of us into the right direction. It feels like anything is possible right now.

We don’t know what school or any part of education will look like next week — let alone next semester or next year or in five years — but I think everyone agrees that our education system is not successful. So to have this moment where most people are accepting that change is needed is exciting. Things can be disrupted in good ways that will lead to more students getting what they need to succeed.

What advice would you give to other women who have an idea for a business?

The biggest thing is just to do it. Most women, and people of color in particular, set really high bars for themselves, because the world does. That holds us back in a lot of ways. In the very early days of a startup, whether you have traction or not, the founder needs to be the champion of that product, that solution or that idea. Articulate your vision for what you want to do and practice that as much as you can. Eventually, you’ll pitch it to the right person at the right time, and that can change everything.

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