Amanda DoAmaral: Founder of Fiveable

Amanda DoAmaral is an educator, activist, and entrepreneur on a mission to make educational opportunities more accessible and equitable for students. After teaching AP World History in Oakland, CA, where she served on the frontlines in the fight to protect an inclusive AP World curriculum, she changed roles to entrepreneur and founder in 2018. DoAmaral expanded the size of her classroom to roughly 40,000 students when she founded Fiveable, a social learning platform for students and teachers to engage after school through live-streamed lessons and Q&As, trivia battles, and supportive communities.

Fiveable has since expanded to offer test prep resources for 15 different AP subjects, helping its students achieve a 92% pass rate on the AP exam. Prior to serving with Teach for America, DoAmaral attended Boston University and earned a Bachelor of Science degree in Social Studies Education.

Tell us about your professional journey. How has your career led you to found Fiveable?

I got my degree in social studies education from BU and then jumped right into classroom teaching out in Oakland, CA. I taught 9th and 10th-grade history through a number of different subjects including Big History, AP World History, and AP Human Geography. That experience is what led me to Fiveable. I really focused on AP World and with my colleagues, we increased the enrollment by 4x and success rates from 17% earning college credit to 70%. So many of our students were reading below grade level, but we made AP possible.

After I left my classroom, I traveled solo in a big loop around the world and then worked as a finance fellow on a congressional campaign. It didn’t take long before I received an email from a frantic former student – “Ms. D, you gotta help us. We’re all gonna fail APUSH.”

And that was the beginning of Fiveable. I started channeling all of my experiences in curriculum design and leadership into this platform.

Why are you passionate about Fiveable? And what should people know about the company?

I’m passionate about what I do because of the very real effect we have on a student’s entire academic trajectory.

As a student, I was not invited into higher-level courses. I didn’t see myself as capable of academic rigor, and even as a teacher, I felt unqualified for AP when it was first handed to me. I know how many other students lay those same misconceptions on themselves. This is a problem that mostly affects women and people of color because the bar seems endlessly high.

As a teacher, I knew the main goal of building AP World was not about the class itself, but to change the narrative for my students that they belonged in this space and they could be successful in it. That’s why I’m building Fiveable.

What does your day-to-day look like – and what you love most about what you do?

Every day is different! I spend a lot of my time working directly with each team member on various projects or laying out systems to make us more productive. I also talk to investors, pitch the business, and raise funds. There’s definitely a learning curve when it comes to raising capital, especially as an underestimated founder, but it makes us think through every little puzzle piece so we can get it right.

I just love being challenged and learning new things. That’s what I loved most about teaching too. I learned so much every day, whether it was about my student’s lives or the history I was teaching. There was always a new obstacle to find a way around. And leading a company is no different. I’m continually learning, adapting, and finding creative solutions. I love that part.

Fiveable Pitch Competition

What was the best piece of career advice you ever received?

This is a tough question. I think I’ve been lucky to have mentors every step of the way that sparked different things within me.

In college, I had an advisor that really shaped my core teaching philosophy into one that truly placed students’ needs first.

At Skyline, I learned a lot from the folks I worked with on what resilience looks like. And in startups, the one thing that’s helped the most is fully understanding that there isn’t always a right or wrong way.

But I’d probably attribute the single best piece of career advice to my mom. In typical mom fashion, she’s always been the voice in my ear, reminding me that everything happens for a reason. That’s been what gets me through the tough times when something doesn’t work out. It gets me to think creatively about what other opportunities might be open. Whenever there is one path I think is perfect, but doesn’t end up playing out, I can always point to something else that came through because of this domino effect. That’s what has made me the persistent leader I am.

What does success mean to you?

I talked earlier about an advisor I had in college, and I learned the answer to this question from him. It was through a tragedy, though. I worked with him for three years, and then he unexpectedly passed away my senior year, and the biggest lesson he taught me was after he had passed. At his funeral, there were hundreds, if not thousands, of former students that showed up. People that he had taught throughout his 40+ year career.

In that moment, I knew that the most important thing you can do in your life is to have a lasting impact on others. Every single one of us in that room continues to carry his torch, and I think about that every time I imagine success. It’s about how many people are impacted by the work you do. And Fiveable is truly my way to expand the size of my classroom and impact more students.

You recently ranked 6 out of 60 startups in the SoGal Summit and Global Pitch Competition Finals (Huge Congrats!!). Can you walk us through your journey with this, from sending in your application to SoGal – up until last weekend’s finals?

It was actually 6 out of 1700 with all of the applicants! I was truly humbled by the passion and talent in the room. I applied back in August and was accepted as a top 15 regional finalist in Chicago. I pitched in the Chicago round in September and placed 2nd, which punched my ticket to the finals.

This past weekend, all of the teams that placed in the top 3 at regionals across the world came together for the final round where 65 founders pitched. I knew I would be up against some incredible talent, so I didn’t expect to win!

What’s the biggest piece of advice that you could offer when it comes to pitching (either in competitions like SoGal or pitching to investors for funding)?

Pitching in competitions is all about stage presence. Of course, you also need to be pitching a great business, but I think competing at this level is also a lot about how you carry yourself and present your idea – conveying why what you’re doing is important.

The early days of startups are so much about the founder and the early team as well. Any investor at this stage is committing to you and your idea, not quite what traction you have yet, so if you can get the audience laughing or relating to you in some way, that helps a lot.

Amanda DoAmaral

Do you have a specific person that’s inspired you or mentored you, that a particular person that’s influenced you?

I’ve talked about a few that stand out, but the others that deserve some credit are my students. I was consistently surprised, challenged, motivated, and inspired by them. No matter how chaotic things felt at our school or how impossible success felt for them, they taught me how to focus on what mattered.

We all get caught up in the process or theoretical sides of things, but my students kept me focused on the tangible outcomes because they needed progress right away. They pushed me to create stronger lessons and develop new opportunities faster.

How do you practice self-care?

This definitely something I need to get better at! It’s hard in the early stages when there’s so much to do, and it’s all so exciting. I also live with several team members, so we’re always on. But I have ways to detach and support myself. I have a little fan group of Survivor that includes me, my mom, and a few friends. We’ll chat about strategy and show gossip. I also deeply follow politics, which is not quite feeling like self-care these days, but I have my favorite podcasts that I retreat to. And I just make sure to take time off for myself. Usually, Saturdays are for recovery.

What do young women, who want to start a technology-based company, need to know.

They need to know that there are absolutely no rules. I see men pitching terrible ideas, getting big checks, and consistently failing forward. As women, we’re underestimated, and sexism is a massive barrier that needs a lot of work. But as a founder, I just focus on what I can control. We as women often hold the bar really high for ourselves because we know how critical others will be of us, making it feel like everything has to be perfect before we can even start. I’ve learned to smash that way of thinking.

I always hold a high bar for myself and for my team, which is what will ultimately make us successful. But I also don’t let that hold me back. You just have to run ahead and do it. Plenty of men were less prepared, less passionate, less hardworking, less creative, and they didn’t question themselves. Just go for the whole thing and adapt as you need, but know that there is no single experience or skill you need before you get to the next step. You just have to get there.

If you could go back and give yourself three pieces of advice when you first started your career – what would you tell yourself?

I’m not sure I would. I think I had and still have a lot of wide-eyed naïveté that gets me to the next step. I remember sitting on a Big History panel in my first year of teaching, and I was up there giving advice to other teachers. I think about that now, and I was so young and inexperienced. The crowd most definitely did not take me seriously. If I had known then what I know now, I might have shied away from that experience.

When people remind me how courageous I’ve been in putting my idea out there, I think about how little I realized the magnitude of that. I’m sure that in 10 years, I will have a whole new outlook, but it would be a spoiler to find that out now. So any advice to myself ten years ago would just be to keep going. Keep making decisions that feel right. And that’s it. Everything else happens for a reason.

What single word or saying do you identify most with?

Trust yourself. I’ve been thinking about putting this on a big painting in my room, so I see it every day. Trust yourself. There’s always a voice inside your head that wonders if you are not good enough or experienced enough. It’s an imposter syndrome that’s very real, especially for underestimated founders. But there’s also a voice in my head that tells me which decisions are right. I fuel that voice with data and mentors and experiences. And when it comes down to knowing what’s next, no one knows my team, my business, and my vision better than me. I just have to trust myself.

What’s next for you and for Fiveable?

Growth! Both in a user sense and in terms of our team and business. In two years, everything has evolved so much, and I can’t wait to continue evolving.

We’re excited to support thousands of more students this spring and beyond. There is so much for us to learn that will help us develop a better product for students and I’m excited about it. All of our product and growth strategies can be summarized in two words: students first. We’ll keep following the path that students layout for us based on what they need.

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