The Boyz of Edtech | K–12 Education Insights

Old Soul
Old Soul
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Explore the latest education business trends, entrepreneurship, and school leadership insights with us. We bring you expert discussions on district leadership, edtech innovation, education policy insights, and K-12 education advancements. Join us for valuable perspectives on edtech trends, startup founders in education, and strategies for effective school operations and relationship building. Hosted by Dr. Rick Fernandez, Jacob Kantor, Jeff Piontek, Ryan Patenaude, Matthew Millstein, and powered by Old Soul.

  1. 3d ago

    What Makes an EdTech Company Built to Last with John Gamba

    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, and ultimately bringing those lessons back to Penn to mentor the next generation of education entrepreneurs.John breaks down what separates promising EdTech ideas from companies that can create lasting impact. His framework focuses on three fundamentals: engagement, pedagogical alignment, and ease of adoption. The conversation explores why strong technology alone is not enough, why founders need evidence behind their claims, and how responsible AI, research, and measurable outcomes should shape product development. John also explains why the footnotes supporting a company's claims may be more important than the flashy slides in its pitch deck. The group then digs into the business mechanics behind sustainable EdTech growth. Instead of chasing district logos and annual recurring revenue at all costs, John advocates for paid pilots, milestone-driven expansion, and a greater focus on net recurring revenue. They discuss why landing a district is only the beginning, how customer experience determines whether a pilot becomes a renewal, and why companies need to intentionally map the entire journey from initial conversation through onboarding, implementation, measurement, and expansion. 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 Moments03:30 Building and exiting an EdTech company to Blackboard 05:05 Bringing entrepreneurship and innovation to Penn GSE 07:15 What John looks for in promising EdTech companies 11:20 The three fundamentals of successful EdTech products 14:35 Why evidence and research belong at the center of the pitch 19:10 Giving superintendents visible wins through technology 23:25 Shifting the focus from ARR to sustainable district growth 27:10 Why successful pilots should lead naturally to expansion 31:30 Mapping the complete customer journey after the sale 36:15 Why customer experience matters as much as customer acquisition 40:05 Paid pilots, milestones, and commitments to growth 44:25 The leadership qualities John looks for in founders 47:10 Balancing humility, coachability, and the will to succeed 50:30 How mentorship and coaching shape stronger entrepreneurs Connect with GuestJohn Gamba: https://www.linkedin.com/in/johngamba Interested in joining the show? Fill out the form: https://forms.gle/SRVhzpXikBombee38 Listen to the episode: https://youtu.be/TGCkPgC94gY

    What Makes an EdTech Company Built to Last with John Gamba

  2. 6d ago

    Beyond the Sale: What School Leaders Really Want from EdTech Partners with Dr. Davion Lewis

    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 first year in Michigan with a major challenge already waiting for him: rebuilding community support for a school bond that had previously failed by just 51 votes.Dr. Lewis breaks down how research, listening, board alignment, and community involvement shaped his entry into the district and ultimately helped turn the bond effort into a grassroots initiative. He also discusses the pressure new superintendents face to make changes quickly, why early wins matter, and how leadership stability can create the conditions for long-term improvement. From navigating conflict with a school board to recognizing when a decades-old problem might not be the right battle to fight, he offers a candid look at the judgment required to lead a district effectively. The conversation also delivers a practical message for edtech companies: do your homework and become a partner, not simply a vendor. Dr. Lewis explains why companies need to understand district budget cycles, state funding priorities, contracts, implementation realities, and the people surrounding the superintendent. He shares concrete ways providers can add value beyond their product, including internships, community involvement, professional development, and proactive implementation support. The episode closes with a discussion of Essexville-Hampton's academic success and why continuity in teachers, principals, superintendents, and boards may be one of the most important ingredients for sustained improvement. 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 03:10 Taking on a school bond after arriving in a new district 05:30 Building credibility by having skin in the game 08:10 Turning a failed bond into a grassroots community effort 10:30 Building a superintendent's first 100-day entry plan 13:45 Why today's superintendent role requires more than instructional expertise 16:15 Knowing when to move quickly and when to slow down change 19:05 Building credibility through early wins and healthy conflict 23:20 What edtech vendors misunderstand about district buying cycles 25:40 Why providers should understand state funding before making a pitch 28:35 The difference between an edtech vendor and a true district partner 35:05 Why the cheapest solution is not always the best partnership 39:10 Making implementation easier instead of creating more work for districts Connect with GuestDr. Davion Lewis: https://www.linkedin.com/in/davionrlewis Interested in joining the show? Fill out the form: https://forms.gle/SRVhzpXikBombee38 Listen to the episode: https://youtu.be/1KiFSgtvvrw

    Beyond the Sale: What School Leaders Really Want from EdTech Partners with Dr. Davion Lewis

  3. Sep 11

    Banning AI Won't Prepare Students for the Future with Jean-Claude Brizard

    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 whether broad restrictions address the real challenges schools face with artificial intelligence.The conversation explores the potential consequences for equity, instruction, procurement, and workforce readiness. Jean-Claude argues that students with access to AI at home will continue learning how to use it, while students who depend on schools for access risk being left further behind. Rather than treating AI primarily as a technology problem, the group discusses why schools should rethink instructional design, elevate pedagogy, and move students beyond answer-getting toward analysis, productive struggle, collaboration, curiosity, and other durable skills. Jean-Claude also examines the procurement and implementation challenges behind education technology. He explains why districts need stronger systems for evaluating whether products are safe, effective, aligned with instructional priorities, and properly implemented. The discussion highlights Digital Promise's work around AI and EdTech assurance labs, continuous efficacy measurement, and the need for shared accountability between districts and providers. The episode closes with a broader look at workforce readiness and global competitiveness. 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 02:14 Why a last-minute AI policy creates implementation challenges 05:12 The equity risks of limiting AI access in schools 08:05 Why EdTech procurement needs stronger evidence and evaluation 12:18 Preparing students for an AI-driven workforce 15:30 Moving from answer-getting to deeper thinking and analysis 18:42 Why instructional design matters more than banning the tool 22:15 What the graphing calculator debate can teach us about AI 28:10 Spending, strategy, and improving student outcomes 34:36 Why schools struggle to replicate successful practices 39:15 The challenge of removing AI from modern EdTech products 43:30 Building continuous AI and EdTech assurance systems 49:20 Why technology should support the instructional program 54:18 Shared accountability through outcomes-based contracting 58:12 Why AI literacy and computational thinking need to start early Connect with GuestJean-Claude Brizard: https://www.linkedin.com/in/jean-claude-brizard-0080a810 Interested in joining the show? Fill out the form: https://forms.gle/SRVhzpXikBombee38 Listen to the episode: https://youtu.be/oEtxATz0hcE

    Banning AI Won't Prepare Students for the Future with Jean-Claude Brizard

  4. Aug 27

    From High Performers to a High-Performing Team with Dr. Miranda Walachowski

    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 performers into a truly high-performing team. Miranda explores why strong teams must make room for individual growth, protect their energy, and create clarity around how they work together. The group gets candid about balancing their businesses, families, and the podcast while identifying where logistics, unclear processes, and future interpersonal conflict could slow their momentum. Miranda explains why team charters, decision-making structures, written agreements, and honest conversations can help teams spend less energy on friction and more on meaningful work. The discussion ultimately turns toward mission, vision, and action. Together, they uncover an opportunity for The Boys of EdTech to create a more interconnected ecosystem between K-12 leaders, entrepreneurs, and education partners while continuing to learn from one another. Miranda challenges the team to treat new ideas as experiments, establish clear milestones, streamline guest selection and scheduling, and build systems that protect both the team's momentum and the humans behind it. 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 Moments05:31 Career advancement in education and edtech 09:46 Finding synergy in a new team 12:58 Integrating podcast insights into work 16:32 Managing work and family energy 18:13 Balancing work and family energy 24:26 Implementing Team Science Lab 26:50 Balancing work and family life 30:58 Learning and growth in education 32:55 Driving positive impact in education 36:20 Collective learning and collaboration benefits 40:02 Balancing personal business growth 45:54 Streamlining scheduling for efficiency 48:49 Balancing show monetization and authenticity 52:05 Meeting interesting people and logistics 56:00 Effective scheduling and guest engagement strategies 57:57 Discussing team assessments and purpose Connect with GuestDr. Miranda Wallechinsky: https://humanarks.com/  Interested in joining the show? Fill out the form: https://forms.gle/SRVhzpXikBombee38 Listen to the episode: https://youtu.be/bjs3cKq0RxY

    From High Performers to a High-Performing Team with Dr. Miranda Walachowski

  5. Aug 21 ·  Video

    Dept of Education Issues New Guidance: What EdTech Founders and Districts Need to Know

    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 strategies, and how to create real impact in education technology. Whether you're a founder, buyer, or education partner, this episode delivers actionable perspectives to navigate the evolving landscape. Note: The letter was published on August 20th, 2026 Key Moments00:00 Evaluating educational tools and evidence 05:04 Evaluating Educational Tools Effectively 07:33 Questioning the need for RCTs 10:37 Discussing investment and educational implementation 16:54 Discussing education and AI influence 18:17 Addressing educational equity gaps 21:03 Auditing and optimizing spending 25:38 Partnering with school districts 30:47 Business marketing and strategy approach 31:48 Discussing past educational initiatives 37:50 Discussing adult habit changes 42:15 Facing pandemic challenges with FEV Tutor 46:12 Evolving outcomes-based contracting in edtech 48:01 Ensuring mutual investment success 52:09 Challenges for education startups 54:01 Communication and support strategy 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/ Interested in joining the show? Fill out the form: https://forms.gle/SRVhzpXikBombee38

    Dept of Education Issues New Guidance: What EdTech Founders and Districts Need to Know

  6. Aug 4

    From Lonely Cliff to Shared Hill: Rethinking How EdTech Founders Build and Scale

    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 founders lose their original vision under pressure from markets, customers, and expectations. He introduces the concept of the “shared hill,” a new way of building companies rooted in authentic vision, long-term partnerships, and collective growth. The conversation dives into why traditional edtech sales and growth models are breaking down, especially in a world where AI is rapidly commoditizing products. Michael emphasizes that trust has been eroded in the market and that founders must now lead with vision, not just features, to create meaningful differentiation. The group explores a new approach to building in edtech, centered on co-creation with districts and partners rather than transactional selling. From replacing demos with insight-driven conversations to designing long-term transformation partnerships, Michael outlines a practical framework for founders to build durable revenue and real impact. The episode also tackles the realities of funding and scaling, including the “missing middle” problem in edtech investing. Michael shares alternative pathways to growth through strategic partnerships, revenue-based financing, and aligned distribution models, challenging the assumption that venture capital is the only path forward. 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 Moments01:20 What a “Founder Jam” looks like in practice 04:30 Why Michael chose education and learning as his focus 06:43 The concept of the “shared hill” explained 09:25 Why edtech products are losing trust in the market 11:03 Vision vs product in a world shaped by AI 14:16 Rethinking the traditional sales process in edtech 16:28 Why cheap pilots fail and partnerships matter more 18:40 What Michael looks for in early-stage founders 20:47 Building durable revenue through deep partnerships 24:16 The co-building sales framework step by step 26:52 Scaling from $100K to $1M through community and movement 34:00 Consortium partnerships and shared accountability 40:08 Alternatives to venture capital for founders Connect with GuestMichael Narea: https://www.linkedin.com/in/mnarea  Interested in joining the show? Fill out the form: https://forms.gle/SRVhzpXikBombee38 Listen to the episode: https://youtu.be/HHnGkrKyUIw

  7. Jul 27

    From Classroom to Systems Change: Leading with Purpose and Precision with Dr. Julia Rafal-Baer

    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, talent, and system-level change. Drawing from her own experiences as a student with non-visible disabilities, she reflects on how early challenges shaped her passion for creating more equitable and responsive education systems. The conversation explores a defining moment early in her career that reshaped her perspective on leadership and systems. From that point forward, Julia became focused on understanding how strong leadership and thoughtful policy can drive real change for students and educators alike. The discussion dives into her work building multiple organizations, including Women Leading Ed, and how she approaches leadership development through personalized support, coaching, and intentional talent building. She highlights the importance of sponsorship over mentorship, the role of self-awareness in leadership, and why strong teams are built through systems, structures, and clarity rather than individual performance alone. The group also explores the future of education, including the growing role of AI, the need for faster and more adaptive strategic planning, and how leaders can navigate complexity while maintaining focus on impact. Julia brings a unique lens that blends discipline from her background as a competitive athlete with a deep commitment to developing leaders who can thrive in high-pressure environments. 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 Moments02:11 Early challenges in special education systems 04:17 Writing to the NYC Chancellor and system-level change 06:08 Applying individualized support to leadership development 07:40 Why women often don't see themselves as ready 10:14 Importance of coaching and self-awareness 13:25 Burnout, recovery, and building sustainable habits 19:02 Growth and impact of Women Leading Ed 21:28 Talent as the biggest system challenge in education 24:37 Balancing focus and avoiding 'shiny object syndrome' 28:10 Leveraging AI across leadership and systems 32:42 Why AI strategy must move faster than traditional planning 38:12 Moving from mentorship to sponsorship 43:06 Personal challenges and high-performance mindset Connect with GuestJulia Rafal-Baer: https://www.linkedin.com/in/jrafal  Interested in joining the show? Fill out the form: https://forms.gle/SRVhzpXikBombee38 Listen to the episode: https://youtu.be/paTeLjxuDCM

    From Classroom to Systems Change: Leading with Purpose and Precision with Dr. Julia Rafal-Baer

  8. Jul 21

    From Relationships to Results: Leading with Impact in Education with Thomas Davis

    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 up in San Diego to becoming a trusted advisor across K-12 and beyond. He reflects on how early experiences, strong mentorship, and a commitment to giving back shaped his path and continue to influence his work today. The conversation dives into the evolution of education leadership, highlighting the importance of mentorship pipelines, cultural understanding, and developing future leaders who can sustain meaningful change. Thomas shares insights from his work with CALSA and other organizations, emphasizing the role of community, representation, and intentional leadership development in transforming education systems. The group also explores the changing dynamics between school districts and edtech providers, unpacking why relationships, storytelling, and problem-solving must take precedence over traditional sales approaches. Thomas offers a compelling perspective on how vendors can become true partners by focusing on impact, embracing performance-based models, and aligning with district needs. 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 Moments02:58 Transition from teaching to edtech sales 05:11 Why hitting quota defines success in edtech sales 06:40 Growth story of CALSA and leadership development 09:48 Mentorship as the foundation of leadership pipelines 12:07 Cultural awareness and diversity in leadership 17:26 Building trust between districts and edtech partners 24:18 Three key shifts in edtech: AI, performance contracts, partnerships 29:01 Current challenges and opportunities in school systems 32:09 Innovation vs. defense mindset in education leadership 38:17 Launch of K-12 Impact Academies and training future leaders 40:27 Keys to success in edtech sales and leadership Connect with GuestThomas Davis: https://www.linkedin.com/in/thomas-aurelio-davis Interested in joining the show? Fill out the form: https://forms.gle/SRVhzpXikBombee38 Listen to the episode: https://youtu.be/Ld2CtmkKKFE

    From Relationships to Results: Leading with Impact in Education with Thomas Davis
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Explore the latest education business trends, entrepreneurship, and school leadership insights with us. We bring you expert discussions on district leadership, edtech innovation, education policy insights, and K-12 education advancements. Join us for valuable perspectives on edtech trends, startup founders in education, and strategies for effective school operations and relationship building. Hosted by Dr. Rick Fernandez, Jacob Kantor, Jeff Piontek, Ryan Patenaude, Matthew Millstein, and powered by Old Soul.

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