The Boyz of Edtech

In this episode of The Boyz of EdTech, Rick Fernandez, Matthew Millstein, and Ryan Patenot take a practical look at Q3 and Q4 in the K-12 EdTech market and why these months can be critical for building momentum. With districts settling into the school year and the holiday season approaching, the conversation explores how EdTech companies can use this window to strengthen relationships, create oppo...

In this episode of The Boyz of EdTech, Rick Fernandez, Jacob Kantor, and Jeff Piontek sit down with Jennifer Womble, Conference Chair and EdTech Advisor for the Future of Education Technology Conference (FETC), for a wide-ranging conversation about where education is headed and what schools need to rethink along the way. Jennifer shares her unconventional path into education, from studying economi...

In this episode of The Boyz of EdTech, Rick Fernandez, Matthew Millstein, Jacob Kantor, and Jeff Piontek sit down with John Gamba, Entrepreneur in Residence and Director of Innovative Programs at the University of Pennsylvania. John shares his journey from building some of the earliest branded websites to founding, funding, and scaling education ventures, including a successful exit to Blackboard,...

In this episode of The Boyz of EdTech, Rick Fernandez and Matthew Millstein sit down with Dr. Davion Lewis, Superintendent of Essexville-Hampton Public Schools, to explore the realities of district leadership, community trust, and what education companies need to understand before approaching school leaders. Dr. Lewis shares his unconventional path into education and reflects on stepping into his...

In this emergency edition of The Boyz of EdTech, Rick Fernandez, Matthew Millstein, Jacob Kantor, and Jeff Piontek are joined by Jean-Claude Brizard, President and CEO of Digital Promise, for a timely conversation about New York City's newly announced restrictions on AI tools in schools. Drawing on more than two decades of experience inside the New York City education system, Jean-Claude questions...

In this episode of The Boys of EdTech, the conversation gets personal as Dr. Miranda Walachowski, Founder of Human Architects, steps into the coach's seat. Rather than a traditional interview, Miranda guides Rick Fernandez, Ryan Patenot, and Jacob Kantor through a live team coaching session focused on the future of the podcast, their individual goals, and what it takes to turn a group of high perf...

In this emergency episode, Rick Fernandez, Jacob Kantor, Ryan Patenaude, and Matthew Millstein unpack the latest Department of Education guidance impacting the edtech industry and K-12 innovation. They explore evidence-based procurement, randomized controlled trials (RCTs), screen time debates, and outcomes-based contracting. Dive into candid insights on district leadership challenges, startup str...

In this episode of the Boys of EdTech, the crew is joined by Michael Narea, CEO and General Partner at the Transcend Fellowship, for a deep and thought-provoking conversation on what it really takes to build, sustain, and scale in edtech today. Michael shares insights from over 12,000 one-on-one conversations with founders, revealing a powerful pattern he calls the “lonely cliff” where many founde...

In this episode of the Boys of EdTech, the crew is joined by Dr. Julia Rafal-Baer, CEO and Founder of Women Leading Ed, for an inspiring and deeply insightful conversation on leadership, resilience, and transforming education systems at scale. Julia shares her powerful journey from starting as a special education teacher in the Bronx to becoming a nationally recognized leader shaping policy, talen...

In this episode of the Boys of EdTech, host Rick Fernandez and the crew sit down with Thomas Davis, Board Member and Educational Innovator at Boz Institute, for a powerful conversation on leadership, mentorship, and what it truly takes to drive impact in education. With a career spanning classroom teaching, edtech sales, consulting, and nonprofit leadership, Thomas shares his journey from growing...

In this episode of the Boys of EdTech, the crew is joined by Jenna Farone, Vice President of Education at Rockwood Search, for a timely and unfiltered conversation on the current state of the edtech job market. Jenna shares her journey into edtech recruiting, from entering the industry with no prior experience to building a strong network and becoming a trusted partner for both candidates and comp...

In this episode of the Boys of EdTech, the crew is joined by Dr. Rick Surrency, Superintendent of Putnam County School District in Florida, for a powerful conversation on leadership, innovation, and what it takes to truly compete in today’s K-12 landscape. With nearly 50 years in education, Dr. Surrency shares his journey from coach and classroom teacher to an elected superintendent navigating one...

In this episode of the Boys of EdTech, the crew is joined by Tiffany Law, COO of the Institute for Education Innovation (IEI), for a candid conversation on what it really takes to build meaningful connections between district leaders and edtech partners. Tiffany shares her unconventional journey into education, transitioning from a 27-year career in the restaurant industry to helping build IEI fro...

In this episode of the Boys of EdTech, the crew flips the script and takes a step back to answer a question they have never fully addressed: who are they, what do they actually do, and most importantly, why do they care so deeply about K-12 education? From former superintendents and operators to go-to-market leaders and relationship builders, each member shares their journey into edtech and the un...

In this episode of the Boys of EdTech, the crew is joined by Jeff Patterson, Founder and CEO of Gaggle, for a deep dive into the origins of student safety technology and how the edtech landscape has evolved over the past two decades. Jeff shares his entrepreneurial journey—from starting businesses as a child to building early edtech tools in the late 90s—and the pivotal moment that led to Gaggle’s...

In this episode of the Boys of EdTech, Rick, Ryan, and Jeff are joined by Amanda Lanicek, CTO of Springtown ISD, for a candid and urgent conversation on navigating a major data breach in K-12 education. Amanda walks through her real-time response to the Instructure incident—from immediately disconnecting APIs and securing systems to communicating transparently with staff and families. She shares t...

In this episode of the Boys of EdTech, Matthew and Jacob are joined by Rob Dickson (Wichita Public Schools) and Kris Hagel (Peninsula School District) to explore the rise of “vibe coding” and what it means for the future of edtech. The conversation dives into how district leaders are increasingly building their own solutions using AI—often in hours instead of months—and why this shift is challengi...

In this episode of the Boys of EdTech, the crew is joined by Dr. Barbara Mullen, Superintendent of Rush-Henrietta Central School District, and Dr. Brittany Miller, leader of the Center for Outcomes-Based Contracting. Together, they unpack what it really takes to align edtech innovation with student success. Dr. Mullen shares her district’s “big rocks,” including facilities modernization, student w...

In this episode of the Boys of EdTech, the crew unpacks what’s actually happening on the ground—from AI overload and vendor noise to what truly cuts through when selling to school districts. The group breaks down why AI isn’t the differentiator anymore, how districts are thinking about build vs. buy decisions, and what vendors are getting wrong in their outreach. From cold email strategies that ac...

Join us for our inagruarl episode where the Boyz break down the ASU+GSV Summit, one of the most influential conferences in education technology in the world. The conversation covers everything from the wild networking opportunities and practical strategies for making the most of your conference experience, to the importance of genuine relationships and being intentional in connecting with leaders,...