Creating Safe Spaces for Real Conversations in EdTech with Tiffany Law

Creating Safe Spaces for Real Conversations in EdTech with Tiffany Law

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 from the ground up. Along the way, she reflects on the lessons learned from stepping into a completely new space, embracing mistakes, and finding her footing in a fast-moving and often overwhelming edtech landscape. The conversation dives into what makes IEI different. Instead of traditional conferences, IEI creates intentional, closed-door environments where district leaders can speak openly about their challenges, learn from one another, and connect with partners in a way that feels authentic and pressure-free. The focus is not on flashy presentations or big budgets, but on real problems, real conversations, and real solutions. Tiffany also breaks down how IEI structures its events to level the playing field between large companies and smaller innovators, using curated matching, real-time feedback, and highly qualified one-on-one meetings to ensure that every interaction is meaningful. If you are in edtech or district leadership, this episode offers a behind-the-scenes look at how trust, transparency, and thoughtful design can transform the way partnerships are built in K-12. 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 02:36 Transitioning from restaurants to education 03:36 Building IEI from the ground up 05:12 What makes IEI different from traditional events 07:47 Inside IEI event structure and formats 11:30 Why closed-door conversations matter 12:44 Creating safe spaces for district leaders 15:33 Connecting the right people through curated matching 18:28 How real-time feedback shapes conversations 22:44 Leveling the playing field between vendors 23:53 Why solutions matter more than budgets 28:23 How partners qualify and prioritize conversations Connect with Guests Tiffany Law: https://www.linkedin.com/in/tiffany-law-coo Interested in joining the show? Fill out the form: https://forms.gle/SRVhzpXikBombee38

The Why Behind the Work: How the Boys of EdTech Are Shaping K-12 from Every Angle

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 unique role they play in helping districts and companies work better together. The conversation highlights how success in K-12 is not about selling products. It is about understanding real problems, building trust, and creating meaningful impact for students. The episode also dives into personal stories that shaped their perspectives. From early nonprofit work supporting schools globally to growing edtech companies from scratch, to firsthand experiences navigating school systems as students. These stories ground the conversation in a shared mission: improving outcomes for students, especially those who need it most. If you have ever wondered what actually happens behind the scenes in edtech, or why relationships matter more than demos, this episode gives you an inside look at the people driving those conversations 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 01:15 Supporting districts and edtech alignment 02:22 Translating complex solutions into clear value 03:49 Opening doors and driving meaningful conversations 04:11 Scaling EdTech companies and go-to-market strategy 05:50 Jeff Piontek’s background in education and leadership 07:10 Why education is the foundation of the future 07:58 Matthew’s nonprofit journey and impact on global education 09:17 Connecting EdTech solutions to real student outcomes 11:14 Supporting underserved student populations at scale 24:08 The mission to close equity and achievement gaps 48:04 Personal experiences shaping passion for education 50:22 Why relationships, not sales, drive success in K-12 Interested in joining the show? Fill out the form: https://forms.gle/SRVhzpXikBombee38

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]