Executive Spotlight: Maura Cunningham, CEO and Founder of Rock The Street, Wall Street

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Stewart: Welcome to another edition of the InsuranceAUM.com Podcast. My name’s Stewart Foley, I’ll be your host. And today’s topic is financial literacy for young women in high schools across the United States, and we’re joined by the founder and CEO, Maura Cunningham from Rock The Street, Wall Street. Maura, welcome.

Maura: Thank you. Thank you so much, Stewart. I’m looking forward to this.

Stewart: It’s going to be fun. Just as background for our audience, we do pro bono podcasts for folks who we think are doing important work. Right? We did a podcast with Jelani Fenton from Safari, that does talent incubation for the insurance industry. We did a podcast with Dion Woods from the DIME Program, who works with 11th and 12th grade youth on financial literacy. And you and I met at a 100 Women’s event hosted by our client, Ninety One, and you were kind enough to give me a T-shirt that said, “Girls Rock Finance.” And I took a picture of it, pointing at my CFA certificate and got something like 4,000 views on LinkedIn. So, thanks for that.

Maura: Wow.

Stewart: Thanks for that. I want to start this off the way we start them all. What was your hometown, your first job ever? Not the fancy first job. And a fun fact.

Maura: Oh my gosh. Okay. All right. My hometown is the Bronx, New York, very proud Bronxite. My first job was at a deli in the Bronx on East Tremont Avenue in Throggs Neck. I was behind the counter and I loved it. I worked on weekends and opened the store from like 6:00 AM till 4:00 PM, I think my shift was. Cut a lot of deli meat and served a lot of people and really, truly enjoyed it, because you got to meet the locals.

Stewart: Absolutely. Yeah.

Maura: And you got to chat with a whole range of people. And I haven’t thought of this in, God, decades, but yeah, I really enjoyed it. And then, what was the last part?

Stewart: Fun fact?

Maura: Fun fact.

Stewart: What’s a fun fact?

Maura: Oh, okay. I would say a fun fact is that most people don’t know that I whitewater kayak.

Stewart: Nice.

Maura: And I love it. I was born and raised in the Bronx and went to Wall Street and we’ll talk about that in a few minutes, but then I moved to Tennessee 20 years ago and I was fortunate enough to take up whitewater kayaking about probably 12 years ago, maybe more. And we’re a great state for whitewater kayaking, particularly down in the southeastern corner, where the Ocoee, the Nantahala, and the Hiwassee rivers are. So, I’ve become a real outdoor enthusiast in my later life, including hiking and biking, and all of the things.

Stewart: Oh, that’s cool. No, that’s a great fun fact. We share a couple of things. You’re not only a first-generation American, but you’re a first-generation college student and I am as well. And I think that’s fueling your passion for this project Rock The Street, Wall Street. Can you tell us about it?

Maura: I’d be delighted. So, you’re right. Coming from the neighborhood that I came from and the Bronx too, most of our parents were off the boat, as they would say. So, our enclave was mostly Italian, Irish, German, and then a little bit at the time, Hispanic, mostly Puerto Rican coming in. Our parents had no clue about life in America, other than what our kids were bringing home from school, but they knew that they wanted a better life for themselves and their kids. So, they came to the United States for that reason.

So, my father literally came to America with nothing more than pretty much the shirt on his back and then saved enough money to send for my mother to come over, for passage for her to come over. And so, she came over about three years later. So, it took about three years for him to save up the money. And so, I was fortunate enough to go to Catholic schools there in the Bronx.

And my father, he worked three jobs and he would, quite frankly, in between the jobs, which were taxi driver, bartender, and soda jerk, as they called them, he would sleep at movie theaters in Manhattan in between the jobs. He wouldn’t be able to even come home.

Stewart: Wow.

Maura: And so, subsequently though, he made his way up to, I don’t know if there is such a thing, but lead bartender at a very well-known pub in Manhattan, that actually they named the street after him on 57th Street and York Place. And among many patrons was Mike Bloomberg.

Stewart: Oh, wow.

Maura: Yeah, I mean, the blue bloods and all of Sutton Place would come. So, he made his way up, but he was again, just the bartender, was not the owner. In any event, I could see he knew nothing about finance. And thankfully though, my mother knew how to keep a checkbook. And so, it was my mother who kept the checkbook. And that’s all that they knew. They really had no idea how to invest and no one really in our neighborhood knew how to do any of that.

And then I was fortunate enough to be paired up with some young women also in school, who were very, very, very bright and we all had careers and then they just throw up their hands when it came to investing. I’m like, “You can do this. I mean, this is nothing more than sixth-grade math.” Right? But they would just throw up their hands at it, and I’m like, “There’s a problem here. We got a real problem.”

And then when I got to Wall Street and saw that I was the only usually producing female in the office, I thought, “Wow, there’s something wrong here.” So, I was fortunate enough to retire at an early age. I retired about 13 years ago, and then I traded options. I traded options for my own account. And then after three years of doing that though, I thought there had to be more to life than this. So, I went back to school and got my master’s in civic leadership, thinking I was going to go into public administration. I did my thesis on girls and math and how we lose them at age nine in the United States, some would say as early as age six in the United States. And we don’t have this problem in China, Russia, India, Asian countries, and even in Eastern European countries. And so, this is clearly a cultural issue, not a capability issue. So, I want the girls back. So, we are addressing this in the high schools where they begin to have a better appreciation for money. We did launch originally at the nine-year-old age, but they really had no concept of money. So, we mopped it up to the high school level for that reason. And then Eureka, I mean we founded this Rock The Street, Wall Street over 10 years ago. We’re celebrating our 10th anniversary actually this year.

Stewart: Congratulations.

Maura: Thank you. And we’re now in 62 high schools in the United States, in 34 cities, I should say, across the United States, Canada. And we just launched in the UK-

Stewart: Good for you.

Maura: … this past fall. Yeah.

Stewart: Good for you. So, what are we doing wrong, losing girls at nine in math? I mean, my background is I taught for a number of years, I found real talent, not only with female students, but underrepresented groups that you see not a lot of on the street. What are we doing wrong?

Maura: So, it’s a great question. I’ll tell you what the research says and I believe it absolutely to be true. So, here’s the result, first, let me tell you what the result is. So, I, in my college math class was the only female in my math class of 34 men and me, and we won’t say how many years ago, but it was quite a few years ago. Let’s say it was, I don’t know, two and a half, three decades ago.

And fast forward, my chief operating officer, who is Ashley Leftwich, she’s a generation younger than me. She was on a much bigger college campus than me. She was at the University of Georgia, 40,000 students. 40,000 students. She was the only female in her math class. And so, this is the silent killer as to why there aren’t more women in STEM. And so, we are bringing the M of STEM to light. We are letting it have the light of day. No one is talking about this. You mostly hear about the T and E, tech and engineering. Well, guess what? You got to get them into math in order to get to T and E.

Stewart: Absolutely.

Maura: So, it starts very young, Stewart. So, the research shows that if mom and dad have a boy and a girl, and if mom and dad have stereotypical roles, mom and dad are still suggesting to the daughter, “Study dance and literature.” And to the son, “Study math and science.” And that’s still happening, still very pervasive.

Then the girl gets to elementary school age, where 90% of the elementary school teachers are female, who have little to no certification in math. And so they will actually say, “I hate math. I can’t do math.” Or, they display anxiety in doing math. And the University of Chicago has done 12-year longitudinal studies on this and they’ve sliced it and diced it a number of different ways. This affects the girls in the classrooms, but not the boys in the classrooms. And so, the girls begin to think that it’s societally acceptable for them to opt out of math.

Now the girl gets to middle school. In middle school, she hears the girls actually saying, “We can’t do math. I don’t have to know math.” And so again, they think it’s societally acceptable for them to not know math, which is not true in those other cultures whatsoever. They are pushed on math. Then the girl gets to high school. So, now she’s heard this for 10 years, a decade of, “We don’t have to know math. We can’t do math. Why even bother.” Right?

Stewart: And she might be behind already.

Maura: Right.

Stewart: Right. Yeah.

Maura: Too. So, now she’s in high school. And even more so the girls are saying, “We don’t have to do math.” I actually heard it said, “Our boyfriends will do it for us.” I’m not kidding. I’ve actually heard this and I’ve had to address this firsthand. And so, no wonder why there are only 1 in 10 women in the finance and economics classes still today. And so, I’ve asked the industry, when I first got this launched 10 years ago, “What is the definition of insanity? Doing the same thing over and over again and expecting a different result.”

Well, the industry keeps thinking that they can recruit women and underserved populations, minorities, at college. Well, you know what? You will never ever broaden the pipeline if you wait until they get to college, because they’ve already opted out. They don’t even know that we exist. They don’t want it. They have no clue that this is something they can do.

As I mentioned earlier, it’s nothing more than sixth-grade math for the most part, 98% of us in the profession, I know we have our algorithms and quants, we’re fully aware of them. Some of them sponsor us. Fully aware. But 98% of us only have to know sixth-grade math. And so, if you tell them that, then they’re like, “Oh, okay, I can do this.” And so, you have to, you must catch them at an earlier age. You cannot wait until they get to college.

Stewart: And that’s amazing to me and it makes perfect sense. Right? My daughter right now is 17 and she has math anxiety. And it’s interesting that you say that, because it really resonates with me. I’m sure she’ll kill me for mentioning her on this podcast, but nevertheless.

Maura: Well, Stewart, the best thing for you to do is intervene. Again, the research shows if mom or dad, either one, intervenes and says, “Here’s why you are thinking this, because you’re hearing it all around you, among your friends, you really think that.” But the reality is, they score just as well and even higher than the boys. But socially, they’re being told, because the teachers don’t know math, and I’m married to a teacher, so please understand I have the greatest respect for teachers, the greatest respect.

Let’s get to this point, 80% of the teachers self-report, self-report that they’re not capable. Now, what’s the word? Competent, that they don’t feel competent to teach financial literacy. 80%. Which is criminal in my mind’s eye. But please go to your daughter now, right? She’s 17. And say, “Hey, where are you getting this impression from? And why do you think that’s true?” Because she’s hearing it among her friends and she may have heard it from her teachers as well. And then get involved with her teachers and say, “This is a problem. What are you doing about it to counteract that socialization?”

Stewart: Thank you. That’s great advice. So, you have female financiers that volunteer for Rock The Street, Wall Street. Can you talk a little bit about what’s resonating with those folks that are volunteering with you?

Maura: I would say the entire program, to be frank. I mean, I was in a silo my entire career, because I was the only female, usually in my department or in my office. So, we were siloed off, to be honest. I mean, truly we were in silos, because there were not many of us. And I was consistently the only female.
So, when I launched this, speaking of silos, I thought, “Oh, okay, I’m going to cross my fingers and let’s see what happens.” And boom, I launched it, and wow, I was absolutely floored by how many women reached out to be volunteers. I was absolutely floored. So, clearly we’ve hit something here.

In addition to the volunteers, just so you have a feeling for this, there are over 100 additional cities that want our program, over 100. And that is not just in the United States. We’re getting interest in … Well, we’re in London now, but also Edinburgh, Dublin, Paris, Singapore, Sydney, and Mexico City. So, we can’t meet the demand.

But back to the volunteers. So, it’s a legacy issue, Stewart, in my humble opinion, because we don’t see ourselves in upper management and we don’t see ourselves in the positions of power. And so, what they want to do is they want to grab their younger selves and say, “Hey, you can do this.” And they want to be the ones that sponsor them, that mentor them to come into the profession. And we create that social capital for these students, 78% of whom are BIPOC, Black and Indigenous People Of Color, 44% are from low-income families. Now, these girls would never ever have these opportunities before. Now we’re giving them that hand to bring them up and in to the profession. And for those girls who choose not to come into the profession, we are making them not only financially literate, but also investment literate.

Stewart: It’s so important. I mean, Dion Woods made this point. If paying the electric bill and the gas bill is a challenge every month, financial instruments aren’t a topic of conversation around the dinner table. Right? And that creates a self-fulfilling prophecy to some extent.

You’re doing really solid work here and I want to talk about how you’re funded and how … I mean, our audience is made up of insurance companies and asset management firms, for the most part. And asset management firms are a way that you get funded. So, can you talk a little bit about your business model and how people can help? Because you’re in 60-odd cities now, you’ve got 100 cities that are interested in joining you, and you need resources to get there. How do we get that done?

Maura: Thank you for asking the question, Stewart. And we are very fortunate in that we have over 50 corporate sponsors. And just so you have a feel, you mentioned the asset managers, we have over 52, I think it is, the share, of the 52, 25 are asset managers. Insurance companies, we have about, I believe it’s one, two, three, we have three if not four insurance companies. And so, the insurance companies include AIG, now Corebridge on our end, on their end, actually. But the ones we’re relating with now are Corebridge, Principal, State Farm, and I know we have some others in the hopper. AON, by the way, too. And I think we put them under asset management on that side.

But in any event, the way that they can get involved, there’s a couple of different ways. If they want to get their employees involved along and into their community, then they would sponsor a school. So, we are a year-long program, we’re not a one-and-done. We go back every year and we have four components to the program. One is a series of fall workshops that are held at the high school. The second is what we call a Wall Street experience field trip, which is held usually before Thanksgiving. And then the third component is the mentor pairing, which happens in the spring. And then the fourth component is the vocational career platform.

So, it’s a year-long program and they can deploy, the employers can deploy their diversity, equity, and inclusion teams, members of their groups, such as a Black ERG, employee resource group, Hispanic ERG, or LBGTQ DEI, diversity, equity, and inclusion, or a women’s group, any of those four. And we see that happening with each of our sponsors that do sponsor a local high school.

We would ask that they consider that in cities where they have a lot of employees, so that we would be pulling from their pool of employees as volunteers. And our staff would be happy to talk to them further about the particulars of the program and so forth. And we recruit by component. So, even though it sounds like it’s a long program for your employees, we recruit by component, meaning each component is a different recruitment.

The other way that they can get involved with us is to sponsor our vocational career platform, which is the newest component and the fourth component, fourth program, we call it. We did a soft launch in August of ’21 and it was like, ‘build it and they will come’. We were extremely, again, thrilled with the response that the industry gave us. So, we only mentioned it to our current sponsors that we were launching this, what we call internship and job portal, the IJP. And within about two months, we had over 267 listings of internships and entry-level positions listed from our sponsors. So, it was a wonderful-

Stewart: That’s fantastic.

Maura: Yeah, it was a wonderful, unbelievable response. So much so that we created the fourth component, which is the vocational and career platform, which includes other things. It sees our girls past high school. So, as we have grown organically for the last 10 years, we track our students, by the way. Our girls are now in college and they’re saying to us, “We need your help in college now, because we are getting in at the age of looking for internships and looking for entry-level positions.”

So, very organically we have grown this VCP. So, now we’re into our second year and we need funding to grow that portion of the program, which is absolutely wonderful because we’re democratizing these opportunities that previous to us, would’ve gone certainly only to the elite schools, right? Because mom or dad is in the business. But we are democratizing that. And so, clearly the industry is seeing us as the go-to place for emerging diverse female talent.

Stewart: And my clients and the folks I talk to want to grow, they want a more diverse workforce, but I don’t think a lot of them … To your point earlier, about doing the same thing, expecting different results, they’ve got to look for different avenues to hire. Right? So, it’s tremendous to know that you’re one of those avenues.

On the back end here, what are your future plans? I will say this, we will make sure that we put up the contact information to reach your team for if anybody’s interested in working with you. But I love how ambitious you are and I can’t wait to hear the answer to this question. What are your plans for Rock The Street, Wall Street?

Maura: It’s interesting you said that, ambitious, because again, having been in the silo for so long, we’re just thrilled with the response. And our plan is to get to the majority of the cities that have interest because we’ve clearly demonstrated that we’re plug-and-play now in any city. And so, the plan is to continue to plug-and-play within the United States, and then also to continue to grow our presence
in the money centered cities such as London, such as in Mexico, Mexico City, Singapore, Sydney, Australia, and there’s another city in Australia as well. And then London, of course, Edinburgh, Manchester, and so on. Paris. And then either Munich or somewhere else in Germany.

But it’s a function of sponsors and of course, the women. So, most of what the growth has been, I would say, easily more than 90%, if not 95%, it has been driven by the women. So, it’s kudos to them rather than me, as far as the growth of our footprint. I’m just a shepherd as far as shepherding the program, but clearly our boots on the ground are the women.

Stewart: That’s fantastic. So, I’m keen to get your answer to this question. We ask this to our podcast guests, but in your case, the answer’s going to be particularly interesting. I want to take you back to your undergraduate institution, when they handed you that diploma. And having gone down the path that you’ve chosen, what would you tell your 21-year-old self? What advice would you give yourself?

Maura: Wow. Wow. That’s a good one. From a career perspective?

Stewart: Yeah, just from any perspective. I mean, you’ve talked about so many aspects of why we struggle to get a more diverse workforce, and you had mentioned earlier that some of your female financiers look at this as an opportunity to go back and grab their 21-year-old selves by the shoulders and say, “Hey, do this.”

There’s so many women, young women, I mean, I’ve had a multitude of women who did really well in my finance class, and I’ve reached out and I haven’t gotten nearly the response, right? And it’s like, I want women to know, and underrepresented groups as well, that there’s a really bright future in the financial services community of the insurance industry, and so forth. What would you tell a 21-year-old Maura Cunningham today?

Maura: Well, I always bit off more than I could chew.

Stewart: I can relate.

Maura: Oh yeah. Yeah. I mean, I always bit off more than I can chew. I was unafraid of being the squeaky wheel. I can’t tell you how many times I was told I was the squeaky wheel. And I would say, “Look, in this environment, what do you expect me to be? Okay. Because if I don’t speak up, you’re not handing it to me. I know that.” Right? So, what would I tell my 21-year-old self? I took on risk. I will say, most women won’t take on risk. I interviewed, speaking of interviews, a woman who is a professor at a university up in the St. Paul, the Twin Cities, Minneapolis. And she’s been teaching there for over 30 years, graduate school finance. And she said to me that, “Consistently, these women who are just as bright, just as capable as the men, want a safe, cushy job rather than to become a portfolio manager. And they think that becoming a portfolio manager is too much risk.” When in reality, as you know, it’s just a function of doing it and you have the tools to do it, and you just have to beat the odds and step up and do it, where they would be handsomely compensated, but instead they take the less riskier positions, and of course, are then less compensated for that.

And again, I did take on risk. I was totally full commission, no salary, probably after the age of 28 or thereabouts. So, I would tell myself though, if it were me telling myself, I would probably try to help other women sooner. I would probably try to help other women sooner. As you well know in this career, you’re so fast, you got to get on track and stay there. Right? But there were so few women that were like me, and it was obvious, there’d be 400 men at a conference and maybe 8 of us women, it was always the same 8.

And maybe approach other women and encourage them to look differently at the profession and to be able to take risk and, why are you so afraid of risk? But I think that’s a cultural thing again, they don’t know what they don’t know. So, maybe introduce them sooner to the concept of risk. And I should have probably taken more time to share that with other women that may have been a high potential or even mediocre potential like the men.

Stewart: Absolutely. No, I get that.

Maura: That would be it.

Stewart: I think that’s great advice. I’d like to introduce you, I want to make our audience aware of this as well, but there’s a group called IWIN, which is the Insurance Women’s Investment Network that’s over 600 members. And that’s somebody that I’d love to network you with. They do a phenomenal job, Sarah Marshock at Wellington, is who we work with most closely there, but there are a number of women on both the buy and sell side at very senior levels. And we partner with them with CFA Institutes doing events and so forth. And we want to do more there.

But I do think that women are willing to help each other in a way that sometimes guys aren’t. Right? And I think it’s really important to network. And one of the reasons I wanted to do this podcast with you was to increase awareness of what you’re doing. It’s phenomenal work. You’re making a huge impact, a great difference, and I just couldn’t wish you more success. Just very happy to have you on, and thanks for taking the time to really walk us through what you’re up to at Rock The Street, Wall Street.

Maura: Well, thank you. I appreciate that. And we would love to get connected with IWIN. I would really love to meet those women and share our story as well. And we’re thrilled to be on this and I can’t thank you enough, Stewart. Those were good questions. Thank you.

Stewart: Yeah, absolutely. And thanks for being on, Maura Cunningham, founder and CEO of Rock The Street, Wall Street, a financial and investment literacy program designed to bring both gender and racial equity to financial markets and spark the interest of a diverse population of high school girls into careers in finance.

Thanks for listening. We appreciate your ideas for a podcast, please drop me a note at podcast@insuranceaum.com. My name’s Stewart Foley and this is the InsuranceAUM.com Podcast.

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