College Isn’t the Only Path: Exploring Gap Year Success

with  Riley Simpson

Riley Simpson - Leap Year

Riley Simpson, founder of LeapYear, believes students shouldn't be rushed into college—or life—without clarity. After experiencing his own powerful, unstructured gap year that transformed his confidence and career direction, Riley created LeapYear: a 12-month structured gap year that helps high school grads build character, critical life skills, and deep clarity around who they are and what they’re called to do.

If you missed his appearance on the Wealth Without Wall Street Podcast,  now’s your chance to discover how he’s challenging the broken education system and replacing it with a new pathway—one built on purpose, self-awareness, and action.

Go Deeper with Riley Simpson

What is LeapYear?

LeapYear is a 12-month structured gap year program designed to help high school grads gain clarity before rushing into college or career decisions. It’s not a break—it’s a launchpad. Each year, a select cohort of students joins a guided journey designed to grow confidence, character, and clarity of purpose.

Leap Year Logo

The Program Includes:

  • Career Prototyping – Students test real roles through internships, projects, and business-building.
  • Core Curriculum – Focused learning in identity, communication, leadership, and real-world problem-solving.
  • Weekly Coaching – One-on-one guidance with a dedicated coach plus mentorship frameworks.
  • Spiritual Formation – Faith-forward reflection on calling, purpose, and life beyond the program.

LeapYear equips students with the tools, mindset, and experiences needed to thrive in whatever path they pursue next—college, entrepreneurship, ministry, or beyond.


Whether you're a student looking for direction—or a parent who knows college isn’t the next right step—LeapYear offers a better way forward. It’s structured. It’s intentional. And it’s built for students who want clarity before commitment.

 Explore the LeapYear Program 

Meet Riley Simpson — Gap Year Strategist & Career Discovery Mentor

Riley's own journey after high school wasn’t linear—it was transformational. Over two years, he tested seven different careers: mediation, real estate, film, entrepreneurship, and ministry. That real-world experimentation—guided by mentors—shaped his confidence, clarified his purpose, and even led him to meet his future wife.

Later, Riley served as Chief of Staff at Learn Capital, a $1.5B venture fund focused on education innovation. There, he saw the shortcomings of a system that pressures young adults to choose a career path before they know who they are. LeapYear was born out of this insight and Riley’s lived experience—offering a better way to launch into adulthood.

Riley Simpson
Riley Simpson

What You’ll Learn From Riley Simpson:

  • Why Most Students Feel Lost (and What to Do About It)
    Hear how 80% of high school grads don’t know what’s next and how LeapYear offers a better approach.

  • The 4 Questions That Matter More Than “What’s Next?”
    Who are you? What do you love? What are you great at? What does the world need?

  • How to Prototype a Purpose-Filled Life
    Learn how students explore career paths through internships, projects, and real-world experiences.

  • How Colleges and Employers Are Catching On
    From Harvard to hiring managers, intentional gap years are seen as an asset—not a delay.

Why Riley Simpson's Perspective Matters

Most students are pressured to choose a career path before they know who they are. Riley Simpson’s LeapYear flips the script, helping young adults gain the clarity and confidence they need to make wise, purpose-aligned decisions about their future.

Backed by experience, insight, and a heart for helping the next generation, Riley is leading the way in rethinking how we launch into life after high school.

Explore Riley's Work Today

Riley Simpson is redefining what it means to prepare young adults for life after high school. Through LeapYear, he’s giving students the clarity, confidence, and skills they need to thrive in a world that demands more than just a degree. Don’t miss this opportunity to explore a bold, purpose-driven alternative to the traditional path.

  • Share this with a student or parent who needs a better option: startleapyear.com

  • Follow Riley for insights on career clarity, education reform, and equipping the next generation to live with purpose: