Can you tell us a little about your background and your company?
My name is Sydney Montgomery, and I am the Executive Director and Founder of Barrier Breakers, a nonprofit dedicated to increasing access to higher education for first-generation students and others who face barriers to entry. As the first person from my high school to go to Princeton University and as a first-generation graduate of Harvard Law School, I intimately understand the challenges students face navigating the admissions process and achieving upward mobility. Barrier Breakers provides pro bono and sliding-scale college and law school admissions counseling, mentorship, and ongoing support to ensure students not only gain acceptance but thrive in their educational journeys. Outside Barrier Breakers, I use my platform to promote educational equity and access. I was named to the Forbes 30 Under 30 2024 Social Impact list, and my TEDx Talk, First Generation Graduates Drive Business Success, has over 140,000 views.
What inspired you to start your business?
Growing up, I didn’t have a roadmap for getting into top-tier schools. Both of my parents were military, and my mom is a Jamaican immigrant. My parents had a non-traditional education path and weren’t sure how to help me navigate the college process. I saw firsthand how much harder the process was without guidance, and I wanted to change that for others. I started giving back to my community, church, and high school in 2012 and then eventually pivoted from practicing law to educational consulting full-time in 2020 to support more students. Initially, I started as an independent educational consultant, but I quickly realized the systemic barriers many students face—financial, informational, and emotional required a more scalable systemic approach. I transitioned Barrier Breakers into a nonprofit to ensure more students, regardless of financial background, could access high-quality admissions support.
How did you create awareness for your brand?
Building awareness for Barrier Breakers has been a mix of strategic partnerships, digital content, and word-of-mouth referrals. We’ve collaborated with undergraduate institutions and law schools, community organizations, and churches to reach students in need. Our annual Break Into Law Conference—the largest virtual event for first-gen pre-law students—has been instrumental in positioning us as a leader in the space. I’ve also leveraged our platform through social media and our podcasts, Break into College and Break into Law School to expand our reach to more students and families. I also leverage public speaking engagements and thought-leadership pieces to amplify our mission.
What strategies helped you secure funding and scale your business?
Scaling a nonprofit comes with unique funding challenges. I’ve focused on diversifying revenue streams, including individual donors, institutional partnerships, and our earned revenue. Securing long-term and unrestricted grant funding is challenging for a new non-profit, and I knew that I did not want to rely only on external funding sources for our sustainability. Our model allows us to leverage earned revenue for additional stability. Every admissions advising package purchased by a student or family with resources allows us to help a low-income student who otherwise would not be able to afford our services. I’ve also emphasized storytelling—helping funders see the direct impact of their support through student success stories and video testimonials.
What have been your biggest successes so far?
One of my proudest achievements is the impact we’ve made on students’ lives. Barrier Breakers has served over 7,000 students across the country in a mix of 1:1 and small group services. I’m incredibly proud of the fact that from 2022 to 2023, we collaborated with the Law School Admission Council to provide free support and resources to 5,800 students. We also have grown our annual Break Into Law Conference, which saw over 2,100 registrants last year, with participation from more than 55 law schools—over 25% of ABA-accredited institutions. We’ve also been able to execute strategic partnerships with organizations like Yale Law School to expand our reach.
What challenges have you faced, and how did you overcome them?
One of the biggest challenges has been navigating the changing DEI landscape. With recent attacks on affirmative action and diversity programs, funding sources have become more uncertain. Another challenge has been managing growth while ensuring financial sustainability. I’ve leaned on my board, sought out strategic advisors, and streamlined operations to maintain efficiency.
What are your plans for the future?
In 2025, we’re expanding our Outreach and Wellness Program to provide ongoing mentorship to students post-enrollment, ensuring they not only get into school but thrive. We’re also on a mission to sustainably serve at least 100 students pro bono yearly with high-touch admissions advising (15-25 hours per student). We’re also hoping to pilot partnerships with churches to offer college readiness programs for low-income youth in Title I schools. Long-term, I want Barrier Breakers to be the go-to resource for first-generation students nationwide, providing not just admissions support but career development and professional mentorship.
What advice would you give to aspiring female entrepreneurs?
- Don’t wait for the perfect moment. Start where you are with what you have. When I left practicing law and started working as an educational consultant full-time, I did not have everything figured out. I did not have a large financial safety net but I knew that this was the work that I was called to do and I knew that I had to bet on myself not to fail.
- Trust your vision. Others may not see it immediately, but stay committed.
- Find your support network. I am a big advocate for women investing in networking and mentorship. Mentorship and peer support are crucial for sustainability. Networking creates circles of influence and opportunity that may otherwise be unavailable.
What are your top three tips for entrepreneurial success?
- Know your numbers. Whether in business or nonprofit work, financial literacy is key.
- Leverage partnerships. Growth comes from collaboration, not just competition.
- Prioritize sustainability. Burnout is real—structure your business so it can thrive without you running on empty.
Who are five people who inspire you the most, and why?
- Tope Awotona – His journey as an immigrant entrepreneur, bootstrapping Calendly into a multi-million-dollar company, reminds me that resourcefulness and resilience can take you further than outside validation. His story inspires me to trust my vision even when the odds feel stacked against me.
- McKenzie Scott – I admire how she gives boldly and without strings attached. Her philanthropy isn’t about control—it’s about trust, impact, and real change. She inspires me to think about how I can create meaningful opportunities for others.
- Suni Lee – Watching her push through a chronic illness to fight for Paris 2024 resonates with me on a deep level. Managing my own health challenges while leading Barrier Breakers is tough, and her determination reminds me that strength doesn’t mean being unaffected—it means showing up anyway.
- Bishop Vashti McKenzie – As a faith leader and trailblazer, she’s shown that leadership and spirituality can go hand in hand. Her work inspires me to lean into my faith while making space for others to grow and lead.
- Dr. Ruth Simmons – As a first-generation college student who became the first Black president of an Ivy League university, she proves that education can be transformative. Her leadership and commitment to expanding access for underserved students inspire me to keep pushing for equity in higher education, no matter the obstacles.
What are your favorite inspirational or motivational quotes?
- “Faith is taking the first step even when you don’t see the whole staircase.” – Martin Luther King Jr.
- “Your playing small does not serve the world.” – Marianne Williamson
- “Do what you can, with what you have, where you are.” – Theodore Roosevelt
Where can our readers connect with you?
- Website: www.sydneyamontgomery.com; www.barrier-breakers.org
- Instagram: @_sydneyamontgomery
- LinkedIn: Sydney Montgomery
