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Sydney Montgomery
Law School Admissions Specialist Working with First-Generation and Minority Applicants
Sydney Montgomery, a Forbes 30 Under 30 honoree, is the daughter of a Jamaican immigrant mother and military parents. She was the first person from her high school to go to Princeton University and later, to Harvard Law School. She has dedicated her life and career to supporting first-generation students in higher education and first-generation professionals in business. She is a professional writer and speaker; her TEDx talk, "Breaking Barriers, Building Futures: The Power of First-Generation Minds to Shape Business Success" centers on tangible ways to support first-generation students and professionals.
Montgomery is the founder and Executive Director of Barrier Breakers®, a nonprofit that has worked with 7,000 first-generation and other marginalized students on the college and law school application process. Additionally, she hosts the Break into Law School® podcast. Previously, she founded Outline It, writing software for students with learning differences, and co-founded College Equity First, a nonprofit that measures the campus climate for Black students at more than 100 colleges.
Montgomery holds a BA in English from Princeton, a JD from Harvard Law School, a Certificate in Independent Educational Consulting from UC Irvine, and a Certificate in Anti-Racism in Urban Education from UNC Charlotte. She is a member of the Forbes Nonprofit Council and has been featured in Inc., Forbes, FastCompany, Medium, CNBC, and others.
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