These Founders Are Building a Start-up That Isn’t All Hoodies and Long Hours

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Taking Care of Business: A week devoted to taking our professional lives up a notch.

This week, Winnie raised $2.5 million. Not the Winnie you might be thinking of — Winnie Harlow, maybe, or Winnie the Pooh — but Winnie the parenting app, a free-to-download Yelp-adjacent app to help parents navigate their world with kids in tow. The company’s two founders, Sara Mauskopf and Anne Halsall, have worked in tech for years (Google, YouTube, Twitter, you name it) and saw a gap in the consumer marketplace. Why weren’t there apps that shared all of the different places where parents could take their kids for a free meal, a changing table, a park with a structurally sound playground?

They built Winnie and made it available for free everywhere — “Not just for parents in San Francisco who can afford to spend lots of money on their kids,” Mauskopf says — and are now in the process of hiring more engineers, moving into an office, and figuring out plans for their new cash flow. So how did a pair of moms launch and fund a parenting app in a landscape of white men in hoodies? Here’s their guidance on launching a great — and diverse — start-up in tech.

Build something that you would use yourself.
Sara Mauskopf: I had my daughter 16 months ago, and at the time I was working with Anne at Postmates. After I had my daughter, I realized there was all this information that I suddenly needed to know. Even though I had been living in the same house for six years, I realized I had no idea where I could go with my daughter, where it would be appropriate to take her, if there would be changing tables in the bathroom or a place to nurse her, let alone if there are activities that would actually be fun to do with her or fun to do as a family. Anne has two children who are a little bit older, so I was always asking her, “Does this get better? Does it get easier?,” to which she said local information is something you always need and there are not really any tools for this. The status quo is that you either go to places that you know and you’re comfortable with, or you learn from other parents and their secret networks. Your world becomes a lot smaller.

Don’t be afraid of the dreaded M-word.
S.M.: Ninety percent of new parents are millennials, and they’re going to demand technology to solve their parenting problems. We were uniquely positioned to solve this particular issue. We were both technical women who had worked on consumer products — I was an early employee at Twitter and have worked at Google and YouTube, and Anne spent four years at Quora — so we could really be the first people to see this opportunity and have the background to solve it at scale.

It’s okay to let your personal values be your driving inspiration.
S.M.: We really feel strongly that caring for children is a job. That is one of our core values, and caring for children is too often considered inconsequential because it’s so often assigned to women. The work of taking care of a child is considered invisible and undeserving of great tools and technology. But we felt that caring for children was actually the most important job.

Anne Halsall: We had to pitch a lot of our investors on the work and the challenges that people who care for children encounter every day. Almost universally that was something that they were not very familiar with. There was a lot of educating that happened when we went out there to pitch. It’s a space that a lot of them don’t take too seriously, and it’s also a problem and a pain that they don’t necessarily feel, even if they do have children.

And it’s important to let those personal values reflect themselves in your company culture, too.
S.M.: We want to build a different kind of company. Some of the companies we’ve worked at in the past aren’t great environments, especially for people who have families. The importance of families is really built into our company culture. We don’t want to build a start-up where people work all hours of the day. We felt that a lot of tech companies have a lot of cultural norms that end up excluding a lot of people. When your company activities are all going out to drinks or elaborate off-sites where you have to be away from home, that excludes pregnant women, people who care for children; it also excludes people who don’t even care for those kinds of activities.

A.H.: When I worked at Quora, they went through this shift when a lot of employees started having children, and I was one of the first. As a company that puts a heavy focus on being hard-core on the engineering and tech side, that didn’t keep them from having conversations about how the culture could be more accommodating to parents. It illustrated to me that your company could have both — a hard-core engineering focus and a culture that welcomes parents.

The day-to-day is just as important as the built-in benefits.
S.M.: I think it’s en vogue to offer great parental-leave benefits, which I think is wonderful and I’m happy about, but there are so many more things that are important to retaining women in tech than just offering great maternity leave. I think the day-to-day is so much more important. Treat people like adults. We don’t count vacation days. We accept that our employees will get their work done. We want them to feel relaxed and go about their daily lives, and that’s why we have a flexible work culture. If you need to work from home or you have doctor’s appointments, we understand that people have lives outside of work. We believe that employees are more effective when they’re able to balance those things. Work hard when you’re working and then you don’t need to be working 24 hours a day.

A.H.: I think that what we’re doing is audacious because we’re doing it this early. One of the things that we set out to prove when we were two people with no funding at all is that we can operate in a way that is highly inclusive without having a ton of money. You can do it.

S.M.: We built these values into our culture early on — the importance of balance and keeping perspective — because we’re in it for the long haul. We’re going to give this idea a real chance to succeed. My husband was diagnosed with cancer early this year, and it was a really difficult time for my family. We hadn’t even launched the app at that point, but because early on we knew that we could operate without needing to be in the office 24 hours a day, seven days a week, we were able to manage even with me dealing with that. It’s given us a great sense of perspective.

Stay visible.
A.H.: When John Greathouse published an article in The Wall Street Journal about how women should use pseudonyms in the tech world, Sara wrote something that I related to a lot. It was about the importance of staying visible and, even better, transparently visible. Sara and I are both very public in our experience as mothers, as people in technology and people working in start-ups. It has only helped us that we are that way. I can’t even imagine what fundraising would have been like without being as visible as we are. We just don’t hide, and I think it’s a good practice. I think it also just helps in making the industry healthier overall. Then people can see that it’s not just young men who are talking about things in tech. Women are part of that conversation, too.

If you want to work in tech, there are never enough engineers.
S.M.: I talk to a lot of young women who are earlier on in their careers and who started off in engineering and computer science. They want to know how to move up the ladder, so they think they have to move into product management or less technical areas than engineering. I would underscore that the most valuable thing for us right now are engineering skills. While our product and design backgrounds are useful, and we need to know how to build consumer products, the fact that we both stayed pretty technical has been a huge asset. I wish I had been even more technical. It really helps when hiring a team. When you have two technical founders, you attract the best and the brightest. I would encourage women especially to stay technical and to not feel like they need to do something a bit softer to have a great career.