With Advanced Placement exams starting this month, the past weeks have kept Amanda DoAmaral working around the clock. As students cram, her team of four has been scrambling to meet the demand on Fiveable, where she and other teachers broadcast live test-prep sessions. Last month, the website attracted more than 60,000 visitors and 3,300 live attendees. One session on AP European History alone got 845 viewers.
“I see Fiveable as a platform that can democratize learning,” says the former teacher who once taught AP classes at Oakland Unified School District. And she’s starting with subjects that she knows best. The company’s name is a reference to the best score possible on the AP exam. In its first year, she claims, more than 90 percent of the 400-plus students on the platform passed their AP World History and US History tests.
On Fiveable, visitors can watch livestreams of AP exam review for free. Each session is one-hour long, featuring a teacher narrating and screensharing test-prep materials. There are also quizzes and online study groups where users can chat. For a $5 monthly subscription, users can access a library of 350 videos of past sessions and practice materials. Today, Fiveable claims more than 7,500 members—1,100 of them paying subscribers.
In startup parlance, those numbers are an encouraging sign of product-market fit, especially for a company that re-launched its platform just this January. DoAmaral says Fiveable’s footprint has spread largely by word of mouth. The growth is also partly due to the steady uptick in AP test takers. More than 2.8 million students took a combined 5.1 million tests in 2018, according to The College Board. Both figures have grown every year since 1999.
DoAmaral’s path to Fiveable has been a test in itself. It is also part of a continuing tradition where entrepreneurial educators start companies to serve their peers and students after leaving the classroom. Former teachers have built tools for reading, writing, financial planning, teacher-parent communication and a myriad other applications in schools.
For DoAmaral, the transition from the classroom was guided by a simple question: “I’m a teacher and I know what students need. How can I bring what I know to more students?”
Around the World and Back to Students
Fiveable was borne partly out of frustration and economic necessity. In June 2017, DoAmaral left Oakland Unified, where she had been teaching AP-level history and social studies subjects for five years. She didn’t want to; the job had been fulfilling in every way—except for one.
“Teaching was ultimately financially unsustainable. At that time I was paying more for my student loans than my rent,” says DoAmaral, who has degrees from Boston University and Loyola Marymount University. “It got to a point where I could keep doing this, or I could take a break and see what else my life could look like.”
That summer she returned home to Boston and bought the cheapest one-way ticket she could find out of the country. That took her to Scotland, and from there she continued further and further east, through Bosnia, Egypt, Nepal and Thailand.
The wanderlust came to an end in November 2017. She returned to the U.S. to work on a political campaign for Pat Ryan, a Democrat candidate running to represent New York’s 19th Congressional District in the U.S. House of Representatives. She moved into a house in Kingston, New York where she and four other campaign workers lived and worked.
The job entailed making fundraising calls, and many of the donors turned out to be startup entrepreneurs. For DoAmaral, it was a glimpse into a new world. “At that point I just had no idea what startups looked like, but I went down this rabbit hole of learning about marketing, product, building a business—all these completely new things for me.”
“All of a sudden,” she recalls, “I realized that entrepreneurship is a thing that people do. That I could have an idea, try it, build it, and pitch it to people.” During down time, she adds, the house was an “incubator of ideas” among her housemates for what they wanted to do next. “We were career-changers, all around the same age, frustrated about politics and the 2016 election, but wanted to do something to change things.”
For DoAmaral, that meant reflecting back on her students and her past career. Her passion remained helping students, and she tapped into what she knew. Her first idea was to create instructional videos, and in her room she recorded 15 videos on AP World History topics.
Deciding to pursue this idea full-time, she left the campaign in January 2018 and moved in with her mother in Maine. What might otherwise have been a humbling experience for a 28 year old was instead a “creative tornado,” in her words, as she and her mom bonded and brainstormed over starting a company. DoAmaral recalls watching “Shark Tank” together to practice how they would answer questions from investors one day.
Her idea got further validation in spring 2018, when she began receiving emails from former Oakland Unified students about their frustrations with their current AP classes. They didn’t like the new teacher, and felt unprepared and stressed. On April 6, she did a livestream session where she answered students’ questions, and pulled up a Google Doc on screen to show them how to write an essay.
That date would mark the birthday of Fiveable, according to DoAmaral. “It was a date I will never forget. It set me on the track I’m on today.”
House Calls and Accelerators
That June, Fiveable was accepted into BetaBoom, a Utah-based startup accelerator that provided $20,000 in capital. Part of that money went toward hosting a virtual professional development workshop for 250 AP teachers, which doubled as an opportunity to build awareness for the company.
DoAmaral’s profile got an unexpected boost that summer. At an event hosted by The College Board, DoAmaral got into a testy exchange with Trevor Packer, who heads the organization’s Advanced Placement program, over a controversial plan to cut AP World World History curriculum to start in the year 1450. The video went viral, and she was interviewed by The Atlantic, NPR and other media outlets.
She did not leverage the spotlight to pitch her startup. “It wasn’t about me or Fiveable. It was about the fact that this organization was making a decision that will affect curriculum for millions of students.” To many historians and teachers, it was also culturally offensive, or plain ignorant, to gloss over the histories of non-white civilizations before European colonization. Among history teachers and historians, DoAmaral became a minor celebrity.
After finishing the BetaBoom program, DoAmaral moved to Philadelphia where she set up the “Fiveable House,” a coliving and coworking arrangement similar to the setup she lived in during Pat Ryan’s campaign, just a year earlier. She put out invitations for “whoever might be crazy enough to join me to live in the house,” offering help with rent, food and equity in the company. Three people answered the call, bringing expertise in web design, SEO, marketing and “other aspects of the business I had just been dabbling in,” says DoAmaral. The team rebuilt and relaunched the Fiveable website this January.
The team packed up again in March 2019, moving this time to Madison, Wisconsin after the company was accepted into another startup accelerator, the gener8tor. The program invested $100,000 in the company. This is where Fiveable is currently based.
This summer, after the AP exams are over, thousands of teachers will converge in Cincinnati, Kansas City, Tampa and other cities to grade the AP exams. DoAmaral, who says she once graded 1,200 essays at one of these gatherings, plans to host Fiveable after-event parties to recruit more teachers onto her platform.
The company is also considering expanding to other tests, like the SAT, and experimenting with other test-prep formats, such as an AP World History trivia game. It is inviting students to nominate teachers to stream on the platform. And it plans to cut down its video recordings to bite-sized chunks so viewers can more quickly navigate to specific topics.
Doing all those things will require more resources than what Fiveable’s team of four currently has. Raising a seed round is a possibility in the near future, DoAmaral says. For now, a couple of friends and family are volunteering on the side. “This is what a ‘friends-and-family round’ looks like when they don’t have money,” she jests. “They donate their time.”
