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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 brought to you by Starbridge. Every year, K-12 districts and higher ed institutions spend over half a trillion dollars—but most sales teams miss the signals. Starbridge tracks early signs like board minutes, budget drafts, and strategic plans, then helps you turn them into personalized outreach—fast. Win the deal before it hits the RFP stage. That’s how top edtech teams stay ahead.

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.