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

Author: By Russ Morgan & Joey Muré
Published: Thu 01 May 2025
Episode Link: https://www.wealthwithoutwallstreet.com/podcast/college-isnt-the-only-path-exploring-gap-year-success-with-riley-simpson

Is the traditional path to college really the best choice for every student? What if college isn’t the best next step? In this episode, Riley Simpson joins Russ and Joey to share how taking a gap year led to clarity, career success, and personal growth.

Riley discusses the growing trend of gap years as a viable alternative to college, offering students the opportunity to explore different careers, build skills, and gain self-awareness without the pressure of choosing a major. He also highlights the anxiety students face when forced to pick a direction too early and offers practical advice on how a gap year can be a purposeful and transformative journey, rather than just a break.

Discover how this alternative education path not only benefits students but also helps them develop the clarity to make better decisions for their futures.

Top three things you will learn:

-Breaking free from college pressure

-Building clarity

-Preparing for the future

About Our Guest:

Riley Simpson has had a fascinating trajectory. He took two gap years before going to college, during which he became a mediator, broke into the film industry, became a real estate broker, started and sold a business (Right Hand Media), and then entered the tech industry.

Riley is currently the Chief of Staff at Learn, the first-ever edtech Venture capital firm that has been an early investor in notable edtech companies, such as Coursera, Udemy, and many more.

Disclaimer: The opinions expressed on this podcast are solely those of the hosts and guests and do not constitute financial advice. Always consult a licensed professional for financial decisions.

This episode is sponsored by a podcast show partner. We may receive compensation if you use links or services mentioned in this episode.

The hosts may have a financial interest in the programs or services mentioned in this episode.

Connect with Riley Simpson:

-Website - https://wealthwithoutwallstreet.com/gapyear

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