Middle School Leadership Program | Summer 2026

Online Entrepreneurship and Leadership Program

The Middle School Leadership Program is a virtual, 8-week experience that guides ambitious 8th graders (rising high school freshmen) through real challenges, real skills, and real leadership so they arrive at high school curious, courageous, and one step ahead.

Are You Up for the Challenge?

Most leadership programs talk about leadership. We believe you become a leader by doing. Over 8 weeks, you'll take on real challenges, talk to real people, solve real problems, and build the habits and skills that leaders actually use. You won't just learn about being a leader, you'll practice it, stumble, figure it out, and try again.

 

Why Focus on Entrepreneurship? 

Entrepreneurship is much more than merely learning how to start a business. It's a mindset—a problem-solving framework fueled by creativity and grit—that challenges you to be a leader. When a student has to pitch an idea, solve a real problem, talk to someone new, or build something in a week, there's no faking it. Good judgment, resilience, and initiative can't be memorized. These leadership skills are earned through trial, error, and trying again.

That's why entrepreneurship is such a powerful context for teens entering high school. The qualities of successful social entrepreneurs are the qualities great leaders need: making decisions without all the answers, taking action despite the fear of failure, and seeking out people and experiences that challenge and stretch you.

We believe entrepreneurship and leadership aren't a one-time event or a title you're given. They're a set of habits and skills that get sharper every time you use them.

 

Schoolyard Ventures

Schoolyard Ventures is a design thinking lab that helps ambitious teens solve real world problems and create positive change.

Over the last 7 years, we've supported more than 3,000 students to launch and lead social ventures through 30+ terms of our UPenn Social Innovators Program (check it out here), supporting teens to build everything from tech companies and fashion brands to community nonprofits and social movements. The more we work with high school students, the more we hear the same thing: "I wish I had learned this when I was younger." The Middle School Leadership Program is our answer to that.

Schoolyard Ventures’ network of advisors is comprised of changemakers, entrepreneurs, and social innovators who have built and scaled ventures across five continents, from affordable housing reform in California to plant-based food systems in India to education nonprofits in Haiti. Every advisor has also started their own entrepreneurial journey as a teenager. They don't just teach this in theory. They live it.

Information Session

 
 
 

Summer 2026 Term

Week of June 8 - Week of July 27th

 

Program Description

This program is not a lecture series. Over 8 weeks, students take on real, skill-based challenges that build their leadership toolbox from the inside out by doing, failing, reflecting, and trying again. Each week introduces a new leadership principle paired with an immediate challenge to put it into action and reflect along the way. 

Students learn and work alongside a small cohort of peers from across North America, supported by personalized guidance from advisors who have built and led projects, ventures, non-profits, teams, and companies themselves.

 
 

Program Format

Who

Current 8th Grade Students (Rising High School Students)

Location

This is a 100% virtual (online) program.

We believe that pedagogically, online learning requires a different model than in-person. This includes much smaller class sizes, an emphasis on action and discussion instead of passive lectures, and a focus on mentorship and personalized guidance.

Time Commitment

The expected weekly time commitment for students is a minimum of 3 hours per week. This includes:

  • Weekly Interactive Recitations (65 minutes) | Mondays 5:00 - 6:05pm ET '

  • Weekly Advisory (65 minutes) | Wednesdays 5:00pm - 6:05pm ET

  • Independent Work | 1-2 hours a week

Click below to read more about each program feature:

 

  • Mondays 5:00pm - 6:05pm ET 

    Each week, students meet live in small groups of no more than 8 peers from across North America, guided by two Schoolyard Ventures advisors. Each session introduces a new leadership principle paired with a real entrepreneurial challenge to put it into action immediately.

    Here's a taste of what that looks like:

    • Try it. Do something you have never done before.

    • Listen to it. Deep dive into the personal stories of those closest to you.

    • Solve it. Tackle an everyday problem you or your family faces.

    • Start it, Stop it. Start a habit worth keeping. Drop one that isn't.

    • Change it. Identify something you can make better for others.

    • Build it. Solve a real problem for one person in one week.

    • Pitch it. Sell an idea, product, or solution to real people.

  • Wednesdays 5:00pm - 6:05pm ET

    Once a week, students will join smaller group advisors (no more than 4 students and 1 advisor) for intimate discussions on their progress, talking through challenges, and setting action plans for the week ahead.

    Need more support? Students can reach out to their advisor directly to set up additional time. But here's the catch: as the entrepreneurs of their own life, they have to make the ask. That's part of the practice.

  • Each week, students complete 1-2 hours of independent work, including weekly challenges, skill-building drills, and written reflections.

    There are no books, no tests, no quizzes, and no grades. The work is taking action and reflecting on what you learned along the way.

    Through our digital platform, students can message advisors, review materials, and collaborate with peers at any time throughout the week. 

  • At the end of the program, students receive a certificate of leadership. But the real credential isn't the piece of paper, it's the challenges you took on, the skills you built, and the story only you can tell.

 
 

Logistics

Information Sessions

We host live information sessions for interested students and families to learn more about the program. If you are unable to attend, please register and we will send you the recording.

Cost

Tuition for the program is $1,695 USD. A 50 percent deposit is due within 15 days of enrollment. Final payments are due by June 15th. 

Financial aid is available to families who qualify using a Clarity application.

 
 

Application Process

Deadline

Application Deadline: Thursday, May 7, 2026 at 11:59pm ET

This is a rolling admissions and enrollment process. The program may reach capacity before the enrollment deadline.

Process:

  1. Written Application: Your first challenge - tell us more about you. Interested students submit a short application (10-15 minutes) to share more about you and what you are interested in learning and doing this summer. 

  2. Phone Interview: Your second challenge - a short 5-10 minute phone interview (audio only) with someone on the Schoolyard Ventures team. We want to get to know you better and how we can best support you this summer. 

  3. Acceptance: Students will be notified within one week of applying for their acceptance into the program.

Contact the Executive Director of Schoolyard Ventures, Reilly Brooks, at (202) 570-4332‬ or reilly@schoolyard.org.

Questions? 

 
Apply Here
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