Tán Ho finds home creating inclusive online community at Fiveable

Tán Ho was technically homeless before he joined Fiveable.   

It was late 2018, and Ho had been sleeping on friends’ couches for months after quitting his marketing job and breaking his lease in Buffalo, N.Y. He was freelancing and working at restaurants but felt lonely and aimless as he struggled with depression, anxiety and issues related to coming out as gay.

"What makes me happy, that I’ve always known, is impacting other people in a good way," Ho told the Milwaukee Business Journal. "When I didn’t get a chance to do that, that’s when things started breaking down."

But things started to align when Ho stumbled upon a Reddit post from Amanda DoAmaral, a former teacher launching a company that offered online Advanced Placement (AP) test support for high school students. DoAmaral was seeking her first employees, but with a catch: She couldn’t afford to pay a salary, but she offered room and board, and the chance to live and work in a shared space while building something meaningful.

Ho said yes.

Nearly three years later DoAmaral and the 29-year-old Ho are still roommates and collaborators as they continue building Fiveable. The Milwaukee-based education technology startup has since grown to more than 1 million unique users in April and has attracted $4.2 million in funding, including investments backed by former U.S. president Bill Clinton's daughter, Chelsea Clinton and tennis star Serena Williams. Earlier this week, Fiveable announced its first acquisition: Hours, a virtual study platform founded by 16-year-old Calix Huang.

DoAmaral is well-known as the company’s CEO and original founder, but fewer people are aware of Ho, the company’s chief experience officer who was officially named a co-founder in March. 

The two Fiveable co-founders complement each other well, with DoAmaral driving the company’s vision of becoming an empowering social learning network, and Ho following up with the execution, said Craig Schedler, Fiveable board member and managing director of Cream City Ventures, one of Fiveable’s investors.

“I think Tán understands the user better than anybody,” Schedler said. “He really thinks like a high schooler in the best sense.”

Ho’s role has evolved since he first joined Fiveable as the chief growth officer, where he focused on search engine optimization and email marketing to increase the company’s traffic and user base. Fiveable recently hit 5 million visitors since its inception, Ho said. High school students are the primary users, but teachers, educators and administrators also use the platform.

Now, as chief experience officer, Ho oversees Fiveable’s marketing, design, community and student success teams. He described the community as the glue that holds Fiveable’s users together with events and programming. Student success includes proactive and reactive customer support.

"I was able to craft my own role," Ho said. "People don’t get to do that often – they get siloed into one thing. But for me, I’ve always found it difficult to just do one thing."

Given his own struggles with mental health, Ho — who is Vietnamese and Nigerian, and identifies as a queer person of color — feels that his biggest opportunity to make an impact through Fiveable is to help support and empower all students, including those from Black, Asian and Latinx communities.

“If you look at our student base, it’s so diverse now,” Ho said. “We want to make sure we’re building something that will enhance lives for all of the students that we want to represent — especially underrepresented communities.”

Under Ho’s leadership, Fiveable has begun offering mental health support for students, including online vent sessions; self-care discussion groups; and access to professional help through partnerships with Crisis Text Line, a nonprofit that offers free, 24/7 support from trained counselors, and Joon Care, a Seattle-based teletherapy app for young adults. 

Ho is a first-generation American from Utica, N.Y., where his single mother raised him and his older brother. Growing up, Ho helped his mom write emails and letters in English, and she taught him her Vietnamese recipes. She was a rice farmer in Vietnam before she moved to the U.S. and began working in casinos. 

“My entire family works in casinos, so my mom was like, ‘You should just become a blackjack dealer,’ Ho said. “But I’m terrible at gambling … Fiveable is the biggest risk I took.”

Ho got his first taste of online entrepreneurship in high school as a creator and seller of layouts for Myspace, a popular social networking website in the mid-2000s. As an undergraduate at Canisius College in Buffalo, he studied marketing, communications, media and design for his bachelor's degree.

After graduating, Ho held a few marketing-related jobs — including at a sausage factory and an architecture firm — for a few years before he found himself feeling lost and struggling with his mental health. That's around the time he met DoAmaral.

"Stumbling across Amanda’s post, that was like the fire I needed to get out of my slump," Ho said.

Upon joining Fiveable, Ho moved to Philadelphia to live and work with DoAmaral and other early employees. Since he wasn't earning a salary at the time, he picked up a restaurant job during the day and worked on Fiveable at night. In spring 2019, they moved to Madison when Fiveable got accepted into gener8tor, a 12-week startup accelerator there.

After finishing the gener8tor program, which provided much-needed seed funding, mentorship and a network of Wisconsin-based supporters, the Fiveable team decided to move their headquarters — and their residence — to an apartment on Milwaukee's east side.

"Being in Wisconsin has really helped ground all of us — at least Amanda and myself," Ho said. "It’s allowed us to really slow down and focus on what’s important, which is the company and our families."

This month, Fiveable is projecting a record 3 million unique users amid AP testing season. As the company attracts a growing number of high school students, Ho feels a greater responsibility to foster a safe online community, he said.

Along those lines, Ho is leading the company's trust and safety initiative, which includes mental health support but is broader than that, spanning departments with the overarching goal of protecting Fiveable's student users. In practice, it ranges from ensuring data security to creating protocols for reporting issues such as a student contemplating suicide in one of Fiveable's public discussion forums.

Reflecting on his journey, Ho said his mental health struggles have been "instrumental" in getting him to where he is today.

"It sucked a lot at the time," Ho said. "But it’s an opportunity now to really take that as experience and then turn it into something actually tangible and useful for our students."

Tán Ho