A Story Behind Every Empty Seat: How Evan Wilsons’ Scaffold Ed is Tackling Chronic Absenteeism with AI
When nearly a third of students stopped showing up to school during the pandemic, it became clear: chronic absenteeism is not just a data point—it’s a crisis. Evan Wilson, co-founder of Scaffold Ed, is working to get to the heart of what’s keeping kids out of school. His AI-powered tool helps schools move beyond attendance charts to uncover the real stories behind student absences. By turning qualitative family feedback into tangible insights, Scaffold Ed helps educators identify and address barriers—things like delayed work permits or MetroCard access—that often go unnoticed but make a real difference in whether a student shows up.Evan’s personal journey through the education system was shaped by early medical challenges. At the age of three, he was diagnosed with cataracts and spent much of his early life navigating school while legally blind. These experiences—often being overlooked, misjudged, and under-supported—fueled his passion for rethinking how schools engage with students and families. For Evan, data shouldn’t just explain what went wrong—it should help shape what comes next.In this episode, Evan pitches his vision to Jin-Soo Huh, a former classroom teacher and partner at The Learning Accelerator. Together, they explore how Scaffold Ed can evolve from a powerful analysis tool into a true catalyst for change—leveraging AI not just for efficiency, but for equity. They dig into how to build trust with families, the importance of anonymity, and how schools can use real-time feedback to deliver more targeted, responsive support.Episode Highlights:02:04 Evan's Educational Journey04:58 Entrepreneurial Beginnings07:04 Understanding Chronic Absenteeism11:06 Scaffold Ed: A Solution to Absenteeism14:19 The Role of Data in Education18:02 Pitching to Jin-Soo Huh 27:16 Key Takeaways Links & Resources:Evan WilsonScaffold Ed Jin-Soo Huh The Learning Accelerator About the Host, Nicole Jarbo:Nicole Jarbo is the host of Pitch Playground and the CEO of 4.0. An entrepreneur and 4.0 alumni herself, Nicole took a side hustle from $0 to $500k per year and founded a fintech startup that empowered Gen Z with their finances. She's passionate about sharing the inspiring stories of the 4.0 community and believes in work that makes the world more livable, creative, sustainable, and fun.About 4.0:4.0 is a hub for education innovators and social entrepreneurs reimagining the future of learning. Through mentorship, funding, and community support, we empower bold thinkers to turn their dreams into reality. To date, 4.0 has helped spark and invest in over 1,800 ideas, and our alumni have impacted over 10M students and families. We envision a future where our education system meets the needs of every family and improves life outcomes for all.We Want to Hear From You!Whether you're an educator, entrepreneur, or just passionate about changing education, reach out to share your story, ideas, or feedback. Visit us at pitchplayground.com, leave us a review and subscribe to Pitch Playground wherever you get your podcasts. Remember to Vote! At the end of this season one of these entrepreneurs will receive $50,000 towards their idea. We want to hear from you, yes YOU, to cast your vote for the idea you think should receive the cash. Sign up for our newsletter at 4pt0.org to stay tuned on when voting will open.
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28:39
One Size Doesn’t Fit All: How Danette Buckley’s Dream Tech Academy Offers Personalized Education
How do you create a classroom that meets students where they are? For Danette Buckley, the answer was to build it herself. Dream Tech Academy, her microschool in Petersburg, Virginia, was born from a personal mission to support her daughter during a difficult medical journey. Today, Dream Tech serves 42 students and is rewriting the rules on what education can look like. Many classrooms fall victim to teaching to the middle—large class sizes necessitate a one-size-fits-all approach to education, leaving students who are excelling or who need additional support without adequate resources. Danette’s school empowers students to thrive on their own terms.Danette is a lifelong learner who fell in love with school at age four and never looked back. After immigrating from Jamaica and witnessing the challenges of U.S. classrooms, she maintained her passion for education but saw that traditional schools often fail to meet the needs of every student. A family challenge brought her back to the classroom—this time as a homeschooler—and her vision evolved into a flexible, tech-enabled school designed to serve kids of all abilities and interests, where students could learn at their own pace. Dream Tech is a place where students are grouped by comprehension, not just age, and where learning is personalized, and joyful.In this episode, Danette pitches her microschool to Kelly Smith, CEO of Prenda. Kelly has helped over 1,000 people start microschools. Together, they explore how Danette can create a sustainable structure for Dream Tech, stick to her policies without losing her compassion, and bring her unique, student-first model to more families. It’s a conversation full of heart, strategy, and hard-earned wisdom for anyone reimagining what school can be.Episode Highlights:02:16 Challenges in the U.S. Education System04:08 Returning to Education as a Parent06:00 Homeschooling and Developing a Curriculum07:18 Growth of Dream Tech Academy09:55 A Day in the Life at Dream Tech12:30 Success Stories and Impact15:36 Challenges and Future Plans19:38 Mentorship and Strengthening the Pitch29:20 Key Takeaways and ConclusionLinks & Resources:Danette BuckleyDream Tech AcademyKelly SmithPrendaAbout the Host, Nicole Jarbo:Nicole Jarbo is the host of Pitch Playground and the CEO of 4.0. An entrepreneur and 4.0 alumni herself, Nicole took a side hustle from $0 to $500k per year and founded a fintech startup that empowered Gen Z with their finances. She's passionate about sharing the inspiring stories of the 4.0 community and believes in work that makes the world more livable, creative, sustainable, and fun.About 4.0:4.0 is a hub for education innovators and social entrepreneurs reimagining the future of learning. Through mentorship, funding, and community support, we empower bold thinkers to turn their dreams into reality. To date, 4.0 has helped spark and invest in over 1,800 ideas, and our alumni have impacted over 10M students and families. We envision a future where our education system meets the needs of every family and improves life outcomes for all.We Want to Hear From You!Whether you're an educator, entrepreneur, or just passionate about changing education, reach out to share your story, ideas, or feedback. Visit us at pitchplayground.com, leave us a review and subscribe to Pitch Playground wherever you get your podcasts. Remember to Vote! At the end of this season one of these entrepreneurs will receive $50,000 towards their idea. We want to hear from you, yes YOU, to cast your vote for the idea you think should receive the cash. Sign up for our newsletter at 4pt0.org to stay tuned on when voting will open.
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31:18
Hard Hats, Soft Skills: How Aaron Frumin's unCommon Construction Prepares Students for College and Career Success
What if students could earn school credit, get paid, and build a house—all in one semester? Aaron Frumin, founder of unCommon Construction, is making that a reality. Based in New Orleans, unCommon Construction is a nonprofit apprenticeship program that places high school students on job sites, where they learn hands-on construction skills while developing the soft skills they need to succeed in life and work. From teamwork and communication to resilience and professional attitude, students walk away with much more than a paycheck—they leave equipped to take on life’s challenges and seize new opportunities.Aaron’s journey started far from the job site. After dropping out of college and joining the Red Cross post-Katrina, he discovered a calling to serve. That calling eventually led him from the classroom to the construction site, and finally to founding unCommon. The organization blends education with real-world experience. Aaron shares how a need to leave a positive “thumbprint” on the world drives his work.He pitches unCommon to Spencer Sherman, principal consultant at Education First, and together they explore the ins and outs of how unCommon’s new community center can serve as an innovation hub and expand the organization’s reach. They dig into the importance of user-centered design, creating sustainable funding models, and what it takes to truly prepare young people for college, careers, and life.Episode Highlights:01:57 Aaron's Journey: Volunteering After Hurricane Katrina 07:25 The Birth of unCommon Construction10:11 A Day in the Life of a UCC Student14:29 Impact Stories: Transforming Lives Through Construction18:50 Expanding the Vision: The unCommon Community Center20:01 Mentorship and Pitch Improvement27:19 Key Takeaways Links & Resources:Aaron Frumin unCommon Construction Spencer Sherman Education First About the Host, Nicole Jarbo:Nicole Jarbo is the host of Pitch Playground and the CEO of 4.0. An entrepreneur and 4.0 alumni herself, Nicole took a side hustle from $0 to $500k per year and founded a fintech startup that empowered Gen Z with their finances. She's passionate about sharing the inspiring stories of the 4.0 community and believes in work that makes the world more livable, creative, sustainable, and fun.About 4.0:4.0 is a hub for education innovators and social entrepreneurs reimagining the future of learning. Through mentorship, funding, and community support, we empower bold thinkers to turn their dreams into reality. To date, 4.0 has helped spark and invest in over 1,800 ideas, and our alumni have impacted over 10M students and families. We envision a future where our education system meets the needs of every family and improves life outcomes for all.We Want to Hear From You!Whether you're an educator, entrepreneur, or just passionate about changing education, reach out to share your story, ideas, or feedback. Visit us at pitchplayground.com, leave us a review and subscribe to Pitch Playground wherever you get your podcasts. Remember to Vote! At the end of this season one of these entrepreneurs will receive $50,000 towards their idea. We want to hear from you, yes YOU, to cast your vote for the idea you think should receive the cash. Sign up for our newsletter at 4pt0.org to stay tuned on when voting will open.
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29:17
Beyond Compliance: How jacob adams’ Inner Spark Learning Lab Cultivates Critical Thinkers
What if education wasn’t about compliance but about discovery? jacob adams, founder of Inner Spark Learning Lab, believes students should have the power to question, explore, and create—not just memorize and obey. In this episode of Pitch Playground, jacob shares his journey from being labelled a “troublemaker” in school to reimagining learning environments that prioritize student agency and self-actualization.jacob’s first teaching job was at a majority-Black elementary school in Brooklyn, where he quickly realized how rigid discipline policies and top-down control stripped students of autonomy. Witnessing kindergarteners being forced into silence, he began to question the foundations of education. His experiences led him to launch Inner Spark Learning Lab (formerly STEM to the Future), an initiative that engages students in hands-on, community-driven learning projects designed to foster critical thinking, self-awareness, and social impact.If jacob wins the $50,000, the funds will support a Dreamweaver position—a dedicated team member responsible for learning about students, their families, and the broader school community to ensure programming meets real needs. He sits down with Niloy Gangopadhyay, Vice President at Teach for America, to refine his pitch and tackle key questions: What role do community facilitators, or “Dreamweavers,” play in ensuring students feel seen and heard? How can jacob provide measurable outcomes that school leaders and funders will recognize? Tune in to hear jacob’s vision for student-centered education. 02:54 jacob's Early Education and Challenges05:07 College Struggles and Overcoming Obstacles06:17 Teach for America Experience07:55 Questioning the System10:13 Creating a New Teaching Approach16:53 Inner Spark's Impact and Future Goals18:47 Pitching to Niloy Gangopadhyay25:57 Final Thoughts and ReflectionsLinks: jacob adamsInner Spark Learning Lab (formerly STEM to the Future)Niloy GangopadhyayTeach for AmericaAbout the Host, Nicole Jarbo:Nicole Jarbo is the host of Pitch Playground and the CEO of 4.0. An entrepreneur and 4.0 alumni herself, Nicole took a side hustle from $0 to $500k per year and founded a fintech startup that empowered Gen Z with their finances. She's passionate about sharing the inspiring stories of the 4.0 community and believes in work that makes the world more livable, creative, sustainable, and fun.About 4.0:4.0 is a hub for education innovators and social entrepreneurs reimagining the future of learning. Through mentorship, funding, and community support, we empower bold thinkers to turn their dreams into reality. To date, 4.0 has helped spark and invest in over 1,800 ideas, and our alumni have impacted over 10M students and families. We envision a future where our education system meets the needs of every family and improves life outcomes for all.We Want to Hear From You!Whether you're an educator, entrepreneur, or just passionate about changing education, reach out to share your story, ideas, or feedback. Visit us at pitchplayground.com, leave us a review and subscribe to Pitch Playground wherever you get your podcasts. Remember to Vote! At the end of this season one of these entrepreneurs will receive $50,000 towards their idea. We want to hear from you, yes YOU, to cast your vote for the idea you think should receive the cash. Sign up for our newsletter at 4pt0.org to stay tuned on when voting will open.
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28:00
Consent-Based Education: How Dr. Erin Flynn’s Hedge School Prioritizes Student Autonomy
What if students had full autonomy over their learning? Dr. Erin Flynn, founder of the Hedge School, is reimagining education through consent-based learning. Located in Texas, the Hedge School is a microschool where students have the freedom to choose what and how they learn, creating an environment that fosters curiosity, confidence, and emotional well-being. Erin’s journey to founding the Hedge School was shaped by her experiences as a teacher, principal, and ultimately, her disillusionment with the traditional education system. She saw firsthand how rigid policies, standardized testing, and lack of student agency stifled learning. Rather than conforming to a system she felt was failing students, Erin took a bold step: she created a school designed around student choice, inclusivity, and self-directed learning. The Hedge School’s approach is radically different from conventional education. Students decide how to engage with lessons, whether that means taking a walk, skipping an assignment that doesn’t resonate with them, or learning in a way that best suits their interests. For Erin, learning should be a collaborative process, not something imposed upon students.With an opportunity to expand the Hedge School’s model, she receives mentorship from Kelly Smith, founder of Prenda, a venture-backed microschool network. Kelly helps Erin refine her pitch and strategize on how to scale. They explore questions like: how can Erin establish satellite Hedge Schools while ensuring each maintains its unique community-driven culture? What support do new educators need to replicate the Hedge School model successfully? How can Erin balance business objectives with her deeply held beliefs about education? Together, they dive into strategies to sustain Hedge School’s mission while expanding its reach.02:01 Erin's Educational Journey07:18 Challenges in the Public School System10:11 Founding The Hedge School11:23 What is Consent-Based Education?13:58 The Micro School Movement20:09 Scaling The Hedge School27:51 Final Thoughts and TakeawaysLinks: Dr. Erin Flynn Hedge School CooperativeKelly SmithPrendaAbout the Host, Nicole Jarbo:Nicole Jarbo is the host of Pitch Playground and the CEO of 4.0. An entrepreneur and 4.0 alumni herself, Nicole took a side hustle from $0 to $500k per year and founded a fintech startup that empowered Gen Z with their finances. She's passionate about sharing the inspiring stories of the 4.0 community and believes in work that makes the world more livable, creative, sustainable, and fun.About 4.0:4.0 is a hub for education innovators and social entrepreneurs reimagining the future of learning. Through mentorship, funding, and community support, we empower bold thinkers to turn their dreams into reality. To date, 4.0 has helped spark and invest in over 1,800 ideas, and our alumni have impacted over 10M students and families. We envision a future where our education system meets the needs of every family and improves life outcomes for all.We Want to Hear From You!Whether you're an educator, entrepreneur, or just passionate about changing education, reach out to share your story, ideas, or feedback. Visit us at pitchplayground.com, leave us a review and subscribe to Pitch Playground wherever you get your podcasts. Remember to Vote! At the end of this season one of these entrepreneurs will receive $50,000 towards their idea. We want to hear from you, yes YOU, to cast your vote for the idea you think should receive the cash. Sign up for our newsletter at 4pt0.org to stay tuned on when voting will open.
How could $50,000 transform learning? On Pitch Playground, we invite education innovators and social entrepreneurs to throw their best ideas at us. From technologies that build empathy to providing affordable childcare and reimagining the way we learn—this is a place for pitches from visionaries. Each episode features an intrepid edupreneur workshopping a $50,000 project to solve a critical problem in education. With support from mentors, funders, and fellow entrepreneurs we'll explore what it takes to turn dreams into reality.
At the end of the season, we award $50,000 to the best pitch we've heard on the show. We're inviting educators and social entrepreneurs to play in the sandbox with us and share their vision for the future of education. We encourage these visionaries to be BOLD—don't just think outside the box; reshape the box itself. Draw outside the lines. It's about making good ideas last longer and go further.
About the Host, Nicole Jarbo:
Nicole Jarbo is the host of Pitch Playground and the CEO of 4.0. A serial entrepreneur, former educator, and proud 4.0 alum, Nicole has a track record of building impactful ventures across a variety of industries, including education, financial technology, and media. Passionate about storytelling and innovation, she’s sharing the inspiring stories of the 4.0 community and believes in work that makes the world more livable, creative, sustainable, and fun.
About 4.0:
4.0 is a hub for education innovators and social entrepreneurs reimagining the future of learning. Through mentorship, funding, and community support, we empower bold thinkers to turn their dreams into reality. To date, 4.0 has helped spark and invest in over 1,600 ideas, and our alumni have impacted millions of students and families. We envision a future where our education system meets the needs of every family and improves life outcomes for all.
Have a Pitch to Transform the World?
We’d love to hear from you! Whether you're an educator, entrepreneur, or just passionate about changing education, reach out to share your story, ideas, or feedback. Visit us at https://pitchplayground.com/ and subscribe to Pitch Playground wherever you get your podcasts.
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