DREAM BIG: Your Dreams Are Your Future

Brought to you annually by the Windward Parents Association and Windward Alumni Office, Dream Big: Your Dreams Are Your Future program began in 2011. Each year Dream Big features prominent, inspirational speakers who share their stories about overcoming obstacles and going on to achieve their dreams. The goal of the program is to engage Windward middle school students and our extended community in an encouraging, interactive event as a reminder that having a language-based learning disability need not hold anyone back from a lifetime of achievement.

2022 Dream Big Featured Speaker: Reed Switzer '19

Reed Switzer is an entrepreneur and rising product leader in the financial technology space. Born and raised in New York, Reed was a student at The Windward School in his early years. He got his start working by bussing tables at a local diner. In high school, he developed a passion for apparel and launched his own brand with a couple of his classmates. He later served as director of operations for a music streaming startup where he fine-tuned his design, marketing, and operational skills.

In 2021, as an undergraduate at The Wharton School of the University of Pennsylvania studying finance and technology, Reed decided to leave school to pursue his entrepreneurial ambitions. He founded and currently leads a venture-backed FinTech startup called Hopscotch. The innovative company enables small businesses and solopreneurs to pay and get paid in real-time without any fees—think Venmo for business on steroids.

Read an alumni profile on Reed Switzer '19, as featured Windward's The Compass, Winter 2022 edition.

View the 2022 Dream Big Event Recording Below

Past Dream Big Featured Presenters Include:

2011 – The Kings Speech Screening
2012 – Dannel Malloy, Governor of Connecticut
2013 – Screening of The Big Picture: Rethinking Dyslexia, by James Redford
2014 - Ben Foss, Lecturer, Teacher, Founder of Headstrong Nation
2015 – Meryl Davis, Olympic Ice Dancer and Dyslexic
2016 - David Flink, CEO and Chief Empowerment Officer of Eye to Eye National
2017 – Jack Horner, Paleontologist
2018 – Meryl Davis, Olympic Ice Dancer and Dyslexic
2019 – Robert Carroll ’04, New York State Assemblymember NYC
2020 - Denis J. O’Leary, III ‘06, Senior Investment Associate at Bridgewater Associates and Member of The Windward School Board of Trustees
2021- Julie Schechter ‘06, Criminal Defense Attorney
2022- Reed Switzer, '19, Co-Founder and CEO of Hopscotch



Learn More & Support Future Dream Big Programs

Michelle Spino Andruss
Alumni Relations Director