Book Sydney on Your College Campus
Sydney Montgomery is a highly-rated college speaker. As the daughter of military and immigrant parents and a first-generation graduate of Princeton University and Harvard Law School, she battled insecurities, financial challenges, and debilitating chronic illnesses to defy societal labels and expectations. She followed her beliefs to start a non-profit organization that has helped 7,000+ students earn more than $490M in scholarships and achieve their higher-education goals. As a TEDx Speaker and Forbes 30 under 30 entrepreneur Sydney inspires other young adults to believe in themselves, find their voice, and confidently pursue their goals no matter their background
signature topics
- Charting Your Own Path: Creating a Career That Fits You
- Resilience & Grit: Thriving Through Challenges
- Social Entrepreneurship: Turning Passion Into Impact
140,000+
TEDx TALK VIEWS
7,000+
Students Impacted
100+
speaking and press features nationally
Resilience & Grit: Thriving Through Challenges
Fueled by my life experiences, challenges, and triumphs, I share personal anecdotes and practical tools to develop a resilient mindset that fuels success in academics and beyond; strategies to overcome imposter syndrome, financial stress, and career uncertainty; and methods to reframe failure as the path to longterm grit and success.
Students Will Learn
- How to develop a resilient mindset that fuels success in academics and beyond
- Strategies to overcome imposter syndrome, financial stress, and career uncertainty
- How to turn failure into fuel and develop long-term grit
Charting Your Own Path: Creating a Career That Fits You
I did everything “right.” I attended Princeton and graduated from Harvard Law—only to realize that the traditional career path wasn’t for me. I reinvented myself, shifting from law to educational entrepreneurship, proving that success doesn’t have to be linear. This talk is for students who feel lost or unsure about their next steps.
Students Will Learn
- How to make confident career decisions even when the path isn’t clear
- Why it’s okay to pivot, change paths, and redefine success
- Practical ways to explore careers, gain experience, and build a personal brand
Social Entrepreneurship: Turning Passion Into Impact
I have launched two successful social enterprises—one in education tech and another in higher education access— without coming from a wealthy background or having startup funding. In this talk I share the real behind-the-scenes of what it takes to build a business that makes an impact and pays the bills.
Students Will Learn
- How to turn a passion into a real business or initiativ
- The biggest mistakes new social entrepreneurs make
- How to balance profitability with purpose
- Real stories of starting with little and growing something big
What Students Say
Background
Executive Director & Founder, Barrier Breakers, Inc.
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Princeton Theological Seminary
Masters of Theology, specialization in Practical Theology -
University of North Carolina, Charlotte
Certificate in Anti-Racism in Urban Education -
University of California, Irvine
Certificate in Independent Educational Consulting - Harvard Law School
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Princeton University
BA English Certificate
French Language
Speaking Experience
Sydney has spoken on national and international stages as a keynote speaker, conference panelist, commencement speaker, workshop leader, and more. She is a member of the Forbes Nonprofit Council and has been featured in Inc., Forbes, FastCompany, Medium, CNBC, and others. If you are seeking Sydney to speak at your next in-person or virtual event, please fill out the speaking request form or email us at speaking@sydneyamontgomery.com
Past Speaking Venues
Sydney pivoted from law to education, scaling two six-figure businesses and founding a nationally acclaimed nonprofit organization. As a speaker, Sydney delivers profound insights on diversity, innovation, and resilience, drawing on her extensive experience as a leader and advocate for first- generation students. Booking Sydney Montgomery means engaging a captivating speaker with a unique blend of personal story, professional expertise, and transformative insights. Each presentation is crafted to not only inform but also inspire, empower, and motivate audiences to take actionable steps toward their goals.
High Schools, Colleges and Universities
- Clarksburg High School Commencement
- Clarksburg High School Advanced Placement Power Scholars
- Princeton University, Career Services
- Princeton University, Entrepreneurship Club
- Princeton Prize in Race Relations
- Stanford Neurodiversity Summit
- American University
- George Washington University
- St. John’s University
- Yale Law School
- MIT Generative AI Summit
- Miami-Dade College
- Princeton University Female Founded Conference
- Indiana University
- University of California, Irvine, Division of Continuing Education
- Marion P. Thomas Charter High School
- Tennessee State University
- Harvard Alumni for Black Advancement
- Rowan College at Burlington County
- Marymount Manhattan College
Professional Organizations, Conferences, and Corporations
- The Independent Educational Consultants Association
- National Association for Law Placement
- The Equity Summit
- Greater Houston Women’s Chamber of Commerce
- Northeast Association of Pre-Law Advisors
- National Black Pre-Law Conference
- Break into Law Conference
- Students of Color for College Conference
- Kappa Alpha Theta Emerging Leaders Institute
- Halcyon Opportunity Fellowship
- TEDx Asbury Park
- Mt. Calvary Baptist Church HBCU College Fair
- Montgomery County Women’s Bar Association
- Innovative Educators Summit
Press, Media Outlets, and Podcast Interviews
- Forbes Media
- WKMG News 6 Orland
- WNBC-TV
- Canada TV
- Business First AM
- Insider’s Guide to Finance Podcast
- Thinking LSAT Podcast
- Status Check with Spivey Podcast
- Taming the High Cost of College Podcast
- The College Scoops Podcast
- College Essay Guy Podcast
- The Inside Scoop Podcast
- Your Teen Magazine Interview
- LSAT Unplugged Podcast
- Law School Toolbox Podcast
- Inc, Magazine
- US News
Faith-Based Organizations
- Mt. Calvary Baptist Church
- Christ Congregation Church
- American Baptist Churches of the South
- American Baptist Women's Conference
It was so wonderful to hear your testimony! It was super affirming, especially as a first-generation low-income Jamaican student. It’s amazing to see a fellow Black woman succeeding as an entrepreneur, child of God, and overall professional!
Hear directly from students
Princeton University and Harvard Law School
Entreperneurship Student, Princeton University
Leadership Workshop Participant, Kappa Alpha Theta