Coworkers live, work together in one Milwaukee apartment
Fiveable plans to grow, establish office culture with additional roommate-teams in other locations
When Amanda DoAmaral decided it was time to hire the first employees for her startup, she decided to look for roommates too.
DoAmaral started her social learning platform, Fiveable Inc., from her mom’s house in Portland, Maine, in April 2018. About five months in, when her site was getting 4,000 hits a month, DoAmaral decided she needed to hire her first employees and move out.
Now from a three-bedroom apartment in Milwaukee, DoAmaral and her team are building what they call the Twitch of education — a livestreaming site focused on Advanced Placement classes for high school students.
Three of Fiveable’s four employees live — and work — from the apartment between Bradford Beach and Downer Avenue.
The Lake Drive apartment is the third home DoAmaral has shared with Claire McHale and Tan Ho. McHale was in Philadelphia doing freelance marketing work when she saw an ad for Fiveable on Craigslist. Ho responded to DoAmaral’s posting on Reddit while he was living in Buffalo, New York.
“It was just something new, an adventure,” McHale said. “I think I’ll grow more from this than doing something I’m really used to.”
“I follow passionate people,” Ho said. He was between leases anyway.
They found an apartment in Philadelphia with a lease starting in December 2018. A Madison cohort of the accelerator gener8tor brought Fiveable to Wisconsin in March. Fiveable picked to move to Milwaukee after that program ended.
They found the three-bedroom, two-bathroom apartment with in-unit laundry and were sold. They moved into the apartment in Milwaukee in June — the same day the team pitched at Summerfest Tech, earning second place in the startup competition and the attention of CNBC star Marcus Lemonis.
They set up one of the two living rooms as an office with desks and a whiteboard. The second living room has couches and a television. There
is a hallway that separates the two, but works slips in there. Boxes in the corner are filled with Fiveable stickers, shirts and pens that are going out as a back to school gift to about 150 student streamers.
It’s convenient to live and work in the same place, DoAmaral said, even if it means no separation between the two.
“I think that any startup at the stage we’re at doesn’t have that,” she said. “They’re living pretty much the same life we are; they may or may not be living together but they’re basically living together.”
The company is less than two years old but experiencing early growth with around 120,000 hits to its website each month.
More than 33,000 accounts have been made on the platform. Around 25,000 students watched one of their live streams during last school year and about 2,400 upgraded to a paid version. Students in 3,000 schools and every single state have logged on.
‘What happens when it’s not fine?’
The idea to live and work together didn’t come from nowhere. DoAmaral spent her first few years after college teaching near Oakland, California, and living with other teachers. Then she joined a congressional campaign and lived with other staffers.
“This experience of living in a house full of people that are all working on the same goal, like I’ve done this now three times,” she said. “Totally different experiences, but it has shaped every part of me. I want other people to have that too. It’s how we can build stronger relationships with each other and get more done.”
Fiveable is gearing up for the school year now, preparing to increase the number of weekly livestreams from about seven to more than 30 for 19 different AP exams. To fuel its growth, Fiveable is raising a $750,000 seed round.
Fiveable also is looking to grow its team with new employees who will start a second Fiveable House. They are seeking four Fiveable Fellows who will all live together from Sept. 1 to Jan. 1, in another apartment in the same building as the original house. The fellows will get free room and board in addition to a stipend.
The original team has decided that living together is a part of the company culture, at least at this point.
There is reason to believe that the intense work-home relationships would aid in team building, said Lisa Pook, an organization development manager with human resources service MRA.
The early stages of team development — known as forming, storming and norming — could be quickly passed with the additional time spent together. That means an earlier arrival at the final stage, performing.
“You become more efficient and effective as you develop those bonds,” Pook said. “It’s a good thing if you can speed up the process.”
It also means that there is little ability to disengage from work, she said. Or that little annoyances could build up quicker.
“You’re engaging with an individual at a whole different level,” she said. “If I’m just interacting with you at work that means that to some extent I can put up with whatever you do. I know that I have at-home time where I don’t have to engage with you.”
Ground rules and expectations need to be set, she said, to diffuse problems.
“It’s fine when it’s fine, but what happens when it’s not fine?” she said.
‘This is a story that we will tell’
The trio realizes the living and working situation is unique, comparing it to MTV’s “The Real World.” They have talked about setting up a confessional booth to post videos to the company’s social media accounts.
There aren’t really typical days for the startup. Ho wakes up first. All three usually find their way to the office room by 11 a.m. But they’re essentially working all the time.
“When I wake up and when I decide to go to bed — that’s when I’m working,” McHale said.
Ho does most of the cooking for the team, who all grocery shop together. Rent for the $1,500 a month apartment and grocery bills are paid for by Fiveable outside of the small salaries the team members earn.
Ho makes sure they don’t forget to eat in the afternoon, making smoothies with greens, mango and cucumber. But, he said, “I have to be careful because they’re picky.”
“We’re not picky,” DoAmaral said. “There was just one smoothie that was kind of thick.”
McHale explained: “We’re just going to tell everyone exactly how we feel.”
They work until 7 p.m. or so. Then Ho makes dinner. A recent favorite is Korean beef bulgogi. They watch “trash TV” while eating dinner. Often, it’s dating shows like ABC’s “The Bachelorette,” MTV’s “Are You the One?” or Lifetime’s “Married at First Sight.”
“Sometimes someone ends up back working, usually me,” DoAmaral said. “Sometimes everyone ends up back. It depends on if we are sparked with some idea.”
They’re still working through some aspects of the alternative situation, like how to make connections outside the Fiveable House when the roommates and coworkers spend nearly all of their time together.
“That’s the hard part about living in a new city, and it’s not like we can make new friends at work and each bring our friends back home,” DoAmaral said. “So we have to find other ways to have friends together but also separate too.”
So far, they said there haven’t been any huge fights. But Ho said he has planned who has to take out the garbage for the next three months on the app OurHome, which rewards users for completing chores.
In the end, DoAmaral, McHale and Ho see this as a somewhat temporary situation once the company starts generating greater revenues.
“There will be a time when we have an office and this will be a story that we tell,” DoAmaral said.
Sarah Hauer can be reached at shauer@journalsentinel.com or on Instagram @HauerSarah and Twitter @SarahHauer. Subscribe to her weekly newsletter Be MKE at jsonline.com/bemke.