For Financial Professionals in the US

Invested in Connecting Women: Rock the Street, Wall Street Sparks Girls’ Interest in Finance


May 13, 2022

On this episode of Invested in Connecting Women, host Olivia Hails speaks with the COO of Rock the Street, Wall Street, a financial and investment literacy program that aims to inspire a diverse population of young women in high schools across the country to pursue careers in finance.

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Olivia Hails: Welcome back to the Invested in Connected Women podcast. Today I am thrilled to be joined with Ashley Leftwich, COO of Rock the Street, Wall Street. It is a booming nonprofit that is laying a red carpet for young women to take interest in financial literacy and really the financial career path in general. I think that their tagline beautifully sums up their purpose: “Change who we invest in to change what we invest in,” and I love that.

I’m your host, Olivia Hails, and this is Invested in Connecting Women.

There’s nothing more that I love than women of action, women who turn their passion projects into visions, into an incredible powerhouse of change for the common good, and that is exactly what Maura Cunningham did nearly 10 years ago when she founded Rock the Street, Wall Street and stepped away from a 25-plus-long career in financial services. So why Rock the Street, Wall Street? Well, according to their research in the U.S., we start to lose girls in math classes as early as age nine. We know that 80% of teachers self-report that they don’t feel competent enough to teach financial literacy in the classrooms. There’s an existing wage gap, say no more. And women make up two-thirds of the student loan debt in the country now. And then finally, women make up an extremely small percentage of our industry. I know what I do for a living as a financial wholesaler, there’s only 14% of us that are women. You look around, it’s 2.5% of hedge fund managers that are women, 8% venture capital partners, 9% mutual fund managers, 12% private equity. I could go on and on.

So with all of that, without further ado, Ashley, thank you for being here with us today on the Invested in Connecting Women podcast. I’m excited for you to be here to share about Rock the Street, Wall Street but also your own personal journey that’s brought you here as the COO.

Ashley Leftwich: Oh, thank you so much for having me. You know, it is an interesting journey and you’re absolutely right as far as that real struggle between being able to do what you’re truly passionate about as your job. And the journey to get here was a very interesting one in the sense that I actually started out on the corporate side. So I was with a Fortune 100 company, was the top salesperson for North America, created brand standards for this company and had the opportunity to transition over to the nonprofit sector. So of course, I seized the opportunity and went ahead and jumped in. After working at another nonprofit, I found my way to Rock the Street, Wall Street, which has been just a perfect alignment for me. I come to Rock the Street, Wall Street very genuinely and, actually, as you and I had discussed before, I was the only woman in my math class at a very large university of over 40,000 students and it was just me and 40 men. So we all have probably seen that exactly. And it is something that I’m personally passionate about because I did grow up in an affluent area and had the opportunities that many of our students did not and I still had no idea that these finance careers existed. So I am so grateful to be with Rock the Street, Wall Street. I’ve actually been here for three years and have taken on the COO role and it is a joy to work with the individuals that we have on our team and with all of our partners.

Olivia Hails: Awesome. So in preparation for this interview, I have been … I mean, I see financial advisors every day in my job, right? So I’ve been kind of dropping the question like, “Hey, do you know Rock the Street, Wall Street?” And it’s been about 50/50. So I’m really excited for this episode too because I just, I’m like shouting from the rooftops. When I found this organization and found out what you all were doing, I was like, “Everybody needs to know this and this needs to be adopted by Washington, D.C. and every single state, every school, especially those that aren’t in affluent areas and don’t have opportunities to see what money can do in a lifetime.” So tell us about Rock the Street, Wall Street.

Leftwich: Rock the Street, Wall Street is a financial and investment literacy program that is specifically designed to spark the interest of a diverse population of high-school girls. So we’re really serving a dual mission both in the financial and investment literacy as well as in diversifying the talent pipeline. And our program actually runs throughout the full academic year and is very comprehensive in the sense that we have financial investment literacy workshops in the fall and then a field trip to a local financial institution, and then mentorship, which I feel like many of the individuals that are listening to your podcast can probably attest to how important mentorship is and having that social capital. And we actually don’t stop there. We continue to connect with them even after the academic year through our alumni connects and an internship and job portal so that they can actually have a pathway into the industry.

Hails: And correct me on the numbers if I’m wrong here, so you’ve been in existence for nearly 10 years. Is the 10-year this year?

Leftwich: This is our 10th year.

Hails: 10th year, alright. That’s amazing, so a full decade. And you’ve had over 4,000 young females graduate through your program, is that correct?

Leftwich: Yes.

Hails: And that’s, I’m assuming, very rapidly growing?

Leftwich: It is. You know, this year, we actually were in 51 schools across 26 cities, one of which was Vancouver, Canada.

Hails: Nice.

Leftwich: Yes, and we are continuing to grow, really thanks to the genuine interest in the industry. Women like yourself have really taken an interest and been able to join us, catapult us, be our volunteers. We actually have 100% female financial professionals that are volunteers in the classroom, which is so important that we have that identity-based modeling for these girls. And the girls are choosing to be a part of it with their friends, which helps us get to that wonderful number that we have been able to reach and just continue to grow. We’ll actually be adding six additional cities next year including Honolulu, which I think is fun.

Hails: Yes, hopefully you’ll get invited to go help train those folks.

Leftwich: Yes, I will take either.

Hails: Yes. Alright, so I want to unpack that a little bit before we do that, just so that our listeners are on the same page. How do you … so when you say you move into a new city, what’s that process – because you are sponsor-based, right? – to enter into a new school? So let me hear a little bit more about that process and then I definitely want to get back to how you get young females involved. Because at high school, it’s a little bit of a herd mentality. So we’re going to jump into that next, but how do you move from, you know, grow into a new city?

Leftwich: Yes, so usually, that is something where we have a financial firm or a foundation or someone that really is passionate about our program and bringing it to that city. So we do look to have a pocket of volunteers, usually from a financial firm that’s sponsoring or from many of the other affiliate organizations that we have relationships with or individuals that reach out to us to volunteer. So if we have a presence there for those volunteers and the support, we do look to launch into that city. And then we look at schools to be able to have the program and really find those that have a genuine interest in what we’re doing.

Hails: Yes. How long does that process typically take? It may be subjective, but I’m just curious.

Leftwich: It does definitely depend. As far as the conversations that individual firms and to have sponsors, that’s often something we’re building a relationship. Sometimes it’ll be something like where we have a firm that comes on board and starts with multiple locations and then continues to grow their footprint or starts with one and continues to additional cities where they have large pockets of employees. So sometimes it’s very organic within an internal network of the firm that that relationship gets built. But oftentimes it is something where those relationships with the affiliated organizations really come in to help us.

Hails: Find the school and, yes, connections. OK, I can see that and I love that. So you’re going in when girls are between ninth grade and senior year and you are offering a year’s worth of an elective of financial literacy, right, to really throw yourself in and learn about a whole side of the world that you didn’t really know about. I know if I think back to my high school days, I mean I actually liked math so I guess I was one of the norms. I know you did, too. We’re both, you know, I work in financial services, but I would have never attributed my enjoyment of math to do something like that. I would want to know if my girlfriends were doing that. And if they were doing it, why and how they get involved? So you know, that can be a difficult group of women to work with. They’re just extremely influential, right? They can be influenced easily. So tell me a little bit about that process of, you get a full class.

Leftwich: Oh yes, there’s a lot of different parts to that one, so I will share that. One of the things that works out so amazing is that we have a great programs team that works out the logistics at the school. And part of that is by having what we call a school champion. So someone that is on the school staff that really gets us, a math teacher, an economics teacher, a business teacher, a guidance counselor, someone that can really be on board and share it to the girls. So that’s probably the first step in making sure that we’re finding that right school partner. And then you are absolutely right as far as it being something that we want their friends to join in with them and see. The actually top two reasons why girls are not choosing to go into STEM professions is because, one, they don’t see women in that particular industry. And two, they don’t see their girlfriends choosing that. Those are the top two reasons.

Hails: Right.

Leftwich: We can address that.

Hasil: Yes, easily, yes.

Leftwich: So our program does that. And really, we have it set up in a sense where it’s something that’s fun for them to participate in with their friends and we accomplish that by a couple of different ways. We always make sure that our curriculum is pulling things straight from the headlines, things that are current events, things that they care about, things that they’re seeing, because if there’s one thing about high school girls, you got to keep it relevant.

Hails: Yes, I did watch your recruitment video, and was like, “Oh, this is so with the times because this is … I feel old watching this.”

Leftwich: I had the same feeling and I was like, “It’s perfect.” It’s the perfect video. So for the different curriculum pieces, we actually do have things that are very relevant to them, they’re actually acting as a financial advisor so they’re doing a hands-on project with a group of other girls. They’re connecting with their friends, they’re making new friends and it really is something where they’re getting to socialize with each other in that kind of more club-like environment, even though it is something that’s usually is during the school day.

Hails: Right. And tell me a little bit about your curriculum because I know you mentioned there’s three different sections. And when I think back to, you know … I’ll just say just for pure reference, my high school experience, there was never finance. There was an econ class maybe, but there was never finance or definitely not personal finance. So when I think back to not only the subject, it was just math or physics, something of that nature. I had absolutely no idea what kind of career paths even existed in the financial world. And it wasn’t until I had been at Janus Henderson for several years that I was like, “Oh, wow, there are so many things you can do here.” And I still feel like every day I’m learning a totally different level of career options. So is there a part … I mean, I know there’s a part where you discuss careers, but tell us a little bit more about that section.

Leftwich: Yes, so we do have the curriculum sets that you mentioned and we have multiple curriculum sets because we like to build a relationship with the school. And we have girls that will re-enroll with us year after year, even though none is a prerequisite for another. So they’re actually learning different concepts in regards to their investment literacy within those. And so they’re, it just depends on how old their client, their fictitious client is that they are advising, and sometimes she’s in her late 20s making decent salary and they’re looking at her long-term and short-term saving and investing and risk assessments. And sometimes she’s later on and they’re doing a stock analysis. So it just depends on that side of things. And in each part of the program, we make sure to talk about those different career opportunities that are within finance because there’s so many. You don’t have to love math and be math nerds like you and I were. I mean you really can, or I should probably say, still our mathematics. You really can just lift the veil on the fact that many careers are not much more than first-year algebra for them. So we do have quants and we do have things that are more embedded into math, but these girls can find this to be something that’s really attainable for them and we’re really exposing them to those opportunities. I mean, with female financial professionals being our volunteers, they’re learning about their careers, what their roles are in finance, but we also have a particular section in the curriculum to make sure that we are showing them multiple different career avenues within finance. And that spring mentorship, that’s incredibly valuable. We actually even have a career test on our website where they go in and see their results for suggested careers within finance.

Hails: Gosh, I wish I could remember what the results of my career path would have been at 18. No, it probably would not have been what I’m doing today and I’d be grateful for that. But I would love to go back and see what those were. But you’re right. The career opportunities are really endless and the reason why I think you rarely see … you know, we always try to address, I know Janus Henderson and several other asset managers, we’re always looking to address why, how do we get more women in the business? The latest statistics I looked at where, you know, 14% female financial advisors. It ranges anywhere from 15% to 20% depending on what source you’re looking at. There’s several of them out there. But at that phase, finance is already intimidating in somebody’s mind, especially a woman, right? It’s like, “That’s too much for me. I’m not a math person.” And that’s when I have to kind of shake my … some of my friends that I have this conversation with, and say, “The world is your oyster in this business.” You know, if you can get yourself licensed and then you start educating yourself and then you realize how almost just infectious it is, like there’s so much to learn. You could just learn every, you learn every single day. And for me, I love that because no two days are the same and there’s always something to learn. And the markets, especially the way they’re behaving right now, they’ve never behaved like this before. This is all new. So there’s just so much that you can get ingrained in, right. So I just absolutely love that you all didn’t say, “Well, how do we solve this problem?” You said, “Well, how did we even get to this problem? And let’s go look at the source of that problem and provide a solution there,” which is exactly what you all are doing, and I just can’t commend you enough for that. And I know it’s got to be fun. But with all of that, because we have numbers in our business so much, how do you measure success at Rock the Street, Wall Street? And I know that’s probably not a one-word answer. But how do you when you all are all together and looking at year-over-year, let’s say, how do you measure success?

Leftwich: Yes, well, you know that we’re data people. So we certainly do like to measure that. And how we do that is, in the fall we have a pre- and post-test to actually gauge what their financial and investment literacy increase is. And we find that the girls actually are increasing on average by 78%. That’s incredible.

Hails: That’s incredible.

Leftwich: And then we continue to track them into college because, as you can imagine, we are looking for these girls to continue on into the industry. So we actually sample them through a company called the National Student Clearinghouse to see what they choose to major and minor in in college. So we look for them to be in finance, economics or a related business computational field, and actually find that our alum are pursuing those degrees at five times the national average for women in college. So it’s great to see not only that they are indicating back to us that they are interested in majoring and minoring, but they actually are choosing these as majors and minors.

Hails: Yes, which is a great measurement, I would say. And with only less than 10 full years, those numbers are just going to continue to grow and get better, I assume.

Leftwich: Oh, absolutely. Because when we started 10 years ago, we were just in one cohort, just one school. And since then, our most growth has been in the recent years. So as we keep getting larger and larger each year over year, we’re going to see more and more girls going into college and really seeing that change.

Hails: Alright, so let’s talk about Ashley as a part of Rock the Street, Wall Street, right. I know that in the short time we’ve known each other, that you wear many hats and that you are pulled in probably more directions than you’d like to be. But what are the contributions that you feel that you’re directly making to the organization?

Leftwich: We have a lot of really exciting things that happened here at Rock the Street, Wall Street and it absolutely is a team effort and I am so honored to be able to be the one that’s a part of the team in that aspect. So we have a programs team, we have a partner engagement team, we have marketing teams, and we’re all working to make these goals happen. So one of the contributions that I feel like we have collectively all come together on is the Student CEO piece. We actually added that this past year and it’s a leadership role that’s within each of the schools. So we typically have two Student CEOs and they actually take on a role in recruitment and a role in organizing and choosing which snacks. You know, these important things that certainly do drive high school students to engage with us. And we actually have leadership summits for them throughout the year. So we’ve had the most recent leadership summit, we had a CEO come and speak virtually across all of our cohorts and really share about what it looks like to be a leader and what pieces they would pass on to them. So these are really incredible opportunities that have just launched this this past year. And then we also had a Rock the Street, Wall Street app. I actually have a probably more unique background in the sense that I did have a formal education in business administration and then went on to get my Master’s in marketing and information systems because both of my parents are computer programmers. So I kind of have like this logic/IT mindset, and we launched an app because that is where the high-school students are, on their phones for a lot of it, so we need to be where they are. And so we launched a Rock the Street, Wall Street app so that they have many resources there right where they are usually looking. And I think that is certainly something that has been a great contribution.

Hails: Yes, I want to talk about the Student CEO just because as you were talking about those girls that you’re choosing and the journeys that … leadership opportunities. And speaking in front of all of these people, do you find that some of these Student CEOs were more introverted before they got the opportunity to do this? Or are you getting those class president leadership [types] already and you’re just further developing them into a field? Or is it both? I’m curious, just because as you’re talking to them, is this pulling people out of their shells as well?

Leftwich: It is. So we actually are seeing both. And it’s interesting whenever we have both in the same school because we do have two. So the girls actually interview with us, which already is something that many of them are stepping out of their comfort zone to do. And it has been incredible because we actually just opened our Student CEO applications for next year and so those interviews are underway and always something that’s exciting to listen in on trying to make sure that we don’t make the students nervous that someone else is listening in. And just such a joy to hear because they are coming from completely different places. I mean personally, I was not the class president, but I was one of the club presidents and I still remember whenever it was time for me to address the whole student population about what my organization, within my club, was doing, and really being nervous. And I do a lot of public speaking now, really being nervous, and I walked up there and then I was just talking from my heart and it was wonderful and glorious and felt so rewarding. So many of the girls share back feedback where they’re, they didn’t think that this is something that they could do. And then they’re like, “No, I can really do this. This is really something that I’m interested in.”

Hails: I love to hear that. I will say when I look back to high school, it’s not the algebra that I remember, it’s not the exact dates of, you know, AP History curriculum or whatever it may have been. It’s those life skills that really carry you through college or entering the workforce or travel that, to me, that’s what gave me the most value and I think prepared me the most to really move into life was those life skills.

You’re absolutely right. And what’s so great about the program, too, is we’re really showing the girls both how it can have an impact on themselves and their families, but also how these skills can have an impact on their community. And how through these careers, through this knowledge that they’re gaining, they can really take that and transpire it into something so much bigger and fulfill their passions through finance.

Hails: Yes, which is just amazing. I get all giddy and get chills about it because it’s just … the opportunity that you’re putting in front of young women is incredible. And I know that people listening to this will want to support you. They will want to get involved. And with that, what’s next for Rock the Street, Wall Street? I know we’re about a couple months into the year – what’s next? What are you most excited about moving forward?

Leftwich: So many things to be excited about. But I think that one of the things that I’m really excited about is that we are expanding again into these additional cities and going transatlantic to London and really starting to see this outpouring from the Students CEOs and from those that are within the schools and really seeing that support line coming from many, not only within the school system, but also within the industry. And we certainly would be thrilled to have everyone engage with us in some capacity by signing up to be a volunteer. If you’re interested in having a “Girls Rock Finance” shirt, we can certainly show you where that shop is and really be able to bring in on the fact that this is something that we have seen this growth and been able to reach more girls because of you. Because you are sharing and getting the word out about Rock the Street and really helping us to not only bring on additional individuals that help us with funding and with volunteers, but also with those connections into firms and affiliate organizations.

Hails: Yes, and I love that you have multiple different layers of opportunity to get involved. A sponsorship level, and then if you become a corporate sponsor, your employees are now eligible to be the instructors and the teachers and the mentors. What other opportunities are there to volunteer if it’s not … let’s say you’re on the corporate ladder and you’re not sure if you can get that sponsorship quite yet, are there any other opportunities to volunteer?

Leftwich: There certainly are. And those opportunities are usually where we have a foundation or find funding that is from a different source than a financial firm. Also, if you can believe this, many of the financial firms that we may have that support us actually don’t have enough women in those roles to volunteer. So then we look to reach out to those that have said that they were interested in volunteering. We also have that internship and job portal that I mentioned, which is seeing massive growth and has over 120 opportunities listed on it. So it’s free to post on. I would welcome everyone to post on that as well because any opportunities that could potentially be for our students to continue on into the careers, whether it be high school or college internships or entry level jobs, those are certainly things that our students and our alum would be interested in.

Hails: OK, so that’s on your website that people can go to and post jobs if they have them or interact through you all internally, or…?

Leftwich: It’s on the website. So you can go to and you can go to Contact Us and select that, and we’re happy to connect with you and walk you through that or you can see the internship and job portal right there and create an employer profile.

Hails: I love it. Alright, and as we always do on the Invested in Connecting Women podcast, we like to end lighthearted and have some fun and just get to know a little bit of “off-the-cuff Ashley.” So we’re going to do my lightning round of questions here. I’m going to throw a couple at you and just give me what you got back as quick as you can. Ready?

Leftwich: Yes.

Hails: All right. What’s the fastest speed you’ve ever driven in your car?

Leftwich: 80.

Hails: Oh, that’s it? Come on. Got to live on the wild side a little bit. Last long that you listened to?

Leftwich: Oh, not lightning round.

Hails: Or one of your favorite songs. How about that? A favorite song?

Leftwich: Yes, probably … my husband is a singer/songwriter, so it makes it really difficult.

Hails: Oh, yes. You’ve got to be careful on this one, huh?

Leftwich: Yes, exactly. But more than likely one of the traditional ones. I do actually really love music. It’s really difficult to choose.

Hails: I would agree with you on that. I would say if I had to choose like a favorite artist, it would probably be Led Zeppelin.

Leftwich: That’s always a good one.

Hails: That’s just like a top down and then go from there. But that’s, it’s one of the perks of living in Nashville is it’s everywhere. You can get good music everywhere.

Leftwich: Yes.

Hails: Alright, one more for me. I like this one a lot. When people stand for an ovation, are you one of the first ones to stand or are you one of the last ones to stand?

Leftwich: Probably the first.

Hails: Yes, join in with the crowd.

Leftwich: I’m enthusiastic, yes.

Hails: Alright, so you can throw a couple back at me if you want.

Leftwich: Yes, hiking or spa day?

Hails: Oh, spa day. I lived in Colorado for 10 years, I got it out of my system.

Leftwich: That’s absolutely … it’s beautiful out there. Milk or dark chocolate?

Hails: Oh, definitely dark. Hands down, dark chocolate.

Leftwich: OK, and then mountains or beach?

Leftwich: See this goes back to Colorado. I definitely got to say beach now because one of the biggest things I missed when I was living out there was, “Okay, this is a reservoir, this is a reservoir, this is a reservoir.” I need to see the ocean, I think there’s nothing that the salty air can’t fix in my life, so we’re going beach, but sure do love those mountains and the fresh air.

Leftwich: Same. I think that is great in both places.

Hails: Alright, Ashley. Thank you so much for your time today. Thank you for the work that you’re doing and setting a path for women that may feel stuck in their roles in life. It is possible to find a role that combines the head and the heart and just does so much good for the community and the community at large – the globe even, right. We’re going to London across the pond so kudos to you and the rest of the Rock the Street, Wall Street. Don’t stop what you’re doing and thanks for being here today.

Leftwich: Thank you.

Hails: Until next time, I’m Olivia Hails and this is Invested in Connecting Women.

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May 13, 2022