Amanda DoAmaral closes a $615K seed round—and opens up about her roller coaster year as a founder

Amanda DoAmaral is the founder and CEO of Fiveable, an edtech livestream platform with a growing user base of teachers and students from every state in the US. She has described Fiveable as Twitch for education: “If kids can get help with video games, they should be able to get help with homework, too.” amanda doamaral headshot

Fiveable focuses on preparing students for AP exams, and—as of November 2019—the platform has hosted livestreams for close to 30,000 unique users. For the 2018-19 school year, Fiveable students reported a 92% pass rate across the seven subjects offered, while the national average was 55%. (Full disclosure: Beta Boom was one of Fiveable’s earliest backers. Amanda earned $20K in capital and a spot in our Salt Lake program in June 2018.)

News hits for Fiveable suggest a near-meteoric rise: after Beta Boom’s early vote of confidence, Amanda posted a viral YouTube video advocating for students in an exchange with a College Board exec, then she and her tiny team earned a spot at gener8tor, a Wisconsin-based accelerator which promises $100K in investment, and in June 2019 she impressed celebrity entrepreneur Marcus Lemonis enough to garner $10K of his personal capital on top of taking second place at the 5 Lakes Pitch competition.

What’s more, the company announced it closed on a $615K seed round just after the new year. But rather than let that money tell her story, Amanda took to the company’s website to speak frankly about how Fiveable almost didn’t make it through 2019. We’ve pulled together some of her notes on the struggles faced and lessons learned on her startup journey so far.

Follow your passion—which sometimes means taking a detour

Amanda joined Teach for America right out of college, moving from Boston to Oakland to teach AP World History and Geography to public high school students. At first she wasn’t sure she was qualified to teach AP courses, but it turned out she loved it. After five years, however, she had to confront the fact that teaching wasn’t financially sustainable for her. “I was paying more for my student loans than my rent,” and Bay Area rental prices weren’t cheap. What she didn’t realize was that staring down her own financial precarity would be the spark for a much-needed startup.

Learn to see yourself as an entrepreneur

Amanda left her teaching job, traveled a bit, then moved back to the East Coast. Her next job involved making fundraising calls to potential campaign donors, and many of the people who gave money were startup founders. At that point, she had only an abstract idea of what startups and entrepreneurship looked like. But she started researching how to build a business, and realized, “I could have an idea, try it, and pitch it to people.” This was 2017, she was living with other young campaigners and looking for a way to use what she’d learned as a teacher. “It was the students who lit the way,” she explains. Kids from the school where she’d taught were asking for support, so Amanda started livestreaming AP history lessons for them. “It didn’t start out as ‘I’m gonna build a startup’—it started out as ‘I’m gonna help people [in the way] I know I can help them.’”

Turn your struggles into an asset

The fact that Amanda hadn’t ever considered founding a tech business is one indication of her “outsider” status in the startup world. But reflecting further on how that’s helped her (and her business) succeed, she notes, “I’ve always felt like I’ve had to work ten times harder to get to do whatever I have to do. Whether it was as a kid or in college, I knew I had to go faster and that’s how I’ve approached founding this company. I think that’s part of the advantage—knowing that people are going to overlook me and so I have to shoot higher than they’re gonna expect so that I can come out on top. I’m pretty sure that all female founders and founders of color operate in that way, and that’s probably what propels these businesses forward.”

Sometimes you need to go a little “nuts” 

From her first unofficial livestream to the day she completed Beta Boom’s startup program in 2018, not even three months had passed. Amanda returned from Salt Lake City with a clearer view of herself as a founder, then promptly moved back in with her mom and got to work on what she’s called the craziest thing she’s done on her startup journey: The Fiveable House. “I knew I needed a team, [but] I didn’t know any marketers or developers. I didn’t know anybody outside of my universe of teachers. The only way I could think to move this idea forward was to rent a house in Philly and convince people to come live and work with me—for basically nothing. It was nuts!” But it worked. The Fiveable house drew in Amanda’s first two employees and has since moved to Madison, then Milwaukee—where Amanda still lives and works with teammates Tan Ho and Aaron Levin.

Let your users be your guide 

As Fiveable expands its course offerings and experiments with new formats, Amanda stays attuned to what students and teachers are asking for, “because they seem to know what I should do next more than anybody.” What’s more, she’s also thinking about generational trends outside her immediate platform, observing, “This generation of teenagers is very connected. We’re seeing this with [activism]—teenagers are running massive movements because they’re connected to each other. But we’re not seeing that with education. When you think about a teenager right now, they’re on their phone, they’re hopping around on YouTube, they’re watching videos on Twitch, they’re on Instagram, Snapchat, TikTok—but where is the learning happening? I think what we’re trying to do is just connect to where kids are right now.”

Don’t be afraid to operate outside of a tech hub

Since starting Fiveable in Maine, Amanda and her team have worked in Philadelphia, Madison, and Milwaukee. Beta Boom seeks out startups that may be overlooked due to geography, and Amanda explains how being based somewhere “small” can be an asset:  “These startup ecosystems are so much smaller than Silicon Valley’s. Even just pitching in a competition [like Milwaukee’s 5 Lakes Pitch] and getting to the final round,” is a unique experience. “I’m not competing against 20 other edtech [startups]. One of the judges [at 5 Lakes] called us the most exciting startup in Milwaukee right now, and there’s no way we’d get that title in the Bay Area, in New York, even in Chicago. It’s worth it for us to be in a smaller place so that we can stand out and all of these different people can help us.”

Find a way to connect with other founders

As she found her footing as a leader and Fiveable continued to grow, Amanda and her team moved to Madison to take part in gener8tor, a “concierge accelerator” that provides three months of business development programming on top of significant capital. However, she’s said that one of her key takeaways from the experience was meeting other founders. “It’s hard when your team doesn’t understand all the pieces you’re dealing with, and neither does anybody else. My family has no idea!” Because she lives and works with her team, Amanda admits it can be hard to expand her social network: “I have to be able to know other people who ‘get it’ in order to feel less lonely. [And through gener8tor] I’ve made friends who are starting their own companies and going through the exact same things but in their own way.”

Be prepared to weather the unknown

On top of the energy that infused her early successes, Amanda remembers a lot of uncertainty—and that hasn’t disappeared even today. This rollercoaster of emotions is one of the first things she likes to mention to would-be founders: “I honestly never knew how high the highs could be and how low the lows could be. Going from on the floor crying, calling my mom, to a total swing the next week—getting opportunities where people would see my vision with me. Just knowing that when you’re starting out, and that it will keep happening, is a big part.”


A Look Back at our SOCAP Diversity & Impact Gathering

As we enter the winter season approaching the end of the year, we wanted to reflect on one of the highlights of the previous season. In October, we attended SOCAP19 in San Francisco. As every year, this impact investing conference created an amazing space for connecting to other change-makers, sharing information and hearing from industry leaders. The reason this year was particularly special was that Beta Boom co-hosted a happy hour mixer that brought together diverse founders, impact investors, and supporters for an evening of conversation.

Our motivation to host was clear. First, SOCAP is a huge conference that can feel overwhelming. After a day of inspirational addresses, panels, and networking it’s important to decompress and talk with people who share our interests. Second, since starting Beta Boom, we’ve had the great pleasure to connect with national organizations that are promoting inclusive entrepreneurship across the US (such as the Kauffman and Case Foundations), as well as many local groups supporting female entrepreneurs and people of color. Our work also builds ties to individuals seeking to invest in more diverse founders. While all these groups are working toward a common goal, they aren’t often in the same room together. 

In short, we hear all the time about the need for greater connection and collaboration between founders, investors, and supporters, so we endeavored to bring them together in a relaxed setting to further build these connections.

Co-host Monique Aiken, VP of Programs at Mission Investors Exchange (MIE) came wearing multiple hats including as a member of the steering committee for the SEO impact investing network and as an alumna of the Tiogo Foundation. In the spirit of collaboration, Monique merged MIE’s 4th annual happy hour event with this gathering, inviting all threads of her connections to attend as “a testament to the spirit of the night.” She encouraged the room to “work in coalition and build community to go further, faster together.” 

The founder conversation highlighted the need to focus on the user and chart one’s own path

In a room overlooking the Bay, with food and drinks in hand, conversation flowed and connections were sparked. We wanted to give our guests a window onto the important work founders and supporters do, and highlight how these roles intersect, so we organized two informal Q&As. Our founding partner, Sergio led the first conversation made up of three founders/CEOs: 

  • Meena Palaniappan of Atma Connect, a non-profit tech company working to build resilience in low-income urban communities worldwide; 
  • Amanda DoAmaral of Fiveable, an EdTech livestream platform that prepares high school students for AP tests; and
  • Erica Plybeah of MedHaul, a company providing transportation solutions for medical patients in low-income and rural urban communities.

They started by discussing the most important lessons they’ve learned as founders. Erica confessed she’d been a perfectionist before she became a founder, “and any founders out there know that doesn’t work well. I also had to realize I can’t do everything in one day.” She advised fellow entrepreneurs to take work/life balance seriously, and explained she spends a couple mornings a month volunteering in her son’s classroom. “I don’t bring my phone, I don’t check my email, which is very tough. It’s a very exhilarating experience.”

Meena continued by noting the lessons her users have taught her, explaining that “purely as a result of the ingenuity and resourcefulness of the people [we serve],” Atma has gone from “a way for urban poor people to share water price information,” to a tool for building resilience to future disasters. “I’m just constantly humbled and amazed by that.”

Amanda, who didn’t come from a business background before launching her startup, talked about how she’s learned that “Everyone is making it up as they go.” While finding investors and advisers who can help you get from A to B is key, she’s also learned that there are really no specific markers of success, so founders should “Just keep going.” She also touched on how her platform can address the immediate needs of her users, saying, “We all think that education needs a big overhaul, and that’s true, but the kids right now need it tomorrow. They don’t have time for us to get it together and overhaul it.”

All three women closed by mentioning how partnerships could help take their companies to the next level. Amanda and Fiveable are looking for a way to help students pay for livestreams. Meena explained that entering the disaster space has brought Atma into conversations with insurance companies like SwissRe, (whose tagline is “Making the world more resilient”) and she’s been buoyed by the realization that there are “big institutional sectors that are driven by the same goals that our users have.” Erica and Medhaul have already partnered with Lyft, and she noted, “Solving issues in healthcare is not something that one company can do,” so she’s open to “nontraditional” partnerships with big companies like Google or Walmart. 

Sergio concluded by reminding the crowd that one thing Beta Boom really believes in is helping entrepreneurs in ways beyond investing capital. Supporters “can provide connections to customers, to mentorships, to strategic partnerships, and there’s also a huge value in providing visibility into the work that founders are doing. So when you do meet a founder I would really challenge you to ask yourself, ‘What other ways can we help them be successful and better serve their users, their customers?’ ”

Investors and supporters challenged us to check ourselves, think of unintended consequences and to perhaps not run fast and break things

Kimmy led the second conversation featuring investors and supporters from innovative organizations:

This conversation zoomed out a bit to address the differences these panelists see between predominant models of investing and thinking about tech and the ways they and their respective organizations see and do things. 

Eliza set the tone in her intro about why she’s currently focused on poverty and inequality in the US, saying, “we’re at a critical juncture… and there’s massive urgency around how we think about and start to shift systems here.” She continued by explaining her approach to investment, adding, “I’m somewhat contrarian in the venture investing world in that I don’t want my entrepreneurs to run fast and break things. I want them to be thoughtful and deliberate and energized.” 

After explaining that her org “believes that dignified job creation is the best way to tackle poverty in emerging-market countries,” Nathalie stressed the importance of “hacking” in a very particular sense: “Working with people who have done [similar work] and are willing to share their results.” This approach is currently playing out in an initiative she’s working on that will integrate gender-equity metrics into the enterprises where NESsT invests.

As one of two developers of the first CRM system and co-founder of the People-Centered Internet, Mei Lin took a moment to emphasize that investing and innovating “isn’t just about getting money and doing things” — it’s also paramount to consider the unforeseen consequences of the technology we are working to create.

Building on the notion of thinking beyond the current moment, Dustin stated that the most important thing he’s learned in the impact investing space is the need to “Check yourself. Always. It is my absolute privilege to be able to work with entrepreneurs that are changing the world, and I come to things from my very own perspective, [which] is white, male, and privileged. I’ve had to learn to actually engage with people and understand what their struggles are and, honestly, to always try to provide value to the other person in conversation.”


New Pattern Spotlight: Amanda DoAmaral, Founder of Fiveable

Amanda started out as a Teach for America teacher in Skyline High School in Oakland, where she taught Advanced Placement U.S. and World History. After leaving the classroom, she still wanted to help all students do well on their AP exams and started tutoring students online.

Amanda didn’t know it at the time, but she stumbled upon a model that really resonated with students and helped students pass their AP exams at twice the national average. She kept growing and evolving her model and went on to build one of the leading online social learning platforms–Fiveable.

In this episode of New Pattern Spotlight, we learn about the highs and lows of running a startup as well as the advantages that underrepresented founders like Amanda have. This candid interview with the founder of Fiveable is a must-watch!

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Fiveable Is Enabling College Success for All High School Students

When students take and pass AP courses, they can save as much as $19,000 in college tuition and other costs. Unfortunately, many students lack both access to AP courses as well as support outside of the classroom, which can greatly improve students’ course completion and test outcomes. Amanda DoAmaral, the founder of Fiveable, has intimate knowledge of this reality having taught AP History in Oakland, California as well as from her experience with Teach for America. While this gap is greatest in school districts with fewer resources, this is a wide scale problem across the United States.

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