What it’s like to launch a startup with friends, according to 3 Gen Z cofounders who created a childcare startup together

Longtime friends Sasha Reiss and brothers Daniel and Josh Andrews launched Playground, a preschool software startup, together.

Sasha Reiss and brothers Daniel and Josh Andrews met over a decade ago in high school. From an early age, the trio worked well together — and now, in their mid-20s, they are in business together.

“Sasha was basically our mom’s third son,” Daniel Andrews told B-17. “Growing up, we all worked in my mom’s preschool — and the three of us realized we could help our family run the place better with technological improvements.”

The Andrews had a strong technical background, with degrees in computer science and engineering, while Reiss had expertise in design.

Together, they founded and launched Playground, a preschool software management startup that handles everything from registration and payroll to attendance. The startup has raised $3.4 million since its launch in 2020.

The trio are part of a growing ‘friendpreneur’ trend that’s particularly popular among Gen Zs.

Research published in July and commissioned by AI photo app Photoroom — which surveyed 6,000 respondents across the US, UK, Mexico, Brazil, Korea, and Japan — found that more Gen Zs are launching startups with their friends. Around 60% of Gen Z founders who were surveyed had involved their friends in the business, compared to 42% of millennials and 21% of Gen X and boomers.

Reiss and the Andrews brothers said that working together as friends has elevated their relationship and provided advantages for their business.

Working as friends has streamlined communication

The trio said they find it easier to discuss business decisions honestly because they are used to organically communicating with one another.

“We’re each other’s biggest fans, but we’re also each other’s biggest critics,” Daniel Andrews said. “So we could take really intense feedback incredibly well, and we’re able to turn things that might come off as a little bit rude into something more constructive because we can read between the lines, having just been knowing each other so long.”

“We’ve been able to operate significantly faster and be honest with each other because we have that initial layer and unconditional love for each other,” Reiss added.

Spending so much time together has also proven to be a business boon.

“I’ve been living with Sasha for four years, and it’s pretty much a 24-hour cycle of hanging out minus sleep,” Josh Andrews said. “But it’s created a really good feedback loop where we take work home, but we also know how to have that separation when we leave the office.”

Reiss said that having an aligned schedule has also helped the three get “ideas flowing naturally” outside an office setting.

“I think a lot of our best ideas were made maybe at a bar getting a drink, or at a restaurant just getting dinner, and you’re not even thinking about work — and I think that’s a big reason why we come up with a lot of novel ideas for our visits,” Daniel Andrews said.

He added that their “shared life experience” has made them more empathetic and understanding of each other.

“We have had a lot of family health issues over the last couple of years as we’ve been on this journey,” he told B-17 “Being a first-time founder, it is incredibly beneficial to work with friends and family who can step up and take on that work. The lowest points definitely feel a lot less low when you have these kinds of people around you.”

Pick friends wisely

Working with friends also poses its own challenges.

“We have similar backgrounds in similar skill sets, and so intentionally seeking out hires that bring a diverse background that’s very different than ours has been much more important for us,” Daniel Andrews said.

Being a part of the same friend group can also pose logistical roadblocks. The trio often get invites to the same holidays or events — sometimes resulting in an “out of office” from all three.

“We’ve definitely navigated that by having people stay behind; we’d be like, okay we can’t all leave right now,” Josh Andrews said.

While the trio is enthusiastic about the concept of launching a company as friends, they agree it’s only worthwhile if they bring out the best in each other.

“If you have friends that you find that are like slowing you down, or like trying to distract you, or other things, those might not be the best friends to launch a startup with,” Daniel Andrews said.

“But there are those friends who are always pushing me to run harder, do that extra like hike, run that mile faster.

“Those are the people that you really want to engage and work on something with. And I think selectively picking up friends who are available and those who are trying to push you to be better is the correct path forward,” he added.