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.
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Données mises à jour le 05/08/2026
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From Lonely Cliff to Shared Hill: Rethinking How EdTech Founders Build and Scale
Épisode 13
mardi 4 août 2026 • Durée 43:50
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 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 01:20 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 Guest Michael 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
From Classroom to Systems Change: Leading with Purpose and Precision with Dr. Julia Rafal-Baer
Épisode 12
lundi 27 juillet 2026 • Durée 46:16
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 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 Moments02:11 Early challenges in special education systems
From Relationships to Results: Leading with Impact in Education with Thomas Davis
Épisode 11
mardi 21 juillet 2026 • Durée 42:18
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 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 02:58 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
The Reality of EdTech Jobs: Layoffs, Hiring Trends, and How to Actually Get Hired
Épisode 10
mercredi 15 juillet 2026 • Durée 49:11
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 companies. She offers a behind-the-scenes look at how hiring really works in edtech today and why relationships matter more than ever.
The conversation dives into the wave of layoffs and restructuring happening across the industry, unpacking what is actually driving these changes. From post-COVID overhiring and shifting budgets to evolving expectations around performance, the group explores why companies are becoming more selective and risk-averse in their hiring decisions.
Jenna also shares practical advice for job seekers navigating this uncertain market. She emphasizes the importance of leveraging your network, being clear about your experience, and avoiding the common mistake of mass applying without a strategy. The discussion highlights how strong candidates differentiate themselves by understanding their strengths, asking the right questions, and treating interviews like a true two-way process.
The episode also explores the role of AI in hiring, the importance of self-awareness in career decisions, and how both candidates and companies can make smarter, more intentional choices. Whether you are hiring, job searching, or simply trying to understand the market, this episode offers valuable insights grounded in real-world experience.
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
04:22 Adapting quickly in new jobs
07:53 Coping with a layoff
Competing for the Future: How Dr. Rick Surrency Is Transforming Outcomes in Putnam County Schools
Épisode 9
lundi 6 juillet 2026 • Durée 38:15
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.
Creating Safe Spaces for Real Conversations in EdTech with Tiffany Law
Épisode 8
vendredi 26 juin 2026 • Durée 46:43
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
The Why Behind the Work: How the Boys of EdTech Are Shaping K-12 from Every Angle
Épisode 7
mercredi 17 juin 2026 • Durée 51:17
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
From “Hotmail for Schools” to Student Safety at Scale: The Evolution of EdTech with Gaggle’s Founder
Épisode 6
mercredi 3 juin 2026 • Durée 33:30
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.
When a Data Breach Hits: Real Talk from a District CTO on Trust, Security, and What Comes Next
Épisode 5
mercredi 20 mai 2026 • Durée 42:39
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
Vibe Coding Is Here: How Districts Are Building Instead of Buying
Épisode 4
vendredi 15 mai 2026 • Durée 21:48
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.
01:23 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
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 Guest Julia 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
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 Guest Thomas 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
10:41 Discussing layoffs and AI impact
13:31 Business growth and funding challenges
16:39 Navigating partnership challenges
19:45 Understanding Sales Hiring Needs
24:59 Assessing Leadership in Job Search
28:38 Finding the right team fit
31:04 Challenges of Founder Led Sales
35:38 Founders doing their own sales
36:47 Technical founders avoiding sales
41:14 Finding strong job candidates
45:20 Finding a specialized recruiter
Connect with Guest Jenna Farone: https://www.linkedin.com/in/jennafarone
Interested in joining the show? Fill out the form: https://forms.gle/SRVhzpXikBombee38
Listen to the episode: https://youtu.be/sGgVHQL46Q8
