Live at the Uncharted Learning Summit: Why Entrepreneurship Is for Everyone
In this episode of the Getting Smart Podcast, hosts Victoria Andrews and Shawnee Caruthers travel to Chicago for the Uncharted Learning annual summit, where they sit down with students, alumni, teachers, a first-year educator, a school champion, and a program director to explore what happens when entrepreneurship becomes the organizing principle of a school community. From Mika Chang discovering her business-minded identity to Connor Boundy reflecting on pitching venture capitalists as a teenager in the very first INCubatoredu cohort, and from Alan Carranza connecting delegation skills to life in the Army National Guard to Spiky founder Abigail turning a product into statewide policy advocacy, the episode braids together voices across generations, roles, and geographies to reveal what Uncharted Learning has built over more than a decade. For the full conversations with all attendees at the Uncharted Learning Conference, check out their audio links below.
The conversation surfaces several layered insights for education leaders. First, entrepreneurship is not a content area but a container for self-discovery, durable skills, and genuine belonging. Second, the program’s design intentionally dissolves the labels of teacher and student, inviting community champions like Susan Hohlman, reinvigorated educators like Megan Gordon, and first-year teachers like Triana Williams into the same learning ecosystem. Third, the pitch competition illuminates how productive friction and even rejection become the real curriculum. For leaders wondering how to re-engage burned-out teachers, connect curriculum to community assets, or bring entrepreneurial thinking to under-resourced districts, this episode offers both inspiration and a concrete on-ramp through Uncharted Learning’s middle and high school programs.
Transcript
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Community, Entrepreneurship, and Uncharted Learning
Victoria Andrews: Hi, and welcome to the Getting Smart podcast. I’m joined by my great friend, Shawnee Caruthers, and we are excited to have this conversation about community. And not just any type of community, but the communities that really catalyze all of the different assets they have access to, from the students on their campus, to small local businesses, to the volunteers that help run them. The excellent vehicle that this happens through is entrepreneurship, and we’d love to highlight and illuminate the work of Uncharted Learning. We attended their summit, and we were able to meet so many members of this rich and vibrant community.
I want to start off, Shawnee, by talking about the students, the young people. Every young person that we spoke to, especially the alumni, didn’t just talk about this amazing entrepreneurship class that some were excited to join and some were not. They talked about the different skills that it unlocked in them. Did you notice that same energy that was just contagious?
Shawnee Caruthers: I did, and it’s something that I notice every time I’m around that Uncharted Learning vibe. Uncharted Learning is based out of Chicago, but definitely has satellite systems nationwide. It’s really known for unlocking the entrepreneurial spirit within each learner. And they do it in such an organic way that learners don’t have to feel anxiety around stepping into this class, because they have strong training resources to prepare both the learner and the facilitator for this type of experience.
I want to get back to the vibe of the students in just a moment, but it all starts with the training. The first thing they do is make a “bug me” list, and I’ve always been intrigued by this. They just talk about all the things that bug them. They don’t even jump into what they want to make or what service they want to provide. Just: what bothers you? What do you notice within your community that maybe needs to be a little bit stronger? And from there, they build on that until learners have this really deep and immersive entrepreneurial experience.
So when we were together at the Uncharted Learning Summit in Chicago this past summer, it was really intriguing to see the energy, like you said, that the young people had. It makes you wonder why all students can’t have this sort of joy and this sort of access, and it reminds you of what’s possible when we just move out of the way and give young people the resources.
Discovering Herself Through INCubatoredu | Mika Chang
Victoria Andrews: We are recording live from Uncharted Learning’s annual summit, and I’m here with Mika Chang. Mika, can you share a little bit about your experience when you went through Uncharted?
Mika Chang: This was really a unique experience. I didn’t exactly know what I was getting into, and I thought INCubatoredu sounded like a really interesting class, but you really get to discover yourself through this class. I would say it’s a different experience for every student, and everyone gets a different takeaway from it. I really discovered myself. I didn’t know that I was kind of an entrepreneur and business-minded until I took this class, and I feel like I’m a changed person now. I have clarity on the direction that I want to go in college and my career and beyond, and I’ll always keep the lessons I learned from my amazing teacher during these two classes.
Teachers Reinvigorated and the First Cohort
Shawnee Caruthers: And being around that kind of energy, it’s not just with the young people. It’s with the teachers as well. We hear so many stories like, “I wasn’t as satisfied with my job as I used to be, but when I started teaching INCubatoredu or MXinc with Uncharted Learning, it reinvigorated my passion for teaching.” So Uncharted Learning’s resources, and the organization in general, are really doing great things for educational ecosystems across the country.
Victoria Andrews: They’ve even built in an on-ramp for students who have gone through the classes to come back and re-engage. We had conversations with students from the very first cohort. They didn’t have the “bug me” list back then, because they were the true guinea pigs, or in the words of business design, the first iteration, the first draft.
The First-Ever Cohort | Connor Boundy
Victoria Andrews: This is Connor Boundy.
Connor Boundy: I was very fortunate to be part of the first ever cohort. Back in 2013, I put my backpack in a cubby, I pitched a bunch of VCs a business I built in a classroom, and I walked out with a check. I never left building startups because of this program. They gave me a bug that I was very, very fortunate to get early. And seeing how far this program has come has been so inspiring for me and all my friends who went through it.
We have basically a quarter million students that have gone through this program, and we were the first. I hop on calls now with investors and founders and tell them the story, and they’re like, “Wait a minute, is that this program?” Yeah, we were the first ones.
More Than a Product
Victoria Andrews: And to hear that they even want to come back, to pour in and serve as judges, to provide insight, or to help build those students’ social capital, that’s a testament to the organization. That’s a testament to the richness of the community, and to all of the teachers and businesses that have been pouring into it for well over a decade.
It’s beautiful to witness, like you mentioned, all of those young people just electrified by sharing, “Hey, this is the product that we’ve built.” And not just, “I’m trying to sell a product,” but “I’m really passionate about my product,” whether it’s matcha, a way to water plants while you’re traveling, or a creative way to protect young people from the dangers of high sun exposure. Whatever it was, it wasn’t just the product. They were able to communicate the process: what they learned about themselves, what they learned about their teammates, and of course what they learned about entrepreneurship, what it means to have an entrepreneurial mind, and where that can take them. Many expressed, “I may not even go into business, but I know so much more about myself, and I have so many more connections when I leave this classroom.”
Learning to Lead and Delegate | Alan Carranza
Shawnee Caruthers: This is Alan Carranza.
Alan Carranza: One of the things I learned about myself is how good I am at assigning tasks to people and delegating those tasks. I could do the work all by myself, and that’s how it was for most of high school. But once I discovered how to delegate tasks and how to lead a team, that changed the game tremendously. It’s very difficult to do, especially if you’re a lone wolf, somebody who just wants to do the task and feels better off working alone. But once you discover it, it’s definitely a game changer, the amount of things you can do, the progress you can make.
Besides college, I’m in the Army National Guard right now, and that’s another thing it’s helped me with: knowing when to lead, and also following orders from the higher-ups.
The Spiky Story: From Product to Policy
Shawnee Caruthers: You talked about the mentorship and the other areas of growth that a young person can experience by going through an entrepreneurial experience, and you talked about some of the products we saw: the matcha, the houseplants, the sun exposure. But I also want to talk specifically about Spiky. We were so impressed with Spiky, and that was one of the first alumni to sit down with us. It was a young person who had a friend who was, I must say, traumatized by having her drink spiked while she was out at an event. And so it allowed this young person, through the Uncharted Learning class, to build a product to protect other young people.
It could have just stopped there, as a product. But instead, she took more of a social advocacy lens. She began to identify the states in which spiking someone’s drink is considered a felony. I believe at the time it was only two states, and she lives in Tennessee. So she began to work alongside her local legislator to ensure that in Tennessee, it also became a felony. She developed a whole range of skills around policy, politics, and legislation, all the things you maybe wouldn’t normally associate with an entrepreneurial experience, but it was exactly an extension of the product she created.
This young lady just started college a couple of weeks ago, and now, even on her college campus, she’s advocating for her campus to adopt this product, not for profit, but for awareness, and to help people feel safe. So there are so many lenses of entrepreneurship. You talked about the entrepreneurial mind, the for-profit component, and now we’re talking about social entrepreneurship. Entrepreneurship is literally for everyone. What each young person receives from it is truly up to them, and it can take them as far as they want to go.
From Middle School to CEO | Paula Chilton
Victoria Andrews: This is Paula Chilton.
Victoria Andrews: And speaking of students starting in MXinc and progressing all the way to high school, you have Abby Goddard, who was a finalist for the National Pitch Competition last year. And she said she started in middle school.
Paula Chilton: Yes, she was one of the first ones in that group. Her idea was like a chef-at-home type of program. It was a hypothetical program, but it allowed her to say, “Okay, I really kind of like this. I want to see what business I can do that I’m really passionate about.” And then here we go. Five years later, she is a CEO. She has her own business, Spiky, and she’s making money. She’s a force.
I remember when she didn’t even have her driver’s license. She would pull up into the parking lot, and her dad was still in the passenger seat because she still had her permit. She was just 15. And here she is. She has raised almost $50,000, and I think she has over $60,000 in revenue. She’s been accepted into her dream school, the Wharton School. I am so impressed with her, and I love her like my own. She is just something special. You have those star students, and she definitely is one of them.
Discovering Hidden Passions
Victoria Andrews: Abigail’s story, as the founder of Spiky, is one where she won the award and received financial backing from the judges. But the pendulum can swing all the way to the other end. We met other alumni, and this is the case even for educators, who were on the fence, like, “I don’t really know what this class is about.” But through the process they uncovered, “I do have a passion for public speaking,” or “I do have a passion for serving other people and serving my community.”
A Tool Belt of Life Skills | Ida Pascal
Victoria Andrews: This is Ida Pascal.
Ida Pascal: Working with seventh graders and 12-year-olds, they really don’t have experience with business and business courses. They may have a parent or family members who have their own business, but as far as their own experience, there’s very little compared to when I taught high school and worked with students who had their own jobs, had cars, and received paychecks. They had a better understanding. These kids don’t have that foundation. So my goal is to introduce business to them, but not only business: the skills that are necessary. You can have many skills that correlate with being in business, but you don’t necessarily have to use them for business, like great communication skills. Yes, you need it for business, but you need it in life. So my goal is to take a tool belt, just like a carpenter’s tool belt, and fill that tool belt with skills that they can use not only now, but later on in life.
A Space for Teachers to Explore
Victoria Andrews: That’s what I deeply appreciate about Uncharted Learning. Whether it’s MXinc in middle school or a course in high school, it’s a vehicle for students to explore themselves, their capabilities, and the possibilities. And like you mentioned earlier, we even saw teachers being reinvigorated. We spoke with one teacher who had truly resigned. Not “I’m contemplating it.” No, no, no.
Our good friend Megan said, “I’m good. Thank you for your service. I’m out.” And because of the wisdom of what her campus leadership saw, they said, “Hey, you might be interested in this.” That was the catalyst for her to become even more engaged. It allowed her to re-explore her skills and bring more of herself into the classroom, and she’s just on fire. Truly electric.
So it’s not just how it can impact young people and alumni, but also teachers. Just like anybody else, you might get tired of doing the same old, same old. But being given a space where you can bring your full, authentic self and your other passions matters. You might be passionate about literature, but also about graphic design, and you may not be able to bring that into every space in the same way. I deeply appreciate that Uncharted provides that space for exploration for teachers as well.
Resigning and Finding Her Spark Again | Megan Gordon
Victoria Andrews: This is Megan Gordon.
Megan Gordon: I was at the point where I loved teaching so much, but I was getting a little burned out. I had been teaching graphic design, yearbook, and digital media to middle schoolers, and I resigned from my job, even though I liked it, because I knew I just needed something a little different. I knew this position existed in our district, but it had a teacher who was great, and I always walked by the room when I’d go over to the special building and thought, “Wow, that must be really cool.”
So I resigned not knowing what I was going to do, which is kind of scary and risky. But the next week, the principal from this CTE campus reached out with a text: “Hey, I heard you resigned. Would you be interested in this?” I said, “Well, I don’t know. Let me think about it.” We talked a little bit about it, and the more I learned about the program, I thought, “Okay, yeah, I think I’m going to do this.”
I’ve always thought it would be so fun to have a job where I come up with ideas and create things, and then other people figure out how to make them work. I love the company IDEO, and I always used it in my English class and my other middle school classes. When this came up, it was almost like my whole class could be a mini IDEO, where these kids are brainstorming. I really enjoy the creativity of the class, and the beginning of the year, when we’re forming teams and learning our strengths.
The Power of Word of Mouth
Shawnee Caruthers: Yeah, I agree. Anytime a program can completely change your mind about wanting to leave a profession, you know it’s powerful. I can’t remember the young lady’s name, Victoria, the one who brought her sister. Mika, thank you.
It’s not just, “I’m a student taking it.” It’s, “I’m telling my little sister about this class, and now she’s going to take it.” We asked the little sister, and she said, “Well, my sister told me about it, so now I’m going to sign up for it.” What is more powerful than that? Word of mouth is about as powerful as it can get, and when students are talking about it, that’s when you know it’s truly catching fire.
So it’s a phenomenal program. It’s not just about a product. It’s about a way of thinking, a way of being, a way of mattering and belonging, and showing up in spaces that you’re able to curate for yourself based on your interests and the interests of your teacher. And when those forces come together, when we remove the labels of teacher and student and begin to work together on solving something meaningful, whether it’s a service or a product, that’s where the true learning begins.
A First-Year Teacher’s View | Triana Williams
Victoria Andrews: This is Triana Williams.
Triana Williams: I’ll be teaching middle school entrepreneurship, and I am thrilled, but also nervous. I’m going to be real. The summit here has been great, but it’s a lot of information, so it’s an overload. But it’s informative. I can’t wait to take it back to D.C. and watch my students’ wheels turn as I teach them new information. And little do they know, we’ll be learning together.
I would tell teachers: just be yourself. Do your thing. However you want to teach your class, tailor it to your personality. This is not the normal content, and you don’t have strict state standards to follow, so you have more flexibility to bring personality to the class.
The Role of a School Champion
Victoria Andrews: Speaking of belonging and removing those labels: if I said, “Hey, Shawnee, do you want to be a school champion?” you might not know what that means or what it entails. But speaking with Susan, who is a school champion, she’s not just a champion for the school. She’s a champion for Uncharted Learning, a voice from the community coming in, and a multi-generational voice too. She has businesses she’s been a part of, and she provides insight and mentorship. She is a faithful volunteer.
I really want to drill down on that sense of belonging for a moment. In conversation with her, you hear a sense of purpose. You hear connection. You hear her ability to bring a level of value and insight that you may not be able to get within the four walls of the school building. I love that Uncharted provides opportunities for volunteers to be school champions: advocates, voices from the community that say, “Hey, this is a problem you could solve,” or “Here’s some insight into your design process that you may not have had.” And Susan is so electric that she’s inviting other people, saying, “We need more school advocates. We need more school champions.” It’s the vehicle of entrepreneurship, bringing in different voices and perspectives from the community and breaking down those walls so that people aren’t siloed.
What a Community Champion Does | Susan Hohlman
Victoria Andrews: This is Susan Hohlman.
Susan Hohlman: As community champions, from my perspective, I’m there to support my classroom teacher, to do everything I can possibly do to take as much off her plate as I can. So we have a nice system. Primarily, what I do as a community champion, separate and apart from promoting us in the community, which I’m doing all the time, is say to the teacher in the classroom: “Tell me what you need, and I’ll get the coaches. Tell me what you need, and I’ll be there to support you. Tell me what you need.”
I’m passionate about pouring into young adults. Somebody poured into me, and we want to pass that on. I’m a servant leader, servant educator, servant business person, and I want to pass on what people have instilled in me to the next generation. INCubatoredu is just an exceptional program. To watch the young adults walk in the door at the beginning of two consecutive semesters, and to see how they grow, how they develop, how they mature, and what they produce at the end of the second semester, it’s exciting.
Joy, Belonging, and the Pitch Competition
Victoria Andrews: What it means to be a learner: every person we mentioned is a learner. The alumni, the first cohort members, the teachers, the school, the CTE director, even the school champion. Everybody’s a learner. All of those voices have a sense of joy and a sense of belonging. And to see the labels, like you said, just torn down is so encouraging, so inviting and welcoming. When you think about community, that is exactly what you want.
Shawnee Caruthers: Yeah, I agree. There was no way you could be in that space over the span of the conference and not feel all that joy. We had the distinct privilege of talking one-on-one with people to really capture their stories, and that was a joy. But even if you didn’t have that opportunity, there were so many other things going on between the sessions and the pitch competition. And I don’t want to leave this space without talking about the pitch competition for just a moment.
We both said we would hate to be a judge, because there were so many phenomenal products being showcased. And it wasn’t about the products. It was about the young people on stage talking about something they felt passionate about. They had put their heart and soul into it, they’d done research, and they traveled for it. They were all so strong. Of course, they ended up narrowing it down to one, but they had the opportunity to award so many others. And while we were hoping multiple teams would win, there’s a life lesson in itself: young people need to understand that not everyone “wins” the prize monetarily, but they all won in terms of growth and durable skills. And then we got to go out into the foyer and see all of the products being showcased.
From 30 Seconds to a 10-Minute Pitch | Jason Roemer
Victoria Andrews: This is Jason Roemer.
Jason Roemer: Just 60 days ago, we had our first pitch contest, to a full auditorium of close to 400 people, which is unbelievable. On August 12th last year, when we started school, none of them would have said they’d be able to pitch with the proficiency that they did. They all killed it. And the community was there to support from day one, and pitch night was the icing on the cake, if you will.
The growth of the students, from day one, when we did our first 30-second elevator pitch, to a 10-minute pitch in the course of one school year, blows me away. Every time I thought the kids were ready to tap out, they would come back the next day with a renewed sense of vigor and say, “No, we’re going to do this.”
Lessons from Rejection
Shawnee Caruthers: So many skills being learned, so much celebration, and so many young people who said they used to not be good public speakers, and now they’re standing on stage at a pitch competition. It’s a wonderful program. The people at Uncharted Learning are so helpful. They are such weavers, such ecosystem builders. Whether something involves them directly or is just going to help education in general, they’re always there. I just love Uncharted Learning so much.
Victoria Andrews: I couldn’t be a bigger advocate as well. I hope they give me the title of school champion, because I really am one. I’ll just double down on everything you mentioned. Given where we are in the world, rejection is very real, and there are more lessons learned from rejection. I won’t even call it failure, just not going to the level you wanted. You can sharpen up your presentation skills. Maybe you change the colors in your slide deck, or maybe you have a conversation with a judge that helps you build your social capital and gets you into a space you weren’t able to reach before. So while the pitch competition is the culminating event, and there’s only one winner declared, there are so many opportunities to learn and grow through that whole process.
Bringing Uncharted to More Students | Jackson Greenstone
Shawnee Caruthers: This is Jackson Greenstone.
Jackson Greenstone: I think students are in a unique stage in this generation, and they’re looking for something new. They’re looking for ways they can be independent and use their skills in new and creative ways. So I encourage everybody to look at the resources Uncharted is providing for districts and how you can tailor them for your populations. I really want to see this come to life in some of our lower-resource districts across the nation, because I think that’s where it can really flourish. Students, regardless of their demographic or background, are curious. They have great ideas. So how do we bring good resources like Uncharted to our students?
Entrepreneurship Is for Everyone
Victoria Andrews: Again, I’m a huge fan of Uncharted, what they’re doing and what they bring into various spaces, and I’m excited to keep watching them grow as they spread across the country. If you or your community is thinking, “We’re really trying to leverage the beauty and the assets of what we have to offer,” please look into Uncharted and reach out to them. They’ll be linked in the show notes. They would love to walk through what your campus offers and how their programs can overlap with what you already have. Whether you’re a middle school or a high school, they have classes and supports for all secondary levels.
Shawnee Caruthers: Absolutely. Thank you for sharing how people can connect with Uncharted Learning. And just a reminder that entrepreneurship is for everybody. We know that sometimes teachers and learners feel a little hesitant because they’re not, quote unquote, entrepreneurs, so they don’t feel comfortable walking into this class or teaching it. But with all the benefits that come from it, like we just talked about, it truly is for everyone. You don’t have to be an expert, and you don’t have to be an entrepreneur. You just have to be willing to open your mind, learn, walk through a process, and be open to what comes out on the other side. Entrepreneurship is truly for everyone. And like Victoria said, check out Uncharted Learning.
Hear the Full Interviews from the Uncharted Learning Summit in Chicago
CTE Director for Frisco ISD in Texas
Alumnus from the first-ever 2013 cohort
Executive Director of CTE Governance and Strategic Initiatives for Washtenaw County, Michigan
High school business teacher in Fredericksburg, Texas
Alumnus of the incubator and accelerator program
District administrator / CTE representative with McAllen ISD in Texas
Middle school educator at New York City Highland Middle School
CTE Director / Assistant Director at the Entrepreneurship Center of Williamson County Schools in Tennessee
Intermediate School District (ISD) leader in Michigan
Alumnus of the Franklin Heights High School
Middle school entrepreneurship teacher at Friendship Public Charter in Washington, D.C.
District CTE and program leader in Leander ISD, Texas
High school entrepreneurship teacher in Midlothian.
Community champion, volunteer mentor/coach,
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