Edtech Insiders

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


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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.

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