Sydney Montgomery
Speaker | Mentor | Entrepreneur
Inspiring success.
Transforming Futures.
I’m Sydney Montgomery
I’m 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.
Speaking
Sydney brings powerful storytelling, lived experience, and actionable wisdom to every stage — from corporate retreats to college campuses. Her talks invite women, first-gen professionals, and emerging leaders to rise with faith, purpose, and freedom.
Courses
These practical, heart-centered classes walk you through the inner and outer work of growth — whether you’re rebuilding confidence, navigating a career pivot, or ready to live with more peace, clarity, and purpose.
Coaching
This is for the woman who’s accomplished on paper but quietly wondering, what now? Through private, high-touch coaching, Sydney helps you clarify what’s next — not just in your career, but in your life, leadership, and walk with God.
Workshops
Whether you’re leading a team or launching your future, these transformative workshops create space for reflection, resilience, and reinvention. With a focus on confidence, identity, and redefining success, each session helps participants grow with clarity, courage, and purpose.
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.
DIG DEEPER
Free Tools to Grow in Purpose — Personally, Professionally, and Spiritually
Whether you’re focused on your career, your confidence, or your calling, these resources are here to help you grow from the inside out. Dive deeper into the themes that fuel lasting change and help you move forward with clarity and courage.
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Build confidence through faith-rooted declarations. Download Here
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Teach strategic, values-aligned networking. Download Here.
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This guide will help you understand that the power to define yourself lies within you. Exlore identity work and mindset reset around hustle, shame, and false success. Download Here.
Engaging Keynotes for a Variety of Audiences
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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.
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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.
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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.
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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.
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 initiative dedicated to dismantling those very obstacles. Through 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.
“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!”
—Gabby G.
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