We recently connected with Sydney Montgomery and have shared our conversation below.
Sydney, looking forward to hearing all of your stories today. Let’s start with the story of your mission. What should we know?
I think I’ve always been an entrepreneur at heart. I started my first business when I was 10 years old, teaching piano to my neighbors…charging…$2/lesson. I continued to teach piano for 10 years (and grew my prices tremendously!) but during high school, I was also a babysitter and a tutor with Peer2Peer Tutors (now Aristotle Circle Peers) tutoring the SAT, French, and essay writing. Despite being one of those students who were highly involved with activities and on the “right” track academically, when it came time for me to apply to college I was completely lost. Neither one of my parents went through the college admissions process in high school. My mother was a Jamaican immigrant, and both of my parents received their degrees only after enlisting in the US Navy. My teachers stepped in and provided me with tremendous support and I ended up becoming the very first person from Clarksburg High School to go to Princeton.
Princeton changed my life in more ways than I can count. When students and teachers at my high school asked me to come back and speak to them about the college admissions process, I jumped at the opportunity. I realized that there was so much misinformation about the college admissions process and not enough resources to help students find their best-fit colleges and I wanted to change that. Year after year, I would help students from my school and church navigate the college admissions process while listening to their hopes and dreams and helping them determine their values. When Princeton’s pre-law advisor left during my first year at Harvard Law School, I started unofficially helping out other first-generation and minority students on the law school admissions process.
I actually did practice law for a bit. After graduating from law school, I clerked for a judge on a family rotation and practiced private family law litigation in Maryland. I pursued my certificate in Independent Educational Consulting from UC Irvine during my clerkship but originally thought that I could not pursue entrepreneurship full-time because of my working-class background and increasing health issues. However, in 2020 I felt that God was calling me to pivot fully into education and give others the guidance that I needed on my path so more students could experience life-changing upward mobility. So even though I began consulting in 2012, and launched S. Montgomery Admissions Consulting in 2018, it wasn’t until 2020 that I pursued it full-time and it has now grown to be a brand underneath the larger Barrier Breakers®, Inc. 501c3 nonprofit with a mission to increase access to and success in higher education for BIPOC and other marginalized students. We’ve been able to help 4000+ students on their college and law school applications, a number that I am extremely proud of.
Great, appreciate you sharing that with us. Before we ask you to share more of your insights, can you take a moment to introduce yourself and how you got to where you are today to our readers
As the Executive Director and Founder of Barrier Breakers®, CEO and Founder of Outline It, I have dedicated my career to helping diverse students pursue new opportunities. I am a graduate of Princeton University and Harvard Law School and received my Certificate in Independent Educational Consulting from the University of California, Irvine.
Barrier Breakers® has helped 4000+ first-generation and minority college and law school applicants achieve placements and full-ride scholarships with the country’s top law schools and colleges. At 29, I am a 2020 IECA Making a Difference Awardee, a 2021 Counselor of the Year (PCACAC), a Kappa Alpha Theta 35 Under 35 awardee, and was most recently named one of Women’s eNews 21 Leaders for the 21st Century.
I come from a working-class background and was the first student from my high school to go to Princeton University. My mother immigrated to New York from Jamaica at fourteen, and my father grew up on the South Side of Chicago before moving to a small town in Michigan for high school. My parents received their college degrees only after enlisting in the United States Navy. Both of my parents work two jobs, and even though I financially supported my then-high school-aged sister, I left practicing law to raise up the next generation of attorneys.
Only 2% of lawyers in this country are Black women. Nationally, only 51% of Black applicants are accepted to law school every year. However, for the students we work with through Barrier Breakers®, 95% of whom are the first in their family to go to law school, not only are more than 90% of our students getting accepted to law school, but 54% of our students are getting into a Top 14 law school. 66% of our students are getting accepted with at least a half-tuition scholarship and 31% percent of our students receive a full-tuition scholarship to law school. We are helping our students break generational barriers and also break cycles of debt and poverty on their road to success.
Understanding that strong writing skills are integral to upward mobility and higher education success, I launched Outline It. Outline is an interactive writing platform and pedagogical tool for students and educators who work with them to help them write better-structured essays faster. Outline’s patent-pending solution and writing process is the recipient of a $200,000 New Schools Venture Fund grant given to innovators with bold ideas to reimagine education and improve outcomes for all children, especially those most affected by racial and economic inequities. Outline has also been recognized as one of the world’s Top 200 Pre-Series A EdTech Startups (Elite 200) by the ASU + GSV Cup/Global EdTech Summit. Outline’s software has already been trusted by 3000+ users and educators across the country.
How did you put together the initial capital you needed to start your business?
The one word that sums up my entrepreneurial journey is faith. I was 26 when I left practicing law and decided to work for myself full-time as an entrepreneur. It also happened to be the week before the world shut down in March 2020. I didn’t have 6-12 months of savings, honestly, I had debt and a lot of looming bills but I knew that God wanted me to take the leap from helping students on the side to making it my full career and I have never looked back. I didn’t have an option of failure. I actually had debt and no savings, so that meant that I had to be successful. I didn’t have time to think about every single move 1200 times before making it and or think and weigh the pros and cons for 3 months before every big decision.
Because there is that myth that you need to have a safety net of at least three to six months (maybe even a year) before you launch full-time, and that you should not expect to see a profit in your first year of business. I think that might be fine advice for those privileged individuals who have that financial safety net before they decided to make that pivot, but I pivoted to entrepreneurship full-time when I was 26. I did not have a safety net. If I had listened to that myth, I probably still would not have launched my business full-time. And I think we need to tell people that yes, you absolutely can be profitable in your first year. During those first six months of going full-time, I was able to gross $102,000 in revenue without sacrificing my values or the population of students that I wanted to serve. I found a way to create a high-value offer with payment plans that made it more accessible to more students and families. I leveraged technology to multiply myself and my work product before I was able to afford to hire a team. I could not have imagined the impact or the magnitude of what I would be building when I started out as a team of 1 and I know that we’re only at the beginning.
What do you think helped you build your reputation within your market?
The lack of access to information about the law school application process can be a barrier for underrepresented groups applying to law school. This can include not knowing how to navigate the application process, not being aware of available resources and financial aid, and not having access to mentorship or guidance from individuals who have successfully navigated the process. This knowledge gap shows up in pretty drastic ways. For example, a 2017 study found that although the majority of non-Black applicants applied to law school in November, the majority of Black applicants did not apply to law school until March. Since law schools are on a rolling admissions cycle, just that 4-5 month delay could be the difference between a student getting admitted with a scholarship and a student being denied. What’s more, Black applicants apply to far fewer schools than their counterparts and often don’t have guidance about which schools would be a good fit.
To combat this issue, we have dedicated our company to being a powerhouse in free content generation. We host the Break into Law School® podcast which has over 33,000 downloads, host a free YouTube channel, and host the annual two-day nationwide Break into Law School® conference which had over 600 attendees last year. We try to also foster community through our Barrier Breakers® Facebook group for first-generation and minority applicants and our Beyond Barriers student and alumni platform that provides mentorship, and a free and engaging community for students throughout their time in law school and even into their careers as attorneys. Through our work with students, we have been able to be part of reshaping the success rates for BIPOC and first-generation students.
Contact Info:
- Website: www.barrier-breakers.org | www.myoutline.com | www.sydneyamontgomery.com
- Instagram: @smontgomeryconsulting | @myoutlineapp | @_sydneyamontgomery
- Facebook: https://www.facebook.com/smontgomeryconsulting
- Linkedin: https://www.linkedin.com/in/sydneyamontgomery/
- Twitter: https://twitter.com/sydamontgomery
- Youtube: https://www.facebook.com/smontgomeryconsulting
Image Credits
For the blue headshot photo ONLY: Photo Credit: J’nae Antoinette