Winnie Founder Sara Mauskopf

Although the internet has bequeathed a bounty of information among new mothers, it still has its downfalls, especially for millennial parents of the tech generation.

Sarah Mauskopf of Winnie quickly realized that problem after her first child. Everything was new. Breastfeeding. Finding childcare. Safety. And when Sara returned to work, the act of childcare became a “never-ending problem to solve…[with] no tools to help.”

This never ending puzzle was rooted in the lack of local information. Sure, she could learn about helping her infant sleep. But where could she find childcare? What could they do on the weekends? And as a tech-fluent citizen, where was the app for parents like her?

There wasn’t.

Returning to work and emerging from the fog of parenthood, Sara realized there was an opportunity.

“We could build something that makes this information accessible and is mobile and personalized. So the big moment for me was having my daughter and experiencing these problems first-hand and realizing that I was well-positioned to solve these problems.”

For Sara, the market was clear. Modern parents didn’t have an easy tech solution for childcare woes. In the most tech dependent generation in history—with 90% of new parents being millennials—there needed to be a solution that provided parenting information at their fingertips.

Of course, the major business question centered around exactly what type of information parents prioritized. All parents face the typical challenges of breastfeeding, potty training, and dealing with rambunctious toddlers, but online guides provide sufficient help.

Sara pinpointed the lack of localized information as the biggest opportunity. Where could parents find parks, playgrounds, open spaces, and kid-friendly restaurants? While parents could ask friends or find obscure blog posts, there wasn’t one place that aggregated all that data at scale for any location across the United States.

Sara’s tech background also influenced the way she hoped to solve the problem. At the time, she and her co-founder worked at Postmates. But before then, she had built consumer products at Twitter, Youtube, Google, and Quora.

Building consumer-centric products inspired Sara’s vision for Winnie. At her previous jobs, the community created “the content whether it [was] YouTube or Twitter.” So Sara foresaw a two-sided solution for modern parenting. Users would drive content creation through posts and conversations. Software features like daycare and restaurant locators would curate customized, local recommendations for those parents too.

The platform would marry human interaction and big data.

Sara had a marketable idea, business model, and a clear opening, but in any other world, she might not have taken the jump. Sara told me that there were two types of entrepreneurs from her experience. Some start businesses from a young age for the sake of doing it. Others never expect to be a founder, but end up being so passionate about a problem that they become one anyways. Sara fell in the second bucket.

“If I felt like there was another company out there that was already working on this problem and I could join them, I think I would have done that. I didn’t see anyone even remotely addressing the problem that I thought existed in the world and the opportunity.”

Venturing out as a first time entrepreneur can be exciting, but nerve wracking. Fresh off the birth of her first child, Sara faced criticism from people around her who said that she shouldn’t start a company with an infant. But Sara knew that if there was any time to transform her idea into reality, it was then, because she would just be getting more busy in the future.

Regardless of others’ opinions, the early days were still exhilarating.

“You have this idea, you’re really motivated, and you don’t have any product out there to maintain or a user base to worry about,” Sara explained. “You’re really optimistic that everything is going to work. Those were some of the most fun times. I also got to write code which I like doing and really focus on the product. The early days are wonderful, and that’s the part of the startup that I’ve always imagined.”

In the early stages, she and her cofounder would chat with their advisors, write line after line of code in a small conference room, and flesh out their idea into a product. First, she looked at her competitors. Parents typically found childcare information on Google or Facebook, but those services were too general. Parenting wasn’t their focus.

Ara and her co-founder Ann Halsall

Instead, Winnie would be a niche platform that addressed the specific issues around parenting, while acting as a safe space for new parents to discuss the trials of childcare. Winnie would focus on the community both in the information it provided and in the user interactions.

Sara wanted to attract that community through a host of helpful features, one of which was the comprehensive daycare and preschool search. The team dove deep and collected countless data points on daycares and preschools, plotted the locations on a map, and allowed users to look at important factors such as price and distance. It was the first comprehensive database of daycares.

In fact, the base of Winnie’s entire product is data driven. While parent-produced content is one of their main attractions, the technology underpinning the entire platform is just as important. They collect data through researchers, automated web scraping, and crowdsourcing. If a provider wanted to update information on a page (or claim it), much like Google, they could get access.

Building a product that integrated seamlessly into parents’ lives was exhilarating, but building is different from deploying.

“[Suddenly] You…have users and you raise money. You get employees and the stakes get a lot higher. It quickly went from being all fun and games to we have a real company that we’re running. And there’s a lot more responsibility.”

Part of the Winnie Team in 2018

Six months in, Sara’s husband was also diagnosed with cancer. Fortunately, he’s fine now, but at the time, Sara was dealing with a whirlwind of emotions. She had a baby, her husband was sick, and yet there was still a company to run.

And she almost quit.

But having a cofounder made the idea of staying a little more palatable. Others could fill in duties while she took a break. So although she had to unplug for some time, her team supported her consistently.

When she returned full time to the company, Sara was barraged with a host of new issues, but none as big as user acquisition.

In the beginning, they didn’t show up in Google searches, had virtually no data for most of their services, and struggled to build up a critical mass of users.

So how did they solve this?

They started by launching their product fast. In their first three months, they built a beta and deployed it. Three months after that, they rode into the App Store. By introducing a suite of ready-to-use features, they made it effortless for any parent to immediately start using their service.

And those early users were crucial in determining where to steer their ship. They offered feedback, provided the initial data on local attractions, posted, and generated interest through word-of-mouth.

After those first few tenuous months, Winnie got rolling fast. “The system just kind of maintains itself because users come onto our service, and they create content. That content can drive traffic through search and social sharing and word-of-mouth. And so it’s just this nice self-sustaining system where we grow through our users,” Sara explained.

But their unique platform features varied from major attractions for early customers to veritable time sucks.

One area where they spent too much time in the beginning was their restaurant locator service. Winnie had acquired deep data on restaurants across the US, indexing factors from changing tables to kids menus and even if kids ate free.

Sara and the team loved the feature. But the majority of parents cared more about affordable daycare and safe play spaces for their kids. After spinning their wheels on the feature for a long time, they solicited feedback and realized parents didn’t care much about finding kid-friendly eateries.

Locating those restaurants was useful, but not highly demanded. It was an important lesson for Sara and her team: to build the most highly leverageable products, speak to the consumer first.

Procuring feedback and data from the community has therefore become the biggest driving force behind Winnie. And that same supporting community drives repeat use for new parents.

“I think that’s really the value of the Winnie community, is that no matter if you are dealing with some obscure issue or a common problem, there’s just this tower in the community of other parents and we help connect you to people who have similar concerns or who are in your area. You just feel less alone.”

These conversations—usefully enough—have become the backbone of Winnie’s SEO strategy. Popular parent conversation topics and posts gain more traction, rank better on search engines, and drive more parents to the platform.

Through this crazy experience of becoming an entrepreneur, Sara’s learned a major lesson: you can recover from anything.

“I didn’t think I could survive my husband having cancer, and I didn’t think some of the issues that we faced were problems we could solve. Then we solved them. For example, how to grow organically. It just took time for Google to index our pages and start ranking. You have to, as a CEO or as a founder, always think about how to give your company the most time to figure stuff out. And money is a part of that, but also building a culture where you’re working at a sustainable pace. If you go too hard at the beginning you might burn out. ”

Winnie’s changed the game for millions of households across the country, and they hope to continue making a difference into the future. Sara sees Winnie becoming the end-to-end tech solution for parents across the country, democratizing access to the best quality childcare knowledge. 

Entrepreneur Advice

“If you have an idea that you’re passionate about, something that you want to do, just go for it and do it. There’s never going to be a better time to do it. There’s never going to be more information that you need rather than just getting started. You’re going to learn everything you need to learn by getting started and that’s going to be the fastest way to figure it out. When I was wavering or deciding whether I was going to start a company, that was the piece of advice that really resonated with me most. There was nothing else that I needed to learn or figure out before starting because the fastest way to learning all that stuff would be too just getting started.”

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