Sydney Montgomery of S Montgomery Admissions Consulting: Why We Need More Women Founders & Here Is What We Are Doing To Make That Happen
…I will never be as prepared as I would like to be. Going along with being a planner, I am also a survivalist; I like to be super prepared. It’s no secret that I am an over packer, that also my house is filled with lots of things on Amazon that is promised to make your life easier. However, I will never be as prepared as I would like to be in business. I don’t necessarily have as much extra cash flow, or staff, or time as I want, at least in this stage of my business. I am not going to be able to over pack for business and have extra sweaters and extra toothbrushes and all those just in case items, that’s not what entrepreneurship is. Entrepreneurship is making the best out of maybe not having quite exactly what you feel you need to be prepared. It’s important to recognize that you do actually have all that you need.
As a part of our series about “Why We Need More Women Founders”, I had the pleasure of interviewing Sydney Montgomery, CEO of S. Montgomery Admissions Consulting, specializes in helping first-generation and minority college and law school applicants. A graduate of Princeton University and Harvard Law School, Sydney works to dismantle systemic racism in education.
Thank you so much for doing this with us! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?
I found myself in this profession accidentally. My parents have always been staunch advocates of my education. They met in the Navy as teenagers, neither one of them having the opportunity to go to college directly after high school. 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. As a military family, we planted roots in Maryland to give me the best chance at a stable education and weathered my father’s deployments as a family.
Unfortunately, my college application process coincided with my parents’ separation and I found myself suddenly lost. Without access to adequate college counseling, I was left to my own devices to devise my college application list. I thought back to years of sitting with my mom in her bed in the master bedroom, eating a fistful of popcorn from an old Tupperware container that had long ago lost its cover, watching episode after episode of Gilmore Girls. There was something comforting about the idea of small-town Connecticut where everybody knows your name. This need for familiarity at a time when my world was becoming increasingly unfamiliar led me not only to apply to Yale to follow in Rory’s footsteps, but also to the University of Connecticut, Wesleyan, and Princeton.
Despite my lack of guidance, I became one of the first students from my high school to matriculate to an Ivy League university; Princeton changed my life in more ways than I can count. When students at Clarksburg 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. 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.
After graduating from law school, I clerked for a judge on a family rotation and practiced private family law litigation in Maryland. While I originally thought that I could not pursue entrepreneurship because of our working-class background and my increasing health issues, in 2020 I felt that God was calling me to pivot and work full-time with students on the application process. While not a religious company, my values, and methodologies are driven by my faith. As a first-generation, low-income student, I know I would not be where I am without the grace of God. I simultaneously feel a sense of responsibility to give back and I believe that God’s calling on my life is to help students through this time, regardless of their religious beliefs.
I absolutely love what I do; While I enjoyed being a lawyer, there is something unique in experiencing the joy of watching a student have a breakthrough with her essay or an ‘Aha!’ moment about his potential major. I feel privileged when students feel comfortable enough to disclose their personal struggles to me through their essay topics and I live for the moments when I can be their cheerleader, celebrating every small victory, every deadline met, scholarship won, and school acceptance letter. My students are inspirational. They are single mothers, second-career women, recovering drug and alcohol addicts, immigrants, construction workers, FBI agents, teachers, college students, students with autism, and everything in between. As a college and law school consultant, I am passionate about helping my students break down generational barriers and step confidently into their future. Only 2% of lawyers in America are Black women and I am committed to increasing that number every day. I love speaking life into my students’ dreams. Helping students with their higher educational journey is without a doubt the best job I could ever have, and the greatest gift God has given me.
Can you share the most interesting story that happened to you since you began leading your company?
I think one of the most interesting things that happened to me when I launched full-time is that I learned to use my voice as a platform. Around the same time as I took part in an event called Think in Color, which empowers people of color with the tools and knowledge they need to succeed, there was a lot of social justice and unrest in this country. I learned that I could use my platform to speak on issues of systemic racism and dismantling systemic racism in higher education. I believed that as an independent educational consultant I could actually encourage others to be part of the solution, that we could use our voice and our relationships with admissions to really fight for equity in the higher education space. The response from that was amazing. I ended up being able to lead a panel this year with the President of the Law School Admission Council on equity in law school admissions to discuss increasing representation for more minority and first-generation lawyers.
Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?
When you go on college visits, as you’re supposed to as an independent educational consultant, oftentimes you go on tours and attend information sessions in order to get a better understanding of the school. However, given my age, I was frequently mistaken for a prospective student. This actually lasted honestly until about a couple of years ago. I was on a tour, maybe in 2019, and the tour guide looked at me and asked me what was I looking for in a college. I had to have that awkward moment of being like, “oh actually I’m an attorney, but yes this is a great school that I’ll tell my students about it.” I think part of why this happened is because I am a survivalist so I came to all these college tours with a backpack in case anything goes awry or I needed a sweater. So the combination of a backpack plus my hair in a ponytail and maybe some good walking shoes screamed “she is not a full adult she’s actually a high school student.”
None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?
It’s hard to just name one person. My family has been such a great support to me, so has my church, my village, my community, and my high school, but really I wouldn’t be anywhere without the support of my coaches and two of them really come to mind. The first one is XayLi Barclay. XayLi has not only pushed me in business, but as someone who is almost 10 years younger than her it’s so inspiring to see a very successful Black woman entrepreneur really doing business on her terms, staying close to her values, and really leading with a heart of service, while also still being profitable and creating the life that she wants to create. We both come from a Caribbean background, we actually have a lot of similarities in our background and so to see her really thriving has been really inspiring and motivates me. The second person that I want to mention is my purity culture coach, Linda Kay Klein. She is the author of the book Pure which discusses her experiences breaking free from Christian evangelical purity culture. She has really shaped a lot of my personal brand and really helped me empower women, especially women of faith, to boldly pursue their higher education and career aspirations.
Ok, thank you for that. Let’s now jump to the primary focus of our interview. According to this EY report, only about 20 percent of funded companies have women founders. This reflects great historical progress, but it also shows that more work still has to be done to empower women to create companies. In your opinion and experience what is currently holding back women from founding companies?
I think that women are still being held back from founding companies because of the unseen jobs that women have on top of their career. When you are an entrepreneur, everyone knows you are working basically two jobs, maybe three, wearing multiple hats. For the first few years of your start-up, you are really grinding. And when we think about someone devoting themselves fully to get their company off the ground, we are usually thinking about someone whose only responsibility is really to themselves. Unfortunately, for most women that’s not the case. Many women are not only trying to get their business up off the ground, but they’re trying to maybe deal with family, maybe they have children or a spouse that they’re taking care of, maybe they’re also helping out their extended family, their parents or their siblings. Women also traditionally bear the brunt of the housekeeping and the homemaking and women are less likely to get help with all of these day to day “life” chores. So when we talk about what’s holding women back, it’s actually this concept that even in a traditional 9 to 5 women are supposed to be able to work their job and then work a full-time home job. Because we have not stepped away from that mindset in a traditional corporate space, it is almost impossible for us to shift from that mindset when we talked about the entrepreneurial space. So in order for us to move into that mindset we really need to start understanding that it is not okay to continually expect women to work multiple jobs, only one of which may be paying them.
Can you help articulate a few things that can be done as individuals, as a society, or by the government, to help overcome those obstacles?
Many of the things that can be done as individuals or as society or the government to help overcome these obstacles, are the same things that needs to be given to women in corporate America. For starters, there needs to be more robust affordable childcare options. In many families, it was disproportionately the woman who was responsible for taking care of the children during Covid and doing the online schooling while also trying to balance their own work from home job. Even when we talk about women entrepreneurs there’s this belief that if you’re getting your business off the ground from your home you can still do childcare. I think that’s incorrect. Nobody can devote themselves to their business and also be a full-time mom at the same time as being a full-time homemaker.
On the individual level, I think there needs to be a greater cultural shift to encourage more men and spouses to step up. If your wife or the mother of your children is trying to get their company up off the ground then you might need to be a stay-at-home dad for a little bit. You might need to be to be the one in charge of managing extracurricular activities or baking the cupcakes for ballet class. We need to have a more thorough understanding of gender roles when it comes to parenting. I think the other thing that we need to do as a society is make more grants available to women who are trying to start small businesses and also make sure that that information is disseminated widely. There are a lot of funding opportunities, but many women might not know about them, or they might not feel like they have the skills or qualifications to pitch themselves to these competitions. I think that’s why companies like Thinkific,and the Think in Color Summit, along with their bursary programs, are so important because they are empowering women with much-needed professional development to show them how to enter a scene that was ultimately not designed for them.
This might be intuitive to you as a woman founder but I think it will be helpful to spell this out. Can you share a few reasons why more women should become founders?
As you mentioned earlier, only 20% of funded companies have women founders, however, women make up 50.8% of the U.S. population. It is important that women are just as represented in the entrepreneurial and business sector as we are in other sectors because when you have women in charge of companies it drastically changes how that company operates. Women have a completely different mindset, I might be biased, but I think that women are a little bit more creative, more innovative, more out of the box. Women just see things a little bit differently than men might and because we have had to fight for our seat at the table for so long, we are not afraid to break down the status quo and buck tradition. I think that women also are a little bit more empathetic in their dealings — not just at the top level, but all the way down even to the consumer base. When you even look at the global pandemic the countries that are run by women have had drastically different solutions and ideas for their citizenry than other countries. So we need more women to be in charge of these funded companies so that we can continue to have the diverse perspectives and representation in the boardroom and so that we can actually start to change the larger corporate culture and shift how companies interact with society.
What are the “myths” that you would like to dispel about being a founder. Can you explain what you mean?
There are two myths that I would love to dispel. The first is a myth that almost stopped me from even starting. And that myth was that you needed to have a safety net of at least three to six months (maybe even a year) before you launched full-time, and that you should not expect to see a profit in your first year 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. I actually was still financially supporting my sister’s academics as both my parents work two jobs. I come from a working-class background. 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. Is it better if you have savings — absolutely! Is it absolutely necessary? No, it is not.
The second myth is that you cannot maximize your profit while also aiming for the greatest amount of social good. I think that there’s this misconception, especially in educational consulting where people think that the majority of the money comes from working with wealthy clients. 91% one of my students identify as a first-generation or as a minority college or law school applicant. And I have tremendous success with them. Over 78% of my students have gone to a top 30 law school, over 56% of my students have received or have tuition scholarship to law school, 98% of my high school students get into one of their top three colleges. I love what I do, and I love the people that I work with, and yes, it is incredibly profitable. You can do good and you can make money at the same time.
Is everyone cut out to be a founder? In your opinion, which specific traits increase the likelihood that a person will be a successful founder and what type of person should perhaps seek a “regular job” as an employee? Can you explain what you mean?
Everyone could be a founder. I don’t think that there is anything intrinsic about someone where I would say no, you cannot start a business or no, you should just stay an employee. Rather, I think it is a mindset. I think that there are so many limiting beliefs that we tell ourselves. I think we tell ourselves that we should wait for permission to do something. Or we tell ourselves that we’re not yet smart enough to do something. Or we tell ourselves that we’re not yet credentialed enough to do something. Or we are afraid to put ourselves out there and all of those limiting beliefs will eliminate your ability to be successful entrepreneur. I think that also sometimes we let perfect get in the way of good. So for me, a lot of my success came from just doing things. When I was 26 and I pivoted full-time I didn’t have an option of failure. I actually had debts 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.
Life comes at you fast when you’re an entrepreneur, and you sometimes have to be able to make fast decisions. As one of my business coaches, Melissa Kellogg Lueck, would say, you make a decision and then you make it right. So if you make a decision and it doesn’t seem like it’s going in the right direction, it’s up to you to make it right. And I think if you have that mindset of, “I’m just going to go for it,” or the mindset that, “yes I trust myself, I’m going to bet on myself, failure is not an option” then it will work out.
You have to be willing to grind it out if you have to, because being an entrepreneur is a lot of work and if you think you’re going to work less than you worked in a nine-to-five, you are sorely mistaken. If you’re not really willing to grind it out for your business then this is probably not for you. I think if you have that grit and ability to bet on yourself you can totally be an entrepreneur. But if you prefer not to do those things and you prefer to just follow advice and check boxes, then it might not be the path for you.
Ok super. Here is the main question of our interview. What are your “5 Things I Wish Someone Told Me Before I Started” and why? (Please share a story or example for each.)
- Entrepreneurship will be the greatest exercise in my faith. Even before I launched full-time, I can vividly remember doing 21 days of prayer and fasting with my church. This was in January and I launched full-time in April/May. But I didn’t even know in January that I would be launching that year, I just knew that l so desperately to pursue consulting but did not believe that I could for all of those limiting beliefs I mentioned earlier. I did not have a safety net, I did not feel like I could afford that, and I had a lot of health issues, so I just felt like it wasn’t in the cards for me. I remember praying to God, and saying “God, if you just don’t let me starve on the streets then I promise I will use my business to expand your kingdom.” And what I can say is the transformation that I had in 2020 was nothing short of a miracle. Could not have been me. But what I didn’t know is that that was just the beginning of taking leaps of faith. At every single stage in my business, I have had moments where I have felt like I was in way over my head. I felt like I couldn’t do this and that it was too hard; I felt like I was going to fail or that I didn’t have enough money and I had to continually make decisions based on faith. I’ve had to continually say I really don’t know how that’s going to work out but we’re going to do it and we’re just going to see, and my faith has carried me through. I have learned that this is kind of maybe how it is as a business owner, maybe not always, but at least at this stage in my business it is all just one big exercise and faith, and I don’t think I really knew that going into it.
- I have to accept the unexpected. I have always been a big planner; I am one of those people that had lots of five year plans and many 10 year plans. However, the way that my life has been the last two years, I expect and accept the unexpected. I mean I will just start Monday and think, okay, I know how this week is going to go, and by Wednesday realize I was way off base because of a new opportunity, opened door, or development. We usually say the phrase expect the unexpected but I’m going to say the phrase accept the unexpected, as this new, unexpected plan might be even better than the original.
- I will never be as prepared as I would like to be. Going along with being a planner, I am also a survivalist; I like to be super prepared. It’s no secret that I am an over packer, that also my house is filled with lots of things on Amazon that is promised to make your life easier. However, I will never be as prepared as I would like to be in business. I don’t necessarily have as much extra cash flow, or staff, or time as I want, at least in this stage of my business. I am not going to be able to over pack for business and have extra sweaters and extra toothbrushes and all those just in case items, that’s not what entrepreneurship is. Entrepreneurship is making the best out of maybe not having quite exactly what you feel you need to be prepared. It’s important to recognize that you do actually have all that you need.
- I do not need to follow someone else’s playbook. When I first started, I really looked to the industry for a lot of my playbook. I am 27, and although I have been consulting since 2012, when I first went full-time was still really looking to other more established businesses for how I should run my business. But I really had to learn that the type of business I am running was not the type of business that is traditional in this industry, and that’s okay. I wish that I would have trusted myself more when I first started, instead of looking for validation and acceptance and approval from the industry and other professionals. I needed to realize that there was no one playbook and while there are so many consultants who coach other consultants on how to run their business, there really is no playbook for your business.
- There are no rules (or rather: I make the rules). The other thing that I wish I would have known is that there really are no rules, or rather I make the rules. This is a slightly different point from my last point. One of the things that I was really interested in doing early on was finding ways to blend my faith into my business. However, I thought that that was against the “rules.” I thought that you had to keep the separation between business and faith or your personal and your professional life. I was working so hard on creating the separation that I think, at the beginning, I didn’t capitalize on what makes my business so unique, and what makes me so unique. However, during the pandemic in October 2020, recognizing how stressful it was in this country, recognizing the stress of the pandemic, the stress of the election, the stress of the application process (law school applications were up over 30% last cycle), I really wanted to do something to ease people’s stress. XayLi had pushed and encouraged me to start doing lives, however, I didn’t know what I wanted to talk about, but I knew that I was tired of people feeling so stressed, so I started doing daily live prayers midday prayers for students, and the response that I received was overwhelming. I received such positive response even from parents and families who were not Christian that just the centering and the mindfulness really seem to help. That moment of doing daily prayers for students actually enabled me to launch my first podcast, Mindful Prayers for Students. When I started leaning into my faith, people started seeking me out. They would say, “oh you’re the girl that prays over the applications, can I work with you?”. Even now in my Facebook group Barrier Breakers: Law School Edition, at the end of every live Break Into Law School episode on YouTube, I end with a prayer. I’ve held waitlist prayers, I’ve held prayers for the LSAT exam, I’ve held prayers for just a number of different things, and it really has just sparked this movement among students and among applicants that there can be peace in this process. I don’t believe that the application process needs to be stressful, and I would love to help infuse more mindfulness into it and more mindfulness into education as a whole. I would not have gotten to this moment in my business if not for rejecting the rule of separation between church and state, and leaned into my religion and into my background.
How have you used your success to make the world a better place?
As I mentioned earlier, over 91% of my students identify as a first-generation or minority applicant for college or law school. Specifically, looking at law school admissions, I have worked with over 100 law school applicants at this point and I think that the work that we’re doing and the success that I’m seeing with my students is going to radically shape the legal profession. In the United States, only 5% of lawyers are African-American regardless of gender. Black applicants borrow more for law school and still tend to make less after law school. In fact, Black applicants on average borrow 97% more than their white counterparts for law school. There is a lot that needs to be done in terms of equity in law school admissions and I believe that my company is part of the solution by providing quality and ethical law school consulting across the spectrum to a myriad of students.
I have a free Facebook group, Barrier Breakers: Law School Edition, which supports first generation and minority law school students and helps increase community for them whether they work with me or not. In that group I also host the free Break Into Law School live stream and podcast. I also have a free 62-page Essential Guide to Applying to Law School, which is my contribution to ethical and quality information dissemination. One of the other things more unique about my company is that I actually have a community called Beyond Barriers that connects my high school, college, law school, and working professional clients and former students together so that they can have mentorship. As a first-generation lawyer, I understand how important it is to have guidance and mentorship, especially when you are the only one or the first in your family to go to law school. I think that community helps you thrive in law school, because it’s not enough that we’re getting more minority students to law school, it’s important that they’re graduating, it’s important that they are making smart career choices, it’s important that they’re making smart financial choices and avoiding unnecessary debt,, and it’s important that they’re able to have upward mobility in their career, and those are the things that my company helps support.
You are a person of great influence. If you could inspire a movement that would bring the most amount of good for the greatest number of people, what would that be? You never know what your idea can trigger.
Actually, this is something that I think about a lot. I know that I speak a lot about diversity and equity in higher education, but the more that I do this work, especially as my company is faith-based, the more passionately I feel that we need to have a shift in mainstream Christian culture and young adult campus ministry. If I could inspire a movement that would bring the most amount of good for the greatest number of people, I would love to start a movement where Christianity and the Church could be seen as a more liberal, social justice, womanist movement where we are empowering young people and inspiring Millennials and Gen Z through encouragement and love. I want to be part of a national conversation reversing a lot of the rhetoric of shame and judgment too prevalent in young adult campus ministries today. I think that there are so many people who are looking for encouragement and looking for acceptance and validation, and perhaps looking for them in the wrong places. Mental health issues are on the rise in this country and they’re especially prevalent with younger students. We see that this a lot more with the pressure high school students face to get into a “good” college. When I was at Princeton, the rate of depression in the student body was over 60%. As an attorney, I see this as well as attorneys have high rates of mental health issues, whether that’s anxiety or depression, and alcoholism runs rampant within the profession.
At the backdrop of all of this, a lot of mainstream Christianity is not actually helping this issue. Rhetoric pushing these feelings of shame and doubt within young people at pivotal points in their life is only pushing them out of the church. I would love to see a movement in which the church could be the hands and feet of Christ, and actually love and encourage people and help people and their brokenness. I think we need more light in this world, whether that is Christianity or Buddhism or Judaism or Hinduism. I think that we are at a place where society is so divisive and anxiety and fear especially with the pandemic and the economy (not to mention global warming and climate change) have taken over. It has been personally frustrating for me to see the church not step in and offer more peace and encouragement during this time, so if I could inspire a movement, I would inspire a new wave of liberal Christianity and Christian theology that actually helps, not just through teaching but also through more service opportunities. This could be helping families on welfare, helping more with the homeless, helping more with child abuse and neglect, helping more with domestic violence victims, helping more with student loan repayment and financial literacy, and even helping with homeownership. I think that there’s just so many more ways that we can be helpful in society rather than continue to exacerbate divisions.
We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch, and why? He or she might just see this if we tag them.
I would love the opportunity to get to talk to Sheryl Sandberg. Last year Bloomberg wrote an article about how Sheryl Sandberg stated that business barriers for Black women were on the rise during the pandemic; she cited a lot of reasons for that in the article. I think that what Sheryl Sandberg has done with Lean In, her work empowering women and her willingness to speak about the barriers faced by Black women in the corporate space publicly is so inspiring to me. I would love the opportunity to learn from her and learn from her wisdom. I specifically remember this moment during my college years; I was in Boston for an internship and went to a Princeton Association of New England Women’s Network event. The women were all talking about Lean In — her book had just come out and it had really empowered them to continue to use their degrees even long after motherhood. When I looked at the statistics of the number of women who left the law or the number of women who were unable to rise in the legal field because of their gender or familial responsibilities, I knew that this was a larger conversation worth pursuing.
Thank you for these fantastic insights. We greatly appreciate the time you spent on this.
Sydney Montgomery of S Montgomery Admissions Consulting: Why We Need More Women Founders & Here Is… was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.