Over the past several months, I’ve had the privilege of quietly piloting an exciting initiative that fuses creativity, entrepreneurship, and emerging technology in partnership with the High School of Art and Design in New York City. While the initiative is still midway through the school year, I've been reflecting a lot on what we've learned so far and wanted to share some of what we've learned thus far.
Introducing the Artist Youth Entrepreneurship (AYE) Program
The High School of Art & Design is a public portfolio high school in NYC, where every student gains admission by submitting a portfolio showcasing their talents in one of several domains: design, animation, architecture, fashion, and more. Walking through the school’s hallways feels like stepping into a vibrant gallery, with student artwork and creativity literally bursting from the walls.
Earlier last year, the school’s principal, Maximillian Re-Sugiura, had a visionary realization: While students were being taught to hone their creative abilities, they also needed to learn how to turn their work into potential business opportunities. In essence, creativity needed to meet entrepreneurship. This sparked the idea of teaching students how to set up and sell their creations online, and Max proposed a collaboration with Etsy—a New York City-based company synonymous with empowering creative sellers.
Along with the leadership team, they conceptualized a new program called the Artist Youth Entrepreneurship Program (AYE), designed to be immersive and collaborative with industry partners and real world experiences. AYE brings together students, parents, teachers, and even banking partners to provide a comprehensive learning experience. Beyond learning the technicalities of setting up an Etsy shop, students gain essential business skills such as storytelling, branding, pricing, and customer engagement—things that will serve them long after they leave high school. As a Career & Technical Education (CTE) school, all students also get compensated for their time spent on this work.
The art of connecting the dots across such disparate spaces (educational curricula, work-based learning, and online selling) in a programmatic way felt like a perfect AI-shaped problem. So we also leaned into the generative capabilities of AI to help us conceptualize and execute our pilot program design this fall. Here's how we approached our pilot phase of this program.
The Challenge: From Toolkit to Classroom
After a few planning meetings, Etsy's team shared the robust Seller Handbook, which includes hundreds of pages of documentation and resources, covering everything from branding and product photography to pricing and taxes. While invaluable, this content felt overwhelming for a high school teaching team already managing a full schedule. Recognizing this as an opportunity, we decided to leverage generative AI to transform Etsy’s resources into a student- and teacher-friendly curriculum.
Working with Playlab, a platform that uses AI to enhance teaching and learning, we condensed Etsy’s seller toolkit into a 10-week unit plan based on the typical unit plan format at the High School of Art and Design. Each week focused on a different aspect of creating and running an Etsy shop, from brainstorming a shop name to understanding taxes.
Here’s the final lineup we landed on for the unit plan:
Artist Youth Entrepreneurship - Etsy Shop Creation Unit Plan
Week 1: Introduction to Etsy & Account Creation
Week 2: Branding & Product Creation
Week 3: Writing Effective Product Descriptions & Keywords with Playlab
Week 4: Product Photography
Week 5: Pricing Strategies
Week 6: Setting Up Shipping Logistics
Week 7: Managing Shipping and Handling Logistics
Week 8: Marketing Your Shop
Week 9: Providing Excellent Customer Service
Week 10: Taxes and Business Expenses!
We designed each lesson to coincide with a 50-minute class period, aligning with the school’s existing teaching framework. We also build a custom lesson plan builder GPT with Playlab, which gave teachers a few starting points to kick around ideas before bringing these lessons into the classroom.
Making Learning Relevant and Engaging
One thing we learned right away was the importance of making traditionally dry topics (like pricing) more engaging for students. To do this, we leaned into the school’s culture and student interest areas. For instance, Comic-Con is a major event for students, and many were eagerly anticipating the release of the second season of Arcane.
So we tapped into this pop culture reference as a learning lens for the pricing lesson, creating a narrative around pricing Arcane-themed stickers for Comic-Con. With the help of additional AI tools, we transformed the topic of pricing into a dynamic storytelling and problem-solving exercise.
Here’s an example slide from that lesson:
Similarly, teachers used AI to enhance creativity and engagement. One teacher developed a custom GPT with Playlab that helped students write better product descriptions for their Etsy shops. The GPT was trained on Etsy’s text box constraints and let students refine their descriptions iteratively, making the process both educational and interactive (and also introduced AI into the classroom).
Industry x Edu Collaboration in Action
It’s highly unusual to have a leadership team at a school that’s so open-minded about entrepreneurial pilot programs like this, particularly ones that require real-time decisions (and mistakes) with a real student stakeholder audience. But each week, assistant principal Ian Pasetsky and work-based learning coordinator Amanda Deebrah met to discuss the lesson plans and rollout strategy for the following week. It’s truly thanks to this continued commitment (despite all the hiccups) that this has been possible.
Similarly, the industry partnerships and connections met the school from the other side. A highlight of the pilot was bringing in representatives from Tech:NYC, Etsy, and successful Etsy sellers to speak with about 300-400 student participants of the program this fall. They shared firsthand experiences of brand marketing, pricing, and their entrepreneurial journeys. This real-world connection gave students valuable insights and inspiration, reinforcing the importance of the skills they were learning.
I'd like to see more cross-pollination between educational institutions and industry leaders over time, as these are the collisions that spur the greatest learning opportunities.
Looking Ahead: The Artist Youth Entrepreneurship Program
By the end of February, we anticipate reaching an exciting milestone: 100 students completing the foundational work to open Etsy shops and commence the selling process. It's been exciting to hear the students' entrepreneurial spirit come across even in what they want to sell–everything from stickers and custom drawings or portraits to fashion pieces. A couple of students are exploring ways to sell pieces that reflect their unique cultural heritage or hobbies at school, such as pottery.
These efforts will culminate at Fanfaire, the High School of Art and Design’s annual celebration of creativity and fandom, which takes place from April 5-6. At this event, students will share their stories and sell their creations directly to the public, bringing their learning full circle in a dynamic, real-world marketplace.
What I love about this initiative–regardless of the outcomes of any online sales–is that it highlights the potential of project-based learning to empower students with entrepreneurial skills, while also introducing them to the tools and technologies shaping the modern creative economy.
We’ve learned a lot about the boundaries and constraints of such an ambitious, school-wide rollout of a new initiative like this. We know we have work to do on improving the rollout, the communications, the teacher education, and the timing (which unfortunately overlapped too closely with college application season). But this is all fixable. We now have a starting blueprint to iterate on for the next season of students, or even the next school.
The success of this pilot at the High School of Art and Design is just the beginning. We hope to expand the Artist Youth Entrepreneurship Program to other schools in New York City and beyond, offering students everywhere the chance to turn their creativity into opportunity. If you have been working on a similar initiative at your school or district, I'd love to learn about it.
This has been such a collaborative group effort from day one–special shout out to the entire team at the High School of Art & Design (in particular, Max, Ian, and Amanda), Bev from Etsy, Bryan from Tech:NYC, Priyanka and Anna for participating in our seller programming, and Yusuf and Wyman from Playlab for leveling up so many educators on AI 101 in the classroom.
