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 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
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 

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

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

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 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

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

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

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

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 

In this episode of the Boys of EdTech, the crew is joined by Dr. Rick Surrency, Superintendent of Putnam County School District in Florida, for a powerful conversation on leadership, innovation, and what it takes to truly compete in today’s K-12 landscape.

With nearly 50 years in education, Dr. Surrency shares his journey from coach and classroom teacher to an elected superintendent navigating one of the most dynamic and challenging education environments in the country. He offers a unique perspective on leading in a choice-driven system, where districts must continuously evolve to meet the needs of students and families.

The conversation dives deep into the district’s transformation, including a dramatic rise in graduation rates and the implementation of robust career and technical education programs. From aviation and advanced manufacturing to dual enrollment and STEM pathways, Dr. Surrency explains how aligning education with real workforce opportunities has given students a clear reason to stay engaged and succeed.

He also addresses the realities of competition, funding challenges, and the growing impact of school choice, emphasizing the importance of trust, transparency, and community engagement. The episode highlights how forward-thinking leadership, strategic partnerships, and a willingness to embrace change can drive meaningful outcomes for students.

If you are a district leader, edtech partner, or anyone invested in the future of education, this episode offers practical insights on building systems that prepare students for real opportunities beyond graduation.

Connect with the 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

03:54 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

In this episode of the Boys of EdTech, the crew is joined by Tiffany Law, COO of the Institute for Education Innovation (IEI), for a candid conversation on what it really takes to build meaningful connections between district leaders and edtech partners.

Tiffany shares her unconventional journey into education, transitioning from a 27-year career in the restaurant industry to helping build IEI from the ground up. Along the way, she reflects on the lessons learned from stepping into a completely new space, embracing mistakes, and finding her footing in a fast-moving and often overwhelming edtech landscape.

The conversation dives into what makes IEI different. Instead of traditional conferences, IEI creates intentional, closed-door environments where district leaders can speak openly about their challenges, learn from one another, and connect with partners in a way that feels authentic and pressure-free. The focus is not on flashy presentations or big budgets, but on real problems, real conversations, and real solutions.

Tiffany also breaks down how IEI structures its events to level the playing field between large companies and smaller innovators, using curated matching, real-time feedback, and highly qualified one-on-one meetings to ensure that every interaction is meaningful.

If you are in edtech or district leadership, this episode offers a behind-the-scenes look at how trust, transparency, and thoughtful design can transform the way partnerships are built in K-12.

Connect with the Boyz
Rick Fernandez: https://www.linkedin.com/in/dr-rick-fernandez-40692434/
Matthew Millstein: https://www.linkedin.com/in/matthew-millstein/
Jacob Kantor: https://www.linkedin.com/in/thejacobkantor/
Ryan Patenaude: https://www.linkedin.com/in/ryanpatenaude/
Jeff Piontek: https://www.linkedin.com/in/jeffpiontek/
 
Key Moments

02:36 Transitioning from restaurants to education

03:36 Building IEI from the ground up

05:12 What makes IEI different from traditional events

07:47 Inside IEI event structure and formats

11:30 Why closed-door conversations matter

12:44 Creating safe spaces for district leaders

15:33 Connecting the right people through curated matching

18:28 How real-time feedback shapes conversations

22:44 Leveling the playing field between vendors

23:53 Why solutions matter more than budgets

28:23 How partners qualify and prioritize conversations

Connect with Guests
Tiffany Law: https://www.linkedin.com/in/tiffany-law-coo

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

In this episode of the Boys of EdTech, the crew flips the script and takes a step back to answer a question they have never fully addressed: who are they, what do they actually do, and most importantly, why do they care so deeply about K-12 education?

From former superintendents and operators to go-to-market leaders and relationship builders, each member shares their journey into edtech and the unique role they play in helping districts and companies work better together. The conversation highlights how success in K-12 is not about selling products. It is about understanding real problems, building trust, and creating meaningful impact for students.

The episode also dives into personal stories that shaped their perspectives. From early nonprofit work supporting schools globally to growing edtech companies from scratch, to firsthand experiences navigating school systems as students. These stories ground the conversation in a shared mission: improving outcomes for students, especially those who need it most.

If you have ever wondered what actually happens behind the scenes in edtech, or why relationships matter more than demos, this episode gives you an inside look at the people driving those conversations every day.

Connect with the Boyz
Rick Fernandez: https://www.linkedin.com/in/dr-rick-fernandez-40692434/
Matthew Millstein: https://www.linkedin.com/in/matthew-millstein/
Jacob Kantor: https://www.linkedin.com/in/thejacobkantor/
Ryan Patenaude: https://www.linkedin.com/in/ryanpatenaude/
Jeff Piontek: https://www.linkedin.com/in/jeffpiontek/

Key Moments

01:15 Supporting districts and edtech alignment

02:22 Translating complex solutions into clear value

03:49 Opening doors and driving meaningful conversations

04:11 Scaling EdTech companies and go-to-market strategy

05:50 Jeff Piontek’s background in education and leadership

07:10 Why education is the foundation of the future

07:58 Matthew’s nonprofit journey and impact on global education

09:17 Connecting EdTech solutions to real student outcomes

11:14 Supporting underserved student populations at scale

24:08 The mission to close equity and achievement gaps

48:04 Personal experiences shaping passion for education

50:22 Why relationships, not sales, drive success in K-12

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

In this episode of the Boys of EdTech, the crew is joined by Jeff Patterson, Founder and CEO of Gaggle, for a deep dive into the origins of student safety technology and how the edtech landscape has evolved over the past two decades.

Jeff shares his entrepreneurial journey—from starting businesses as a child to building early edtech tools in the late 90s—and the pivotal moment that led to Gaggle’s creation. After a simple conversation with a teacher about the risks of student email, Jeff saw a clear gap in the market and built one of the first safe, school-controlled communication platforms.

The conversation explores how edtech has shifted from basic tools to critical infrastructure for student safety, including monitoring communication, identifying risks, and supporting student well-being. The group also discusses the responsibility that comes with handling student data, the balance between innovation and protection, and why trust is everything in K-12.

Along the way, the episode blends humor, real talk, and hard-earned lessons about building in education—where relationships, long-term value, and solving real problems matter far more than hype.

Connect with the Boyz
Rick Fernandez: https://www.linkedin.com/in/dr-rick-fernandez-40692434/
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

01:28 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