Amanda DoAmaral of Fiveable

An exclusive Tech Tribune Q&A with Amanda DoAmaral (co-founder and CEO) of Fiveable, which was honored in our:
Tell us the origin story of Fiveable – what problem were you trying to solve and why?

I was a high school teacher for five years and after I left my school, my former students started reaching out to me for help. They were feeling unprepared for their upcoming AP US History exam, so I started building study groups for students to support each other. The more I worked on solving this problem, the more I realized that the students were tapping into an overlooked need in educational spaces. Students were craving a way to connect with peers who were studying the same thing at the same time, and if we connect the students, then we can help them overcome any obstacle they face due to lack of resources or school limitations.

What was the biggest hurdle you encountered in your journey?

In the early days, the most difficult challenge was fundraising because I was a “startup outsider” and traditional investors saw us as “too risky”. Meanwhile, white, male founders with degrees from Stanford were more of a “pattern match” and had an easier time raising funds. In order to overcome this, I had to spend more time building relationships and really impress folks with our execution, which we did. COVID shook things up for as well because the idea of a social learning platform quickly went from a pipe dream to an inevitable future of edtech. The biggest hurdles we face now are much more around building the team and scaling operations.

What does the future hold for Fiveable?

We have a deep conviction to social learning and we plan to be the leading platform for students to learn together. We’re focused now on integrating the recently acquired Hours platform and growing our content library to cover every topic a high school student would need. Our hope is that by creating space for student-led communities, we will also empower young people to collectively advocate for educational reform on every level. Students have power in numbers and social learning can help them unlock that power.

What are your thoughts on the local tech startup scene in Milwaukee?

The Milwaukee startup scene has grown immensely over the last decade, led by creative and passionate tech leaders. There are thriving communities of founders and investors, as well as a number of resources built up for every stage. The biggest challenge here is that the city is still very segregated and the startup scene is too. While there are incredible supports that exist, they don’t always reach the black and brown communities across the city. I think the conversations in the last year have led to intentional ways to create equity, but there is still work to be done, just like in every city. With that said, I’m very excited about the future of tech in Milwaukee.

What’s your best advice for aspiring entrepreneurs?

I always advise founders to internalize two things: 1) There are no rules and 2) Trust yourself. In startups, there is no one way to get things done. There are so many different paths that can form and the reality is that there are no rules as to which you have to take. You don’t have to reach milestone “x” before you can unlock opportunity “y”. There’s just the will to build and as a founder, you have to find a way to make it happen. What becomes the most important is your ability to trust yourself and the decisions you make. The founder’s job is really just to make decisions, and most of the time, there is no clear right answer. You gather the data, talk to stakeholders, and eventually just need to trust that you are making the best decision at the time.


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