SYDNEY MONTGOMERY
Speaker | Mentor | Entrepreneur
Hey There!
I'm Sydney Montgomery
I’m Sydney Montgomery, a Forbes 30 Under 30 honoree and a first-generation graduate of Princeton University, Harvard Law School, and Princeton Theological Seminary. As the daughter of military and immigrant parents, I bring a unique perspective on perseverance and success.
As a two-time six-figure social impact entrepreneur and founder of a national nonprofit, I empower students to pursue their passions, develop resilience, and build meaningful connections to thrive in their careers and beyond.
I know firsthand what it’s like to navigate challenges—whether as a first-generation Ivy League graduate, an entrepreneur who rebuilt my career from scratch, or someone who has faced personal and financial hardships, including chronic illnesses. I don’t just talk about bouncing back—I share how to keep going when it feels impossible.
Download The Free Guides To:
EMPOWER YOUR COLLEGE AND CAREER JOURNEY
Mentorship, networking, and finding my authentic self were pivotal to my journey as a two-time 6-figure entrepreneur, Forbes 30 Under 30 awardee, and TEDx speaker. In these free guides, I give you the tools to find the right mentors, build confidence, and grow your network. Download these expert guides to unlock your full potential!
- Finding Your Mentors: Learn how to connect with mentors who will help you succeed.
- Breaking Free From Labels: Discover your true potential and let go of limiting beliefs.
Networking for College Success: Build connections that open doors for your future.
TEDx: First-Generation Graduates Drive Business Success
With over 140,000 views, this talk centers on the experiences and power of first-generation college students to drive business success and innovation and tangible ways we can support first-generation college students in their professional careers.
140K+
TEDx Talk Views
7K+
students impacted
100+
speaking and press features nationally
Sydney, you have blessed our lives with your
wisdom, experience, and vulnerability. So many
things you have told us have been infinitely
insightful and will change how I live my life
forever.
Sydney, words can’t describe the depth of
gratitude I have for the knowledge, kindness, and
authenticity you shared with us. I can
wholeheartedly say that you have made this
experience such a blessing. Thank you for
standing in your empowerment and being such a
wonderful example of who we’re trying to be. You
are the goodness of the world.
Dear Sydney, I didn’t think it would be possible
for me to come to this 3-day conference and
learn so much, and you are a huge reason for this.
You have so much incredible experience and
wisdom, along with genuine encouragement and
the true definition of empowering leadership.
Thank you for changing my life (quite literally)
Hear directly from students
I’m a visionary leader, a woman of faith, and a relentless advocate for first-gen success.
I’ve walked the path of breaking barriers, and now I’m committed to helping others do the same—empowering them to navigate education, career, and entrepreneurship with confidence and purpose.
- Nonprofit Founder & Leader
As the Founder and Executive Director of Barrier Breakers, I lead a national nonprofit that empowers first-generation and underrepresented students on their journey to college and law school.
- Keynote Speaker & Workshop Facilitator
Helping women grow and scale their impact-driven ventures with clarity and confidence.
- ENTREPRENEURSHIP COACH
Helping women grow and scale their impact-driven ventures with clarity and confidence.
- THOUGHT-LEADER & Writer
Contributing to the conversation on equity, education, and entrepreneurship through articles for the Forbes Nonprofit Council and other publications.
ENGAGING KEYNOTES FOR A VARIETY OF AUDIENCES
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.
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.
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.
Leadership, Networking, and Mentorship Strategies for Young Adults
I am passionate about helping. young adults feel confident in their leadership skills, redefine leadership and success for themselves, and realize that the key to success involves growing their support circle through networking and mentorship. As a first-generation student, my success came in large part because of the village that supported me and I’m thrilled to demystify networking for the next generation.
Not 100% sure where to start? get in contact...
Supporting First-Generation Students Through Barrier Breakers®
As a woman of color who navigated both Princeton and Harvard, I intimately understand the obstacles faced by first-generation and marginalized students in achieving educational and career success. This inspired me to found Barrier Breakers, an education nonprofit dedicated to dismantling those very obstacles. Through high-touch admissions advising from current and former deans of admission, continued mentorship, access to vital resources, and strong advocacy, we empower students and professionals to overcome systemic barriers and achieve their full potential. Join us as we build pathways to success that are inclusive and equitable.