For many parents, finding qualified child care feels less like a choice and more like a high-stakes scavenger hunt. Add the affordability component, and the process becomes even more stressful. As Strategos Group’s Managing Partner and Capital Class host, Adam Giery observed in his interview on the subject, “If you’re a parent, you know the challenges of finding quality child care and early education. The pain is real.”

What was once a system run on word of mouth has evolved into a highly professionalized, increasingly data-driven industry. Yet, despite increased investment and decades of increased attention, the search for reliable early childhood education remains a highly stressful experience for many parents.

In 2016, two mothers (both tech professionals) decided to fix that. Their frustrations became the spark for Winnie, a platform that now helps millions of parents and providers across the U.S. connect to essential early education marketplaces.

“Two moms decided enough was enough,” Giery said on his podcast. “They realized the same tools built for commerce and content didn’t exist for our youngest learners. Thus, a business was born.”

An Accidental Entrepreneur

When Sara Mauskopf co-founded Winnie, she wasn’t trying to be a startup CEO. At the time, she was working at Postmates and navigating new motherhood. “My co-founder Ann and I were just talking about how hard it was to balance work and family,” she recalled. “We didn’t set out to build a child-care marketplace. We just wanted to help parents.”

Their first concept wasn’t even about child care, but rather an app for family-friendly activities. “It was free, and people didn’t hate it,” Mauskopf laughed. “But it wasn’t growing on its own.” The breakthrough came when users began using the app for daycare searches.

“People would download the app and search for preschools and child-care centers,” she said. “It took a long time before we realized—this is what people actually need.”

That moment of recognition transformed everything. “We realized everyone just needed childcare,” Mauskopf explained. “All those other things, such as playgrounds and restaurants, were nice to have. But you need childcare so you can work.”

Winnie evolved quickly from there, pivoting to become a full-fledged marketplace dedicated to child care and early education.

The Evolution of an Industry

When Giery asked Mauskopf how the industry had changed in the past decade, her answer reflected both optimism and realism. “Ten years ago, most centers had almost no technology,” she said. “Now they rely on it to run their business. Maybe not as much as I wish they did, but it’s a start.”

What’s changed most, she added, is perception. “When I was growing up, daycare was kind of a dirty word,” she said. “My mom stayed home, and that was the norm. If you put your child in daycare full-time, people judged you.”

Today, that stigma has reversed. “Now you might be seen as a bad parent if you don’t expose your child to early education before kindergarten,” Mauskopf said. “It’s seen as a good thing, as it should be, to have your child in a group environment, learning from a teacher and other children.”

More widespread buy-in exists that values early education less as custodial care and more as a critical stage of lifelong learning.“Parents want their children to be ready for kindergarten, not just academically, but socially and emotionally,” Mauskopf said. “That’s a big change.”

Transparency and Trust

Still, the logistics remain daunting. “When I was a kid,” Giery said, “the bar was low. If your neighbor ran a daycare in their basement and your mom thought it was safe, that was enough.”

Today’s parents want more: licensing verification, reviews, and transparency—especially around cost. “You can get more price transparency buying a car or a house than you can for child care,” Mauskopf said.

That’s where Winnie stands apart. “A big reason people come to Winnie is to assess quality,” she said. “They want to see licenses, read reviews, and understand pricing. Price transparency is one of the last frontiers in this industry.”

But progress has been slow. “We’re trying to encourage more providers to share prices,” Mauskopf added. “It’s better for consumers and the industry overall.”

The Affordability Component

To Mauskopf, affordability and value should not be conflated when discussing early childhood needs. “I believe we should stop asking how to make child care cheaper,” she said, knowing that for some it might seem like a radical concept. “It should be expensive—because it’s incredibly valuable. It allows parents to work. It prepares children for the rest of their lives. Its importance should make it more expensive than college. The problem isn’t that it costs too much—it’s that families can’t afford it.”

Her solution? Shared responsibility. “There should be other payers in the system besides parents—government, employers, maybe new models altogether,” she said. “We need to stop undervaluing something this essential.”

Giery agreed, noting that providers “operate on razor-thin budgets while managing multiple layers of regulation.” Mauskopf sympathized: “These businesses aren’t rolling in cash,” she said. “Most revenue goes to staff pay, facilities, and day-to-day operations. You have to love doing this work. But it can be sustainable if you treat it like a real business.”

Balancing Mission and Margin

For many providers, sustainability is the missing ingredient. “I always tell smaller centers and home daycares: you can’t run this out of the goodness of your heart,” Mauskopf said. “If you go out of business, every family you serve loses care.”

Her advice is simple but firm: “Set your business up to succeed. Charge what it costs, establish real policies—late fees, payment schedules—and make it sustainable.”

The result is a delicate balance between purpose and practicality. “You can run a great business and do good at the same time,” Mauskopf said. “Those things don’t have to be in conflict.”

Building a Marketplace on Trust

Winnie’s two-sided platform connects parents seeking care with licensed providers looking to fill openings. “We only work with licensed providers,” Mauskopf explained. “That helps establish baseline trust because we’re building on the regulation that already exists.”

Beyond licensing, user feedback reinforces accountability. “Even if a center looks great on paper, parents want to hear from other parents,” she said. “That feedback loop is essential.”

Giery noted how this model mirrors successful marketplaces in other industries—balancing scale with human experience. “It’s one of the hardest markets out there,” he said. “But you’ve created a structure where trust is built into the foundation.”

From Startup to National Presence

What began as a side project in San Francisco is now a national platform. “We expanded quickly because we could integrate state licensing data,” Mauskopf said. “It made sense to go nationwide instead of city by city.”

Initially, Winnie was free for both parents and providers. “We wanted traction first,” Mauskopf said. “Then providers started reaching out, saying, ‘You’re sending us a lot of families—can we pay you per listing?’”

That organic revenue model proved sustainable. “We didn’t even think to charge that way,” she laughed. “Providers came to us. It was validation that the marketplace was working.”

The Resilience Behind the Brand

Winnie’s journey hasn’t been without turbulence. “Every day I think, I can’t believe we’re still doing this,” Mauskopf admitted. “We’ve been through so many things that almost killed us.”

One of those moments came during the Silicon Valley Bank crisis, when Winnie temporarily lost access to its funds. “We thought we might have lost all our money,” she said. “But even then, we realized we could rebuild. The experience made us stronger—and it’s what pushed us to become profitable.”

Giery reflected on the lesson in resilience. “Pressure evolves over time,” he said. “What once felt impossible becomes just another part of leadership.”

For Mauskopf, that perspective defines endurance. “Challenges don’t scare me anymore,” she said. “We’ve seen too many to let them derail us.”

A Healthier Model for Leadership

In an era that glorifies hustle, Mauskopf has chosen sustainability. “When we started Winnie, my co-founder and I decided to build it in a way that we could do for a long time,” she said. “I rarely work weekends unless I need to. I want to be present for my kids and still love what I do.”

Her approach emphasizes consistency over burnout. “I don’t believe in the ‘go hard then crash’ model,” she said. “I have three kids. Life doesn’t pause.”

She also encourages her team to prioritize health. “If I get proper sleep and exercise, I’m superwoman,” she said. “I tell my team, if you need to recharge—take a walk, take a nap. You’ll come back sharper.”

That philosophy extends to transparency. “My husband works for Winnie, too,” she said. “It’s truly a family business. I don’t hide any part of my life, and that makes everything more sustainable.”

Giery called it “a refreshing kind of leadership,” contrasting it with the old startup mythos of endless work. “That model burns people out,” he said. “What you’re describing is how you actually last.”

Beyond Early Childhood

Winnie’s scope continues to expand. “This year we added K–12 schools, camps, and after-school programs,” Mauskopf said. “We see child care as the first step in a child’s educational journey.”

Her vision is for Winnie to become the comprehensive hub for families. “One day, I want parents to find everything—daycare, tutoring, after-school care—in one place,” she said. “We’re not there yet, but that’s the dream.”

The Power of Authentic Purpose

What began as a conversation between two working mothers has become a national platform, one that has subtly reshaped how parents and providers connect.

Giery captured the spirit of Mauskopf’s journey best as the podcast wrapped: “As parents, we’re all better off for a service like Winnie,” he told Mauskopf. “But more than that, your story reminds us that entrepreneurship often starts with something deeply personal.”



Mauskopf’s journey isn’t about disruption for its own sake—it’s about solving a problem she lived firsthand. “We didn’t set out to start a company,” she said. “We just wanted to make life easier for parents. Everything else grew from that.”