Sydney Montgomery, Esq.
Executive Director & Founder of Barrier Breakers®
As the first lawyer in her family, the first person from her high school to
attend Princeton University, and a Harvard Law School graduate, Sydney Montgomery (Forbes 30 Under 30) has used her platform since 2012 to help students break down generational barriers and step confidently into their future. As the Executive Director and Founder of Barrier Breakers®, issues of diversity, equity, and inclusion are incredibly important to her.
Sydney holds a B.A. in English from Princeton University, a J.D. from Harvard Law School, a Certificate in Independent Educational Consulting from UC Irvine, and a Certificate in Anti-Racism in Urban Education from the University of North Carolina at Charlotte. She is a member of the Independent Educational Consultants Association and the Northeast Association of Pre-Law Advisors. Sydney is currently an MDiv/MACEF candidate at Princeton Theological Seminary. She speaks and leads workshops on issues of educational equity and diversity, equity, and inclusion in higher education, corporate, and faith-based settings. Sydney is a member of the Forbes Nonprofit Council and has been featured in Inc., Forbes, FastCompany, Medium, and CNBC, among others. Her TEDx talk, “Breaking Barriers, Building Futures: The Power of First-Generation Minds in Shaping Business Success” will be available online at the end of May 2024.
National Board of Advisors
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Ayana Dow, Esq.
Associate, WilmerHale
Ayana Dow advises broker-dealers, financial institutions and other global and domestic financial entities on a broad range of regulatory and enforcement matters. Ms. Dow also regularly counsels companies on compliance issues relating to Commodity Futures Trading Commission, Securities and Exchange Commission, FINRA, and other self-regulatory organization rules and regulations
Prior to joining WilmerHale, Ms. Dow was an associate in the financial services group at another international law firm in Washington DC. She was previously a policy fellow in the Office of Congressman James Clyburn.
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David Sullivan, Esq.
Partner, Ropes & Gray
David is a partner in the asset management group. David focuses his practice on the representation of financial services firms, including open- and closed-end registered investment companies, private investment pools, registered investment advisers and broker-dealers. He represents a number of non-U.S. investment advisory firms.
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Robin Ladd, Esq.
Associate, Haynes and Boone
Robin Ladd is an associate in the Finance Practice Group in the Dallas office of Haynes and Boone. Robin has represented both borrowers and lenders in a variety of transactions. Her practice focuses on subscription secured finance, acquisition financing and syndicated credit facilities.
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Sam Andrews
With over two decades of experience in clinical research and higher education, Sam is responsible for the development of clinical evidence strategies to secure market access and global expansion of medical devices with Smith+Nephew. Prior to pursuing a career in the medical device industry, she led the first Orthopedic Research and Innovation group in Hawaii, providing research opportunities to current and aspiring medical students and residents. Sam holds a PhD in Kinesiology and Rehabilitation Science from the University of Hawaii and a MS in Athletic Training from the University of Kentucky.
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Kaysia Early, Esq.
Founding Attorney, Earley Law Firm
Kaysia Earley is known for achieving exceptional results. As a Christian Attorney whose moral compass is grounded in faith and fellowship, she has gained a well-deserved reputation as a fierce litigator who zealously fights for her clients’ fundamental rights. Founding attorney for Earley Law Firm, PLLC, she focuses on both criminal and civil litigation and is a strong advocate for her clients. In 2022, she was honored as a member of The National Black Lawyers Top 40 Under 40.
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Michael Hogan, Esq.
Michael F. Hogan is an executive with over 40 years in the financial services industry. He is currently an adjunct professor at Bryant University and a course facilitator at Cornell University. He holds a Juris Doctor from Suffolk University Law School; Master of Art History from Lindenwood University; and a Bachelor of Arts in French Language and Literature from Bates College. He is currently a PhD candidate at the Institute for Doctoral Studies in the Visual Arts where his scholarship concentrates on the aesthetics of displacement in street art in context of twentieth and twenty-first century continental philosophical thinking. Michael splits his time in Truro, MA, Boston, MA and Miami, FL
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Cynthia Rivera, Esq.
As a law school admissions consultant, Cynthia is dedicated to helping law school applicants discover their strengths and craft a personal narrative that maximizes their potential. She obtained her B.A. in History from Cornell University before earning her law degree from the University of Virginia School of Law. While attending Cornell, Cynthia was a student recruiter with the undergraduate admissions office. At the University of Virginia, she was a student member of the Admissions Task Force. She later returned to UVA, where she worked as a reader with their law school admissions office reviewing and assessing numerous applications. Before working in admissions, she worked as a financial advisor for a wealth management firm and as an attorney with the Equal Employment Opportunity Commission Office in Washington, D.C. Raised in Puerto Rico, Cynthia is fluent in both English and Spanish.
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Aja Flewelen
Vice President, Diversity Talent Acquisition, TD Cowen
Aja Flewelen leads diversity talent acquisition at TD Securities supporting campus and lateral recruitment. Aja is responsible for the firm-wide strategy, strategic partnerships framework, and colleague engagement model that enable TD Securities to attract, engage, and hire multicultural professionals.
Prior to joining TD Securities, she led the Diversity Talent Acquisition Strategy and Sourcing team at American Express. In her most recent role, she served as Chief of Staff to the President of Enterprise Strategic Partnerships as a member of the Executive Committee Support Team.
Ms. Flewelen brings over a decade of experience in the Human Capital and DEI space across the non-profit, public, and private sectors. Aja is also a proud and active member of Delta Sigma Theta Sorority, Incorporated. She earned a Bachelor of Arts in Sociology from Loyola Marymount University and a Master of Science in Urban Policy from CUNY Hunter College.
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Karen Ali, Esq.
Karen Ali is the president of the Board of Trustees of the New Jersey State Museum Foundation and serves on the boards of The Auxiliary to the Isabella McCosh Infirmary (Princeton University), the Association of Black Princeton Alumni (ABPA), the Latin American Legal Defense and Education Fund, Our Kids Read, and Passion of Hope International-US.
Karen is also active in Princeton alumni activities. She is Co-Class Agent for the Class of 1978 and a member of Princeton’s Annual Giving Committee. In 2018, Karen received ABPA’s Alumni Service Award. In 2013, she volunteered through Princeton AlumniCorps’ ARC Innovators program for Good Grief, Inc. and edited an anthology of children’s essays, The Invisible Tattoo: True Stories about Children Grieving, Living, and Loving After Loss (2014). For more than 25 years, she has served as an administrator for the Fred Fox Class of 1939 Fund, a program that provides grants to students for academic-related projects.
In December 2020, Karen retired from the New Jersey Hospital Association, where she served as senior vice president for community partnerships and prior to that role, general counsel.
Karen received her A.B. in Sociology, magna cum laude from Princeton University and her JD from the University of Michigan Law School. She is a member of the New York and Virginia State bars and the United States District Court for the Eastern District of Virginia Federal Bar.
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Carl Weatherspoon
Carl Ivy Weatherspoon Jr. is an educator, entrepreneur, and community advocate, currently serving his hometown of Gary, Indiana. Ever inspired by possibilities, Carl prides himself on growth, innovation, and athleticism; which is evident in his most recent entrepreneurial ventures, Supa Sportz LLC, and Stack it up—a robotic weight stacker bound to revolutionize the health and wellness industry.
Carl began developing his leadership skills as the oldest of four siblings, and he continued to develop them on the court and field. Carl, affectionately known as “Spoon,” graduated from the historic Gary Roosevelt High School, where he lettered in four sports. He went on to play at Purdue University where he lettered in two sports, Baseball and track. Carl earned dual Bachelor’s Degrees in Computer Technology and Liberal Arts. He also has an Associate’s Degree in Electrical Engineering Technology. Those academic experiences led him to opportunities in professional and independent sports with the Gary Rail cats. He also has experience in corporate America with Schwans Food Company and the Chicago Whitesoxs.