From “Hotmail for Schools” to Student Safety at Scale: The Evolution of EdTech with Gaggle’s Founder

From “Hotmail for Schools” to Student Safety at Scale: The Evolution of EdTech with Gaggle’s Founder

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 creation. After a simple conversation with a teacher about the risks of student email, Jeff saw a clear gap in the market and built one of the first safe, school-controlled communication platforms. The conversation explores how edtech has shifted from basic tools to critical infrastructure for student safety, including monitoring communication, identifying risks, and supporting student well-being. The group also discusses the responsibility that comes with handling student data, the balance between innovation and protection, and why trust is everything in K-12. Along the way, the episode blends humor, real talk, and hard-earned lessons about building in education—where relationships, long-term value, and solving real problems matter far more than hype. Connect with the Boyz Rick Fernandez: https://www.linkedin.com/in/dr-rick-fernandez-40692434/ [https://www.linkedin.com/in/dr-rick-fernandez-40692434/] Matthew Millstein: https://www.linkedin.com/in/matthew-millstein/ [https://www.linkedin.com/in/matthew-millstein/] Jacob Kantor: https://www.linkedin.com/in/thejacobkantor/ [https://www.linkedin.com/in/thejacobkantor/] Ryan Patenaude: https://www.linkedin.com/in/ryanpatenaude/ [https://www.linkedin.com/in/ryanpatenaude/] Jeff Piontek: https://www.linkedin.com/in/jeffpiontek/ [https://www.linkedin.com/in/jeffpiontek/] Key Moments 01:28 Neighbor jokes and opening banter 02:50 Jacob’s “shoe shed” and personality moment 03:16 Jeff Patterson’s early days in edtech 04:02 Entrepreneurial journey and early failures 05:13 Discovering education as a market opportunity 06:26 The teacher conversation that sparked Gaggle 08:18 Why student email was a safety concern 11:34 Identifying the gap in school communication tools 16:22 Building the first version of Gaggle 17:18 “Hotmail for schools” concept explained 22:18 Evolution of edtech over time 29:44 Shifts in communication, safety, and responsibility Connect with Guests Jeff Patterson: https://www.linkedin.com/in/jeffhpatterson [https://www.linkedin.com/in/jeffhpatterson] Interested in joining the show? Fill out the form: https://forms.gle/SRVhzpXikBombee38 [https://forms.gle/SRVhzpXikBombee38]

When a Data Breach Hits: Real Talk from a District CTO on Trust, Security, and What Comes Next

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 the tough reality of operating with limited resources while making high-stakes decisions that impact student safety and district trust. The conversation dives deep into where vendors fell short, especially around communication and transparency, and what districts actually need in moments of crisis. Amanda emphasizes the importance of proactive security measures like MFA, geofencing, and continuous education—not just for staff, but for students and parents as well. Beyond the breach itself, the episode explores broader implications for edtech: build vs. buy decisions, the future of cloud vs. on-prem infrastructure, and how districts should rethink partnerships moving forward. The group also highlights the human side of leadership—empathy, community collaboration, and showing up for others during high-pressure situations. This episode is a must-listen for district leaders, edtech vendors, and anyone responsible for protecting student data in an increasingly complex digital landscape. Connect with the Boyz Rick Fernandez: https://www.linkedin.com/in/dr-rick-fernandez-40692434/ Matthew Millstein: https://www.linkedin.com/in/matthew-millstein/ Jacob Kantor: https://www.linkedin.com/in/thejacobkantor/ Ryan Patenaude: https://www.linkedin.com/in/ryanpatenaude/ Jeff Piontek: https://www.linkedin.com/in/jeffpiontek/ Key Moments 01:09 First response: securing systems and disconnecting access 02:40 Where vendor communication broke down 04:06 Preparing schools for phishing and cyber threats 06:02 Security basics every district should implement 07:25 What effective crisis communication should look like 09:05 Why acting early matters more than avoiding disruption 11:29 How breaches spread through connected systems (APIs explained) 13:39 Real-world risks: phishing, scams, and data misuse 15:05 Build vs. buy: rethinking edtech reliance 16:52 How districts make high-stakes decisions during crises 18:10 Safer alternatives for data sharing and integrations 21:58 The power of community and shared best practices 27:23 Teaching digital safety to students and families 34:56 What makes a great (and terrible) cold email Connect with Guest: Amanda Lanicek: https://www.linkedin.com/in/amandalanicek Interested in joining the show? Fill out the form: https://forms.gle/SRVhzpXikBombee38

Vibe Coding Is Here: How Districts Are Building Instead of Buying

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 challenging the traditional edtech vendor model. From custom-built apps tailored to specific district needs to saving hundreds of thousands of dollars through internal innovation, the guests share real-world examples of what’s now possible. Rob and Kris unpack the broader implications of this movement, including the idea that software has reached a maturity point and is evolving beyond human-centered design. They also explore how AI is flattening the software stack, enabling districts to rely less on complex integrations and more on intelligent systems closer to the data. The episode also addresses critical concerns around data privacy, cybersecurity, and decision-making—highlighting the balance between leveraging AI’s power and maintaining human judgment in education. As districts rethink build vs. buy decisions, this conversation offers a glimpse into a future where educators are not just consumers of technology, but creators. Connect with the Boyz Rick Fernandez: https://www.linkedin.com/in/dr-rick-fernandez-40692434/ [https://www.linkedin.com/in/dr-rick-fernandez-40692434/] Matthew Millstein: https://www.linkedin.com/in/matthew-millstein/ [https://www.linkedin.com/in/matthew-millstein/] Jacob Kantor: https://www.linkedin.com/in/thejacobkantor/ [https://www.linkedin.com/in/thejacobkantor/] Ryan Patenaude: https://www.linkedin.com/in/ryanpatenaude/ [https://www.linkedin.com/in/ryanpatenaude/] Jeff Piontek: https://www.linkedin.com/in/jeffpiontek/ [https://www.linkedin.com/in/jeffpiontek/] Key Moments 01:23 Kris Hagel’s first experience building with AI 03:24 The shift beyond traditional software models 04:00 Building for your district vs. building to scale 05:20 Rise of inbound AI-built solutions from individuals 07:21 Going viral and saving $250K through internal builds 10:18 Are edtech vendors becoming infrastructure providers? 12:09 Real-world applications and AI-driven workflows 13:21 The future of decision-making: build vs. partner 16:02 Data privacy and security challenges in AI adoption 17:11 Flattening the software stack with AI 18:07 What’s next: AI agents and automation in schools 19:20 Intelligence vs. understanding in education 20:43 Why this moment is different for district leaders Connect with Guests Rob Dickson: https://www.linkedin.com/in/showmerob [https://www.linkedin.com/in/showmerob] Kris Hagel: https://www.linkedin.com/in/krishagel [https://www.linkedin.com/in/krishagel] Interested in joining the show? Fill out the form: https://forms.gle/SRVhzpXikBombee38 [https://forms.gle/SRVhzpXikBombee38]

Outcomes Over Everything: Building Better EdTech Partnerships with District Leaders

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 wellness, and improving math and writing outcomes—grounded in a long-term strategic vision. She emphasizes the importance of infrastructure, data maturity, and thoughtful change management in driving meaningful progress. Dr. Miller dives deep into outcomes-based contracting (OBC), explaining how districts and providers can move beyond transactional relationships toward true partnerships focused on measurable student outcomes. She highlights how aligning pricing, implementation, and accountability creates stronger, more sustainable impact. The conversation challenges both districts and edtech providers to raise expectations, define impact clearly, and embrace accountability. From the realities of scaling innovation to the importance of rigorous measurement and change management, this episode is a must-listen for anyone serious about improving education systems. Connect with the Boyz Rick Fernandez: https://www.linkedin.com/in/dr-rick-fernandez-40692434/ [https://www.linkedin.com/in/dr-rick-fernandez-40692434/] Matthew Millstein: https://www.linkedin.com/in/matthew-millstein/ [https://www.linkedin.com/in/matthew-millstein/] Jacob Kantor: https://www.linkedin.com/in/thejacobkantor/ [https://www.linkedin.com/in/thejacobkantor/] Ryan Patenaude: https://www.linkedin.com/in/ryanpatenaude/ [https://www.linkedin.com/in/ryanpatenaude/] Jeff Piontek: https://www.linkedin.com/in/jeffpiontek/ [https://www.linkedin.com/in/jeffpiontek/] Key Moments 06:58 Updating facilities for innovation 08:11 Upgrading facilities for climate readiness 12:13 Focusing on student-centered outcomes 14:33 Free open-source resources and research 20:19 Future-focused partnerships and data insights 21:56 Urgency in education strategy 26:44 Embracing outcomes-based contracts in EdTech 29:52 State investments in educational tech 31:32 Importance of all-inclusive pricing 35:07 Understanding competitive advantages in ed tech 38:17 Defining impact and engagement metrics 41:46 Discussing change management strategy 45:29 Challenges with agreed outcomes in construction 48:06 Challenges in implementing education assessments 51:26 Hesitancy around student learning metrics Connect with Guests Dr. Brittany Miller: https://www.linkedin.com/in/brittany-miller-phd-290a13b3 [https://www.linkedin.com/in/brittany-miller-phd-290a13b3] Dr. Barbara Mullen: https://www.linkedin.com/in/barbara-a-mullen-ph-d-91bb4116 [https://www.linkedin.com/in/barbara-a-mullen-ph-d-91bb4116] Interested in joining the show? Fill out the form: https://forms.gle/SRVhzpXikBombee38 [https://forms.gle/SRVhzpXikBombee38]

Inside EdTech Networking: Lessons from ASU+GSV, AI Advances, and Building Lasting Partnerships

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 actually work to the importance of relationship-building over transactions, this episode is packed with real, tactical advice for edtech founders, sales teams, and anyone trying to navigate the K-12 space. They also explore what meaningful relationships look like in practice, how to stand out in a crowded market, and why understanding district priorities (down to contracts and funding plans) can make or break your success.  If you're in edtech, business development, or district leadership, this episode delivers unfiltered perspectives from operators who are in the trenches every day. Connect with the Boyz Rick Fernandez: https://www.linkedin.com/in/dr-rick-fernandez-40692434/ Matthew Millstein: https://www.linkedin.com/in/matthew-millstein/ Jacob Kantor: https://www.linkedin.com/in/thejacobkantor/ Ryan Patenaude: https://www.linkedin.com/in/ryanpatenaude/ Jeff Piontek: https://www.linkedin.com/in/jeffpiontek/ Key Moments 04:03 Reflecting on conference interactions 07:54 Importance of Learning Efficacy Data 10:07 Casual networking event insights 15:56 Building authentic professional relationships 20:07 Networking strategies at events 22:20 Balancing work and family time 25:16 Tailoring pitches for different personas 30:45 Understanding school funding transparency 33:20 Evaluating client relationships 37:58 Choosing the right business partner 41:28 Allocating education funding strategically Interested in joining the show? Fill out the form: https://forms.gle/SRVhzpXikBombee38