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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.
Nicole Jarbo:
This season of Pitch Playground, we heard stories from bold visionaries solving some of the biggest problems in education. In this mini episode, we're going to take you on a journey through the whole season. We'll give you a reminder of our participants, their pitches, why their ideas matter, and how they'd use the $50,000 if they win. Soon, you'll have an opportunity to vote for which idea you think deserves to win $50,000. Visit pitchplayground.com to cast your vote. Voting will be open June 15th to the 30th, and the winner will be announced shortly after. When the playing field isn't level, learning becomes a privilege instead of a right. First, let's look at the entrepreneurs we met this season who are working to remove systemic barriers that prevent students from thriving. These innovators are redefining what equitable access really means. When Lisa Maria Rhodes was an educator in New Orleans, she saw firsthand how the justice system can be a barrier to learning.
Lisa Maria Rhodes:
Every day during the first five minutes of class I would send a text message to any absent student and their parent just to say, like, "I see so-and-so's absent. Can you still come?" About once a week, I would get a response from a parent that would say, "My son has been arrested. My son is incarcerated."
Nicole Jarbo:
New Orleans is often referred to as the mass incarceration capital of the world. More people are incarcerated there per capita than in any other state.
Lisa Maria Rhodes:
The kid who is arrested and there's no probable cause still sits in jail for 60 days. They miss two months of school, enough for them to fail that year.
Nicole Jarbo:
Alas advocates for students impacted by the justice system and immigration courts.
Lisa Maria Rhodes:
My big question was like, "How do educators interrupt this school-to-prison pipeline?"
Nicole Jarbo:
A vote for Alas will mean $50,000 will go towards increasing access to their services.
Lisa Maria Rhodes:
10 schools, over 1000 students would get support that otherwise they won't have access to.
Nicole Jarbo:
Over 1000 miles away from where Lisa Maria is working in New Orleans. Another education entrepreneur is tackling education equity from a different lens.
Jonathan Santos Silva:
When I think about education, the data supports that we are filling Native students chronically, habitually, and at a rate higher than any other subpopulation.
Nicole Jarbo:
That's Jonathan Santos Silva. He's the founder of The Liber Institute.
Jonathan Santos Silva:
On Pine Ridge where I lived and taught, according to the UN, we had the worst quality of life indicators of anywhere in the Western Hemisphere outside of Haiti.
Nicole Jarbo:
As an educator, Jonathan saw how rural and Indigenous communities are disadvantaged when it comes to access to education.
Jonathan Santos Silva:
I have gone to schools where the building is literally condemned, not figuratively condemned. It's on a federal list that's saying it's condemned and kids are still being educated in it. That wouldn't be allowed anywhere else in America. That would not be allowed.
Nicole Jarbo:
He's working to change that through providing leadership coaching, storytelling work and design thinking.
Jonathan Santos Silva:
The Liber Institute's mission is to embolden and equip Indigenous young people, families, and educators to transform schools in the communities they serve.
Nicole Jarbo:
If Liber wins the money, they will be putting it towards their POWER framework.
Jonathan Santos Silva:
We can begin to expand not just to serving in the places where we can reach physically with our small team, but begin to reach places virtually that by distance could be prohibitive.
Nicole Jarbo:
A crucial aspect of access is making sure that families have the support they need to keep showing up. That's where Jaime-Jin Lewis's NYC-based Wiggle Room enters the picture.
Jaime-Jin Lewis:
The first iteration of Wiggle Room was actually a parent-facing product where we helped them build their care circle in advance. This is not a moment of personal failure when your child care arrangement falls through, this is a structural issue.
Nicole Jarbo:
When the COVID pandemic happened, the work Jaime-Jin was doing took on a whole new sense of urgency.
Jaime-Jin Lewis:
I remember calling some of the moms that we were working with and saying, "Hey, do you have backup child care? What would you do if your kid's school closed?" By the end of March 2020, we had set up a hotline. It was called Workers Need Child Care, but I also wanted to understand what was going on with child care providers themselves.
Nicole Jarbo:
Now, Wiggle Room is working to help more families access affordable child care by leveraging their tool, Auto-Enroll.
Jaime-Jin Lewis:
Wiggle Room is backend daycare operations simplified. We take all of the complex and confusing rules and regulations that daycares have to comply with, and we put them into simple workflows that any person who's running a daycare can easily manage.
Nicole Jarbo:
$50,000 would help Wiggle Room to expand to more communities.
Jaime-Jin Lewis:
Right now, we're still largely focused in New York, so $50,000 would enable us to do anchor events across the state and really build community outside of New York City.
Nicole Jarbo:
From youth impacted by the justice system to Indigenous students in rural schools to families navigating child care, these entrepreneurs are reshaping what equity and education really means. Once students have access, safety, and support, the next question is what comes after? The entrepreneurs in our next section are building bridges from the classroom to the world beyond it. As a guidance counselor, Victoria Chen was encouraged to make sure that every student applied to at least three, four-year schools. One day she encountered one of her students in the hallway.
Victoria Chen:
I was literally chasing him out the hallway, down the hallway, like, "Christian, hey, hey, let's chat." He's like, "Ms., I don't want to go to college. Stop hounding me on this."
Nicole Jarbo:
A four-year degree isn't right for every student. There could be financial barriers, caregiving responsibilities, or simply a lack of desire to go down that path.
Victoria Chen:
If the whole purpose of education is to set a young person up for economic mobility, then we have to show them the various pathways they can take to get there. The four-year degree is one way, but it's definitely not the only way.
Nicole Jarbo:
That's where Victoria's nonprofit BridgeYear comes in. They have a program called Career Test Drive, which helps students get hands-on experience to well-paying careers before they jump into the workforce.
Victoria Chen:
Because you should never buy a car without test-driving it, and you should never choose a career without giving it a try either.
Nicole Jarbo:
BridgeYear opens doors to career opportunities without the time and cost of a traditional degree. If Victoria wins the 50K, she'll be putting the money towards MorePathways, a BridgeYear initiative that allows people to find vetted and trusted workforce programs.
Victoria Chen:
One thing that we would love to do is build in some more capabilities that really make it user-friendly, that allow students to almost engage with it on its own and take on its life of its own.
Nicole Jarbo:
Sometimes career pathways after high school are less about deciding what path you want to take and more about making sure you have the right skills and mindsets to excel wherever you end up. That's where Aaron Frumin comes in. Aaron's idea came out of his experience with education, both as a student and a teacher.
Aaron Frumin:
The walls and constraints of a classroom never really worked for me. The ones that I was trying to operate within and create for my students, it wasn't working for either of us, so I started thinking differently about the walls of the classroom.
Nicole Jarbo:
It was through thinking outside of those walls that Aaron's idea for UnCommon Construction was born.
Aaron Frumin:
We're a nonprofit apprenticeship program where students from different high schools get paid and they earn school credit for building a house or another project together. We sell the house and match their paychecks with a scholarship.
Nicole Jarbo:
Through building houses together, UnCommon teaches students skills that can help them excel no matter where they end up after high school.
Aaron Frumin:
We really hang our hard hat, so to speak, on the development and demonstration of soft skills. We focus on teamwork ethic, problem solving, professional attitude, communication.
Nicole Jarbo:
If Aaron wins a 50K, he'll put the money towards the UnCommon Campus, a 5000 square foot facility being built in the heart of New Orleans where they're based.
Aaron Frumin:
We'll be able to roll out new programs that engage even more students, more schools, and even an adult learner population in our community through that centralized hub.
Nicole Jarbo:
Through mentorship, skills training, and exposure to real-world work, both Aaron and Victoria are building career pathways for the next generation. Now, these next entrepreneurs will look at what happens when extended reality and artificial intelligence meet the classroom. Jonathan Teske first started experimenting how headsets can perform in a classroom when he was the future of education lead at Meta. He did a lot of research and testing in the virtual reality space.
Jonathan Teske:
Every time we put a teacher in a headset, they had typically three responses, which was, "This is awesome. My kids are going to love it. How the heck am I going to teach with this product, this tool, this technology?"
Nicole Jarbo:
Jonathan used what he learned about virtual reality or VR and started working on how mixed reality or XR could improve upon it.
Jonathan Teske:
With ReFrame, we allow any teacher, any school to build a mixed reality immersive learning hub, which gives you 90% of the great things about VR. The other 10% is an immersive environment that you typically don't interact with anyways when you're in VR.
Nicole Jarbo:
If Jonathan wins a 50K, he'll work on building the infrastructure and ecosystem to allow this technology to grow.
Jonathan Teske:
Where we would really focus is really helping any developer have access to building and deploying in ReFrame. We need to get to that next step, and that's where we'd start to focus on.
Nicole Jarbo:
Our next entrepreneur, Evan Wilson, is using technology to help get students back in the classroom. During the pandemic rates of chronic absenteeism nearly doubled. That was nearly a third of students not showing up to school.
Evan Wilson:
There's always a story behind that empty seat, and those stories come from a lot of the deeper challenges that we have in education.
Nicole Jarbo:
In one school, they realized that students were only showing up to school on certain days of the week. At this school, they supplied Metro cards to the students. The team realized...
Evan Wilson:
That students' parents were using their Metro cards on certain days because they needed to get to work. For families, that meant prioritizing either a parent keeping their job or a child going to school.
Nicole Jarbo:
That gave the school something tangible to work on. With Evan's product ScaffoldEd, he's helping schools find patterns and family feedback to get kids back in school.
Evan Wilson:
We're giving them clarity over the specific needs that their families, their students, and even in many cases their teachers have so they can create solutions that actually move the needle in their districts.
Nicole Jarbo:
Evan and his team are looking to take ScaffoldEd to the next level, allowing decision makers to have insights right at their fingertips.
Evan Wilson:
What $50,000 can do is help us embrace the future and give them essentially the power of AI agents to start to implement solutions for these challenges.
Nicole Jarbo:
These two entrepreneurs are using cutting-edge tech to reach students in new ways, one through immersive virtual environments, the other through AI-powered insights into attendance and engagement. In our last section, we're bringing you entrepreneurs who are creating learning environments that prioritize teaching students how to think over what to think. These innovators are offering personalized education. As a principal with the ambitions to become a superintendent, Dr. Erin Flynn recognized that the school environment was not a safe space for all students.
Dr. Erin Flynn:
There were decisions being made at the legislative level and also at the board level at my own school that I thought were actively harming students.
Nicole Jarbo:
Erin's school was in Texas where anti-trans legislation was coming into play. Erin decided that she wanted to create a school that prioritized safety for all students and embrace what she calls consent-based education.
Dr. Erin Flynn:
Consent-based literally means the student gives their consent to do what we're asking. Our goal is to allow the students to have autonomy in their own education.
Nicole Jarbo:
Erin wants to open satellite campuses to expand the Hedge School.
Dr. Erin Flynn:
I would invest that 50 grand in finding other educators who would like to do what I'm doing, do what the teachers in my school are doing, and families who would be interested in sending their students there.
Nicole Jarbo:
Along with creating a safe environment that prioritizes consent, our next entrepreneur believes that cultivating critical thinking is crucial to reimagining what education can be. When jacob adams was a teacher at a majority Black elementary school in Brooklyn, he was shocked by the level of discipline that he was expected to administer to young students.
jacob adams:
The kindergartners would come the first couple of days before anybody else came. They got to sit there with their hands folded. As soon as kids take their hands apart, people are walking over and taking the kids breakfasts. We're just controlling these kids.
Nicole Jarbo:
jacob's Inner Spark Learning Lab helps students learn to think critically rather than just follow rules.
jacob adams:
Inner Spark Learning Lab is creating a way of teaching that allows elementary and middle school students to go through this process of self-actualization, learn more about who they are, who they want to be, and how to create the change that they want to see in themselves, in the neighborhood and in the community.
Nicole Jarbo:
With 50K, iacob would hire for a new role called a Dreamweaver.
jacob adams:
Their role is to be learning as much as they can about the kids at the school, their families, and then the more broader school community. Then they're using that information to figure out what unique needs does the school have, and then what connections do we have in the community that can help meet them.
Nicole Jarbo:
Our final entrepreneur's journey began when her daughter went through some medical challenges that took her out of school for an extended period.
Danette Buckley:
Once she was well enough to come back to school, she would go to class, and I think she was able to stay there for an hour at a time. She would just be exhausted.
Nicole Jarbo:
The school was unable to adapt to her daughter's needs. She started falling behind. Danette decided to homeschool her. Gradually, parents of other students started reaching out, asking if Danette could homeschool their kids too.
Danette Buckley:
I've always had a passion for learning and just a firm believer in one size does not fit all, and that education should be flexible in how students learn when they're learning and where they're learning.
Nicole Jarbo:
With that Danette's microschool, Dream Tech Academy, was born. They prioritize personalized and flexible learning rather than teaching to the middle. Danette has big ambitions for how the 50K could help her school in Petersburg, Virginia.
Danette Buckley:
A big part of this would go to offering discounts or scholarships and open up our services to as many students as possible. My second goal would be to increase our technology in our school. Then my final piece of the pie would go to increasing our teacher's salary.
Nicole Jarbo:
What all of these stories share across classrooms, communities, and technologies is a deep belief in the power of new ideas. It takes courage to question the way things have always been done, and even more to build something better in their place. Whether they're creating space for belonging, rethinking family support, or disrupting systems that hold students back. These entrepreneurs are building bold new futures for education. At the heart of every bold idea is a belief that change is possible, and it often takes one person brave enough to try. This is Pitch Playground from 4.0. You can hear the full stories of these entrepreneurs and read more about them at pitchplayground.com. Head to pitchplayground.com June 15th to the 30th to cast your vote and help decide who will receive $50,000 to take their idea to the next level.