Pod Insights How I Built This with Guy Raz How I Built Resilience: Jessie Woolley-Wilson of DreamBox About this episode Guy speaks with Jessie Woolley-Wilson, CEO of DreamBox, an online math learning program for K-8 students. The platform has added two million new users during the lockdown, but that rapid growth has created "stretch marks" and new challenges for leadership. These conversations are excerpts from our How I Built Resilience series, where Guy talks online with founders and entrepreneurs about how they're navigating turbulent times. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Transcript Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.
0:00 Guy Raz? We get support from US Bank. A question I love asking founders. What's the one decision you almost didn't make? The one that changed everything? Because it's never the obvious stuff. It's never, I decided to start a company. It's the small, boring, Tuesday afternoon decision you barely remember making until you realize it's the reason everything after it either worked or didn't. Say you're 18 months in. Business is growing. You've got expenses coming from six directions. Gas for the van, office supplies, your phone bill, team lunches that are actually client meetings. And you're putting it all on whatever card you grabbed in year one. You're not thinking about it. Why would you? You've got bigger problems.
0:45 Guy Raz? But here's the thing. Path A, you keep going like that. End of the year, you're sorting through statements, trying to figure out what went where. You've left hundreds, maybe thousands, on the table in rewards you never earned. Money that could have gone back into the business. Path B, you pause and get the US Bank Triple Cash Rewards Visa Business Card. Now, you're earning 3% cash back on gas and EV charging, office supply stores, cellphone service, and restaurants. You pick up an extra $750 cash back as a bonus. And you've got a low APR on purchases and balance transfers for 12 months while you're scaling. Same business, same expenses, two completely different outcomes
1:30 Guy Raz? based on one small decision. Visit usbank.com/business to learn more. The creditor and issuer of this card is US Bank National Association, pursuant to a license from Visa USA, Inc. Some restrictions apply. Our presenting sponsor today is Anthropic, the team behind Claude. Every founder on this show started with a hard question. Not the marketing plan, the 2:00 AM kind. Is this idea any good? Am I the one to build it? Should I quit my job? Anthropic got built the same way. A public benefit corporation founded on one Hard question. How do we make sure AI goes well for people?
2:14 Guy Raz? So they asked over 100,000 people their hopes and their fears and are publishing what they find, even the uncomfortable parts. Me? I've got my own hard question about AI. Here it is. If everyone has access to something that can help them write the business plan, build the prototype, analyze the market, maybe even come up with the idea. What separates the people who actually build something from everyone else? I don't have a clean answer yet, so I've been sitting with it with Claude. There's hope in hard questions. Ask yours at claude.ai/hibt.
2:54 Guy Raz? Does your team want a website that looks and feels handcrafted but is still fast to ship? Well, Framer is built exactly for that. With Framer, you design on a visual canvas with responsive layouts, hosting and a CMS built in, so the work is production ready from day one. And you can get it done with help from Framer's AI agents. Framer is the AI website builder that helps creators, teams and businesses ship production-ready sites faster than ever while getting every detail right. Prompt, inspect, edit and publish in one place at a whole new pace. AI agents and humans work together.
3:36 Guy Raz? The agents bring speed and scale and people bring taste, judgment and control. Learn how you can get more out of your site from a Framer specialist or get started building for free today at framer.com/built for 30% off a Framer Pro annual plan. That's framer.com/built. Rules and restrictions may apply. AI isn't just opening new business opportunities, it's changing the way businesses get work done. The questions they ask, the decisions they make, the routine tasks they can hand off. That's the idea behind NetSuite Next, the next generation of NetSuite with AI woven into the tools your business already relies on.
4:21 Guy Raz? NetSuite Next surfaces insights exactly when you need them, puts agents to work on routine tasks and problems, and lets you ask complex questions in plain language, like talking to a knowledgeable colleague. But technology is only part of the story. AI is also reshaping how people and teams work together, and that shift is already underway. That's why NetSuite wants to put a new, expert-created business guide in your hands today. It's called Aligning for the Agentic Era: How AI is Changing Everyday Work. And right now, it's yours, absolutely free. Inside, you'll discover how AI could reshape work across your entire organization, and how to position your business to prosper from it.
5:06 Guy Raz? If your revenues are at least in the seven figures, get NetSuite's free business guide, Aligning for the Agentic Era: How AI is Changing Everyday Work, at netsuite.com/built. The guide is free to you at netsuite.com/built. netsuite.com/built. Hey, everyone. Welcome to How I Built This: Resilience Edition. On these episodes, we're talking with entrepreneurs and other business leaders about how they're meeting this very challenging moment in new and creative ways. And today, we're going to hear from Jesse Woolley Wilson, the CEO of Dreambox. Dreambox is an online learning platform that uses educational games to teach math to kids. And it's become more popular than ever
5:52 Guy Raz? as many schools in the US are opening back up, but only online. Jesse joined me from Dreambox's headquarters in Bellevue, Washington. So for people who aren't familiar with it, can you just kind of give us a description of Dreambox?
6:06 Speaker 01 Sure. Dreambox is a K through 8 math program. That delivers personalized learning for every child on it. So it's engaging. Kids think they're doing games, but they're actually doing very serious math learning.
6:19 Guy Raz? So you have, I think, about 270-plus employees now. How are you managing the staff remotely?
6:27 Speaker 01 It's been a lot of change for us. So there were two phases of this evolution post-COVID. First phase was to survive. And the second phase was to thrive. And in the survive phase, we were guided by our company values and by three principles, really. The first is, what do we do to take care of our employees? We want them to be safe and secure. And we closed the office early, early March, before many other people did. And then the second was, what do we do to take care of our school customers? Our kids and our teachers and school administrators. And we figured if we took care of our, our staff, then we could take care of our customers. And then the third piece was, if we take care of our customers, then we will take care of our company. So the default was not, what do we do to take care of revenue?
7:12 Speaker 01 The default was, what do we do to take care of our talent so that we can take care of our customers? If we do that, we will do everything we can to protect revenue in the company.
7:20 Guy Raz? So, you know, as the pandemic began to unfold and as schools really began to shut down quickly, what was the economic impact on, on your business? I mean, was there a slowdown? Was there a rush to sign up? What, what, what happened?
7:35 Speaker 01 So in the beginning, we didn't know what was going to happen. So we decided to prepare for the worst and hope for the best. And so we cut back on all of our expenses dramatically. We moved everybody to work from home. That meant we weren't spending as much money on travel. We didn't go to any conferences. There was a lot of education conferences where we meet, you know, principals and district administrators. We cut out all of those. And we really cut out everything that we have relied on for the past 10 years to cultivate customers. And we didn't know what was going to happen. Then I got together with my team and I said, what do we do to help teachers through this? We have to figure out a way to demonstrate our partnership. And they said, what we should do is open up the platform for free throughout the whole school year.
8:18 Guy Raz? Wow.
8:19 Speaker 01 They have many, many things. To worry about, they won't have to worry about math instruction. That will be one thing they won't have to worry about. So I went to my board. I said, the thing that we should do is to open up the platform so that if a district had, you know, three of fifty schools on Dreambox, they could put the remaining forty seven on for free through the end of June, just so that they could keep their kids learning at home. And we figured the best thing to do was to go to our existing customers because they were already trained. They had people in the district who could be resources to parents and to children, and we didn't know if we were going to be able to train them. So we did that, and within six weeks, we nearly doubled the number of students and districts were really desperate.
9:03 Speaker 01 So fifth in five weeks. So that was over two million students that were added.
9:08 Guy Raz? So, so to two million students added in five weeks. How much, so how many total students are using the platform?
9:15 Speaker 01 So over five million.
9:16 Guy Raz? Wow.
9:17 Speaker 01 Students, uh, K through eight are using Dreambox through our schools.
9:20 Guy Raz? Yeah, what does that mean for your product team and the engineers who are, who are all of a sudden onboarding two million kids in five weeks?
9:28 Speaker 01 So I love that question because when I say that, most people say, oh, that's so great. You know, you had exponential growth. And what I say in response to that is when you grow really fast, you get stretch marks. And we got stretch marks.
9:40 Guy Raz? Yeah.
9:40 Speaker 01 So our stretch marks were our support system was overwhelmed. And this was at a time when they were usually, it was a low period typically. So gearing up for the fall, busy back to school season. And so we looked at our team and we said, you're going to have to sprint now. And it was very, very difficult because it meant that we had to stretch ourselves. And the one thing I didn't mention earlier as part of our cost reduction, we moved everybody to a four day work week.
10:06 Guy Raz? Wow.
10:06 Speaker 01 And so at the time that we moved them to a four day work week, expecting very low volumes, expecting no sales, expecting nobody to use the system, we had an explosion of new customers, an explosion of kids on the system. And I just told the team, you know, there's a lot that we don't know. I'm going to tell you what I know and I'm going to tell you what I don't know. We're going to meet every month instead of every. Quarter and I hope that with every successive month, what I know is gonna start to creep up and be more than what I don't know.
10:37 Guy Raz? Yeah.
10:37 Speaker 01 And a lot of people said, you can't lead like that. You can't tell people what you don't know. But people already know what we don't know.
10:43 Guy Raz? Right.
10:44 Speaker 01 They will, they need to know that you're gonna be, you know, authentic about that and they appreciated that, even though I didn't have a lot of answers for them.
10:50 Guy Raz? So are you hiring? I mean, have you opened up positions?
10:54 Speaker 01 So we put a hold on hiring for that survive phase. And now we have, we, everybody's back to work. We came back earlier than expected and early July, we came back a hundred percent. And so now we are starting the recruiting process again.
11:08 Guy Raz? Wow.
11:09 Speaker 01 So I will tell you, Guy, though, we expected that all the schools were gonna open up at least partially and maybe have, you know, Monday, Wednesday and Friday in school and Tuesday and Thursday at home, or some other kind of hybrid model. But in the last two weeks, we've seen an acceleration of schools deciding that they're gonna stay one hundred percent remote through the end of the calendar year. So that means that the teachers that we were gonna train so that they would know how to use Dreambox are not in schools. So all of our professional development had to be put on hold or used with a Zoom, for example. And it's really, as soon as you think you have something understood, you have to adapt because it changes and you just have to stay flexible.
11:47 Guy Raz? Yeah. One of your, I mean, your main sales strategy is you deal with school districts and administrators, not parents. I guess, when you joined the, the company in two thousand and ten, there was this kind of hi- more hybrid model where, parents were targeted, the consumer was targeted, and now it's really school districts. I wonder whether now, if, you know, many parents decide to homeschool, or to kind of opt out of virtual learning through their schools. Um, is there a world where, where you start to pivot again and focus on consumers again?
12:19 Speaker 01 Well, it's such a great question, Guy, because a lot of people don't realize, you're right, in two thousand and ten, we started to move toward the B two B model. But I didn't shut down the parent channel, the consumer channel. We knew that there were teachers there and administrators there in the parent channel, and we thought that if we could win their confidence, it would help the institutional side of the business. So the. Other thing that we did is that we opened up Dreambox through the end of August now for parents. They could get a free trial so that parents who were working from home and being overwhelmed while they were at home would know that they could find a solution that was proven to be effective, that was engaging for their kids for mathematics with Dreambox for no cost.
13:02 Speaker 01 We offered that trial for parents and I don't think we're ever going to move away from parents. We think parents are the X factor. And we think technology should never be designed to replace teachers. Forty percent of the employees at Dreambox are former educators. We don't think that technology should replace the learning guardian. We think technology should do what technology does best, which is to help understand the thinking process of children and to give them actionable insights so that they can modify their instructional strategy and personalize it to be more high impact for every child.
13:37 Guy Raz? Let me go to a question from our audience. This is from Jaguna Hillary. She says she is volunteering as a teacher. She's been working with kids since schools have shut down. One disturbing thing she says she's noticed is that a lot of kids don't have access to online learning opportunities or their parents may not even know about them. How do you make what you do and sell available to every kid?
14:00 Speaker 01 So there's two things I would like to say here. It's really important. The one thing that keeps me up at night when I think about online learning is that it might widen the gap between the haves and the have nots. And we all as a society have to be very intentional about making sure that we don't lose sight of that and that we work very hard to make sure that every child, regardless of their zip code, frankly, has access to great learning experiences. So one of the reasons we moved from the consumer approach to the institutional approach is to bring Dreambox to every child. We brought Dreambox to where all kids were, in schools. Not just to the parents who happen to know about it,
14:43 Speaker 01 but to institutions and communities where parents might not be aware of it. So that's one, one thing. But we need to make sure. That some structural impediments like broadband access and device access are targeted to the least well-served communities. And what I'm encouraged by is that the CARES Act and a lot of what districts are using with federal funds is to address device and broadband access. Now, the good news is that almost 90% of kids have access to broadband and devices, but that doesn't help the 10% that doesn't. So we need to work with libraries and we need to work with foundations and we need
15:27 Speaker 01 to work with private-public partnerships while we develop policies and funding mechanisms to close those remaining gaps. The last 10% is going to be the hardest, but we can never let up on that.
15:41 Guy Raz? When we come back in just a moment, Jesse tells us how a hybrid of in-person and online teaching can help all types of students do their best work. Stay with us. I'm Guy Raz, and you're listening to How I Built This, Resilience Edition from NPR. Hey, welcome back to How I Built This, Resilience Edition. And I'm talking with Jesse Woolley-Wilson. She's the CEO of Dreambox. It's a platform for learning math online. This is a question from Noah Thomas. He asks, do you think that, given that the marketplace for remote learning is already
16:24 Guy Raz? shifting and will probably shift even more post-pandemic, do you imagine just an explosion of opportunity for educational technology companies in the next five, 10 years? Maybe an accelerated series of opportunities?
16:39 Speaker 01 I absolutely did. One of the things that we did several months ago was we studied the marketplace and we studied industries that had V-shaped recoveries that were anticipated, U-shaped recoveries, and L-shaped recoveries. So maybe a cruise line is not going to come back. It's an L shape. Maybe an airline is a U shape. But we really feel like- Like education technology is a V shape. And we're seeing that now. We've had explosive growth in users, as I mentioned. And we we expect that that is going to continue for the future. Because we feel like people who were trying out learning technologies as a nice to have complement. Now have been forced with distance learning to see it as a must have.
17:20 Speaker 01 And so if they have good experiences and they see that it complements what they want to do in the classroom and at home. We don't see any end in the growth opportunities for proven effective, engaging and reliable learning technologies.
17:35 Guy Raz? Yeah. Are there um are there public schools or school districts that you may know of? And I'm sure that you're consulted from time to time. Is is there a part of places in the United States that might potentially be ready to open that you know of?
17:52 Speaker 01 So this is such a hard question. I think that in the absence of a national strategy that will optimize frequent testing and tracing. It's very, very difficult to anticipate when a school will be safe. That's the first thing. The second thing is there are conditions and requirements for the learning environment, just like the home environment or the office environment. That you would need to have in place. So do you have sanitizers? Do you have enough masks? How do you mitigate the risk with distance requirements? So all of those things need planning.
18:32 Speaker 01 And I think the support of a national strategy in order for parents, for teachers to feel safe going in there. For parents to feel safe sending their child there. And I don't think that many districts feel that level of confidence yet. As I said, a month ago, I probably would have anticipated that 50% of the districts will be returning in some hybrid model. I think that number is closer to 10% now. And so I feel right now we're in a pause. And I feel like the next window is really after January to see how we get through the fall and the winter. And once there's a vaccine in place and once there are effective treatments in place, I will have a different answer for you.
19:12 Speaker 01 But in this moment, I am not aware of any many districts that are confident that they can send their kids back to school full time now.
19:22 Guy Raz? This is a question that we're also getting from Jitor Moy Day via LinkedIn. Can remote learning truly work for all children? And can it ever replicate or even replace or be as good as in-person classroom instruction for children?
19:39 Speaker 01 So there's a lot of research that shows that the most important variable for student success is their teacher. I don't think that's going to change in the long term. I think there are things that humans will do and continue to do that technology will not be able to do. I fundamentally believe that technology should be used to support human beings, humanity, versus the other way around. That being said, I think that we will not return to how things were before COVID. I think we're all moving and marching toward a new normal. And that new normal is going to have blended learning as a permanent feature of the best learning.
20:18 Speaker 01 Because technologies can understand what is happening in a very nuanced way. And technologies can help personalize learning and give learning guardians actionable insights. What should I do to support Sally's growth in this moment? Dynamic information that changes and adapts to what a child needs moment to moment. And it's that modality that will help kids with special needs as well as, quote, the gifted and talented. I think all kids are talented. But for kids who need acceleration and are ready for more advanced work, the system can help alert the teacher that when the child is ready and what specifically that child is ready to do.
21:03 Speaker 01 It's very difficult for even the best teacher in the best resourced school to be able to personalize learning instantaneously for 30 kids at once. But the nimble personalized learning technologies can do that very effectively at scale. And so the trick is to connect what the technology can do with the in-person learning experience to bring it to a new level. That's the trick.
21:30 Guy Raz? Yeah. You know, I'm so inspired by these ideas you're talking about, right? This idea that all these incredible innovations now happening can make learning more accessible and more efficient. But a big part of me is also so worried because I think of kids who rely on school as a safe place. School is probably one of the safest places for most kids they can be during the day. It's where so many kids are fed. And I looked after, you know, and so I had very mixed feelings about what's happening now as a parent myself and seeing it with my own kids, you know, seeing all the remote learning they're doing.
22:08 Speaker 01 Well, I would say that it's you're justified to be concerned. But I would always also encourage you to be very hopeful about what might happen. We're at a precipice now, and so we can reduce the waste. We can reduce the frustration of children who are bored to tears because they've already mastered a concept and they're ready to move forward, but the teacher isn't aware of that. And we can move to a model where the teacher can use the data from a system like Dreambox to organize her class and do rotations so that kids who are advanced can be in one group or kids who are struggling can be in a different group. And she can modify her live instruction to make sure she delivers exactly what that
22:52 Speaker 01 smaller group needs when they need it. I fundamentally believe that talent abounds and talent lives everywhere. It's that opportunity doesn't. And what we're trying to do at Dreambox is to bridge the gap between talent and opportunity. We believe all kids are mathematicians. We believe all kids have a spark. And we need to make sure that their learning environment is structured in a way and is designed in a way that we can show that not only to everybody else, but more importantly, to that child. We want that child to know that they can do anything that they want to do.
23:27 Guy Raz? I want to ask you one last question before we let you go about your leadership style. You've been at the company for 10 years. You're obviously experiencing incredible growth right now. You've led with a concept that you call benevolent friction. How does it work?
23:42 Speaker 01 So benevolent friction is trying to capture the importance of courageous conversations. We want to be hard on ideas, but soft on people. We believe our work is so important to democratize learning opportunity that we want to try to leave our ego aside and be willing to subject what we think is the best idea, our best innovation, to the scrutiny of our peers who share our mission and share our values about unlocking learning potential. And so in order for you to do that with confidence, you have to be willing to subject yourself to the scrutiny of your peers and to hear that there are ways to make something good better. We're in pursuit of greatness for all kids. So benevolent friction is really
24:25 Speaker 01 a signal that says, I'm going to have a hard conversation with you, but it's not really about you. It's about the idea. And it's about the idea that we think will help accelerate our growth so we can serve more kids and, most importantly, accelerate the impact that we can have to make sure that every child is successful in learning math on Dreambox.
24:45 Guy Raz? Love it. Jesse Woolley-Wilson, CEO of Dreambox, thank you so much for joining us.
24:50 Speaker 01 Thank you. Happy learning math.
24:52 Guy Raz? That's an excerpt from my conversation with Jesse Woolley-Wilson, the CEO of Dreambox. To see our full interview, you can go to facebook.com/HowIBuiltThis. And if you want to see any of our other past live interviews, you can find them there or at youtube.com/NPR. If you want to find out more about the How I Built This Resilience series, or join us live, or hear about other virtual NPR events, you can go to nprpresents.org. This episode was produced by Candace Lim, with help from Will Mitchell, Tyra Lockhart, Matt Adams, Gianna Capadona, John Isabella, Julia Carney, Neva Grant, and Jeff Rogers. Thanks for listening. Stay safe, and I'll see you in a few days. I'm Guy Raz, and you've been listening to How I Built This.
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