Early Education Crusader: Chris Bennett, Co-Founder and CEO of Wonderschool

Laura Spaventa Lewis
Aug 27 · 7 min read
Chris and one of the inspirations behind Wonderschool, Yoli, who ran his sister’s in home childcare program

Editor’s Note: Welcome to our new Unusual Founder Spotlight series! The goal of this series is to introduce the technology founders in our portfolio who have the rage to master and are currently building the future across categories and industries.

With over 24 million children under the age of five in the U.S., early education is a $57 billion market in tuition dollars alone. Numerous studies have shown how critical early education programs are to improve student outcomes over time. And yet, parents across the country are scrambling to find both convenient and affordable options for their children. This is due in large part to a severe shortage of early educators, thanks to below average salaries and the rising cost of living, particularly in major metropolitan areas.

Inspired by his co-founder’s struggle to find early childhood care and his own early education experience, Chris Bennett, the Co-Founder and CEO of Wonderschool, recognized there was a huge opportunity brewing. This led to the formation of Wonderschool, a platform to help both educators and caregivers start, operate, and grow their own high-quality in-home preschools and child care programs, giving them a sustainable career and parents a marketplace of better options. In a little under three years since its founding in 2016, Wonderschool has expanded to four cities, provided hundreds of early education programs for children, and has helped educator-entrepreneurs get their childcare businesses off the ground.

We were excited to sit down with Chris to learn more about how his dad and early teachers inspired him to start Wonderschool and why he’s on a mission to provide quality early education for every child under five.

Unusual: Can you give us a little bit of background on yourself?

Chris: Born and raised in Miami, I grew up very much influenced by my parents who immigrated from Honduras and our large extended family. When I say large, I mean it — I have 31 cousins alone. The majority of my family members ran small businesses, so I was surrounded by entrepreneurs from a very young age. Not only am I one of the few in my family to graduate college, but the only one to go to an Ivy League. While at Wharton, I studied entrepreneurship and started a company that made it easy for students to sell their textbooks on the Internet called LiquidBooks.

Though very interested in entrepreneurship throughout my time at Penn, I decided to take a break from it and took a job in private equity in Chicago. After being in private equity for two years, I went on to try a number of different things. I thought I wanted to be a doctor, so I went and did a postbac in Miami. Then, I thought I wanted to join the US Foreign Service, so I explored that. None of them appealed to me. That’s when a friend told me about a place called Silicon Valley where people came to start companies. I didn’t know there was a place like this, so I came to visit nine years ago and never left. Well, I went home for two weeks to pack my bags and came back. I’ve been working on startups here ever since.

https://www.wonderschool.com | Chris Bennett

Unusual: It sounds like entrepreneurship has been a big part of your life, but it took you a few pivots to realize it was really for you. When did you realize you were an entrepreneur and/or ready to lean in?

Chris: When I was doing my postbac, I realized I didn’t want to be a doctor after I shadowed a few and didn’t like it. Then, I worked in an organic chemistry lab and thought I wanted to potentially work on a cure for cancer. I realized that wasn’t right for me either. During this time I was reading a lot of books on startups, and the opening paragraph of one of my favorites said something along the lines of, “Every company was a startup at one point — Coca-Cola, American Airlines, etc.” When I read that, it all sort of connected. I thought, “Oh…” because I wanted to make sure that if I was going to spend a lot of time on something, it would impact a lot of people. So, when I read about this idea of starting a company as big as Coca-Cola or American Airlines, it clicked that I can accomplish doing good and having a big impact on the world through a startup. It was that moment when I thought, “This is what I’m going to focus on.”

Unusual: What was your “aha” moment that led you to work on Wonderschool?

Chris: My co-founder was having a hard time finding childcare and I didn’t understand why there were not enough options. I started doing research and I realized there was a huge shortage of child care options not only in California, but the entire country. I reflected back on my childhood and the in-home program a woman named Yoli ran that I went to for after-school care and my sister went to for Pre-K. Yoli’s program was a huge success and I thought, “Yoli’s business is still thriving, so why don’t more people start what she’s doing?”

After additional research, I realized that it’s actually really hard for people to optimize their child care businesses the way Yoli has. She’s sort of an outlier in that she has both the business and education aptitude needed. I recognized that we had an opportunity to help people build the right child care businesses. From that “aha” moment, we actually rented a home, hired a teacher, and started our own school in the Berkeley Hills. I realized we were onto something when people started to enroll — the picture became clearer around how this teacher was going to change all of these people’s lives and how we were able to add value from a business perspective.

Unusual: What excites you the most about the potential of Wonderschool?

Chris: There are 24 million children under the age of five and there are a ton of statistics that show early childhood education is incredibly important to a child’s life. One study in particular, the Perry Preschool Project, went into a low income community and gave only half the kids access to preschool. When the researchers looked at the performance of both groups in second grade, they found that there was no difference between the kids who did receive access and those who didn’t. However, when the researchers checked back in with the two groups of children later in life, they found that the kids who went to preschool were more likely to graduate from college, get a job, get married, and less likely to go to jail. The researchers also found that the kids who went to preschool shined in non-cognitive skills like grit, perseverance, delayed gratification, and other skills that don’t show up on a SAT or IQ test — all of these benefits just from going to preschool.

The mission of Wonderschool is to ensure all children receive access to the early education they need to fulfill their potential. When we execute on that mission, there will be so many positive externalities that are created because of it. We will create more jobs. We will create a lot more entrepreneurs. The kids who go through our programs are going to have much better outcomes in life. The parents of the kids will benefit from children who have better outcomes. There are just so many positive outcomes that will occur if we are able to execute on our mission and that potential excites me the most.

Unusual: For you personally, who has been your biggest influence and inspiration?

Chris: Biggest influence? That’s an easy one — my dad. He immigrated from Honduras with not a lot of money and made many sacrifices for my sister and me growing up. He taught me a lot about thinking for yourself, making decisions for yourself, and being accountable for the things you choose to do with your time and life overall. He passed away 10 years ago from Leukemia, but I still utilize a lot of the things he taught me on a daily basis.

Chris and his father Christopher

Unusual: What’s the hardest thing about being an entrepreneur that nobody warned you about? And on the flip side, what’s the most fulfilling aspect of being an entrepreneur?

Chris: In terms of the hardest aspect of being an entrepreneur, I guess I didn’t realize how much the company would change every time we hit an inflection point. When I was running a two-person company, I didn’t realize how much my role would change when I would run a 10-person company versus a 20-person company versus a 50-person company. There’s just a lot of growth that needs to occur as an individual to have the ability to continue scaling with the company. That’s been a big learning for me.

The most fulfilling aspect of being an entrepreneur is seeing the real impact we have on our customers’ lives. Seeing the delight of your customers when you know that they’ve benefitted from something you built with your team is so fulfilling. For example, we had a Company Summit the other week where we invited parents to come and speak about their Wonderschool experiences. One of the parents tried more than three other preschools and she finally found a preschool that was a fit on our platform. She just gushed and even got emotional about how much this meant to her, her child, and her family overall. That moment was so empowering and made the struggles that come along with being an entrepreneur worth it.

Learn more about how Chris and Wonderschool are executing on their mission to ensure every child under the age of 5 has access to early education to help them realize their potential

Unusual Ventures

Your best partner for the journey ahead.

Laura Spaventa Lewis

Written by

Director of Marketing at Unusual Ventures

Unusual Ventures

Your best partner for the journey ahead.

Welcome to a place where words matter. On Medium, smart voices and original ideas take center stage - with no ads in sight. Watch
Follow all the topics you care about, and we’ll deliver the best stories for you to your homepage and inbox. Explore
Get unlimited access to the best stories on Medium — and support writers while you’re at it. Just $5/month. Upgrade