Stay Rooted in Your Mission: Interview with Chris Bennett, Founder and CEO of Wonderschool

I recently went one-on-one with Chris Bennett, founder and CEO of Wonderschool.

Adam: How did you get here? What experiences, failures, setbacks, or challenges have been most instrumental to your growth?

Chris: I owe a lot of my personal growth and success to my upbringing. I was raised by incredibly hardworking immigrant parents. My dad 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. I also had a really impactful experience with early education that sparked my interest in becoming an entrepreneur.

I worked in private equity and had a few other startups before I came up with the concept for Wonderschool. Through the different paths my career has taken, I’ve realized that you gain something from every experience. Learning what you don't want to do is just as important as figuring out what it is you want to do. 

As Wonderschool has grown, I’ve learned a lot from how my role as CEO has changed. Every time we hit a big change or milestone my responsibilities as a leader shifted. As my team increased in size, I was faced with new leadership challenges that I had to adapt to. There's just a lot of growth that needs to occur as an individual to have the ability to continue scaling with the company. 

When building and growing Wonderschool, I realized the biggest challenge that many individuals wanting to start childcare businesses struggle with is navigating the different complexities and nuances of local and state regulations. Starting a business can be really overwhelming, and many aspiring providers don’t realize that they do not need a formal background in this to have a flourishing childcare program. I realized that my opportunity to add value and help create a solution was through analyzing what the key barriers are, using relevant and timely data, and then working directly with state leaders to create state-specific programs to accelerate and streamline the process of building a business for new entrepreneurs. We work hard to build strong relationships with state governments and focus on our shared goal of improving regional childcare landscapes.

Adam: How did you come up with your business idea? What advice do you have for others on how to come up with great ideas?

Chris: Ever since I was a child I knew I wanted to be an entrepreneur. I’d been in the VC and startup realm for a period of time, I started Wonderschool after hearing what a hard time friends of mine were having with finding childcare when I started to visit childcare programs to see what they were facing with connecting with those parents or growing their business I knew I could help. One of the things that fueled my passion in the early years was when someone told me that 90% of the brain develops by age five. I see child care as a way to help economies and also a way to help children thrive. Although I was a child of two hard-working immigrants I was given the opportunity to attend a local home-based childcare program in my neighborhood with a passionate, driven provider, who was becoming a successful entrepreneur.  Reflecting on my past experiences, I also saw how inaccessible quality child care was to the majority of families in the US. I realized the lack of supply in child care could be solved by increasing the availability of local home-based programs. Wonderschool was founded to help solve the childcare crisis by creating more quality childcare options for families around the country, and simultaneously empowering individuals to become entrepreneurs in the childcare industry, as I witnessed my own childcare provider do. 

I think that great business ideas come from a combination of passion and commitment to the long-term goal of what you’re aiming to do, and the data to back up why it’s a strong opportunity. 

Adam: How did you know your business idea was worth pursuing? What advice do you have on how to best test a business idea?

Chris: After I recognized that an opportunity existed to help people successfully build childcare businesses that met the needs of their communities, we gave the idea a real test run, actually renting a home, hiring a teacher, and starting our own program in the Berkeley Hills. When enrollments started happening, I realized we were onto something — it became evident that this teacher was going to have a positive impact on the kids' and parents' lives and that by providing resources to support operations and licensing, our team was able to add value from a business perspective. I think finding an effective, real-world context to test the business model is a really key part of understanding what’s going to work, and where you need to rethink certain ideas.

Adam: What are the key steps you have taken to grow your business? What advice do you have for others on how to take their businesses to the next level?

Chris

  • Do thorough research to develop a deep understanding of the market you want to break into, its challenges, the data surrounding it, and how it’s changed in the past one, five, and ten years. This is the key to understanding how your business can add value and how you can curate an offering that makes your company different from existing offerings.  Never stop asking how you can continue to make solutions scalable, closer, and better for your audience.

  • Find a way to test the idea in the real world to really understand the ins and outs of what the business needs to succeed, and what the public response is. We had an initial Wonderschool program that we started and were able to really see what the operational needs of running this type of business are, and what we needed to do to make our company the best possible resource

  • Assemble a strong investor team to advise business strategies and help create a sustainable business model. 

  • Build a strong team of individuals who have the background and skillset to propel company growth. We have employees with Ph.D.s in early childhood education, experience working in the public service space, etc., who can advise and provide valuable insights that deepen our understanding of market needs. 

  • Make strategic acquisitions to expand and enhance offerings, and additionally strengthen the company workforce. The focus is always on “how can we make our platform as valuable as possible for those who are using it.” We’ve made a number of acquisitions that have allowed us to join forces with great company leaders and leverage existing infrastructure and technology that’s proven successful to better serve our customers. 

Adam: What are your best sales and marketing tips?

Chris:

  • Take time to understand current and future needs and characteristics of your target market.

  • Make data-driven decisions when approaching a new market and ensure that you have a strong framework for gathering and analyzing data.

  • Foster customer loyalty by providing continued service to existing customers/users. Referrals from happy customers are a powerful marketing tool because they come from people who trust and believe in your company and can speak to its market value firsthand.

Adam: In your experience, what are the defining qualities of an effective leader? How can leaders and aspiring leaders take their leadership skills to the next level?

Chris: As a leader and founder, I find the most fulfilling part of my role, and what keeps me inspired, is seeing the real impact Wonderschool is having on our customers’ lives. I think it’s key to make sure that all employees across the organization are able to see the real-world benefits of something they’ve had a hand in building to help them feel driven in their work. 

Part of being an effective leader is ensuring that employees are empowered to think creatively, and understand and feel connected to our business goals. At Wonderschool we regularly share the incredible stories of our customers, childcare providers who have flourishing businesses, and families who are able to find care through our platform, to keep the team motivated and excited about the work we are doing. 

Adam: What is your best advice on building, leading, and managing teams?

Chris: I think that to effectively build, lead, and manage a team, there are a few core principles to keep in mind: 

  • Prioritize open communication amongst the group, to foster a culture of collaboration and creativity

  • Have clearly defined business goals that tie into the company mission and vision

  • Ensure everyone understands their roles and responsibilities and feels empowered to execute their best work.

  • Be flexible and willing to adjust strategies and plans as needed based on changing circumstances and market dynamics. 

Adam: What are your three best tips applicable to entrepreneurs, executives, and civic leaders?

Chris:

  1. Stay rooted in your mission: Being an entrepreneur and leader comes with a lot of challenges, but staying rooted in the company mission and focused on the positive outcomes that result from executing it is a great way to stay excited and creative. Wonderschool’s mission is to ensure all children receive access to the early education they need to fulfill their potential. When we execute 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. 

  2. Don’t fight the market; go where the market takes you: It’s integral to stay flexible in all businesses and it’s something that is especially pertinent in the childcare space. We initially had the idea of being consumer-focused and were pretty committed to this. But with increasing interest from government customers, we shifted to go in the direction of where the demand for our services was taking us. By making this market shift, I realized that we were actually able to better scale the business and help more families around the nation, and government partners are now the biggest source of business for us. We stay flexible too–making sure that we are aware of where the market stands at any given moment in time, and having a framework that allows us to pivot when needed, is essential.

  3. Build strong partnerships:  Investors, business partners, government partners, etc are all so important to creating and maintaining a successful business strategy. It’s important to have a collaborative relationship with partners to strengthen your business playbook. At Wonderschool our government partnerships are especially critical, as we work with leaders on the most impactful way we can serve the child care needs of regional communities and align with their individual regulations. 

Adam: What is the best advice you have ever received?

Chris: I was actually interviewing for a real estate private equity role, and the interviewer told me “If you want to start a company, you should do it now.” His candor and openness propelled me to kick start my entrepreneurship journey and ultimately the founding of Wonderschool. 

Adam: Is there anything else you would like to share?

Chris: When I was considering an industry for my next company, I had an initial idea to start an app in the cleaning service industry. I had an investor ask me “Chris, do you really want to be doing that for the next 10 years?” and thought “No, I don’t.” I realized that working to improve the child care landscape was something I felt passionate about, and from that built a business model. I wake up every day excited about Wonderschool and the impact that we are having on families across the nation. It’s not just that the company needs to have longevity–the passion you have as a leader in your industry needs to remain steadfast as well.


Adam Mendler is an entrepreneur, writer, speaker, educator, and nationally recognized authority on leadership. Adam is the creator and host of the business and leadership podcast Thirty Minute Mentors, where he goes one-on-one with America's most successful people - Fortune 500 CEOs, founders of household name companies, Hall of Fame and Olympic gold medal-winning athletes, political and military leaders - for intimate half-hour conversations each week. A top leadership speaker, Adam draws upon his insights building and leading businesses and interviewing hundreds of America's top leaders as a top keynote speaker to businesses, universities, and non-profit organizations. Adam has written extensively on leadership and related topics, having authored over 70 articles published in major media outlets including Forbes, Inc. and HuffPost, and has conducted more than 500 one on one interviews with America’s top leaders through his collective media projects. Adam teaches graduate-level courses on leadership at UCLA and is an advisor to numerous companies and leaders. A Los Angeles native, Adam is a lifelong Angels fan and an avid backgammon player.

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Adam Mendler