Wes Moore
Bestselling author, combat veteran, social entrepreneur
“The people who are closest to the challenge are oftentimes the ones who are closest to the solution. They're just hardly ever at the table.”
Summary
In this episode of Leadership Matters, Alan and his good friend Wes Moore discuss what makes someone a successful leader, including looking beyond yourself and finding purpose.
They discuss how Wes grew up in Baltimore in 1978, “not just in the shadows of the Civil Rights Movement, but frankly, because of the light.” After his father died in front of him just five hours after being released from the hospital, Wes moved with his mother and siblings to live with his grandparents in the Bronx.
His tough childhood led him to a troubled adolescence, pushing his mother to send him to military school. There, Wes learned his purpose and got his life together, finally understanding what people had sacrificed for him and that people were rooting for him. With 130 cadets under his command at just 18 years old, Wes learned to be a leader.
As Wes got older, he became a Rhodes Scholar and started to invest his time in exploring social causes and racial inequity, leading to his books The Other Wes Moore and Five Days: the Fiery Reckoning of an American City.
Wes Moore is the CEO of Robin Hood, one of the largest anti-poverty forces in the nation. He is a bestselling author, a combat veteran, and a social entrepreneur.
Mentions & Resources in this Episode
The Robin Hood Foundation has been working for over thirty years to find, fuel, and create the most impactful and scalable solutions to lift families out of poverty in New York City.
The Other Wes Moore is a book by Wes Moore that explores how his own life compares to a kid in the same area with the same name who is now serving a life sentence in prison.
Five Days: the Fiery Reckoning of an American City is a book by Wes Moore that explores the reaction to the murder of Freddie Gray, an African American man, by police in Baltimore.
The Rhodes Scholarship is an international postgraduate award for students to study at the University of Oxford. It is the oldest graduate scholarship in the world and is considered among the most prestigious scholarship programs.
Sergeant Prothero was shot and killed while pursuing suspects after a jewelry store robbery where he was working overtime in Baltimore on February 7, 2000.
Guest Bio
Moore was born in Takoma Park, Maryland in 1978, to a highly respected American broadcast news journalist and a daughter of Jamaican immigrants.
Moore attended Riverdale Country School where he encountered academic and disciplinary struggles. When Moore's grades declined, his mother enrolled him in Valley Forge Military Academy. After high school, Moore graduated Phi Theta Kappa from Valley Forge Military College, a junior college in Pennsylvania. He went on to attend Johns Hopkins University where he studied International Relations and Economics and graduated Omicron Delta Kappa and Phi Beta Kappa in 2001. He then attended the Wolfson College, Oxford as a Rhodes scholar where he earned a master's degree in International Relations.
Moore started a career in finance at Deutsche Bank in the international trade and finance division, but in 2005 he left to join the 82nd Airborne Division of the United States Army in Afghanistan. Moore led a team of paratroopers and special operators who were trained in civil affairs, psychological operations, information operations, and various other special operations command disciplines. Among the many awards he received was the Combat Action Badge.
Upon his return to the United States, Moore was accepted as a White House Fellow. He placed within the State Department's Office of U.S. Foreign Assistance Resources where he tracked foreign aid to ensure it was being used properly.
Moore's first book, The Other Wes Moore, was published in 2010. It is the story of two young Baltimore boys that share the same name and race, but largely different familial histories and they travel down very different paths. While both grew up without the consistent presence of their biological father and got into trouble as youth, one, who was raised by his grandmother and grandfather and was born to two parents with college degrees, became a Rhodes scholar and leader, and the other, who was raised by a single mother who dropped out of college, was convicted of murder and is currently serving a life sentence. Wes Moore sets out to answer what made the difference through telling the story of young men trying to find their way in a seemingly broken world. The Other Wes Moore has been on both The New York Times and Wall Street Journal bestseller list.
His next book, The Work is also New York Times Bestsellers. Additionally, Discovering Wes Moore is a Young Adult edition of his bestselling book, and This Way Home, his first Young Adult novel, was released in the Fall of 2015. Library Journal named last year's book Five Days: the Fiery Reckoning of an American City, one of the very best of 2020.
Moore is also the Producer of Future City, a series on Baltimore's WYPR station. He was the host for Beyond Belief on the Oprah Winfrey Network, as well as the Executive Producer and a Writer for Coming Back with Wes Moore on PBS.
He is the Founder and CEO of Bridge Educational Foundation, a social enterprise dedicated to reinventing the Freshman year and creating a smoother transition to higher education for students entering their Freshman year of college.
Moore is a vocal advocate for serving those who served in the military overseas. He has worked with various veterans’ groups, including Iraq Afghanistan Veterans of America and Things We Read, and is a member of the Veterans of Foreign Wars (VFW). His TED Talk titled How to Talk to Veterans About the War has nearly 2M views.
From 2017 to 2021 Moore served as the CEO of the Robin Hood Foundation. On June 7, 2021 (after this show aired), Moore launched his campaign to become the Democratic candidate for Maryland Governor.
Follow Wes on Twitter, or on his website WesMoore.com
Clips from this Episode
On what lies ahead for him, as he prepares to step down from his role as CEO
On the experiences that inspired his book, The Other Wes Moore
About his love for a challenging America: "This Country Was Made To Be Tested!"
Clearing up misconceptions about poverty and why the recent relief bill is historic
Episode Transcription
Alan Fleischmann
You're listening to Leadership Matters on SiriusXM. I'm your host Alan Fleischmann. I'm here with a very good friend, Wes Moore. It's rare to find someone like our guest today who can speak with such authority about the incredible social challenges we face and face as a country – and certainly what we faced during 2020. When the pandemic pushed us into deep recession, my guest was there running one of the nation's largest charitable organizations in the world, administering relief as millions fell into poverty. In the wake of protests for racial justice last summer, the same guest was publishing a book about a reckoning that occurred in Baltimore after the death of a Black man in police custody in 2015. I'm grateful to have Wes Moore with us today to provide insight on an unprecedented year and to offer his outlook for 2021 and beyond. Wes is a Rhodes Scholar, a combat veteran, former White House fellow, and the current CEO of the Robin Hood Foundation. Wes first came to national attention with his book, "The Other Wes Moore," which tells the story of another Black man of the same name whose life took a very different path. Library Journal named last year's book "Five Days: the Fiery Reckoning of an American City," one of the very best of 2020. Wes just announced that he'll be leaving Robin Hood Foundation in May. So there's a lots of talk about what he'll do, and a lot of reflection about his leadership journey thus far. He is a very close friend, someone I look to for advice, and someone who I admire greatly and have for years. I am so grateful for you to join us today. Welcome to Leadership Matters, Wes. I look forward to talking about not only the journey that got you to where you are today, but also the journey that I know will be with you on for many tomorrow's. So thank you for joining us today.
Wes Moore
Listen, this is my joy, man. And listen, you can't understand my journey without understanding the journey that my wife plays, and you can't understand the journey that my wife plays without that understanding you. So this is a long time coming, my friend, I appreciate you.
Alan Fleischmann
Well, it is true that one of my greatest joys and accomplishments is that I had the wisdom of seeing you many, many years ago speak, and I immediately thought – Dawn was working with me at the time, this is going back many years – and I thought "oh my gosh, Dawn, you have to meet Wes." I think it's so bad that I think I texted her, or I think I paged her, I don't even think we had text at the time. But I think I paged her and said "you gotta get over here" and she didn't even know why, and then you two met. I take full credit for that moment, I do. I will say you have married and you have a beautiful family, and I know your mother as well. You've got wonderfully strong and wonderful women in your life, your wife and your mom, but your wife really is something special. So Dawn is certainly a big part of the equation. But let's start talking about your mom. Let's start off by talking about your early years. You were born in 1978 in Baltimore, in the shadow of the Civil Rights Movement, I'm just curious, how much of an influence that have in your upbringing? And was there a figure in the movement you particularly looked up to? Now, obviously, in 1978, it was years after, so I don't want to pretend that you grew up right in the shadow. But you grew up with a legacy, and I'm sure that there were some heroes in there.
Wes Moore
No, I think that there are huge heroes in there. And I think that for each and every one of us, we grew up not just in the shadows of the Civil Rights Movement, but frankly, because of the light.
Alan Fleischmann
The light, that's a good way to put it.
Wes Moore
I think about how that moment really did just change and alter not just what happened within African American families and African American communities, but also just how the larger community viewed our measure of progress, our measure of what it means to be American in that moment, because I think that was a crowning example of this idea of what Dr. King talked about that the moral arc of justice is long, but it bends towards justice. But the Civil Rights Movement was a perfect example that it doesn't bend there because of inevitability, right? That it actually bends there because there are people who are on the other side, who are pulling justice, who are pulling this arc towards justice. And so when I think about people who I know had a marked influence on the movement, I actually don't have to even look that much further than my own family. I say proudly that I come from a lineage of preachers and teachers, and I think about my grandfather, who was born – first one on my mother's side of family actually born – in the United States. He was born in South Carolina, and his father, my great-grandfather was a minister and he was a very vocal minister, to the point that he was so vocal that the threats started coming in. Initially, they started off as as verbal threats, then eventually physical threats to the point that literally, when he was just a toddler, in the middle of the night, his father picked up his family and move them back to Jamaica. Most of my family never had an intention of coming back to the United States, but my grandfather did, because my grandfather always felt he said, "Listen, this is my home, and no one has a right to run me from my home." And so my grandfather then came back to the United States, in 1950, he became the first Black minister in the history of the Dutch Reformed Church. He was an activist. He was a missionary. He was our rock and our beacon. So that's why I think about the legion of folks in the Civil Rights Movement, who spent their life, gave their entire time on this planet, to make sure that the time that other people could spend on the planet could be a little bit better, and a little easier. I don't have to look that much further than even just my grandfather to see the influence that he made, not just on us, but the influence that he made on our larger society as well.
Alan Fleischmann
That's the bright light you're talking about. Rather than talking about shadows – you're right, it's not shadows, it's light. And I guess the brightest light – I've heard you talk about your grandfather before. What a great thing that he lived a life the way he did, but his legacy still lives on, still influences, still inspires, everyday, which is amazing. You know, you've enjoyed such extraordinary success, and the one thing about you that I find so extraordinary is that with all your success that you've had – and we're going to talk about a bunch of it on the show today – you also are probably the one person I could speak to who also shows extraordinary humility, empathy, gratitude, you bring confidence to everything you do, but you always make sure that it's not about you. Knowing enough about where you come from, knowing your mom, I just gotta say, it comes from there. But I also know that your success didn't come easy. You worked hard, and your dad died when you were very young, which I'm sure for your mom and for your whole family just turned everything on its head. To take us back to that point, I want to take this to the book that you wrote "The Other Wes Moore", but I want to start off a little bit with what led to that, because your journey could have gone a whole other way.
Wes Moore
Yeah, you know, I only have two memories of my dad growing up, and the second one was when he died in front of us. He was actually a journalist in Maryland. We were living down in Maryland at the time. I was born in Colombia Hospital for Women – which is not around anymore. But after I was born – I was about three and a half years old, I was months from my fourth birthday – and my father, who again, he was in radio and he was a journalist, and so he made his living with his voice. But he started complaining about his throat, how his throat was bothering him. He tried to make it through the night, it was so bad that he really had difficulty sleeping. The next morning, he said, I gotta go to the hospital. He went to the hospital and my mother, who was working at the time, said "I'll meet you there." She met him, after getting some time off from work, at the hospital and they were getting ready to release him and they were asking her questions like, "Is he prone to exaggeration?" They looked at his clothes and made assumptions about whether or not he had proper insurance. He was released from the hospital with the simple instructions of "Get some rest, and if it continues to feel worse, just come on back." He never made it back to the hospital. Five hours after he was released, he died in the house.
Alan Fleischmann
What was the diagnosis there?
Wes Moore
He died of something called acute epiglottitis. And so what that is, is the epiglottis in our throat, it sits on our windpipe and every time we breathe or we talk or we chew, the epiglottis goes up. And what it does is it's allowing air into our windpipe, it's allowing oxygen to flow through. What acute epiglottitis is, is essentially when the epiglottis becomes so swollen that it just sits on top of the windpipe and it's so heavy that it's not able to lift itself up off of the windpipe. So in essence, his body suffocated itself. You know, the irony and the beauty of it is when I think of my mom and this idea of turning pain into purpose – back then, emergency technicians did not know that if they had someone who had that ailment, they did not know that there was a way you could actually go inside of the throat, lift up the epiglottis, provide the air, etc. My mom, also with the aid of of my father's family as well, now made it so that all emergency technicians are trained on this technique of if you find someone who's suffering from that the ability to actually go in and do the process that would have saved his life. But I think about it in context with my mom, where she was just amazingly unprepared for the fact that instantaneously, and surprisingly, she was now about to become a widow with three children that she was going to raise on her own. That wasn't the life that she prepared for or dreamed of. So, she had a really difficult time with the transition, had a really difficult time with the fact that this was now going to be her life. Eventually, she called up my grandparents, her parents, who were living in the Bronx – my grandfather, who I mentioned earlier, he was a minister in the South Bronx, and my grandmother was a school teacher. Their house was barely big enough for them, but they figured out a way to make it big enough for all of us. And so after a few years of trying, my mom eventually decided that she needed more help, and she moved us up to go live with my grandparents in the Bronx. And so that was my journey up there.
Wes Moore
Wow, and how long did you live there?
Wes Moore
We lived there probably until I was about 14 years old. We moved back down to Maryland at that point, but what happened to me prior was, you know, that was a hard time for me. Because I think I very quickly found –
Alan Fleischmann
You have two sisters, right? You have two sisters?
Wes Moore
Yeah, an older sister and a younger sister. But I very quickly found myself picking and choosing which days were worthwhile to go to school and which ones weren't.
Alan Fleischmann
Your choosing?
Wes Moore
Oh right, exactly. Exactly. I mean, that's right. That's right. The first time that I felt hand cuffs on my wrists was when I was 11 years old. When I was 13, I found out that when my mom makes threats that she's not kidding, because I'm 13 years old and she decided to send me away to military school. And, Alan, I mean, I hated every minute of that place when I first showed up. I ran away multiple times.
Alan Fleischmann
This is Valley Forge Military Academy?
Wes Moore
Valley Forge Military Academy in Wayne, Pennsylvania. When I first kept on trying to run away, they would go and they'd find me and they'd bring me back. The second to last time I tried to run away was actually because they drew me a map on how to get to the train station, because it was so pathetic that I kept on getting lost. They were like, "Just go," like "Why is it so hard?" Until I realized that the map was actually fake. The map took me to the middle of the woods, and they just enjoyed watching me – you know, watching a flashlight in the middle of the woods do this. They brought me back to campus and they said, if we don't change this up, we're going to lose him, so they said, "We're gonna give you five minutes, and call whoever you want, we don't care. But you've got five minutes." I call the only number that I knew, which was my mom. When I called her, I explained her, I said, you know, "Mommy, I don't want to be here," and "Can you come get me?" And that's when she told me, she said too many people have sacrificed for you, and too many people are rooting for you. You have to understand it's not all about you. I listened to her talk. After the five minutes they told me my time was up, I gave them back the phone, they hung up the phone. Honestly, it didn't sink in at first, Alan. I mean, I tried to run away the next day. It's like, I wanted to go home so badly. But eventually I began to understand what she was talking about and understand this idea that we lived in a completely interconnected society. By the end of the first year – I had a mandatory year there– but by the end of the first year, I had a chance to go back because I wasn't on probation anymore. I was actually doing okay in sports, and my grades were okay, and I felt like for the first time in my life, when people asked my mom "How's Wes doing?" she could say "He's doing okay," and not be lying. And that actually meant something. So I had a chance to go back to school at that time down in Maryland, because we moved back down to Maryland. And I said, if it's okay, I'd like to sit tight. I actually ended up staying in military school to the point that I actually graduated from high school there and then ended up joining the army right out of high school.
Wes Moore
So that became the right path. It wasn't just the corrective path, it became the right path.
Wes Moore
Absolutely, absolutely. It was the path that just gave me a much greater sense of – it allowed me to remake my identity. It allowed me to rethink my place, my space. It allowed me to think differently about the type of life that I wanted to live. It allowed me to get a better definition of what leadership was. I think all those things kind of happened and mattered there, but it's interesting you bring that up, Alan. I think sometimes people think that "well isn't a great you got sent away?" As if that was the answer. It's like, what we have to do is pick kids up from one place and put them into a different place, and that type of thing. In many cases, it's not that simple. It's not that easy. And in some cases, it's the wrong answer. What happened to me was the fact that I was picked up and moved around. What happened to me was the fact that I found myself surrounded by people. First, starting with my mom and my grandparents, but eventually leading to this amazing string of teachers and principals and role models and mentors and parents of friends and coaches and ministers. People who helped me to understand that the world was bigger than what was just directly in front of me. And that mattered.
Alan Fleischmann
Was part of this, also, is that where you started to learn, I would argue, a life of service, of purpose?
Wes Moore
Yeah, very much so. I began to understand and I started thinking about what felt good to me. What places and spaces did I actually feel good in? One of the clear answers was, for me, the military, where even when I finished high school, I had a chance to go play basketball in college and do all that kind of thing, and I said, actually, what I'd really like to do is lead soldiers. I'd lead cadets up until that point. By the time I finished high school, I was a company commander, so I had 130 cadets under my command. I'm 18 years old with 130 people under my command. And it felt good. So when I thought to myself, I was like, "Alright, so what do you want to do with your life?" The first quick answer was, "I want to lead soldiers." A big part of that was responsibility, and a big part of it was the fact that I thought about so many of the men in my life, particularly men in my life, at that moment, who I had this deep level of respect and admiration for. There was one thing that for many of them they had in common: they all wore the uniform because of military school. So it became a thing for me that I was like, well, maybe this is where I'm supposed to be, and what I'm supposed to do, and it just felt right, to be able to go through that process and do it.
Alan Fleischmann
I want to get into that and talking about when you were a Rhodes Scholar, which is skipping ahead, and you wrote the book, "The Other Wes Moore" obviously later on in life with reflection, but I wonder whether it's not a perfect place right now to talk about those defining moments that you had, which you're talking about right now, that would differentiate the other Wes Moore a little bit. Why don't we jump in there a little bit? What you did with that book, and then subsequently, what that created, was a major shift. It was an extraordinary shift of mindset, because you live very few blocks away from each other, had the same name and so much in common, and yet, because of those decisions, because of your mother helping you make some of those decisions against your will – but then you embracing those decisions and realizing that they were your own – that your journeys were very different. If you could mention a little bit more now about "The Other Wes Moore" now, that'd be interesting.
Wes Moore
So, when I first learned about the other Wes Moore, it was actually through my mom. She called me and at that time, I was actually overseas. I was doing a study abroad in college in South Africa, and my mom calls. And you know, that was back before FaceTime audio and all that where everything is now free. This is when a long distance a phone call – an international phone call – was like, $4 or $5 a minute. This is crazy. Like, what are you doing.
Alan Fleischmann
Every word mattered.
Wes Moore
Every word mattered. And so when she called, I was like, "Mommy?" She said, "I have something to tell you." She said, "There are wanted posters all over your neighborhood." And I'm like, "That's crazy." But I was like, "But I'm still not sure why that justifies a long distance phone call?" And she says "Because they have your name on it." That was the first time that I learned about Wes. I learned more about the case, I learned about the story, and what happened where you had one day, four guys walked into a jewelry store in Baltimore. The first two guys walked in the jewelry store and they reached their coats and they pulled out guns. Then the second two guys, when they walked in, they reached their coats and they pulled out mallets, and the ones with the guns were keeping everybody on the ground while the ones with the mallets were smashing out jewelry cases and taking out watches and rings and necklaces. They got about $400,000 worth of jewelry. One of them yelled let's go, and then all four then ran out of the center of the jewelry store to get outside. One of the people that was in the store that day was an off-duty police officer who was moonlighting as a security guard. He was a 13-year veteran of the Baltimore police force. He's a three time recipient a police officer of the year. He was also a father of five who just had triplets. The reason he was working that day was because it was his day off from the police force, and he took on a second job as a security guard to make extra money for his family. I know you, Alan, you were very – and still are – very heavily involved in Maryland. And so you remember, I mean, that was a big case in Maryland, the murder of Sergeant Prothero. There was a 12-day national manhunt for those four guys, and finally, after 12 days, all four guys were caught. One of the people that the police were looking for that they eventually captured and tried and convicted and sentenced for this crime was a guy whose name was also Wes Moore. The more I learned about Wes, the more I learned about this crime, the more I learned about this tragedy and the murder of Sergeant Prothero, the more I realized how much more Wes I had in common than just our names. At that time, we were literally living in the same area just blocks away from each other. We both grew up in single-parent households, both had academic and disciplinary troubles, both were around the same age. I knew there were questions I wanted to ask, and Wes was the only one that could answer them. So one day, I just decided to write him a note, and literally the first note that I wrote him – he's over at Jessup Correctional Institution – first note that I wrote him was like, "Hey, Wes. My name is Wes. Here's how I heard about you." And a month later, I got a letter back from Jessup Correctional Institution from Wes Moore. That one letter turned into dozens of letters, those dozens of letters turned to dozens of visits. I have now known Wes for close to two decades. He's now in year 20 of his life sentence. But it was really through that relationship, through the friendship that we built throughout all these years, that I think I didn't just learn a whole lot about him, but I learned a lot about myself. I learned about my own path and my own journey. I think it was one of the things that really helped to add and cement a greater sense of how I want to spend my time and the issues that I want to work on and the things that I want to get done. And a lot of that came to be through this relationship that I built with Wes.
Alan Fleischmann
You also did something very profound with that book. It was so striking and so profound that it became such a big bestseller. But you exploded myths and you transcended conversations around race. All of a sudden, there were people having conversations around the kitchen table – and the boardroom table – about issues of opportunity, equality, and humility. Because what you did in that book by the way you made the contrast – and I've read the book more than once – is you actually profoundly made the point that "if it weren't for the grace of God, that would have been me." That makes all of us who read the book go, "if it weren't for the grace of God, that would have been me," and how vulnerable we all are in our journey and how deliberate we need to be to help one another in order to make sure that we have options and opportunities. It's in the book. That's in the book. Then you get to see why you do and why you've done what you've done. So take us now – we're going back, I guess, a little out of order here. But you're now in that life of service that came from the Valley Forge experience, that came from you being the commander of all the cadets, and then you went on to college. Tell us a little bit about that. And then that led you to be a Rhodes Scholar. I also love this story that I don't think you've shared widely at all about how you didn't even understand what a Rhodes Scholar was because to 90% of people who ever hear of the Rhodes Scholar, they know "well, that's prestigious," but they have no idea what it is. I would say maybe 98% of the world, and I'm talking about people who are really connected in the world, too. They have no idea. But they know it's prestigious. "He's a Rhodes Scholar. He's a Nobel Prize winner." But it is, it is one of the most prestigious achievements one could ever get. It's so difficult to get. But you were in an internship – tell us about that – got exposed to that, where all of a sudden, someone said to you – tell us who that is – "That could be you."
Wes Moore
That's right. So I did my first two years in college, actually, at a junior college. So I got my associates degree, and went to Valley Forge Military College, and I got my commission in the army, and then I transferred to Johns Hopkins University. As I started doing my work at Johns Hopkins, I was doing well academically and doing a lot of extracurricular activities. But then in my junior year at Johns Hopkins, I did an internship, which eventually turned into two internships, with (at that time) the mayor of Baltimore, a gentleman named Kurt Schmoke. After my second internship occurred, Mayor Schmoke calls me into the office, and what's really interesting, Alan, is that, you know, he wasn't the kind of leader that had a photographer around him at all times, right? He's a very, very humble, humble servant, but it just so happened that a photographer happened to be in the office at that time. He was like, so you know, "Thank you for your work," kind of, in some ways, almost the obligatory idea that "The intern has his last day. Can you spend a little bit of time with him, boss?" "Got it." But then he starts saying, "Listen, I got a chance to look over your resume and your transcripts," and he said, "Have you ever heard the Rhodes Scholarship?" And I was like, "I've heard of it." But it's kind of like what you said, I don't know a whole lot about it. He walks me and he says, "Let me show you something." He walks me over to his wall, and then he starts pointing up in his wall, and what's beautiful about this is, I actually have a picture that now sits in my office of Mayor Schmoke and me in his office, and he's pointing up in the wall. What he's pointing to, that was the moment that he was pointing to the picture of his Rhodes class. He's showing me where in the picture he was. That's when he then turned around and told me "I'd like for you to consider applying for this." I went back, and I started doing the research and fast forward, I ended up receiving a Rhodes Scholarship. But I think about that, and the reason that I keep that in my office is had it not been for that conversation – and sometimes those amazing and that photograph– it's like sometimes, the most amazing conversations we have our life, it's not people are there capturing it. But that's one of these moments where you had a transformative moment in your life that was actually captured on camera, where he's telling you about this scholarship. But it goes back to this idea that had he not taken that time, taken that vested interest, done that, I would have never experienced it or known about it or gone to do the research and gone done the work. So it just shows how important individual mentorship, involvement, concern, support are in these times, because sometimes it can be just the simple conversations that can change the trajectory of an entire life. That story, really, for me, that story underscores that exact reality.
Alan Fleischmann
If we lived our lives as if everyone were watching, – and in essence, they are –if for Kurt Schmoke, and knowing him as I do, I have to imagine he purposely wanted to show you that photo. And I think he was the only Black face on that photo, if I recall. But he wanted you to look at that photo and say, "That could be me."
Wes Moore
Yes.
Alan Fleischmann
I think we don't always live our lives where we're realizing, whether it's our children or our colleagues or wherever we work, that everyone's watching. You can be either a beacon of hope and direction, or you could be the opposite, where you're truly an obstruction. But, I know that for you, many people are inspired and aspire to do different things because of the things that you've led and done, and certainly the opportunities you've created. But also, frankly, like the books you've written, like the work you do at Robin Hood and elsewhere, you just kind of shine a light. Then people go "Okay, oh, I didn't see that before." That's actually pretty amazing, actually. I can see how the purpose in your life started to become palpable through these internships, and I think part of being a Rhodes is purpose. You have to figure out, it's not just academic achievement, it's societal achievement. What is your role? What is your direction? What are you going to do to achieve purpose and show that purpose? Right?
Wes Moore
It's one of these things where if you look at the will of Cecil Rhodes, which is interesting, and we can talk about that, too, but it's like, the will he talks about how he wants people who yes, do well, academically –
Wes Moore
– right? But there's something specific that he asked for, and that's people who are willing to fight the world's fight, which is a really interesting line in there. So yes, he asked for physical rigor, or academic achievement, but he wants people who are willing to fight the world's fight. And that was this thread that you then identify and find – all people who all in their own individual ways and their own respective ways, were willing to go in and fight that world's fight. So that was kind of a guiding principle that we all really had to translate and had to find our way into defining that in our own hearts.
Alan Fleischmann
– athletes.
Alan Fleischmann
That's amazing. When you were in the military, did you experience racism? I'm just curious whether that came. You know, you talk about racism, but it's never about you. You're talking about overcoming systemic inequalities in our society that transcend race, frankly, the way you talk about it, certainly you look at vulnerable communities, and you look at underserved communities. But you describe it in ways that make it where you create tables where people come together. But I never really hear you talk about the adversity that you overcame as much. I'm just curious, did you encounter racism yourself?
Wes Moore
Oh, yeah. I mean, the military is a microcosm of our society. It's not like the military in any way is protected from the images and the things that our society that are still very present and unfortunately, very real. But whether it's talking about how the kind of names and nicknames that people were given – and even the way that whether we were talking about the places we were going in and fighting, the names that were just randomly given to Iraqis and Afghans, without understanding how incredibly offensive the names and the nicknames that are being given out, for anybody to be able to utter them and think that – there was a measure of a degrading of humanity that came in how people were being described. I think it's also important to recognize and remember that, that while the military has actually been ahead of the curve, in many cases, for our society – there was a desegregation of the military before we had the desegregation of society. The military did equal pay for you to work before society did it. So the military has actually been ahead of the curve on a lot of these things, but I also trained on military bases that still to this day are named after Confederate generals. I think about my time when I was training at Fort Bragg or Fort Benning. Fort Bragg was named after Braxton Bragg. Braxton Bragg was a Confederate general – and not a very good general by the way, but a traitor. The base that is the home of the 82nd Airborne is also named after a Confederate general. So, it's important for people to understand the weight that that takes on, and the unfair weight that African Americans and people of color, or any type of undervalued or underrepresented community group, feels when we're being asked every single day to experience that and feel bad and to just smile.
Alan Fleischmann
And ignore it.
Wes Moore
And ignore it.
Alan Fleischmann
The betrayal to yourself personally, or the questions you're asking yourself, "Why am I ignored? Why am I being subjected to this, but why am I ignoring it? And why is everyone ignoring it?"
Wes Moore
I think about it, Alan, where, you know, I received the Rhodes Scholarship. The Rhodes Scholarship's named after Cecil Rhodes. Cecil Rhodes was a virulent racist. Someone who literally at some point became the richest man on the planet through diamond mining. The way to diamond was essentially a slave trade of Black Africans who were going in mines, and we're literally talking thousands of people, thousands of bodies. That's how he made his money. I'm a recipient of the Rhodes Scholarship. I attended Johns Hopkins University, and it just recently came out about four months ago that the history of Johns Hopkins – Hopkins actually did an investigative report on the history of Johns Hopkins, because we'd always heard that Johns Hopkins was this great abolitionist. Johns Hopkins – the history we were being told was incomplete. Johns Hopkins was a slave owner. And so I found myself realizing that all these places that trained me were either founded by or named after people that despised me. So, this issue of race, we have to remember that it's not just an act. Racism is not just that oh, a person attends a white supremacist rally, therefore that's racist. I got it. Yes, that's racist. A person use the n-word. That's racist, correct. That's racist. However, racism is not just an act. Racism is the fabric of a system. That's what we have to have the courage to be able to uncover. That's what we have to have the courage to be able to unpackage. It's a system that allows discrepancies and these disparities to continue to exist. It's a system that allows us to have to walk and be trained on military bases named after these people.
Alan Fleischmann
Ignoring the models of excellence that they're supposed to be, when in reality they should be examples of what we ought not to be.
Wes Moore
That's right.
Alan Fleischmann
You're listening to Leadership matters on SiriusXM. I'm your host, Alan Fleischmann, and I'm here with Wes Moore. We're talking about his life experiences, but also lessons in leadership and observations of how we all collectively, frankly, can do better. You've obviously made personal sacrifices for our country. You served in our military, you volunteered for things, you write about the things that are broken in America, but you don't write in a way that makes you feel like it's broken and not fixable. What I always admired about you, and how you chronicle things that you write, and the work you do at Robin Hood Foundation, it's all about acknowledging what's broken, but acknowledging also what needs to be done to fix it, and then investing in that. So, how do you not be a pessimist in so many ways? When you look at the weight of the things, like the systemic racism, the injustice when it comes to economic and social disparities that exist in our country that you were just talking about, which in many ways people just turn their head and ignore, you don't. You seem to be someone who always seems to say, "Okay, let's move on." Not to move on away and ignore these problems, but let's move on in ways to focus on healing and solutions at scale. Tell me how you do that. How do you love an America that challenges us? What is your vision for America, when you think about it?
Wes Moore
It's actually one of the beautiful things about this country – this country was made to be tested, and it was made be questioned. Right? We have to always remember the history of this country, that this was a country that, yes, this country was founded on a racial hierarchy. It was founded on stolen labor with stolen land, and all those things are very much ingrained within the DNA of the country. We have to be able to understand that and really reflect on what that means. We also have to understand that this country was also built and born of revolution. It was built and borne on an idea that we can have something better, that we can have something different, and that we can push for it, we can fight for it, and we get ourselves to then a better day. Now, the history of this country is remarkably uneven. Truthfully, the history of this country at times has been remarkably unfair. But the other thing that I know, which keeps me very centered on what it is we're trying to get done, is I feel like I exist in this vise grip of purpose. And one side of the vise grip is history. It's the fact that I know what my grandparents endured in order for them to have a sense of pride in this country that they did. My grandfather, a man who literally had this deep Jamaican accent his entire life, he died with a deep Jamaican accent, and was probably the most American person I've ever met in my life. I think about the history of Ropes and Tubman and Chisholm and Jordan and all these people who came before who were willing to fight and advocate so that I could see things that they never had a chance to see. So you have this vise grip on one side of history, and on the other side, you have future. And that's where I look at my children. That's where I look at the kids that we work with. That's where I look at communities. There's this vise grip of purpose that puts this intense pressure on us that says, "You must move forward." That hope is a choice. That in this moment, anyone could easily curl up in a fetal position if we chose. We could say "Listen, this thing is horrible. It's terrible. It's racist. It's sexist. It's xenophobic. It's homophobic. It's this, it's that, and give up." We could. That is a choice. I choose to actually listen to the vise grip of purpose. I choose to be able to understand that it is not perfect by any stretch of the imagination, but what that means is, is we've got work to do.
Alan Fleischmann
One thing that strikes me so much – I should mention this, too – your experience is very rich and diverse. You've been on Wall Street, you understand the world, what makes the economy work. You've seen the role of capitalism and the deployment of capital. You've been a philanthropist, but even then, you brought your private sector acumen, I would argue, to how you approach your philanthropy. You've been a leader in the military. You've been a White House fellow. When it comes to public sector, private sector, and civil society leadership, your experience has been extraordinary, and your exposure has been much. And I would argue, then you think back and you say, "Wow, I made it. I got it." How many people can say that they have lived a life that you've had? And yet one thing that strikes me is that when you – and I think it was a kind of 'aha' moment for yourself – you live in one of the most beautiful neighborhoods in Baltimore, and you went for a jog last year, just as this thing started happening. You just finished your book "Five Days," the whole country – the whole world – became so focused on the aftermath of George Floyd's murder, and you had been coming into the same time period, wanting to shine a light on the legacy of what happened to Freddie Gray in Baltimore. And you're going for a run. If I'm right about the story, you purposely go running and you put your Hopkins sweatshirt on and you're wearing Hopkins. I tell the story where it's like, here's a guy who, you know, everything's going great, great leader, lives in a beautiful area, loves the city of Baltimore, loves the state of Maryland. But then when he goes for a run, he makes sure that he has Hopkins on there. Why? So that if anybody from the police were to see him, or anybody were to see him jogging, they would not assume that he is displaced or misplaced in that neighborhood.
Wes Moore
That's right.
Alan Fleischmann
I don't know how conscious that was, or how subconscious that was, but that does tell you how much work you've gotta do.
Wes Moore
It does, and how real it was. I remember that came right off of the heels of Ahmad Arbery. When you hear his mother – because he couldn't speak for himself because he was killed – when his mother talks about how he went out and he was a runner and he's going out for a jog, and how his killers, men said, "Well, you know, we thought he was running from a crime or running from whatever it was." You think to yourself, "This is a young man who was going for a jog and never made it home." There was this thing where it's like you realize, and this is that weight that is important for people to understand and recognize, that I don't have time in a situation where I'm being profiled. And this is why this kind of work matters so deeply, that we have to be able to be important. It's important that we be so cognizant of the type of laws we put in place and the protections we put in place, because I don't have time to show somebody my resume if they see a six-foot-two Black man running in their neighborhood.
Alan Fleischmann
You're not able to say "Hey, by the way, I'm a former Captain of paratroopers. I served in Afghanistan. Look at me." No, in fact if anything, they just look at you and say – all the stereotypes, all their prejudice – they say, "what are you doing in this nice neighborhood?"
Wes Moore
That's exactly right. So I found myself – it wasn't by itself, it was actually very intentional – where I'm digging through my drawer trying to find what shirt I want to wear, and I immediately go to my Hopkins shirt, because I'm like, "Well, at least if I'm wearing the Hopkins shirt, I won't be seen as a threat to someone who doesn't know who I am." But to think that I actually have to take time to pick out my wardrobe to go for a run to say "what's the least threatening thing I can wear today?" It just is a reminder that this weight and this burden is real and it is present. And so, our ability when we hear these kinds of stories, and frankly when we saw Mr. George Floyd's name being added to a much longer list of other names, to include names such as Walter Scott, names such as Freddie Gray, and Anthony Anderson, and Chris Brown, and Laquan McDonald, and Breonna Taylor, and Sandra Bland, and Tamir Rice, and Trayvon Martin. It's important for us to understand that the fears that people feel in many communities, it's not hyperbole. It's not making stuff up. It's not exaggeration. These are very real and sincere and long-felt fears that people have about communities they move and maneuver in, and what is exactly that people see when they look at them. And that becomes all of our collective responsibility, to be able to understand that, embrace that, and figure out what we can all do to be able to address that.
Alan Fleischmann
I think actually what happened – you and I have talked about this a lot – what happened last year is, yeah there are bigots and hateful people and we've got to figure out what to do with hate and bigotry in this country. There are an awful lot of people, and you've heard me talk about it on this show, and talked about it with you, there an awful lot of people who are ignorant that just need to understand why they're implicit racists. There's a form of racism where when somebody walks down the street and an African American male is walking towards you and you cross the street. What is that? What does that mean? That's an implicit racism. Then there are other people who are indifferent, which I don't think there are as many as we think, but there's a whole lot of people that are uncomfortable, and I know you're very much into figuring out how we bring people who really want to be part of a movement in that then creates the best of what America is and what it should be? And expose them to that purpose and all that. One of these I wanted to ask you about – again, you've written so many things that I love – but one of my favorite, ever, interviews was Oprah Winfrey, and I'm a Baltimore boy like you. A Marylander. I grew up with Oprah, she was friends with my mom. I feel like Oprah is one of our greatest exports to the world.
Wes Moore
That's right. That's right.
Alan Fleischmann
And she does hold on to Baltimore as a key place for her life journey, but she adores you. One of my favorite interviews that she's ever done under the oak tree on her Sunday show that she does, which is Super Soul Sunday, she interviewed you, and I think it was about a book you did, "The Work," if I'm not mistaken. Am I right?
Wes Moore
That's right.
Alan Fleischmann
And, I think that's one of my favorite things you've ever written. But tell us a little bit about that book. The title didn't actually match all the things that are in the book, and I look at that as a blueprint of where we need to go in public life and private life and civil society. In many ways, it's the Wes Moore guide to what we need to address in our world, in our community, in our country, and our state. Tell us a little bit about that book.
Wes Moore
Well you know, I say that the book almost came from me just sitting on a couch with my publisher, like we were having a session where he was talking a bit about "So what's what's happened with Wes, since the book's been published and what's happened with you?" And I said, "You know, the really interesting thing is that I could write about how Wes's life has changed on a postcard." Because it really hasn't, right? I don't know what time it is right now, but if I knew, I could tell you what Wes is doing right now, because I have his schedule memorized. And it hasn't changed.
Alan Fleischmann
The other Wes Moore?
Wes Moore
Sorry, yes. The other one. And he said, "That's so interesting." He said "During this time that you wrote 'The Other Wes Moore,' you were working in finance, and you were in the military before, what have been those lessons?" And that was really through those conversations with him that I was kind of like, maybe that's really what I want to understand. It's what were the lessons of all these experiences that I've taken in that time? And then also, who were the people that motivated me throughout them? Whether it was looking at people like Dale Beatty, who was a military combat vet down in North Carolina who actually lost both of his legs, and when he came home, he realized how difficult it was for people to be able to find housing. And you know, he had a community that came together and helped to build him a home with ramps, and so he was able to kind of move and maneuver, and then he got together with one of his other soldiers and they created something called Purple Heart Homes, which is now going around the country building homes for disabled vets. Whether it was someone like Esther Benjamin who was a Sri Lankan refugee and immigrant who came over to this country and then rose to become the person who's second in charge of the Peace Corps. People who, in just different walks of life and for different reasons, they found their point, they found their purpose. I wanted to try to highlight them because they really served as really core and key inspirations to me about how I thought about how I wanted to spend my time.
Alan Fleischmann
I really looked at that and it was very inspiring. Again, it goes back to this conversation we had about Mayor Schmoke. You didn't just tell us what we need to do in that book, you've showed us people who are doing it. There is a quality of humility in everybody you just talked about, as well, I would argue, which is a big part of it. So you're very young, but you've accomplished a lot. You have a young family, two kids, you're very committed to community life. Tell us a little bit in the last few minutes we have, the two things I want to talk about is what are you taking away from the Robin Hood experience? I'll tell what you've done with Robin Hood, Robin Hood Foundation from what I know is pretty extraordinary. It's a bunch of very financially successful people who came together years ago to say, "We have to do more." It was very New York City based, very New York City focused, and it was about using the best of data, the best of resources – financial and human – to really come up with solutions at scale to make a difference in the New York area. Then you come along as CEO several years ago, and you say, "Okay, we have a lot here to share with the country, and there are partnerships that need to be forged." You took the best of Robin Hood, which has truly grown tremendously under your leadership, and you said, "Okay, I'm taking this on the road." You've taken it to Maryland, and I've talked to people in Maryland who have been partners with you in Robin Hood. I've talked to people in Minnesota, and I talk to people literally across the country who I've gotten to know who will say, "Well, you know Wes Moore, you know Robin Hood Foundation," so it's become the model. I'm curious what your takeaways are there. I know that even in Baltimore, the Weinberg Foundation talks about the work that you do at Robin Hood as if it's around the corner and down the street. So, tell us a little bit if you could about the lessons you've learned as you're – I guess you have two more months left in this CEO-ship? – and what are you taking away from that?
Wes Moore
I'm so proud of what this team has accomplished in our time here. If you look at where we were versus where we are, our reserves are up 6x from where we were before. Our donor base is up 20x. We built out new frameworks, we built out new platforms for the organization. The organization has a greater sense of community and a greater sense of connection than it's ever had. Our founder, and our mutual friend, Paul Tudor Jones, will say this is the strongest that Robin Hood has been in 32 years. But when I think about the things that we're gonna look back, and we're gonna say, "that was all right," I think about the fact that we were able to stretch our wings. While Robin Hood is New York based, and New York focused, and New York bred, poverty is not a New York issue. Being able to really forge strong partnerships with all these other partners who are around the country, whether it is our friends at the Constellation Fund over in the Twin Cities, or Tipping Point in the Bay Area, or the Lever Fund in Washington, DC, or Slingshot in Memphis, or Better Chicago in Chicago, really able to say and understand "what are the best practices we all need to incorporate into our work to show that we are doing doing the work together?" We think about ideas and concepts like the relief fund, where in the process of last nine months, we have allocated north of $70 million to New Yorkers at a time when we knew that the impacts of COVID-19 were going to be most distinctly hit. So we started focusing on things like how do you build up the social service sector? And also how do you do things like emergency cash assistance, and just getting cash in people's hands, because we knew at that moment, that's exactly what they needed. Or whether it was the Power Fund, a fund that we built exclusively focusing on organizations that are that are led by people of color, because there's a distinct difference over the past 20 years – there has been a 400% increase in philanthropic giving and during that same time, only about 10% of dollars have gone to organizations that are led by people of color. So it shows us that there's not only a bias in the way that philanthropy does its work, but also it doesn't make sense. The people who are closest to the challenge are oftentimes the ones who are closest to the solution. They're just hardly ever the table. We think about how one of the big takeaways, and one of the things we tried to solve for, was this issue that philanthropy alone cannot do it. It does go back to this question of "Why do people think that we have poverty in the first place?" And if people say, "Well, it's because of a lack of opportunity, and this and that," I got it. But even with that, it still means we're putting an unfair onus on the individual. Going back to this idea that poverty is a choice – I can tell you right now, I don't know anybody who wakes up and is like, "This poverty thing is really cool. I love this poverty thing." Poverty is a choice, but it's not a choice of the individual who has the weight of poverty in their shoulders. It's society's choice. It's our choice.
Alan Fleischmann
It's about access to opportunity and capital, access to mentors, access to ways to actually have the ability to be out of poverty.
Wes Moore
That's right. That's right.
Alan Fleischmann
Inequal access in our country does not work.
Wes Moore
It does not work, and so we have to be able to use and leverage our power and share our power to be able to really drill home, what is the role of policy? What is the role of advocacy? What is the role? I looked at the recent bill that was just passed, Alan, and honestly, I think this is going to go down as one of our proudest moments. The recent bill, the recent relief bill that was just passed, there was something in the relief bill that that might seem small to people, but the adjustment that happened on the child tax credit, which we've been fighting for, for a year, the child tax credit is a is a tax credit that was given to families who are living in poverty and basically having a certain allowance for every child that a person is raising. It was $2,000. But the challenge was that it was not fully refundable. What that basically means is there had to be an income threshold that people had to hit in order to hit the child tax credit. The problem was that anywhere between 24-27 million children were being left out of that benefit because they were too deep into poverty, which never made any sense, right? So we have a poverty fighting bill and a poverty fighting tool that excludes the ones who are the deepest and poverty. So, we've been pushing and advocating for this basic adjustment to the child tax credit that's basically saying not only now, in the most recent bill, the child tax credit was up to $3,600 for children under the age of six, it's $3,000 for children who are for six for six and above, but also it's fully refundable. That bill alone, Alan, has now almost cut child poverty in half with the stroke of a pen. Child poverty in African American communities has just essentially been cut about 55%. In the stroke of a pen.
Alan Fleischmann
This shows, again, what leadership can do at all levels. And obviously your advocacy played a role, because if you don't have voices speaking up and using the spotlight of power – I like the way you how you can harness our power and direct our power? – it does matter, and leadership. So, we only have about two minutes left in the show, which is really bumming me out because I'd love to go on for another hour. But I will say, we started this conversation talking about light and shadows, and you very clearly redirected the conversation to the lights, the opportunity. You have been a champion of bringing private sector to the table, creating tables where, frankly, folks don't come together. What you've done at Robin Hood is proof of that. Your leadership is now being speculated now. What do you do next? What is the next thing you do? You're someone who has accomplished so much in the private sector, in public sector, in civil society. You are a uniter and you hold people accountable. You're a champion of bringing people together, but you're not bringing them together for people to actually rest on their laurels, I'll say it that way. What is Wes Moore's next move?
Wes Moore
I think the next move is, well first, it's going to be very consistent with my prior moves. I told people, what's the old investment analogy? Prior performance does not indicate future returns? In my case, it's gonna be very different. The things I've worked on for my entire adult life will be the things I'm gonna work on next. I'm really looking to say, "Okay, I want I want a big problem with a big budget." I don't want a small problem with a big budget. I don't want a big problem with a small budget. I want a big problem with a big budget. I'm very seriously looking at and considering the idea of running for governor of my home state, of my birth state, the State of Maryland in 2022. I'm thinking about how exactly can we really build a really interesting coalition to take on big challenges? And to do it in a way where knowing that what we're trying to get done is not zero sum, but not trying to get it done will be zero sum, and that becomes our fundamental mission. So I haven't decided yet, I'm really thinking hard and spending time and trying to figure it out. But I just know that my time in the fight is nowhere near over.
Alan Fleischmann
Well, the great thing is you bring a lot of people with you, no matter what you tend to do. The humility around your sense of purpose and service is contagious. If we're going to create a better America, that better state of Maryland, that better neighborhood, we have to do in a way that actually takes those lessons to heart and builds coalitions that actually can make the choices, deliver the the resources, and inspire people along the way. So I am thrilled. I would urge people to read – I need to talk about your last book. I would urge people, if you really want to know about Wes Moore and what his thinking is, read his books. All of them. Watch him in these interviews, especially the one that Oprah did with you. You've had several interactions with Oprah, but the one that you that you did about "The Work," I think is a real understanding of what you think we all need to do. It's still very necessary today to kind of absorb what you said then. And, you know, we're gonna have you back on the show. I hope that we can do great things together. This is a show about leadership and how it matters. So I'm grateful for your service today and I'm very excited by the service to come. So thank you very much Wes Moore.
Wes Moore
Bless you, brother. Thank you so much, man.
Alan Fleischmann
Talk to you soon. Thank you.
