Chris Bennett Makes Money Empowering Others. Some Of The Biggest Names In VC Are Backing Him On Mogul Watch

Ebony Grimsley-Vaz
Written by Ebony Grimsley-Vaz

This is one in a Moguldom original series that shines the light on the founders featured on MogulWatch, our comprehensive list of startups that have received venture capitalist funding. Find out how much money they have received from whom, and news and data about their company. 

Chris Bennett’s two tech companies, Soldsie and Wonderschool, have collectively raised $29 million in funding.

Bennett found a way to make money by empowering others to make money, and some of the biggest names in venture capital are backing him.

Soldsie began in 2011 and focuses on helping brands sell their products on Facebook and Instagram. Its payment system enables merchants to monetize their Facebook page by allowing customers to purchase through comments. The company has raised $5 million in capital with a $1-million seed round and a $4-million a Series-A round led by First Round Capital. Investors include Charles Hudson.

Wonderschool started in 2016 and offers a platform for people who want to begin infant, toddler programs and preschools out of their homes. This allows teachers to live where they work in difficult housing markets like San Francisco. Wonderschool raised about $24 million in three rounds. The most recent round in August 2018 (for $20 million) was led by Silicon Valley venture capital firm Andreessen Horowitz.

Chris Bennett
Chris Bennett, founder and CEO of Soldsie and Wonderschool. Photo provided by Wonderschool

This serial entrepreneur recently invested in YoGov, a tech company that helps people to use and get access to government services. Bennett is also one of the founders of Black Founders, an organization on a mission to increase the number of successful Black entrepreneurs in technology.

Bennett has a bachelor of science in economics from the Wharton School at the University of Pennsylvania and has chosen to grow his businesses in Silicon Valley.

“One of the biggest challenges in education today is that there’s not enough early childhood education. We had this idea that one of the ways to do that was to start to invest in creating more early childhood education options for families. So we started Wonderschool. We find teachers, we help them start schools out of their homes and then we help fill their schools.” — Chris Bennett, founder and CEO of Soldsie and Wonderschool.

Bennett spoke to Moguldom about his ventures and how he manages to run multiple businesses.

Moguldom:  It’s difficult for entrepreneurs to find enough time to run one business. What are some of your secrets for being able to run two?

Chris Bennett: I find strong leaders that I can work with to help to run the multiple businesses. We hired a strong COO at Soldsie, and he’s been running Soldsie as I focus on the operations of Wonderschool.

Moguldom: You already had one growing business, Soldsie, when you started Wonderschool. What inspired you to do that?

Chris Bennett: I think a big inspiration for me was early childhood education and figuring out ways to help fix education. What we’ve found is that one of the biggest challenges in education today is that there’s not enough early childhood education. We had this idea that one of the ways to do that was to start to invest in creating more early childhood education options for families. So, we started Wonderschool. We find teachers, we help them start schools out of their homes and then we help fill their schools.

Moguldom: How do you help parents find the right matches?

Chris Bennett: We built technology that helps parents search for the right school and then helps the parent enroll in the school. We have a quality and safety promise. We do this by vetting all the teachers with background checks and home inspections. They also get assigned mentors. We give our teachers a lot of resources to help them onboard, and then once their school is up and running, we work with the teachers on an ongoing basis to make sure they’re running a high-quality program.

Moguldom: You’ve had three funding rounds. Did it get easier to raise money as a founder your second time around?

Chris Bennett: I think it’s been easier because Wonderschool is a really good company and business model. It’s a great team working on a great concept, so I think that we benefit from having a good offering for the market.

Moguldom: What are some of your notable wins?

Chris Bennett: All the schools we’ve started and all the students we’re serving. The fact that we’ve been able to do it in multiple markets is incredible.

Moguldom: You mentioned that finding the right people is important to help you to continue to run. Are there any tips you can share on building a good team?

Chris Bennett: We interview for 110-percent adaptability and communication. We’re looking for folks who are open to changing on the job, who are excellent communicators and who go above and beyond. That’s what we’re looking for when interviewing for positions.

Moguldom: What does success look like for you?

Chris Bennett: Building a company that is going to serve hundreds of millions of children. That’s the goal, and we’re focused on achieving that.

Moguldom:  How do you manage to keep the creativity flowing to make the best services or products for your clients?

Chris Bennett: A lot of it is making sure the team is working well together and making sure we’re able to create an environment for our team to do its best work. I’d say that’s one of my biggest focuses.

Moguldom:  What type of environment are you looking to create?

Chris Bennett: One that’s inclusive, where people feel they can do their best work, be open and honest and communicate across the organization. An environment where people feel like they’re growing inside the organization.

Moguldom: What do you think the next five years look like for Wonderschool?

Chris Bennett: I think the big thing is just continuing to start more schools and enroll more families. That’s the big focus.

Moguldom:  What do you think people would say about your leadership five years from now?

Chris Bennett: I think people would say I’m not the most hands-on leader. (I’m) focused on just getting the right people together and empowering them to do their best work.

Moguldom: You’re working with both Soldsie and Wonderschool, and you recently became a part of YoGov. Can you explain your relationship with that organization?

Chris Bennett: YoGov is just an investment I’ve made. Ryder Pearce is the founder of YoGov. I’m excited about the mission of YoGov (a tech company helping people use and get access to government services) and the vision of it, and I’ve just been supporting him in growing. It’s been awesome.

Moguldom: You started and are operating several successful businesses. Do you see yourself juggling even more in the funder role?

Chris Bennett: It’s a great opportunity to learn, and connect with other founders, so I’ve found that to be helpful. I really enjoy it.

Moguldom: Do you find yourself having to do a routine to balance everything that you’re doing? How do you keep up?

Chris Bennett: I love what I do. I love it. It’s fun, and so far, I’m keeping up.

Chris Bennett
Chris Bennett, founder and CEO of Soldsie and Wonderschool. Photo provided by Wonderschool