The Boyz of Edtech

Old Soul
  • 5.0 (39)
  • Education

The Boyz of EdTech is a fast-paced, insider-driven podcast that explores the evolving world of K–12 education through multiple lenses—district leadership, entrepreneurship, operations, and relationship-building. Hosted by a dynamic panel that includes a former superintendent, startup founders, and edtech operators, the show blends frontline experience with candid conversation about what’s really happening in education today.

Episodes

  1. 5d ago

    Competing for the Future: How Dr. Rick Surrency Is Transforming Outcomes in Putnam County Schools

    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 of the most dynamic and challenging education environments in the country. He offers a unique perspective on leading in a choice-driven system, where districts must continuously evolve to meet the needs of students and families. The conversation dives deep into the district’s transformation, including a dramatic rise in graduation rates and the implementation of robust career and technical education programs. From aviation and advanced manufacturing to dual enrollment and STEM pathways, Dr. Surrency explains how aligning education with real workforce opportunities has given students a clear reason to stay engaged and succeed. He also addresses the realities of competition, funding challenges, and the growing impact of school choice, emphasizing the importance of trust, transparency, and community engagement. The episode highlights how forward-thinking leadership, strategic partnerships, and a willingness to embrace change can drive meaningful outcomes for students. If you are a district leader, edtech partner, or anyone invested in the future of education, this episode offers practical insights on building systems that prepare students for real opportunities beyond graduation. Connect with the BoyzRick 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 Moments03:54 Why Dr. Surrency chose education 04:49 Rethinking innovation and student outcomes 06:20 Building CTE and STEM pathways for real careers 08:19 Challenges of school choice and funding shifts 10:15 Competing in a choice-driven education system 12:14 Supporting student mental health and safety 15:48 Navigating AI adoption in schools 17:27 Evaluating edtech through ROI and outcomes 18:53 Leveraging partnerships and consortium buying power 20:26 How districts can pilot new solutions 26:06 Why CTE is driving graduation success 28:28 Funding and sustaining CTE programs 30:24 Creating real career opportunities for students 33:34 AI tools improving district operations Connect with GuestDr. Rick Surrency: https://www.linkedin.com/in/rick-surrency-221a69a5 Interested in joining the show? Fill out the form: https://forms.gle/SRVhzpXikBombee38

    38 min

  2. Jun 26

    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 BoyzRick 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 GuestsTiffany Law: https://www.linkedin.com/in/tiffany-law-coo Interested in joining the show? Fill out the form: https://forms.gle/SRVhzpXikBombee38

    47 min

  3. Jun 17

    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 BoyzRick 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

    51 min

  4. Jun 3

    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 BoyzRick 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 Moments01:28 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 GuestsJeff Patterson: https://www.linkedin.com/in/jeffhpatterson Interested in joining the show? Fill out the form: https://forms.gle/SRVhzpXikBombee38

    34 min

  5. May 20

    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 BoyzRick 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

    43 min

  6. May 15

    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 BoyzRick 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 Moments01:23 Kris Hagel’s first experience building with AI03:24 The shift beyond traditional software models04:00 Building for your district vs. building to scale05:20 Rise of inbound AI-built solutions from individuals07:21 Going viral and saving $250K through internal builds10:18 Are edtech vendors becoming infrastructure providers?12:09 Real-world applications and AI-driven workflows13:21 The future of decision-making: build vs. partner16:02 Data privacy and security challenges in AI adoption17:11 Flattening the software stack with AI18:07 What’s next: AI agents and automation in schools19:20 Intelligence vs. understanding in education20:43 Why this moment is different for district leaders Connect with GuestsRob Dickson: https://www.linkedin.com/in/showmerob Kris Hagel: https://www.linkedin.com/in/krishagel Interested in joining the show? Fill out the form: https://forms.gle/SRVhzpXikBombee38

    22 min

  7. May 6

    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 BoyzRick 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 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 GuestsDr. Brittany Miller: https://www.linkedin.com/in/brittany-miller-phd-290a13b3Dr. Barbara Mullen: https://www.linkedin.com/in/barbara-a-mullen-ph-d-91bb4116 Interested in joining the show? Fill out the form: https://forms.gle/SRVhzpXikBombee38

    56 min

  8. Apr 27

    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 BoyzRick 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

    45 min

  9. Apr 10

    How to Survive and Thrive at ASU+GSV 2026 with the Boyz of Edtech

    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, founders, investors, and non-profits. Whether you’re a first-time attendee or a seasoned pro, you’ll get actionable advice on how to navigate the overwhelming environment, maximize your ROI, avoid “party pipeline,” and focus on lasting connections. Tune in as the Boyz share their personal stories, pro tips, and what they're excited about for this year’s event, all while keeping it real, relatable, and fun. If you care about the future of edtech, building meaningful relationships, and learning from those who are shaping the space, this episode is for you. Connect with the BoyzRick 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 Moments00:00 Big education conference this weekend 03:43 Networking at a unique conference 08:01 ASU conference energy and connections 10:49 Surviving long event days 14:31 Prioritizing key meetings and goals 17:21 Planning for conference success 22:49 Building genuine, deeper connections 26:01 Networking and event strategy 30:09 Balancing a packed schedule 31:04 Navigating events and networking 37:14 Helping startups and sharing advice 38:48 Connecting with AI and LinkedIn network 42:34 Upcoming changes with ASU and BET 45:34 Networking and career opportunities 50:06 Attending conferences for career growth Interested in joining the show? Let us know: https://forms.gle/SRVhzpXikBombee38

    52 min
  • 9 Episodes

5
out of 5
39 Ratings

About

The Boyz of EdTech is a fast-paced, insider-driven podcast that explores the evolving world of K–12 education through multiple lenses—district leadership, entrepreneurship, operations, and relationship-building. Hosted by a dynamic panel that includes a former superintendent, startup founders, and edtech operators, the show blends frontline experience with candid conversation about what’s really happening in education today.

Information

  • Channel
    Old Soul
  • Creator
    Old Soul
  • Years Active
    2K
  • Episodes
    9
  • Rating
    Clean
  • Copyright
    © 2026 Old Soul

More From Old Soul

You Might Also Like