Finding Leadership in Service with Wes Moore

And in this four part series, you'll hear from these individuals as they share their unique experiences in the military and the lessons they learned that carried them into their new roles in civilian life. You may know westmore as the CEO of Robin Hood, one of the largest anti poverty forces in the country and the largest poverty fighting

organization in New York City. But long before West was the CEO of this incredible organization, West was a kid struggling to find his way and creating a lot of trouble for his mom. Eventually, she sent a thirteen year old West off to military school, and despite running away from school on five separate occasions, West eventually came to appreciate the structure and it became an environment where he

would grow amateur. Fast forward a few years and West is graduating from Valley Forge Military College and later Johns Hopkins University. From there, he wanted to serve as a captain and paratrooper with the U. S. Armies eighties second Airborne Division. After leaving the military, West worked with former Secretary of State Condolee's Rise as a White House fellow, founded the tech company, wrote a best selling book, and hosted a TV show on a national network. West how

are you, man? I am so good. It's great to talk to you. Thanks so much. Good to talk to you too. Before we kind of get into the nitty gritty, um, you know, you obviously served you have such an important job now, uh, CEO of of robin Hood. I actually have been to the foundation event a couple of times, which is some of the cooler experiences I've ever had in my life. Now, before I talk about that for

a second, tell everyone what what robin Hood does. So. Robin Hood is one of the largest poverty fighting organizations in the country, and for the past thirty years, robin Hood has really used data and analytics and metrics to be able to identify and find and fund some of the most innovative poverty fighting organizations UH in the City of New York, and then also beyond where we have allocated over three billion dollars into everything from education to housing,

to mental health to criminal justice reform. So we're everywhere where poverties, either the cause or the consequences, we have really built out and funded. I just wanted to start off by saying that love what you've done as far as your service for our country. UM, talk a little bit about because I know you were in the one of the airborne divisions. Talk about that for a second exactly which one? Yeah, I was in the eighties second Airborne Division. So we're how's that out of Fort Bragg,

North Carolina? And what was that like in the early stages when you are going, you know what, I'm gonna be airborne? Like, who around your close friends or family? Like, what in the world did they thing? Because that doesn't sound like the safest of all the things. It wasn't and it was actually was crazy. Was that you know, My first exposure to the military actually happened when I

was thirteen, and it was at military school. It was on the on the fact that you know, I I got into a lot of stuff when I was younger, to the point that I was kicked out of schools and I was young, I felt I felt handcuffed my risk. By the time I was eleven years old, and my mother had been threatened me to send me away ever since I was like eight because of just all all the things I was getting into. And finally she kept

on threatening me. I kept on blowing her off, and when I was thirteen, she said to me, she was like, I'm not gonna I'm not playing these games anymore. And she's like, I'm gonna send you away, and I thought she was still kidding, And then she told me that she was sending me next week, and she told me to pack my stuff up and start getting ready. And she sent me to a military school in Pennsylvania. And I hated it. I mean I hated every minute at place. I ran away five times in the first four days

when I first showed up. But it was something where the longer I was there, the more I started appreciate creating the experience. And so by the time I had a mandatory year there, I had to be there one year. By the end of the first year, I was actually doing pretty well academically and I could play sports because it wasn't appropation. And when I had the chance to go back to school in Baltimore, my mother she asked what I wanted to do, and I said, if it's okay,

I'd like to stay. And so by the time I was seventeen and I was getting ready to finish high school, I thought to myself, and you know, at that time, I actually had basketball scholarship offers and everything like that, but I thought, like, what actually gives me joy and what actually makes me it makes me excited about next steps. There was only one thing that kept on coming up, and that was the chance to lead soldiers because I actually really enjoyed it. And and so I made the

decision at seventeen. In fact, I was too young to do it myself. I had to get my mom to sign off on it. But at that point it's when I decided that I wanted to actually join the army. And then pretty early in that experience, I realized that I wanted to be a paratrooper. And that's what let me down to four break. You know, when I read your story, it is so inspiring. You grew up in Baltimore, and the Bronx. You're raised by a single mom, How

did that shape your life as to where you are now? Everything? Man? You know, I think my little sister said it best too when she said, you know, our mother wore sweaters so we could wear coats like you know, well, I'll never I'll never forget the kind of sacrifices that my mom made, that your grandmother made. You know, It's just how people were willing to see something in us before we saw it in ourselves. How people were willing to sacrifice their time here on this planet so we could

have a better experience on this planet. How it influences me now and my work now is it just highlights the level of unfairness that we still have because I know, I think about it in the case of my mom, in the case of my grandparents, who also I spent part of my childhood with that These are people who were some of the hardest working, most patriotic, most beautiful people, and smartest people, most creative people, most entrepreneurial people that

you'll ever be around. And still I witnessed the sacrifices and the pain that they had to endure. And so it's one of these things that it just completely reminds and it highlights the fact that we still have a massively inequitable society that we still have to contend with when you have people who are that good and still have to work that hard just to keep their head above water. And I think it's really the things that helps to motivate me even in the work that I do. Now,

what was it that inspired you to actually grow? Because it wasn't like you had a lot of options or a lot of people around you that even new options were available. So what was it as a kid you think that got you to that next step at actually being healthy and motivated. I feel like part of the thing that happened was I got a chance to actually understand that the world was bigger than what was directly

in front of me. Even as I got put and exposed into these different situations and these different circumstances, you you realize like wow, like there are actually things outside of what I see every day that are real for people. And that was that was just very eye opening to me.

And I think the big thing that I know I received from military and military school was people often said they're like, well, was it the fact that they woke you up early, or they yelled at you, or they gave you discipline, and I mean, like all that's really like, yeah, they woke up early, Yeah you did push ups and whatever. But that wasn't the thing that changed me. I really do believe the thing that actually changed my thinking was

was the introduction of leadership. And that's what they specialized in. It was it was this idea that they were going to put you in charge of something early, and it was very intentional, and it was because they wanted you to taste that, they wanted you to feel that, and they knew that that feeling was intoxicating, and so you know, they'll put you in charge of something small. First of put you in charge of a hallway, and they'll tell you if the hallway is clean, will congratulate you. If

the hallway is dirty, then Lord help you. And they noticed that the hallway was clean, and they're like, all right, more, good job, man. Now you're gonna get promoted. Now you're a squad and now you're actually in charge of people.

And then if you did a good job in that role, you got promoted, and then now you're in charge of more people, and then more people, and you started actually yearning and craving that feeling of being responsible for something, for leading, for being in charge of something bigger than yourself. And I really think that was part of the thing that helped to change my psychology and my thinking was I knew I was going to get it at some point. It just so happened that it was the military, and

it was that experience that got to me first. But getting through the military it was no simple task. It was along and argebous road. For West, however, his military education started to have a profound impact on him. He started to take academic seriously and it was paying off. West thought he would be a career military man, but as we know, it was only one chapter of his incredible story. Because I think I was in such unchartered waters.

I wasn't sure at that point. I mean I really did think that, especially if you if you talk to me coming out of high school and even coming out of college in any ways, I thought it was gonna be a career military officer. I thought I was gonna spend thirty years and rise up through the military ranks and you know, maybe at some point end up with

a star on my shoulder or something like that. And then I think that it goes back to even when I was talking about with exposure, where the more exposure I received, the more I started thinking about the things that I wanted to do. And you know, I still have a deep amount of love and respectnomorration for those

who do choose to make it a career. Some of my deepest friends are people who chose to to get a career and are stealing right now and our people who actually have figured out a way to get those stars on their shoulders. And I think as I started going through the process and moving up, I started realizing that there were different things that I wanted to contribute, There were different things that I wanted to try to

make realities in my life. And that's when I started, you know, whether it was working in finance or starting an organization that eventually we uh, you know, we we sold are now working in robin Hood. I just feel like the increased exposure in the adaptability were all things that just really led me into thinking differently about the kind of contributions that I wanted to make in the world.

You served as a captain and paratrooper with the U S Armies eighty second airborn, including a combat deployment to Afghanistan. What did that job entail for you? And then how much of your mind versus just outright strength do you have to use in that position? I mean, it is It's one of these things where I I thought I was walking in prepared because I studied everything about the region. I learned about the different tribes, I learned about that terrain,

I learned about the altitude. We trained up, we did all this kind of stuff, and then you land in country and you realize how much of that training just goes completely out of the window because there's nothing that anyone can do that can prepare you for it. It's nothing that anyone can do to prepare you for the first time that you are in a tick troops in contact, which is, you know, in exchange with with with enemy forces.

There's nothing you can do to prepare you for the environment and the smells and the sights and the things you hear that that just sit with you. It really in the first couple of days that I just realized how the thing you have to be comfortable with is the fact that every single day is going to be different. There's this expression in the Middle Terry where we say stay frosty and um, and it kind of means stay cool,

because don't worry. Everything's gonna change quick. No matter where you're where you're at, things will change up real fast. And I think that that stay frosty was very much the mindset and very much the way we existed and

lived for our entire deployment. I think at the same time, though, it was also the experience where I saw some of the most remarkable human beings doing some of the most amazing things I've ever seen in my life, some of the most courageous things, some of the most fearless things, The way people looked out for each other, the way people take care of each other, and the most extreme circumstances.

That level of commitment to people, that level of commitment to your brothers and sisters who were staying to the side of you. That's something that I also know that I'll never forget again and and something I always have

the deepest levels of appreciation for. While people always acknowledge the soldiers and the sailors and the airmen and the marines, and rightfully so, it's the families who actually have it tougher, and I don't think I fully grasped that or appreciated that until I saw my family and the fact that you you know, when we were overseas deployed, we had good days and we had bad days, but we always

had each other that we leaned on each other. We could talk to each other, We had things that were unspoken because everyone understood, so you didn't have to go into full detail about things because everyone got it. And this was something when you're talking about family where they were having to process all this on their own, you know, at that time. I remember it was relatively early in the wars, and you know where maybe you got a chance to call home once a month, maybe you got

a little bit more than that. It was usually very quick that you didn't have a lot of time to say hi and or whatever, and those this was pre skype or whatever, so you didn't get a chance to actually see people. And it was a really hard experience for us. But I can't even imagine what it must have been like also for family who were just watching the news and hearing about death tolls and this and that and just hoping that they did not receive a phone call or hoping that no one in uniform showed

up at their door. And I think that that level of appreciation for, you know, not just what we were going through, but what family members back home are going through. I think it's something that end up fueling how I just think about, you know, the things that we're asking people to endure right now as well. So I would assume that that it's safe to say you return from

Afghanistan with a different view of the world. Yeah, and and and definitely a different view of the world, a different view of warfare, a different view of combat, a different view of what the implications are of that of that combat, a different level of appreciation for the type of challenges that we're asking people to endure. And I think it is one of these things where you know, we are we are asking people to sacrifice everything, We're

asking their families to sacrifice everything. And so I came back knowing a few things. One is, every time we are asking people to do this, we better be clear about what we're asking them to do, and we better be clear about how we're communicating it to not just them, but to the entire country. And the other thing was is that we better make sure we're keeping our promises. And that was one of the things I think fueled

my energy and advocacy when I came back home. It was on this idea where I felt like we were breaking promises. You know, when people signed up to serve, they signed up with a commitment that our country would support them and their families, not just when they were overseas, but when they came back home. And I found when we were overseas, we got everything that we wanted as

soon as we asked for them. But then we were coming back home and I had soldiers who were waiting nine months to see a doctor, And I'm like, this is crazy, because when when when their country asked people to raise their hand and volunteer and sign up. These are people who didn't tell the country, Okay, well you know, hold off, hold off nine months because I'm finishing something up, or or give me a little bit of time, or not quite now because this isn't the right time in

my life. These are people who just raise their hands and served. And so the frustrating thing for me when I came back home was wondering why the same people who did not ask the country to wait, why was now the country asking them to wait when they came home and it was time for them to receive the benefits that they rightfully earned. And so that was one of the things that I think really fueled my advocacy and the work that I wanted to do when I came back home to be able to fight for the

basic earned rights of veterans. The idea of advocacy and fighting for the basic earned rights of veterans is an idea that West takes very seriously. The notion of thank you for your service, What did that mean to you then versus what does it mean to you now? And how you're trying to help kind of spread that message.

I think what it means is and how I wanted to frame it out was I wanted people to understand that thank you for your service should should mean more than just the ending of a sentence that I want to thank you for your service, to actually be the beginning of a conversation and not always the end of it. Because you'd see people who would say, you know, they would say thank you for your service, almost in passing right, thank you for your service, and uh, you know, I

gotta go catch my plane. Thank you for your service and I, you know, let me go grab a you know, let me buy you a cup of coffee. But there wasn't an interest in actually learning more about what people's

service actually was. And I think it was this level of I think it was this level of rustration that people actually had and that I think for a lot of soldiers had because there wasn't that curiosity to actually learn more about it and to learn more about what we were actually asking our service people to actually endure. And frankly, I think, you know, it's all even with my own family, where there wasn't the level of curiosity

to ask what exactly was your experience? And I think part of it was coming from a place of people saying, well, you know, I don't want to ask the wrong thing, I don't want to trigger anything, or I don't want to say anything offensive, so therefore I'll ask nothing or I'll say nothing. The problem with that was the interpretation that we received was it wasn't that you were trying to figure out what was the right thing to say.

The interpretation that we took and interpretation that I took was you didn't even care that you're not even curious about what was one of the most instrumental and pivotal moments of my life, and what impact did it have on me? And so I felt like there was always this idea that people were talking past each other by not talking and so thank you for your service, and you know, almost this uh, this very this very mixed

feeling that people in many veterans have around it. It is on this idea of saying, we appreciate the fact that people are thinking as for our service, but we want them to know what our service actually was. I want people to ask me questions. I want people to to to be curious. I want people to, you know, say hey, even in fear maybe saying something incorrect or whatever. And trust me, if you say something incorrect, I'll tell you.

But I'd rather you at least ask, because I think for many soldiers and sailors and AIRMoN and marines, you know, we are we're we're we're thankful for an experience that made us who we are today. We're all processing what that experience was. And I think for many of us, myself included, I will process it forever. I don't think

I'll ever have it fully processed. But that's okay. And at least I want people to understand that the the the ask that was made of me and the ask that was made of many of my other you know, brothers and sisters, that it was an ask that we you know, at least want to be able to share and express to people what it was and why it's

meaningful to dous. What is your one piece of advice that we that I that anyone listening to this could use as we are talking to events, I think one of the main things and one of the most important things for people to do is is first remember that we still have conflicts that are going on as we speak, I mean literally as we're having this conversation. There are

missions going on. There are people who are overseas right now, away from their families and still serving on behalf of this country, and Silver Herb still serving on behalf of us.

And I think for a lot of people there there is this thought, because it's not the main thing on the news, or it's not the main thing that's on the headlines, that somehow these things are over and first it's important for people to remember that's not true, even though we're not right now in the middle of it where we were at the height where we don't have hundreds of thousands of troops in Iraq and tens of thousands of troops in Afghanistan like we had at our

peak and we had at one point. We're still talking about only one percent of the population that our veterans of Iraq Afghanistan. We're still talking about a a much smaller percentage of the population than people realize or recognize. And I think for that smaller percentage of the population, regardless of how you feel about the war, it's important

that we respect the warriors, you know. And I think it's I think it's something that I give a lot of credit, a tremendous amount of credit, even to our our brothers and sisters from the Vietnam era, because I do believe that part of the reason that we have received the support and treatment that we've received is because of them. Because when they came back, they were spat at, and they were called names and all this kind of stuff. And and I think that that treatment that they received

was never forgotten by them or by anyone else. And the and the horrific thing about the Vietnam War in particular was that that was where people were being drafted in. It wasn't like people even it wasn't like that was all volunteer war people are being called out from their you know, their jobs and saying here we need to go put on a uniform and serve. And that's how

they were treated when they came back home. And I respect the fact that it was really because of the Vietnam Era and those vet's that in many ways they have led with a philosophy of never again will we have that kind of treatment to these men and women and individuals who raise their hand because the country asked them to. You can feel whatever you feel about the war.

I have personal feelings about these wars, but I still never conflate my feelings about the war, whether it should have happened or how it was executed, with my respect for the men and women and the individuals who raise

their hand because the country asked them to. That is important for this country to understand and for our country to understand that we can't conflict those two things, you know, with you talking about soldiers coming home the different wars, you know, I'm always curious and I have a lot of friends who has to have served and had to reintegrate into society with you in your situation. Did you feel like you had to establish a completely new identity

coming out of the military and out of a war. Mhm, I uh, it's it's such a good question. I didn't think I needed to, but I did because I was a different person. I think that, you know, it's it's not that everybody comes back damaged, but it's that it's

impossible for you to come back unchanged. And now part of it was this the There was just some basic things that had to change, right, I mean, like, for example, you know, and I'm very public about the fact that when I came back, I had a very difficult time

with lights and I didn't expect that. And even as I was speaking with my doctor about it, you know, he was he actually added a lot of context to it, where he said, you know, you were in a place that had light discipline for almost a year, and so you should understand that you should and you should give your brain a little time to say, how are you going to go from a Sadabad or Jelalabad or coast

and then two weeks later you're in Times Square. Give yourself a little bit of permission to know that that is going to be a little bit of a trip for your brain, and that's going to take a transition a place where white lights were faint because of how while I was overseived, because how far away you can see white lights. So that's why we always use green lights and red lights because you could not you can't see those from far away. White lights I can see

from miles away. And so the reason that we've done enough white lights was because if you had white lights, that means enemy could could just launch indirect fire all night long and they know exactly where you are because just look for the white lights. And so we didn't have white lights, and so to go from that to a place where everything is lit up, you can imagine how it takes a little bit for your brain to process that. I think that part of it was just

giving myself permission to be able to adapt. Don't punish yourself over it. Understand it is completely natural and just completely normal, no matter what it is that you're dealing with. And then I think it was about the fact that it's almost like a you know, a snake shedding of skin. And I feel like in many ways that's it's a description of how I looked at the way, how the way I processed it, and I came back home. It's

not that I was a different person. I just had to shed skin, and so I just moved and maneuver differently because that portion and that experience, it informed how I navigated the world. It informed how I approached everything from that point on. But the reality is I still came back changed because of the experience, and that's okay. When West came back from Afghanistan, he applied for and

one the prestigious White House Fellowship. This experience gave West an inside look at how policy was made, setting the stage for his work at Robin Hood and the incredible impact that he's had on million is. I came back and had that experience with Secretary Rice right after I came back from Afghanistan, which is crazy. And I remember I applied for this thing called the White House Fellowship,

which is a non political, nonpartisan fellowship. But I did it right after I came back, while I was in Afghanistan. And it's because my deputy brigade commander, who was also one of my best friends. He's actually a two star general now, which is underpaivable. A guy named Mike Fenzi, who I just loving a door and and he was a former White House Fellow. And I remember one night I came back from a mission and he called me in to his office. He was who I was a

captain at that time. Actually I was a first lieutenant at that time. I hadn't even promote. I hadn't been promoted yet, and he was a lieutenant colonel. And he said, hey, how's it going. I want you to apply for the White House Fellowship. I'm I'm, I'm, I'm in month three of my deployment and um swamped and frustrated and all this kind of stuff. And I said, I don't know if I can get my head around all this. And

he kind of reminded me that he wasn't asking. It's like, I want you to apply for the White House Fellowship. And his point was, he said, you know, I want you to. It's important that they see and understand what you're seeing and seeing. He was absolutely right, because I end up putting together the application, I ended up getting accepted to it. I think I was home for two weeks maybe three weeks when I got final word and I had my interviews and I got find a word

that I was selected. But it was an amazing experience to have that and have that time working with Secretary Rice and Dina Pale and other people who have still come become and then still still remained the longtime friends and mentors, because you see the disconnect often times between

how policy is made and how policy is implemented. Because I spent this year deployed seeing how policy is implemented, seeing what it's like for soldiers on the ground who are implementing a war fighting policy, right who were who had a war fighting posture, And then I spent the next year at the State Department seeing how policy is made.

And one of the things that was amazing to me was watching you know how a you know, you have just these these remarkable people, remarkable human beings, are remarkable public servants, both the career folks and and and many of the political folks who dedicated their life to this and too, and to doing the right thing and trying

to make the right policies. And at the same time the amazing disconnect oftentimes between how policy is made and then once it works its way down the chain, how things can go from Washington all the way down to the Eastern province of Afghanistan, and how a whole lot

can get lost in translation in that process. And that was the really interesting dynamic where you realize that so much of the things being debated it and discussed and and argued about, that once it finally works its way down to the environments in which all this has taken place, that you see there still is a pretty remarkable disconnect.

I want to encourage everybody listening to this because we'll have a few minutes left, but you can check out his West's book Five Days, which is out right now. And you know, you have such an impactful job as CEO of Robin Hood, And I wonder you know what you took from the military that translates into your work

with Robin Hood. Mm hmm. I think I use the things that I learned from the military every day in Robin Hood and and and part of it is, you know, the basic tenants of organizational management, leadership and all these other things that I think we that I think the military helped it not just teach me, but but really instilled in me and how I view management and leadership. But I think the other thing, and one of the other big takeaways that I took that I try to

incorporate into our work. Robin hood is the importance of proximity. You know, there was a there was an uh, General Petraeus who used to be out a commander for all operations, used to have this expression that I think was actually pretty apropoem pretty appropriate, where he said, uh, you know, you can't commute to work here, And what he meant by that was, if you want to be a FOB creature or BOB is an acronym for forward operating base, and that's kind of like the base that people are on.

And Uh, if you just wanted to spend your time on the in the green zone or spend your time in the FOB with all the creature comforts there, and think that you could just go out and run missions and leave and come back, you're never going to be able to accomplish what it is we set to accomplish, because if you aren't connected to the community, if you don't understand the communities in which you're serving, if you weren't building relationships with those inside the community, you'll never

be seen as anything except for people who are just you know, hiding under guys of being here to save people and these faux saviors, and frankly, all the altruism that you think that you are bringing to the job, your altruism will be viewed as something else in the community. And I think it's the same type of approach that we bring to the work at robin Hood, where this idea is, we don't have the luxury to commute to work if you aren't working with the community, if you

aren't actually working closely and tie with impacted communities. If impacted communities don't just have a voice, but if they don't have a vote in the way that you're allocating your dollars and the way you're thinking about the basic resources and the ways you're talking about supporting, then trust me, you will be seen as something other than helpful. And

I think the military really tried to reinforce that. The military was one of the first examples that I got a real, a real clear understanding at least from that side, because you know, up until that point, I felt like I was always in communities were where we are the recipients of philanthropy, even though we really know that, man, but I think the military really was one of the first on the ground examples of understanding that if you don't change your lens nor your mindset, you don't understand

that it's not that you're not making progress, you're actually moving backwards without even realizing that. And I think that's just the type of mentality that I think we try to bring to this work. Now. I really appreciate the time. You guys can follow West I am Westmore. You can also check out five Days, and I would encourage you to see what Robin Hood is all about. Really fantastic work that you did, that you're doing, and that you

have in your sides to continue doing so. West. I really appreciate the time and hope you have a real great rest of the week. Bless you, appreciate you man back at you. Thank you. West has led such an extraordinary life, and he's only one of millions of US veterans here in the United States and abroad, each of them with their own unique story. I think we can all do our parts board our troops by learning more

about their experiences. You can learn more about Robin Hood by visiting robin Hood dot org or on Twitter at Robin Hood n y C. You can find Westmore on Twitter at I am Westmore. Thanks for listening to Vets you Should Know. Check out our other episodes from more great stories from inspiring vets who continue to work selflessly and tirelessly in civilian life to make positive change. If you like what you heard, please rate and review the podcast.

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