Edtech Insiders

Redefining School Discipline with Technology and Empathy with Nathan Maynard of HighFive

• Alex Sarlin • Season 9

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Roosh X is an investment arm of Roosh Investment Group.

Nathan Maynard is the CEO and Founder of HighFive, a company using mobile technology to foster connected school communities and reduce recidivism for negative classroom behaviors. With over 11 years of experience as a youth worker, teacher, and school administrator, Nathan co-authored the best-selling book "Hacking School Discipline," and is a global thought leader in reimagining discipline practices in education.

💡 5 Things You’ll Learn in This Episode:

  • How Highfive uses technology and empathy to reshape school discipline.
  • The importance of creating a sense of belonging to reduce negative behaviors.
  • Nathan's journey from youth worker to edtech entrepreneur and thought leader.
  • The impact of AI on real-time behavioral interventions in schools.
  • How Highfive is expanding its reach across the U.S. with new partnerships and funding.

✨ Episode Highlights:

[00:01:46] Introduction to Nathan Maynard and Highfive’s mission to transform school discipline.
[00:03:34] Building connected school communities to reduce negative behaviors.
[00:05:43] How real-time technology supports teachers in managing discipline
[00:08:13] From "Hacking School Discipline" to scaling Highfive’s impact
[00:21:26] Using AI to address systemic bias and improve behavioral insights
[00:24:34] Highfive’s expansion strategy across key U.S. states.
[00:27:55] Partnership with Roosh X to support growth and mental health initiatives.
[00:34:22] Promoting positive behavior with Highfive's virtual "high fives" system.

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🎉 Presenting Sponsor:

This season of Edtech Insiders is once again brought to you by Tuck Advisors, the M&A firm for EdTech companies. Run by serial entrepreneurs with over 25 years of experience founding, investing in, and selling companies, Tuck believes you deserve M&A advisors who work as hard as you do.

[00:00:22] Nathan Maynard: Instead of it saying, Nathan, you know, your teachers are referring Hispanic females more than these other different groups, like do something about it. It may say, That same data, but then it gives actionable things that the school administrator Nathan could do to talk to the teachers about instead of saying, Are you guys doing something that's racist?

Because like that just creates opposition and then people aren't opened up to it. So when you give something constructive because it may be racism, but likelihood there might be systemic type something going on. So then you are curious behind the behavior which teachers appreciate. Instead of somebody looking at them and saying, what are you doing wrong?

[00:01:06] Alex Sarlin: Welcome to ed tech insiders, the top podcast covering the education technology industry. And funding rounds to impact AI developments across early childhood, K 12, higher ed and work. You'll find it all here at ed tech insiders. 

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[00:01:46] Alex Sarlin: Nathan Maynard is the CEO and founder of High Five, which uses mobile technology to create connected school communities and reduce recidivism for negative classroom behaviors by re-imagining discipline practices. When Nathan was younger, he struggled in school. He was diagnosed with oppositional defiant disorder, ODD, and ADHD combined with a large amount of trauma.

Nathan was motivated as a child by fitting in and pursued that by associating with paths to criminality. And these lived experiences later helped him become a successful youth worker, then a teacher and school administrator for over 11 years. As a youth worker, Nathan won youth worker of the year in Indiana after being nominated and voted for by the youth he worked with in the juvenile justice system.

He became a teacher and later an administrator in two cutting edge charter networks at Goodwill's Excel Center and Purdue's Polytechnic High School, where he was the Dean of Culture and helped found the first high school. These experiences inspired him to co write the best selling book Hacking School Discipline, which has been recognized internationally as a bestseller in 23 countries and used in over 400 universities.

Nathan is now a global thought leader in discipline. He combines hard lived experience with research to understand how trauma impacts students, learning environments, and brain development, and puts all of that to work in his work at Hi5. Nathan Maynard, welcome to EdTech Insiders. EdTech Insiders Hey, thanks for having me.

Yeah. So for those listeners who may not yet be familiar with what you're doing with high five and removing fear from the school community, tell us a little bit about high fives mission and what you're all about. 

[00:03:34] Nathan Maynard: Yeah. So a high five is actually in the K through 12 discipline space in education. The way we're framing this is we're focused on creating connected school communities.

We looked at factors like, you know, the sense of belonging for kids, the sense of belonging for adults. And when people feel like they belong in their environment, we see less disciplined behaviors take place. So we sort of modeled our program around that. In the discipline space, though, you understand that kids make mistakes.

Adults make mistakes. Kids need to have opportunities to fix the wrongdoing when they make those mistakes and to repair harm. So what that does is focus on building the skill of empathy. And then from there we focus on what does it look like a paths of forgiveness with the educator when they're repairing those harms.

[00:04:15] Alex Sarlin: Yeah, it's really important work and I'm sure you're taking some cues from the criminal justice work because your echoes in everything you're saying of, you know, being less punitive and more understanding and sort of really trying to build connections. Do you take some of your cues and some of the research from the criminal justice system 

[00:04:32] Nathan Maynard: into your 

[00:04:32] Alex Sarlin: work?

[00:04:33] Nathan Maynard: Yeah, absolutely. So my first seven years and when I got started, I actually worked in the criminal justice system, the juvenile justice system in tip new county in Indiana. So I was a youth worker for seven years and I worked with kids that were incarcerated or was placed by the Department of Child Services.

So I learned a lot about trends. It opened my eyes up to the school to prison pipeline in the district mhm. Portionality around that data. So it really got me motivated to do something differently in school. So we do look at a lot of those different trends because one of our biggest things we're trying to not just disrupt, but end is that school to prison pipeline.

That 

[00:05:05] Alex Sarlin: makes sense. So, you know, when people think of school discipline, I'd be maybe depending on their generation, they probably think of things like. You know, detention, staying after school, getting a note sent home to parents, you know, obviously there was corporal punishment way back in the day, extra assignments.

There's all these things. And almost across the board, they're all punishments, right? Just everything I just said. Tell us your approach. You know, if a student does something in a school that requires, you know, quote unquote discipline, how would high five help the administrators, the teachers and the student and maybe even the family?

Um, Sort of wrap around that student, make the discipline more effective. And I'd also love to hear about how technology supports that. 

[00:05:43] Nathan Maynard: Yeah, absolutely. Yeah. Technology is how we like have really centered the success of a lot of this different work to make it a little bit easier for us. But I think sort of like going really macro for a moment, just so everyone understands, you know, discipline has a lot of connotations behind that word.

You know, the way that we look at. Discipline, though, is sort of the root word of it, which is discerna, which is the Latin word, which means discipleship to model, to learn, to teach what are we doing to really teach our kids when they make mistakes, how to fix things and censoring things around that sense of belonging just makes everything.

Cohesive and easier to manage. So, you know, looking at discipline, what we do is we really look for those different opportunities. We understand though, sometimes in the classroom, what starts to happen is things move quickly and you may say one thing and then have to go, you know, ask, can these use a restroom, a parent calls, these different things take place.

So what ends up happening is sometimes those things start to fall off. What we want to do is use this technology to really help out and model people. To the teachers to give them this opportunity to showcase how to have a conversation. What is an intervention look like in the classroom? There's all this trends around MTSS and now it's MTSSB and it was RTI before this, but coming from the school and being in the school for now over 15 years, what we see from the classroom point of view a lot of times is that there needs to be something actionable there.

And all these platforms that are out there, they may. Quantify things and show you, okay, here's your highest need kids. And here's your, the kid's highest performing and lowest performing there. But like the school still has to take action steps. And then it goes down to the teacher that sometimes they're not even involved in some of the professional development.

So they're at a loss. So the technology automates that for us. So being out there, you know, for several years and working around, we've learned sort of what that was in there. And we built that into the technology to make this process easy for the teachers. 

[00:07:31] Alex Sarlin: Gotcha. So it really connects multiple stakeholders in the school community around this sort of disciplinary moment.

And I agree with your definition of discipline. You know, it's a teaching moment. It's not meant to be punitive. You're a relatively new company, and you have over a million and a half students served globally, which is really a big deal. Amazing. And hundreds of thousands of hours of administrative time saved, which is one of your key metrics.

So that's success. I mean, obviously this is, there's something about this approach to discipline that's really resonating with the school community. What do you attribute the early success to? And what do you hear from schools when you come to them with this different vision of what school discipline could look like?

[00:08:13] Nathan Maynard: Yeah, absolutely. And just to be sort of clear for everyone on here about the journey and those numbers, you know, when I first got started, I left the school position I was at. I wrote a book called Hacking School Discipline. At that time, the book was number six in the world when it first came out, a bestseller in over 23 countries.

And it really amplified my voice. So I amplified the voices of a lot of people around me. I developed a lot of communities and built Things up. So at that time I developed a technology that was used at my school, a couple different area schools here in Indiana, where I'm located at. And then from there, I had a consulting company that started to scale up.

We've merged those two together, taken that in, and that's where that impact that's been scaling around there. When we're thinking about where the success is coming from, I think being the thought leader in the space of discipline right now around that book, hacking school discipline, and being someone that's been in the field for over 15 years as a consultant, you know, I worked in over 30 different 36 states across the United States, and sometimes in the lowest performing schools, and sometimes some of the most dangerous type of schools are, you know, having different issues taking place.

And, you know, I think that what that did was really developed a reputation around, this is how you can do this differently and showing data behind it. 

[00:09:18] Alex Sarlin: That's really, really interesting. And I want to ask more about the book and your experience with that. Cause that's really fascinating. But before we even get into the book, let's dig into that a little bit, because I know a lot of the entrepreneurs who listen to this podcast are always looking for ideas for how to get noticed in a crowded space or how to build trust with potential customers or how to have people sort of coming to you and asking you for solutions.

And it seems like, you know, I imagine it wasn't your original intention to start a discipline company. But as you say, by thinking about it a lot, by writing about it, by speaking about it, consulting on it and becoming a thought leader in the space, you built obviously a really, a big audience and a lot of trust with exactly the type of people who would want to adopt this kind of tool in their school system.

So we'll work backwards here. You know, What does it look like to go from that thought leadership to entrepreneurship? And then I want to go into the thought leadership in the book. Cause it sounds really interesting. 

[00:10:13] Nathan Maynard: Yeah, it's been a big shift, you know, to start out like, you know, cause I got into youth work early on because of my lived experiences.

You know, I had a lot of stuff that's going on in my early childhood and, you know, I was able to navigate that now successfully, but, you know, I wanted to be in kids lives that had a similar upbringing that I had. So, you know, I always want to stay close. So then the more, you know, sort of traction this type of work has gotten, the farther it Felt like to be away from it, but what I think is good for the listeners to think about is I always say censored in this work, even once a month, I'm still going to some of these really tough schools, I'm doing consulting work with them just even two, three days.

Just so I stay fresh on my skills that I can talk to families. I can talk to students. I can talk to teachers, admin, anybody that's those different stakeholders. I'm understanding a little bit of their perspectives and how to speak to those different groups and understanding their needs. I think when you're looking at.

You know, having a product and you're trying to get it into the market and you're trying to see like how to be in this crowded space. I think understanding the stakeholders needs in a deep manner helps you become not just someone that has a cool product that's meeting a problem. It's that you're the thought leader over you understand the stakeholders.

I think that's what's drawn in a lot of different attention to to thought leadership around this space. 

[00:11:28] Alex Sarlin: Yeah, it's so interesting, you know, as we mentioned in your bio, and you just mentioned sort of in passing, you had a lot of issues and trauma as a child, you were sort of on the other side of this disciplinary system.

So I imagine that you find a lot of ready. Ears among students who are dealing with discipline. And then of course, doing all this consulting and working in the school world, the administrators, you know, you've done that too. So you've been on sort of both sides. What does that look like? That's so interesting.

It feels like you have a really deep and multi sided empathy with all different players in this system. 

[00:12:04] Nathan Maynard: Yeah. And I appreciate you noticing that. Like, I think that, you know, I don't sort of like showcase it a bunch, but what it does is it really helps me understand, like, what's best for kids. Because I think that sometimes we get in the weeds with stuff, you know, like, what's this, what's that?

Like MTSS, RTI, that like this labels and like the teachers are like my head spinning, like, what's this? And then all of a sudden, like, then the last thing that it's about, like the kids. And then sometimes it's like the underserved and underprivileged kids too, that are like even the last thing. Once that gets something, so then things start to be standardized or pushed in a certain direction.

So like, I think understanding things and really being part of something when I was younger has helped me sort of understand, like people can have success longterm, even if you have had challenges. And I think that. Those kids that I work with in the juvenile justice field and in Lafayette, they saw that and a lot of them are still successful.

And now to like, even with my scaling journey, we have targets to even hire a lot of these kids. I used to work with when they were youth because they can do what I do. They can empathize with the people there. And when I've talked to some of these kids that are now like in their twenties, you know, and I talked to him, I'm like, what would you tell a teacher nowadays?

And they would say like, you know, when that teacher got mad at me for not charging my laptop, I would tell him like, yeah, You know, my lights weren't on the last three days and I haven't eaten or if my mom just got arrested, you know, like, that's what I understand. Those kids understand teachers sometimes understand, but we lose it sometimes with a product, you know, so that it's really important for us to high five.

[00:13:29] Alex Sarlin: Yeah, that's really, really interesting. There's so many. Complex issues happening inside a school building, many of which reach far outside of the school building in terms of families, in terms of students, upbringing or other pressures they have in their lives that all often come out in school. And every educator knows this and has experienced this.

They know that their students have a lot going on, but you're right. This is something that doesn't often sort of make its way into the ed tech world at all. So let's talk about the book. Yeah, yeah. Yeah. We were going backwards here. So let's talk about the book, hacking school discipline. It's been a bestseller in 23 countries.

As you mentioned, it's used in many universities, obviously really, really, really hit something very new. And you mentioned the school to prison pipeline as something you obviously think a lot about. Give us a little bit of an overview of some of the book. We'll put a link to the book, of course, in the show this episode, but Tell us a little bit about that and how you came to write it and what effect it's had.

And what are some of the key points and what is some of the effect it's had on the world?

We'll be right back. This season of EdTech Insiders is again proudly sponsored by our M& A partners, Tuck Advisors. Thinking of selling your company? As experts in mergers and acquisitions in education and EdTech can help. At Tuck Advisors, their motto is, Make hay while the sun shines. If you want to start planning the harvest contact tuck advisors now.

[00:15:02] Nathan Maynard: Yeah. So like the book came about in sort of a really cool natural way and it felt good at the time. Like I didn't have any social media stuff, had no companies, nothing at all. I was just straight and educator. Like I didn't know any side hustle type stuff. Like I was just trying to make it, but you know, I had a couple of mentors in my space that were seeing some of the stuff that I was doing that helped me out.

And you know, one of them at the time, You know, he had an opportunity to write a book that he already had a contract with over some science stuff, but he was seeing what was going on in our school and his name was Brad Weinstein and he was like, Hey, we should go and you should do the discipline book and I should talk about this stuff.

You should talk about that. So we started having the conversation and at the time he was seeing it getting modeled in the school because he was at our district office, but I was one of the school administrators. And what he was seeing, and it was a really cool school. It was called Purdue Polytechnic high school.

It was like a very innovative type school. And we had like the XQ foundation was a part of it from Emerson collective. Like it was just a really special thing. And the leadership there was really scaled that across, but in the beginning of it, we were just trying to make it work. Like, you know what I mean?

Like here's this. New type of set up. Kids don't have classes. They have these workshops, these dojos, they're signing up for stuff. It was amazing. Kids were excited like it was fun, but I was in charge of the discipline. I was the dean, so I was having to deal with some of the big things that were still going on in all these kids lives because we were focused on underserved and underprivileged kids like we really focused on making sure it worked best for them.

So writing that book, I was able to utilize a lot of the stories from myself as a youth worker all the way as a teacher, School administrator, like, you know, all the way across the board. And then also in live time, like we were seeing these types of stuff play out in a brand new school, in a brand new environment.

We were like in the food court, like, or right above the food court in the busiest mall in Indianapolis, but like, it was so special and now it's scaled across with great leadership. So that's really how the book got started was, you know, in that sort of thought tank there. And then from there, I remember, We got a message and it was like in the middle of June and it was like, Hey, you know, your book's number six in the world right now.

And I was like, what? And like, I remember like I have so many screenshots on my phone and like, you know, it still gives me goosebumps to this day thinking about it and stuff. And I just remember thinking, I was like, what do I do? Like, you know what I mean? Like it's like, This, and then one of my friends, her name's Connie Hamilton.

She started mentoring me at the time. She's in Michigan and another book, like an author and stuff. And she was telling me, she's like, Nathan, you got to go speak and you got to do this stuff. And I'm like, I can't speak. And I was bad. Like, I'm not joking, man. Like I wasn't that bad at speaking. Like she gave me this list to Applebee's like the first time I went to her district and it was like, slow down, don't do this, blah, blah, blah, like this stuff.

But then I took that and I kept doing it and doing it. And. You know, even recently I did a keynote speech and like LeVar Burton was the other keynote speaker. Like, I feel really special to like get into that world. And the book has just helped that thought leadership across and seeing it sort of transcend in different countries as well.

You know, it's really special saying like, Hey, behavior is not that different. Like it's empathy, it's belonging, forgiveness. Like that's what we need. 

[00:18:04] Alex Sarlin: Yeah, so interesting. One of the things that has sort of plagued the disciplinary system in the U. S. Is racial discrimination, right? We know lots and lots of studies that students of color are much more likely to get suspended.

They're much more likely to get in trouble for all sorts of different kinds of things. But your book obviously is not just, you know, it's in 23 countries now. It's not just about that, but I'm sure it talks about that a little bit. You know, tell us about that. Yeah. Just your thoughts on that part of this world.

This is one of the really, you know, shameful parts of the education system at large in the U. S. Is the inequality and the racial inequality and socioeconomic inequality. But the discipline is sort of the front edge of that. It's where it happens in the classroom every day where police are called into the schools for certain types of students.

Tell us about your thoughts on that and how people reacted to it, how the people who were Reacted and embraced your ideas about discipline dovetail with that type of problem. We see in the system. 

[00:19:01] Nathan Maynard: Yeah, absolutely. And I, I think that, you know, just pointing out in the very start of the hacking school discipline book, the very first data you see is the school to prison pipeline.

So like, it's very censored in that. And like, Yeah. You know, when I was a youth worker, I didn't understand what it was, you know, like I would see the patterns when you go to the court system, see the kids flowing into our treatment care center. I really didn't understand. Cause like I grew up in a tough environment, but I'm a white male, you know what I mean?

So like, I didn't understand that. Like there's also systemic oppression. There's systemic issues taking place. So I think that's where a lot of this lays. So I think that it is a very shameful, embarrassing, sad, Disappointing, horrible thing that's going on with this disproportionality. But I think teachers, school administrators and schools as a whole are trying their best.

I see to try to do something, but sometimes we're not hitting the mark. And I think what's going on is there's an issue between systems and processes of going on. I think we're improving our processes, but our systems are outdated. I think if we can update our systems and have really clear, here's the evidence Here's how we understand what success looks like.

Cause even with technology products, new programs, you're testing efficacy, you're going through, but now we're talking about inequality around civil justice. You know, like there's some stuff we have to really frame around this of what's metrics of success and where's the issue. Because even my co founder, he doesn't call it the school to prison pipeline.

He said, Nathan, it's a school to prison production line because what's happening is it's doing exactly what's always been done, you know, like, but the processes and those educators are trying different things. Things, but the systems are tough for those kids. Even when you see in just the student handbook.

That goes through and it says something like a fender and victim. These are kids, you know what I mean? Like, you know what I mean? Like sometimes it's that level, you know, of criminal justice, but sometimes it's a victim in a fender for a kid that like poked his girlfriend or boyfriend or something like that.

Like, you know, we've got to calm down our language because we're labeling kids. And when you label kids that are historically marginalized. You're putting a double thing on them. And I think that's when the discipline system needs to be disrupted. 

[00:21:03] Alex Sarlin: Yeah. So among the sort of early adopters, it's not that early.

You're talking about 1. 5 million students, but among the relatively early adopters, the people who have really embraced high fives technology solution, do you see some Coming from that perspective of saying, you know, we're trying to improve our processes. We really care about this, but you know, we can't move the needle enough and we really want, you know, technological help.

[00:21:26] Nathan Maynard: Yes, absolutely. So I think that when our first product hit the market, it was called behavior flip. And when that first got into the market, The number one reason schools were reaching out to us was they were getting flagged for disproportionality around the referral or suspension data, and they didn't know what to do with it.

So then that led to a lot of professional development, and then the technology was sort of a separate type of thing. What High Five has done is sort of combine those two things together. So there's a training aspect involved, there's upskilling of teachers around different skills, but then on the other side, too, there's a tracking system that helps sort of quantify things and drop that down.

You know, our AI tool that we have is, is really innovative with how the reports come out. So what that starts to do is instead of it saying, Nathan, you know, your teachers are referring Hispanic females more than these other different groups. Like do something about it. It may say, That same data, but then it gives actionable things that the school administrator Nathan could do to talk to the teachers about instead of saying, are you guys doing something that's racist?

Because like that just creates opposition and then people aren't opened up to it. So when you give something constructive, because it may be racism, but But likelihood there might be systemic type, something going on. So then you are curious behind the behavior, which teachers appreciate instead of somebody looking at them and saying, what are you doing wrong?

Which like, sometimes they're not doing anything wrong, but there's something else taking place. 

[00:22:52] Alex Sarlin: Yeah. You know, it's so interesting because I hear you talk about the different roles that you've played in this world, right? As a youth worker, as somebody working in criminal justice, a youth justice, as a teacher, as a thought leader and author, and now as a tech entrepreneur, and it really feels like.

All of these efforts sort of come together. They tie together in a really interesting way by helping surface the disproportionality and the issue, and then provide some solutions in your book and start to say, Hey, let's think really differently about discipline. You sort of create an interest and people realize how this is a serious issue.

And they start to look at the data and they start to realize, Oh no, we're part of the problem because we're doing this. And then you say, Hey, we're working on solutions and we do impressionable development, but we also have technology solutions. And so it's really very impressive how many different sort of impacts you are having in this incredibly important.

[00:23:42] Nathan Maynard: Yeah, it's fun to do it. And I think the most critical thing too, is like making sure that we're thinking about the educator and the student involved in this process the whole time. And I think when people do that, that makes things a lot more successful. 

[00:23:55] Alex Sarlin: Yeah. And this is such a loaded, I mean, discipline issues can be seen as zero sum games, right?

They can really raise tensions that, you know, obviously parents are sort of implicitly involved. Teachers are involved. Administrators are involved. Other students are involved. It just, they cause such. Issues. So the idea of really understanding all the different players in any different moment and trying to support them with actionable insights is really key.

So you're about to expand across five key States in the U S and as always, as you mentioned, you're focusing a lot on low performing K 12 schools or schools that have a lot of disciplinary issues. Tell us about this expansion and what you expect to see. 

[00:24:34] Nathan Maynard: Yeah, definitely. So, you know, we have had a product on the market with, you know, that past company for about four years.

And we just updated that and made that iterations, got some funding in for that and got amazing tech partners with ruchex to help us with that. Developed out that tech. And then what we did was we launched the new version of that tech to 16 schools. Got those 16 schools on boarded, got a lot of success with that.

Now we're up to within a couple of weeks, we got up to about 30 schools. Now we have 75 additional schools sort of in the pipeline. And that's just for, you know, my home state here in Indiana. And then from there, we got some traction going in Texas, Florida and Michigan as well. What we're trying to do right now is.

Just have the schools, we're doing some thought leadership exercises across those different states. And we're bringing in round table thought leaders, such as like parents, stakeholders, students, stakeholders, just the way I do everything else. So we're just doing that the same thing as sort of our go to market, you know, making sure everything's structured in a way that everybody understands what we're doing in these different schools.

And we're getting people interested, but we've had an overwhelming amount of educators from district leaders to principals reaching out to, you know, Test this new version of this product out there to go through since the other version did have traction on the field and those stats that you're mentioning earlier.

So we're really excited about, you know, what this next step looks like for us. 

[00:25:51] Alex Sarlin: Yeah. I mean, when we think about product market fit and education and an ed tech, the key question is always, you know, is this a vitamin or medicine, right? Is it a painkiller or a vitamin? Is this something people are really struggling with?

They really feel the pain of on a daily basis. And I think disciplinary issues. Definitely are. This is something that digs schools, all sorts of different people in the school system suffer from issues. So it's not a surprise to me that you have a sort of lineup to try the product. Right. In Texas, Florida, these are very big markets.

You mentioned just in passing there, you have a tech partner and investor with Roosh X and Roosh X is an unusual player in the ed tech space. They're actually Ukrainian VC firm. How did you connect with them? And what does that relationship look like? 

[00:26:35] Nathan Maynard: Yeah, definitely. So I met two of the managing partners over there.

I met them in California. There's just an event around biohacking around like eating healthy, drinking good and stuff like that. You know, I've had a lot of personal journey about being healthy. So I met them over there. And then from there, we just became, you know, sort of friends. We chatted for about a year.

Yeah. Yeah. Probably about a year and a half, just as friends. And then, you know, from there, they said, Hey, Nathan, we're looking to get into the ed tech space. They've done a lot of investments across the United States. They've done 12 different investments with Sequoia. They've had a lot of different traction over there.

And 75 percent of their companies are here in the States, but not a lot of ed tech traction. The two guys that I met was Sergey and Din. And when I Was talking to them about the empathy, the forgiveness and what was going on. It was also during the time of the war, we had a lot of conversations around mental health, resiliency.

And I think I have a big heart right now for Ukraine. And I think that if we can create some mental health resiliency supports for those kids that are displaced from the war right now, we're after about. 400, 000 students that are displaced over there. And these two gentlemen can help us with some foundation stuff, some impact work, do some efficacy testing, and to make sure that we can give the educators what they need over there with our product.

So there was a lot of lined up with it. And then when they also offered to be our first investor too, I mean, like it, that was a huge blessing because their network is very extensive. You know, we're extremely excited about them. 

[00:27:55] Alex Sarlin: Yeah. And obviously, you know, having a little bit of money in the bank allows you to really continue your efforts to expand more, to have more product development, more marketing, more user research, you know, everything.

And it sounds like the technology has been really a good area of partnership with this investor. And obviously other investors who are listening to the pod, you know, take note, this is Roosh X R O O S H. Then an ex Ukrainian generalist VC firm, but moving into ed tech and a high five just got their seed investment, but lots of traction already over a million students just in a short amount of time and not that many districts yet.

So it's amazing. So let's get a little more in the weeds about what a high five and maybe even your previous iteration of your product really is doing in a school. Just because, you know, you've explained it a little bit, but I want to really I want our listeners and I want personally to really be able to envision sort of at what point high five sort of disrupts the traditional disciplinary punitive action that happens in a school that can sort of have ripple effects.

You know, can you just like give us a truly like walkthrough, like you mentioned that, you know, a boy pokes his girlfriend in a school, take us from there. How does high five support? 

[00:29:07] Nathan Maynard: Yeah. So let's say that, you know, a boy pokes his girlfriend in class, the girl screams in class, the teacher redirects the girl and says, you know, Hey, why are you screaming?

And she goes, he just hit me. The teacher says, don't hit. And then continues to teach what the teacher would then do is just maybe jot down, you know, let's say the boy was Nathan and, and jot down Nathan, you know, hit Sarah. And then he put that down. What the teacher would continue to do. Let's say they continue to interact.

Across the class, there's a couple other kids that may have done some stuff that was positive around there based on some of those high fives that are the positive things that we recognize, which is empathy, communication, some of those future workforce development type skills, but also lines with like being a good human, right?

Like, you know, stuff around there. So they would write some of those positives and some of those additional sort of negative behaviors. They would go through the app, right? And what they do is they just click either the high five for the positive ones to recognize that, or they do the negative one.

There's quick dropdowns for them to choose the different behavior that that was, but then that's the typical sort of format that, you know, our last iteration would do. And then what we would do is we're a quantify those at a time. And then after so many, we'd give the teacher something to do after that.

Now, what we do is we do that in live time. So then what happens is when the teacher put that in there, that's The kid poked something, the tip that will come up will be something around logical ways to redirect that behavior or to can connect with the kid, depending on sort of around what took place. So then the teacher has a quick tip that they can use.

So if they want to wait until the end of the class, they can get it. They can get it in live time too, or they can do something where they continue to click these, and then they do some of the corrective behaviors down the road with that kid. So some of those examples of what they could do with the kid is.

With cognitive behavioral therapy, they talk a lot about getting behind the behavior. So one of those different practices. So let's say you're, you're an elementary teacher, you know, cause like hopefully our high school kids aren't poking people like that, but they do sometimes, right? Like, so elementary kid, they did something.

What the teacher could do with that kid is they could give them the iceberg activity so that the app tells you how to do this activity draws up an iceberg at the top. You write the behavior that the kid has done. And then underneath it, they unpack the different behavior behind it. This is typically stuff that teachers are already doing in the classroom.

But they have to have their own layouts in their handouts or they have to figure out, well, that kid did this, this kid did this, what's logical, what makes sense to get good effects on their discipline. A lot of brain power goes into it. And the educator makes a ton of decisions. So we've just tried to automate that, but then also quantify the process around it.

And then the cool thing is we also have our needs assessment that quantifies sort of our five pillars of behavioral neuroscience, a trauma informed work, restorative practices, belonging metrics, that type of work. But then what the app does in the needs assessment is it helps gives you a good sort of score and the pulse of the school as a whole.

So it's a really good sort of interactive thing that's like very deep. Different for the market. It's like we built it as sort of like behaviorists and educators for something that we feel like was needed. And a lot of educators helped us in that journey. So it's been fun to give them what they wanted around this.

[00:32:16] Alex Sarlin: Yeah. Right. So that makes a lot of sense. And the educator can react in real time. As you said, they can wait till the end of class. They can sort of craft a plan to move the behavior over time or change the behavior over time. But in essence, you're taking some of the training that might've happened. Four months before, right?

A professional development session about this and bring it all the way to the moment, contextualize it, help make sense of it, and then take the data and be able to put it together for the entire, I'm sure for the class, but also for the whole school and maybe even the school system. That makes a lot of sense.

So 

[00:32:49] Nathan Maynard: it's a mobile application. Yeah. Mobile web based, we got both with that. So, you know, and then we have our, our assessment, you know, so like, it's just a very easy to use type of app for the teachers to use. And it's just a simple interface. You know, we try to keep things simple with it. And then we get a lot of sort of feedback around ways to make that usability even better.

But we feel like what we're doing right now is also going to help even individual students too, with like IEPs and sort of the listing of behaviors taking place. Because I see what these teachers have to do every day. And they're given like Three kids with IEPs in one class sometimes like and then they have like five of those classes and they have to record down every single time that kid does positive this back and forth.

So we have this in the teacher's normal workflow instead of a special education, you know, type of thing. I think it makes the workflow way easier because I also see that like there's a lot of things coming out there that I think that is going to create more workflow. Potentially we're trying to make it less.

[00:33:44] Alex Sarlin: Right, right. So remove some of the paperwork or administrative work that comes with disciplinary, you know, action or the disciplinary, just tracking the behavior as well. Tell us a little bit about the positive side of this, because obviously the company is called high five. You mentioned high five is sort of the positive reinforcement part, which I'm sure is incredibly valuable and useful and terrific also is probably not the main reason people are coming to you.

They're probably coming to you for the negative, but they're probably very excited about the positive. Tell us how those two sort of interact, how the team. Tracking of negative disciplinary and the sort of ability to give virtual high fives in various ways for all these different positive behaviors.

How do they interact in a classroom? 

[00:34:22] Nathan Maynard: The way that we really frame this is we focus on the research that says that 80 percent of the time for classroom management should be proactive, which is relationship building and community building. And only 20 percent should be responsive or reactive. So even though, you know, those customers are coming to us, we're like, Hair on fire, sometimes around discipline, we make sure that during the training and during the implementation that it's focused around the positive.

And that's what high five does. So, you know, I explained to sort of the classroom management type side of it, but what we do is we have these different circle prompts for the teachers. So then what they do is they can cycle through them. If you're a high school teacher, you know, you can try a couple of different ones to get the best responses.

They have a quick little bar that they can do from like a hundred percent engagement to 0%. So then we can cycle out the ones that don't have very much for it. So what that does is helps the teachers build community in their classroom. And then that's that 80 percent proactive. So we really framed things around.

What do you do to build relationships with kids? Like, how do they know you? Because like, even when we were talking earlier about like my lived experiences, like the teachers I behaved for are the ones I liked. They weren't the ones that like scared me. Like nothing really scared me as a child. You know what I mean?

Like, oh, you're gonna call this person. Okay, like You know, like as a kid, you don't think like that sometimes when you're just like, got a lot of stuff going on. So like, I think that what we want to do for the teachers is help them with something that's more like that grasp on. And it's sort of like that old, you know, you don't want to make someone sort of disappointed.

You know what I mean? Because like that disappointed means they care about you. And that's what like, you can't even say disappointed if you don't have a relationship with a kid. So like, it all starts with that. Like, do you know your kids names? We use John Hattie's research about greeting kids in by the door and, you know, letting them know that here in their name, Within this amount of time, like we structure all of those positive things into this app.

So then it's just cycling those stuff through, because like you said, like the professional development goes one year out the other. And when I would do these like full one day, two day thing for years over these different steps. States. After the book, what I'd realized is they would only remember like the one thing around like the biggest kid behavior that they had in the classroom, the teachers would, and they would forget that it's all around relationships.

Like, you know what I mean? Like that thing won't work without this, right? Like, but the app will help with stuff like that. 

[00:36:35] Alex Sarlin: It's so interesting. So as I hear you talk about this sort of two sides of this, the building a strong relationship, greeting kids at the door, really giving, being able to give them these virtual high fives and also making sure that you're being proportionate and not being overly punitive.

It feels like there's maybe a natural match here for the charter school movement, which has often gotten in trouble in the past for some of their rigidity in discipline. Have you gotten any traction there or talk to, I'm sure in your time, you've talked to many different charter networks. What does that look like?

[00:37:04] Nathan Maynard: So the majority of our current schools that we have on board right now are charter schools. So they are ones that with high needs stuff going on. We do have a good differentiation from private, public and charter, but I would say the majority are charter schools. So we have seen that, you know, coming straight from two different charter schools.

You know, the first one I worked at was the Excel Center, which is a charter school network here in Indiana, but it's also national too for high school dropouts. But then the Purdue Polytechnic one, which was an innovation school, the XQ one. So I think I've seen how they've handled discipline. They went through and like, I think it, it's been amazing.

Like I love the programming and, you know, I helped with the Purdue Polytechnic on their very first building, build some of that. And then. The Excel center, I helped them with some keys to success that I designed with it, but they did something really small, and I think it made really big impacts. I think the charter school networks can do the same right now, though, we're, you know, we're just making sure that we get good product market fit metrics in and go through.

And then we want to it. Share that, you know, message out, do some good efficacy studies. I think it's really important as being a thought leader and with someone that like very close to the chest with this stuff that we get this right. So, you know, the charter school networks is definitely a dream for us to get into, but I think right now we're getting this out there and we're, we're really excited about getting this inferred in the first 200 schools and then continue to scale it up that way.

Yeah, it makes a lot of sense. It's really interesting to hear. 

[00:38:24] Alex Sarlin: When I hear this idea of, you know, behavioral intervention in real time, it makes me feel like there are some other populations that might have benefit from that kind of thing, including parents and police people. So I know, you know, you don't want to be distracted and move away from your, your school product, but I'm sure you've thought a lot about discipline.

How do you think this kind of approach might work for those kinds of populations? 

[00:38:45] Nathan Maynard: Yeah, it works very well for both. So like, and I say this from, you know, just seeing different things out there. Cause like I been part of it. So I would say like in Lafayette, I went to a training one time when I was a youth worker called policing the teen brain.

And what that was doing was teaching police officers, like. How the brain actually works for kids. Like, you know, you might tell a kid no or stop, but their brains, like it takes them smaller times to process their prefrontal cortex isn't developed. Their amygdala fires quicker. If you're talking to kids from trauma, their amygdala goes boom, boom, boom.

Like, you know, it taught them how to deescalate something from the mindset of regulation. And like, I don't know the stats of that, but I know that that's now a national program and there's amazing people behind that helping police officers. I would say when it comes to parents. Parents are definitely very big on this.

Like, even with hacking school discipline, a lot of parents have purchased that book and I get a lot of messages like, Hey, it doesn't really relate in the home. And I'm like, well, it's meant for teachers, you know, and stuff like that. But like, there's a lot of synergies that where it does sort of relate into it.

So that is sort of an avenue that we've always had, even with our behavior flip product, we had skills that would go to parents too, because one of the biggest things when we first launched the product five years ago, Was we were getting teachers and parents to both give compliments on the product saying like now I know what's actually going on or now I'm talking to this person or it's not just coming from this person or this like there was direct communication instead of through me as the school administrator.

So I think that, you know, when we can streamline stuff like that, it really opens up those doors for collaboration. 

[00:40:17] Alex Sarlin: Yeah, very much so. It feels like some really interesting adjacent markets that have some of the exact same problems with some of the exact same kids. But it's really exciting. So listeners will probably notice that if you have teachers in the classroom giving these high fives out, building these positive relationships, also tracking disciplinary moments, also doing, you know, as you mentioned, these sort of positive activities and tracking whether they're engaging or not.

A lot of data is being generated at any given time. And when we talk about a lot of data being generated, naturally want to think about it. So you mentioned AI in passing before, but how do you see AI contributing to high fives mission to improve school discipline? And especially when it comes to sort of real time reaction, cause that is one thing I can speed up reaction time in context more than many things.

[00:41:03] Nathan Maynard: Yeah. Let me tell you my dream world, you know, for AI. Cause I, I think that we're in the dream world right now, right? Like it can do this type of stuff. I think that teachers right now, if they had something where. They came through and they said, okay, first period, you know, here's your three kids that remember last period or yesterday they did these two things and just like quick little tips.

It gave them sort of real time type stuff. Hey, remember after lunch, those kids are going to be a little bit more dysregulated cause they're coming back from recess than lunch. You should do this one minute mindful video, just like real quick tips like that with actionable things around the behavior.

From predictive things from one student to the macro, and that's what high fives doing right now, but we're doing it through the, the evidence, you know, so we have some really amazing people in our circle right now. One is like the learn launch accelerator, Jean Hammond and her crew has been just mind blowing for us, like helping us so much, but we have groups like that, that are really making sure that when we do include something like AI.

That there's safe processes, that the data is protected, that we're doing that in this way, but then my, my high hopes, you know, can be sort of expressed there with some really good veterans in the field that are mentors. 

[00:42:14] Alex Sarlin: Yeah, that makes a lot of sense. We love Gene Hammond and the LearnLaunch Accelerator as well at EdTech Insiders.

They are good friends and have do amazing work. Yeah, and it makes sense. You know, AI can make sense of context. It can remember forever and, you know, adapt. What's happening now to what's happened in the past. You can imagine that high five, you know, halfway through a school year would really know a lot about the disciplinary journey that every kid has taken, that the class has taken in general, you know, across those five dimensions of positive reinforcement that you're talking about.

So there's a lot of potential. And I love that the way you say, you know, in my dream world, it would be this and Hey, the dream world's here. I can do some of this already. Yeah. I feel like that a lot these days. So, you know, that's a dream world vision, but you're still relatively early in your trajectory and you're expanding a lot.

And now you have some money to do it with, you know, how do you envision high fives platform evolving over the next few years? What would you really like to see high five be able to do as it expands, but also as it gets, you know, more technologically savvy and can do even more to meet its mission of a better form of discipline.

[00:43:19] Nathan Maynard: Yeah, I think that there's a lot of opportunities in the risk assessment space to make that sort of a safe space, because I think that anytime that you're getting a lot of data for kids or especially disciplined data or that it can be weaponized, it can be used wrong, it can be used for the negative, like there's ways that things have to be sort of process in this and what we see right now in the student information spaces is a lot of people are interested in these early warning indicators or this, but what we're noticing as behaviorists is, you know, It may be very biased.

Like there might be some other structures going in. So I think looking at high five, we're very interested in what does it look like to potentially plug into stuff like that in the future, look at student information systems and help them sort of quantify something that's more actionable and less prescriptive.

That might be biased. And that's what we feel like we could do with with the current product out there on the market, pulling a lot of data, getting collections in, having university partners with efficacy studies. We could be something that there could be always the trends to protect That type of stuff out there.

So we're really interested in doing this the right way from stakeholders. And like I said, in those different key States, we're talking people from legislation all the way to like parents to like, you know, decision makers, foundations, family offices, like we want to do this in the best structured way. But I would say in, in that next scenario, you know, there would be something we could plug in with student information systems and have a really nice way to say, like, this is how, you know, school stays safe because I know even with some of the school shootings that have taken place, the greater connection grant came about.

And that Greater Connection Grant has talked about one of the number one ways to offset school shootings is to improve the teacher and the student relationship. So that's something that, you know, we want to do with those upscaling, but at the same time, we're going to have some really awesome data. What can we do to keep this protected, safe, and then help other educators and youth workers and students?

So that's why Student Information Systems, LMS, 

[00:45:11] Alex Sarlin: Yeah, that interoperability and integrations within the school systems would be a turbocharge for a platform like this. And it makes a lot of sense. And, you know, we were talking about the sort of poking scenario as, as one form of in class behavior or disruption.

And, you know, obviously school shootings are the other end of the spectrum, right? But what's interesting about what you're doing, you know, it's painful all the way down, right? I mean, obviously a school shooting can disrupt a whole community. A whole state, you know, it's just unbelievable what it can do.

But every problem in a classroom has ripple effects. And so there's so many, you know, there's just so much difficulty that comes from behavior management, classroom management, working with undeveloped prefrontal cortexes year after year. Actually, I, I'm almost surprised that there aren't more people doing this kind of work, but it feels like it's difficult.

It's difficult work. Yeah. Well, keep on doing what you're doing. It's really, really exciting. Thank you. So when you think about that type of early warning, you know, predictive analytics to help flag somebody who might be doing some, you know, be at risk of doing something bigger, even if it's not something as extreme as a school shooting, just something bigger in the classroom, maybe, you know, a serious fight, how do you think about the sort of putting together the pieces like you were before about the positive actions, right?

The thing is, what's so interesting about what you're doing with high five is that even though it's You know, reducing the punishment and the actions on the student's behalf is one of the core goals. One of the core ways you do it is through all this positive reinforcement and proactive. Do you think that that kind of positive reinforcement might actually circumvent some of these bigger incidents?

[00:46:46] Nathan Maynard: We strongly believe that. So my co founders and I, you know, Luke Roberts, Laura Morton, we believe that what we can do is really drop down violence by increasing a sense of belonging. And that's something that Luke's done across the UK with some of the most violent prison settings. Instead of focusing on all these other prescriptive type things, Focus on, do people feel like they belong?

Not just the inmates when he was working in the justice system, but also like the, the guards at the time. We need this same thing with the schools. Do the kids feel like they belong and do our teachers and our educators feel like they belong? Cause when I talk to teachers and they say stuff like, I don't know the teacher across the hall, Nathan, like, you know, like I'm trying to my best over here, but they, you know, so we really want to make sure that if we can frame those belonging metrics, That is the shape of what we believe will drop down violence, increase attendance, drop down these discipline issues and all this other macro stuff.

Can we really focus on the metrics of belonging? 

[00:47:42] Alex Sarlin: There's so much amazing research about this kind of thing that never makes its way into the classroom, or if it does, it does through PD, you know, in a slide. So the idea of being able to get it into those key moments. Into the actual, you know, live processes in the classroom is really amazing.

So I want to thank you so much for being here. Nathan Maynard is the CEO and co founder of high five. They just got their seed investment from Ukrainian venture capital firm, Roosh X and are expanding with their new vision of school discipline and Disrupting the school to prison pipeline. Thanks so much for being here with us on EdTech Insiders.

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