The Boyz of Edtech | K–12 Education Insights

What Makes an EdTech Company Built to Last with John Gamba

Old Soul | Edtech & K–12 Education Experts — Thu, 17 Sep 2026 08:00:00 -0400

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 Moments
03:30 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 Guest
John 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

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

Old Soul | Edtech & K–12 Education Experts — Mon, 14 Sep 2026 08:00:00 -0400

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

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 Guest
Dr. 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

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

Old Soul | Edtech & K–12 Education Experts — Fri, 11 Sep 2026 10:00:00 -0400

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 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

02:14 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 Guest
Jean-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

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

Old Soul | Edtech & K–12 Education Experts — Thu, 27 Aug 2026 12:00:00 -0400

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.

Key Moments
05:31 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 Guest
Dr. 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

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

Old Soul | Edtech & K–12 Education Experts — Fri, 21 Aug 2026 16:56:08 -0400

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 Moments
00:00 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 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/

Interested in joining the show? Fill out the form: https://forms.gle/SRVhzpXikBombee38

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

Old Soul | Edtech & K–12 Education Experts — Tue, 04 Aug 2026 09:40:04 -0400

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.

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

Old Soul | Edtech & K–12 Education Experts — Mon, 27 Jul 2026 08:00:00 -0400

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.

Key Moments
02:11 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 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

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

Old Soul | Edtech & K–12 Education Experts — Tue, 21 Jul 2026 12:00:00 -0400

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.

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

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

The Reality of EdTech Jobs: Layoffs, Hiring Trends, and How to Actually Get Hired

Old Soul | Edtech & K–12 Education Experts — Wed, 15 Jul 2026 14:30:00 -0400

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.

Key Moments

04:22 Adapting quickly in new jobs

07:53 Coping with a layoff

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

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

Old Soul | Edtech & K–12 Education Experts — Mon, 06 Jul 2026 10:00:00 -0400

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.

Key Moments

03:54 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 Guest
Dr. Rick Surrency: https://www.linkedin.com/in/rick-surrency-221a69a5

Interested in joining the show? Fill out the form: https://forms.gle/SRVhzpXikBombee38

Creating Safe Spaces for Real Conversations in EdTech with Tiffany Law

Old Soul | Edtech & K–12 Education Experts — Fri, 26 Jun 2026 09:00:24 -0400

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.

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

Old Soul | Edtech & K–12 Education Experts — Wed, 17 Jun 2026 09:30:00 -0400

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.

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

Old Soul | Edtech & K–12 Education Experts — Wed, 03 Jun 2026 10:07:12 -0400

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.

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

Interested in joining the show? Fill out the form: https://forms.gle/SRVhzpXikBombee38

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

Old Soul | Edtech & K–12 Education Experts — Wed, 20 May 2026 10:10:18 -0400

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.

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

Old Soul | Edtech & K–12 Education Experts — Fri, 15 May 2026 09:32:01 -0400

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.

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
Kris Hagel: https://www.linkedin.com/in/krishagel

Interested in joining the show? Fill out the form: https://forms.gle/SRVhzpXikBombee38

Outcomes Over Everything: Building Better EdTech Partnerships with District Leaders

Old Soul | Edtech & K–12 Education Experts — Wed, 06 May 2026 10:30:00 -0400

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.

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
Dr. 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

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

Old Soul | Edtech & K–12 Education Experts — Mon, 27 Apr 2026 10:00:00 -0400

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.

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

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

Old Soul | Edtech & K–12 Education Experts — Fri, 10 Apr 2026 09:12:10 -0400

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.

Key Moments
00:00 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