Since its founding in 2018, Milwaukee education technology startup Fiveable has raised more than $14.2 million from investors.
Those dollars have come from venture funds backed by Serena Williams and Chelsea Clinton, investments from Wisconsin angel groups and venture firms, and fundings by several coastal investors, including a $10 million Series A round announced Tuesday.
But Fiveable also has encountered investors that declined to invest at least in part because the company's founders are both people of color, Fiveable CEO and co-founder Amanda DoAmaral told the Milwaukee Business Journal in a Tuesday interview.
Fiveable is a social learning platform designed to help high school students form communities online, regardless of where they live and the quality of their school system. It also aims to support students in dealing with the increasing stresses of high school.
With a diverse, growing team led by DoAmaral and Fiveable co-founder and chief experience officer Tán Ho, the startup has become known for its inclusive online community that empowers students to excel in school, develop emotional wellness and plan for the future.
Both co-founders are based in Milwaukee but the Fiveable team is fully remote. In the following interview, DoAmaral discussed the company's presence in Milwaukee and the challenges of being a person of color in the local startup community.
This interview has been edited for clarity and length.
What has been the biggest challenge with building Fiveable?
"There's a lot of them. I wasn't in startups before. Coming from a classroom, in the early days, my mental models for what this could look like were very different than the reality of it. It's just been a lot of really fast learning. Especially in the early days, things like fundraising were really hard because I didn't know how to navigate the ecosystem. I didn't have the network. I didn't know exactly how to pitch ourselves.
"Every step of the way, it's just leveling up as fast as I can. Being able to hire a team and support a team and really evolve the vision over time and make decisions... I have to sort of balance the learning while I'm building. Like, the airplane took off and we're building it while we're in the air."
Do you plan to stay in Milwaukee and keep the company here?
"Yeah, we're here. I don't have any plans on leaving. It's been a surprise for me how much I like Milwaukee — I didn't ever think that I would live here. I grew up in New England and didn't have any connections to Wisconsin... It's become this perfect place to be... I have some friends that are here, and to be in the same city as (Tán), those have been really awesome.
"I also think that the way in which Milwaukee will change over time is going to be directly related to how work is changing and how the climate is changing, and I think this is a pretty ideal place to be considering both of those things."
Do you mean the environmental climate?
"Yeah. All of my friends live on the East and the West Coast and it's like, hurricane or fire... Here, we seem to be in a good position, just considering how things will keep going. I wouldn't want to move to a coastal city right now."
Are you considering getting office space in Milwaukee?
"Not at the moment. We really like remote work and we've found that you can hire talent from anywhere — it's really opened up our ecosystem. Also, I just generally think that remote work allows for people to be at their best... I personally love the freedom of just being able to work from home or travel if I need to go someplace.
"We don't have any plans to get an office space and we'll instead focus on finding ways to get the team together. So like next week, we're bringing the whole team to northern Michigan for training."
I'm curious what it feels like to be one of Milwaukee's "startup darlings," if you will, especially given that Fiveable's team is remote.
"It's also pretty wild. Like I said, I didn't have connections to Wisconsin before, so to have that now is very cool. I think it's a reason why we wanted to stay, too — we just felt like if we were in a really big startup scene, we would get lost in the noise.
"It's a really interesting city because there's so much potential. Obviously, I've only been here for a few years, but I can see how much it's grown and how powerful this tech community can be... We just need to really invest in the community that's already here.
"There's so much untapped potential, people who are just not brought into this conversation — this was me a few years ago — I had no idea what startups were, how to raise money, how to build different platforms. So the more that we invest in this community, the better. There's a lot of great work that could come out of that."
Are there specific companies you're referencing or founders you think there should be more investment in?
"I just know that there's a lot of investors and some founders that have been working on really bringing the talent and the ideas from the community here, especially the communities of color here that are not often brought into the conversation.
"One of the things that is hard for me — you know obviously, people know us here — but it can be difficult because, for Tán and I, we're both founders of color and when we walk into rooms, a lot of times we're the only ones. That's a really stressful position to be in, and in the early days, there were people who passed on our rounds because we were seen as too risky for that exact reason. That is still happening at a level that is ... it's just wild.
"I think what's important is that we don't just create a closed-off space. We don't want the wealth to just be recycled between the same groups of people. The only way that we can really build up all of the communities here is to invest in them.
"For me, if I can talk to folks and support them — and even just if they see me and see what I've done — I know that can make a difference because I certainly didn't see myself in founders before. I didn't know that was a thing I could do. So even just that representation for me and Tán to be here and to have that, I think it's really, really important."
