Starts Right Here: Will Keeps on Courage, Leadership, and Healing in Des Moines

Will Keeps, born William James Holmes, grew up on the South Side of Chicago, facing immense hardship from a young age. Surviving childhood abuse, gang involvement, and a near-death experience, Will transformed his life to become a passionate advocate for at-risk youth. Now based in Des Moines, Iowa, he is the founder of Starts Right Here, a nonprofit dedicated to empowering young people through education, mental health support, and positive community involvement. Will’s story of resilience and his commitment to changing lives have earned him local and national recognition as a beacon of hope for struggling communities.

In this powerful episode of Courageous Crossroads, Will Keeps shares his harrowing yet inspiring life journey—from a troubled upbringing in Chicago’s gang-infested neighborhoods to becoming a force for good in Des Moines. Will opens up about the traumas of his past, his struggle with PTSD, and how those experiences shaped his mission to support at-risk youth through his nonprofit, Starts Right Here. He also reflects on the challenges of fighting negativity, the importance of community, and what true courage means to him. This episode is a deep dive into resilience, redemption, and the power of using your own story to uplift others.

Thank you for listening! We hope you feel inspired and encouraged by our conversation today. If you did, be sure to share this episode with others.

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See you in the next episode! Be blessed!

Full Transcript

Intro:
Welcome to Courageous by Crossroads Apologetics, a look into what motivates us to step out in courage and the everyday bravery of men and women like you. In each episode, we hear a personal story of bravery centered around this. What’s the most courageous thing you’ve ever done? And now your host, founder of Crossroads Apologetics, Jeff Johnson. 

Jeff Johnson:
Hey, everybody. Welcome to another edition of the Courageous Crossroads. If you’ve been around the Des Moines community for any length of time, you’ve undoubtedly heard the name Will Keeps bannered about. Will, originally from Chicago as a transplant to Des Moines several years ago, has done amazing work with helping youth get back on their feet here in Des Moines, probably the best way to put it. And I had the opportunity to sit down with Will in his home and discuss his ideas on courage and a whole lot of his backstory as well. And I can’t wait for you to hear Will and be inspired by him. And this is one in particular I want you to click around and pay attention to the show notes. It’s got a link to his charitable organization, starts right here, which deserves a lot of your attention. 

Jeff Johnson:
And Will’s also come out with a book that you should purchase and give that a read, too, to hear more about this amazing man and the courage that is within Will Keeps. So here’s Will. 

Will Keeps
My name is William James Holmes, you know, better known as Will Keeps. Born in the south side of Chicago, my father left when I was, like, 2 years old. My mom remarried. She brought in a man who we thought that was a good guy. And, I mean, I had an older brother and an older sister. And he came in, and we was looking at him as being our father. Well, this man decided he wanted to molest me and my sister, which caused me to have all these issues with anger, pain, and have all these issues that I didn’t even know I had. You know, it just. I was this happy, go, lucky kid. And all of a sudden, when I got touched, it was just. I became different. And so that led me to believe that I wasn’t protected in my own home. 

Will Keeps
And so I felt like I needed to be protected somewhere else. And so I chose the streets, and I felt insecure about myself. And this is all back in Chicago. All back in Chicago. 

Jeff Johnson:
Yeah. 

Will Keeps
And I literally was looking for attention from my mom. I wanted her to just see me, but my mom could never see me. So I’ll try hard and try hard to the point where I’m trying so hard to get attention from my mom. She pushed away from me even more, which Hurts me even more. And so now I feel like that my family is in the streets and. And my family is not in my home. And so I just became this guy who. Who felt like I needed people to protect me. And so I joined the gang. 

Jeff Johnson:
And how old were you when you did that? 

Will Keeps
I had to been about 12 to 13 years old. You know what I’m saying? When I joined the gang. Well, not really joining it, but feeling like because this was on my block, the gang was on my block, I decided to be a part of the block. So basically, yeah, join the gang. And that’s kind of my life in Chicago. Just constantly kept getting in trouble. I did finish high school, though. You know, I got kicked out of all the. The public schools in Chicago. 

Jeff Johnson:
Really? 

Will Keeps
Why’d you get kicked out? I was never going. You know what I mean? 

Jeff Johnson:
Just truancy. 

Will Keeps
Truancy. And my grades wasn’t that great. And I was. I had a situation where I was left for dead at 15 years old where I had a friend get killed in front of me. And they thought I was. They thought I was dead, too. So I played like I was dead. And that changed my life, too. And you know, the crazy thing is that as an adult, I hear about ptsd, and so that put a lot of PTSD in me, and I didn’t know what it was. So I’ve been living with PTSD for a long time, you know what I’m saying? And not really got the help. Not really got the help for it. But yeah, that’s a little bit about me, you know, Chicago. 

Jeff Johnson:
Okay. So I know you after you came to Des Moines, and you and I become friends, and, you know, you’re of quite a bit of notoriety around town because of what you’re doing for the community and all the outreach and the help that you’re giving to the youth and the community. But you’re married, you got kids? 

Will Keeps
Yes, my wife is Jay. I got three kids. Be honest. Got four because I took care of my nephew. He came from Chicago as well. 

Jeff Johnson:
Nice. 

Will Keeps
But we’re empty nesters now, so we are home alone. Wow. Yeah. 

Jeff Johnson:
And you’re a happy man now? 

Will Keeps
I’m happy with my marriage. I’m sad. I’m sad. You know, I realized doing good can be so painful and doing good can hurt. You know, I’m sad that there’s so many people out there that are struggling, and I’m sad that negativity is stronger than positivity, and I’m sad that you. 

Jeff Johnson:
Still see that as being True. 

Will Keeps
Yeah. Because I’m sad that people look at positive as. You have to do it from the bottom of your heart. You know what I’m saying? But positive people supposed to do it from the bottom of their heart. But positive people need that empire, that army to fight against negativity that’s already built huge. And we constantly keep fighting against something that we’re not prepared to fight against. 

Jeff Johnson:
Well, okay, let’s hold on a second because you’re. There’s a lot of facets to will keeps. And one of the first events I ever went to was in support of starts right here, which is your endeavor to help kids. Help kids that have failed in the school system are trying to get through school and get back on their feet again, which is an amazing thing. I was at a meeting where I saw the governor get up and just applaud you from the bottom of her heart. Talk about wonderful things about you. I saw the police chief get up and talk about how there’s a lot of people that start things, but very few people stick with things. And you’ve been doing this without anybody’s help for a long time. I saw the superintendent of schools get up. 

Jeff Johnson:
I mean, you had some powerful business people around and all sorts of people that were talking about what kind of a man you were. So that’s the will Keeps that I just got to know. But maybe tell people you came from Chicago and you came here to Des Moines, and then you got rooted in the community, and now you’ve started. This endeavor starts right here. Could you talk about the motivation behind that a little bit? 

Will Keeps
So I was working. I came out here and I started working for the post office. And I hated the post office, but it was a good job, take care of my family. It wasn’t that I hated the post office. I hated some of the management there. They treated me like garbage. And. But then I got hurt and at the post office and there was a situation where there’s a kid named Terry Harris who was friends with my son, my nephew. He was actually friends with the family, but he was close friends to my son and my nephew. They didn’t do some chores around the house, but they supposed to be over Terry house that day to go hang out with him. They didn’t get some chores done around the house. And so I made them stay home or I made them. 

Will Keeps
They couldn’t leave until the chores was done. Well, Terry got killed that day in his own home, where my son and my nephew supposed to have been that day. 

Jeff Johnson:
And had you not had them doing chores. 

Will Keeps
Yeah, they supposed to been there. Yeah. And he got killed. And my son and my nephew was crying. It was upset. And they asked me to do a song about what’s going on in the community. And I said okay. I went upstairs in my studio and did a song called Wake up Iowa. When I did Wake Up, Iowa, I had no idea it was going to be where I had a voice, where people was listening to me. There’s people that hated what I said and people that love what I said, but most of the people that hated what I said was some of the gang bangers that was out here in Des Moines. And I had no idea that my voice was going to start being in the news, being in the papers, you know what I’m saying? 

Will Keeps
Being on the police website, police Facebook page. I mean, people started hearing what I had to say. Then I did another song called We Fight and we would fight. We fight. Talked about what was going with the black community and the police, which was a controversy song as well, Controversial song as well. And. And that got me on CNN and Fox News and stuff like that, where people were starting to listen to my message. But I had no idea that all this was going to steer into a nonprofit, which I didn’t even know what a nonprofit was, you know, it steered into a nonprofit. 

Will Keeps
And I thought that I was just probably gonna just get a building and, you know what I’m saying, do some after school programming and do a community site, you know, where kids can come in, play some video games, you know, just stay off the street. But I had no idea that I was going to form a school where kids can actually get their education and get wraparound services and be able to change their mindset and be able to get mental health, you know, and to. To be in an environment that they always wanted to be a part of. Even though some of these kids got great homes, but being in this environment, for them, it’s more. It’s more of a peaceful place. Cause we deal with a lot of. 

Jeff Johnson:
Kids that in your starts right here. 

Will Keeps
Yeah, we deal with a lot of kids that always like to fight, argue, and they’re going through all types of trauma, but that starts right here. They relax, they chill. I mean, of course we got our knuckleheads, you know what I’m saying, here and there. But most of them come in, they relax and they chill and they just want to get their work done. And we built that environment of love, respect, you know, holding them accountable. 

Jeff Johnson:
And how long has starts right here been around starts right here. 

Will Keeps
Been around since 2018. 

Jeff Johnson:
Okay. And how many kids have successfully navigated the program? 

Will Keeps
We graduated 54 kids. So we’re at a 58% success and with loss with the lost kids and dropout prevention kids. That’s unbelievable. 

Jeff Johnson:
So you provide education for them, Tutoring services. 

Will Keeps
We work with the more public schools. So the more public schools bring in teachers, science, math, social studies, reading. And they come in and they’re credit based teachers where the kids can actually get credits and actually be able to get a diploma. 

Jeff Johnson:
And how do they, who are people that come to your program? What’s the, what’s the situation that occurs that they come to? Starts right here. 

Will Keeps
The kids. Yeah, you got kids that are dropped out with the dropout prevention kids. You have kids that get suspended, kids who just can’t be in a big school setting and they want more of a smaller setting. So we get those kids. And how we get those kids is the more public schools gets us. The kids that are being suspended, they’re called DE students. And most of the option kids we work with, Options Academy most and those with the more, that’s. That’s umbrella under Des Moines Public Schools. 

Jeff Johnson:
Okay. So now if those 54 hadn’t graduated, hadn’t come through starts right here, they. 

Will Keeps
Would still have been out here and not going to school. They still would have been dropout kids. If we didn’t have this program, those kids still would have been dropout kids. 

Jeff Johnson:
Wow. Wow. So that’s really doing some good. Now you’ve. I’m going to put information about starts right here in the show notes so people will know how to get involved and help out that program. But you’ve also, you’ve just recently written a book. 

Will Keeps
Yes, wrote a book called Willpower. 

Jeff Johnson:
Nice. 

Will Keeps
It’s about my life and I’m surprised it does. It did very well. So already, you know, I wrote a book about my life, man. Because at first I didn’t want to do it because it was too expensive. But a friend of mine named Brent Cook, he said that he was gonna pay for. He wanted me to do this book so bad that he said that he wanted to, he was gonna pay for it with no problem. And he did, you know, he paid for it. The book is out written by Danny Byer. We’re under Book Press Publishing. And so it’s. People say they read the book and it took them only a day or two to read it. Cause they couldn’t stop reading it. 

Jeff Johnson:
Wow. 

Will Keeps
It was unbelievable. 

Jeff Johnson:
Well, you got an amazing story, Will. So the Courageous Crossroads podcast is about the subject of courage. A couple questions. How do you define courage? What does courage mean to you? When you hear that word? 

Will Keeps
Courage means to me is to keep. Even though life can have you take so many steps backwards, courage is that person who would learn from those steps you took backwards and use those steps to move forward even further. That you never give up. Especially when you’re. I would say it’s not about what you’ve been through, but it’s how you get through, you know? And courage is to keep getting through and to actually let others see. Because there’s a lot of people who will think they don’t have courage, but they do because they’re not understanding that waking up every day and constantly keep moving every day through the pain you’re going through, that’s courage, right? So courage can. Courage can be so many different angles, you know, and so I want to be able to teach people that you’re not. 

Will Keeps
Because I used to think I was weak because I used to let people get to me. People used to bully me when I was younger, you know, my family, you know, I was bullied by my stepfather, you know, and I used to think I was weak, but I had no idea that I was showing strength because I was getting up every day. Moving forward. 

Jeff Johnson:
Who do you admire when it comes to courage? When you think about courageous individuals, who do you think about? 

Will Keeps
I see these. I see these kids that we work with when their mindset changed and they start realizing who they are. It’s like. It’s like they be. It’s like they were Spider Man. See, my favorite cartoon character is Spider Man. It’s like they were Spider Man. Spider man got bitten by this. This spider. And he had no idea how to use this gift. And his strength and his abilities that he already had with the spider just enhanced them, but he still didn’t know how to use it. A lot of these kids today, they got these superpowers and these abilities that they don’t even know how to use. And so when I see that we help these kids be able to use that ability, that’s empowering to me. 

Jeff Johnson:
So these kids represent courage to you? 

Will Keeps
Yes. Then you got. Some kids don’t care about courage. They just care about whatever. We gonna speak the good, and we’re gonna speak the bad. Nobody wants to talk about the bad. You know what I mean? Because I’m in this. I mean, I’m doing this job and doing what I’m doing because there’s a lot of bad out there, and there’s a lot of. There’s a lot of people who. Who just don’t get it. When it comes down to courage and moving forward. And no matter how you try to help them, if they’re not helping themselves, my help is a waste of time. 

Jeff Johnson:
Yeah. 

Will Keeps
One young lady, I had her for about two to three months, and she was causing so much problems inside the building, where her mouth attitude was making people uncomfortable. Every time she got in trouble, she blamed everybody else. Other than holding herself accountable to the point where I gave her so much grace because she was actually improving in other things. But that one thing, when it comes down to her behavior, like talking about smacking teachers, you know, I’m saying, I’m gonna fight somebody. I don’t care about this person. You know, starting. You know, starting things with other students and staff to the point where I had to tell her she had to go. You know what she said to me? She said, you guys said you was gonna be there for me. I trusted y’all, and now y’all gonna let me go. 

Will Keeps
What I said to her was, is that I trusted you, and you can’t even see what you’re doing. That’s hurting yourself and hurting others around you. So she wasn’t ready to be a part of this program, so I had to let her go. So she’s hurt. 

Jeff Johnson:
Well, you’re on the front lines with these kids that are having a difficult time. Well. And like you said, your success rate is what, 54, 58. 58%, which is wonderful. But I can see how your heart would break for the other 42%. 

Will Keeps
Yeah. 

Jeff Johnson:
That aren’t making it. That would be difficult. 

Will Keeps
It does break, you know, because my mindset is to help everybody, and I don’t want to put a band aid on the issue. I want to do surgery. So that’s why I was saying in the beginning of this conversation that we’re fighting an empire, a full army that’s been growing for centuries, and that’s negativity. And we expect to fight this negativity with the positive. The positive. Okay. We talk about God. God is in our life, in our heart. God is the empire. Right. But if we do not follow everything that God wants us to do, when it comes down to fighting this negativity, how are we gonna win? And that doesn’t mean just me as being a leader. That means that people like you or other people that can actually help me fight has to step up. 

Jeff Johnson:
Right. 

Will Keeps
Is that making sense? 

Jeff Johnson:
It’s Making sense. And do you know what I love so much about your heart, Will, is because this has been around since 2018, and you’ve been doing this stuff before then, too, but, you know, just starts right here. Proper has been around since 2018, and you’ve had great success with it. I mean, these are lives that otherwise would be out on the streets or they’d be destitute, they’d be doing something else. And now they have an opportunity. You know, they have a positive trajectory. But I can understand why being as close to it as you are, you can see the need is so much bigger and you need so much more help to keep going and to keep growing and to reach everybody. That. Yeah, I mean, I can hear your heart clearly in this, Will. 

Jeff Johnson:
Let’s come back to this main question, Will, that I came over here to ask you. So Will keeps. What’s the most courageous thing you’ve ever done? 

Will Keeps
Was to get shot, See two kids die and get back up and be mad about it. Be mad that I seen two kids die and not run away from it. But to understand, I have to run towards it. 

Jeff Johnson:
Share as much of that story as you feel comfortable sharing, Will. 

Will Keeps
I had three kids who was in opposite gangs. Well, they all said they weren’t in the gang, but we know they were. Situation happened where? Outside of the school where one of the kids, Preston, was upset with Gianni and Rashad, and he came into the school and had a great day. He wound up killing those two. And because I tried to stop him, he almost killed me as well. Shot me twice. 

Jeff Johnson:
That starts right here at the school. 

Will Keeps
He shot Gianni 13 times, shot Rashad nine times. He killed him, and I had to watch that. I lost three boys that day. I tell people that Preston, you know, he was. He was. He only had two days left to graduate because I had him for about two and a half years. He had two more. Two more days to graduate. He was going. He was going to ice this test because he was doing good with that. Learning how to. I think it was math. He was doing good with math, and he was going to ice that test. And to see. To see that happen in front of me was the worst thing that ever happened to me in my life. And I’ve been through a lot. 

Will Keeps
And I think the reason why I was the worst, because it happened in a safe place where I was supposed to be the one who protecting them. So it broke my heart and it almost crushed me. 

Jeff Johnson:
And you have physical wounds that came out of that. 

Will Keeps
Yeah, I was shot in the hip. It went through my body. The bullets launched on the other side. I still have nerve damage down there where I’m not the same. And I got shot. I had my hand on my heart, and as I was falling, he kept shooting and shot me in four of my fingers. 

Jeff Johnson:
Because you were trying to get between him. 

Will Keeps
And I realized that Preston might have a gun, so I went towards Preston and tried to get Preston out the door. Preston came. He came under my arm, and he started shooting. Rashad ran my way. He shot 30 rounds in seven seconds. Rashad ran my way, and I didn’t even know. Rashad ran past me, and he already shot Gianni Becker, Another. Supposed to have been three dead that day. Becker ran out the back door. As he turned around to shoot at Rashad Moore. I was right there. So I already lost three seconds because of shock, because I’m like, what is happening? But I was in that fourth second, I was trying to figure out how I was going to get to Preston, But Preston already turned the gun around within that four seconds. 

Will Keeps
And as he was shooting Rashad, he shot me twice in the process. And as I went down, my hand was on my heart. He shot four of my fingers, and the bullet went through my ring finger. And I had this ring on that I never wear. I wore it that day. Never wear that ring. And the bullet hit that ring, and it created that bullet to not go into my heart. 

Jeff Johnson:
Wow. That’s a miracle. 

Will Keeps
Yeah. People. People was telling me that we don’t. We wouldn’t blame you if you quick. If you gave up, wouldn’t blame you. But I couldn’t see myself quitting, giving up. I saw myself, like I said, getting mad like, y’all, don’t try to kill me. Oh, okay. We finna. We finna go harder. We finna fight even harder, you know. 

Jeff Johnson:
So that’s a form of courage of itself. 

Will Keeps
And I always thought that I was some punk growing up, you know what I’m saying? And I’m thinking to myself, and a lot of kids think they’re some punks. Sometimes they’re afraid, but they don’t realize that sometimes not saying something, not doing something, is more brave than doing something. 

Jeff Johnson:
That’s right. 

Will Keeps
It’s crazy how God has helped me to be strong when it comes down to fighting my pain. He find ways to get me to really see things different than my pts Is trying to show me. You know, some people say, how do you even make it through that? Because a lot of people would have crumbled behind all that. I’ve been through so much of my life. I feel like God prepared me for this moment. 

Jeff Johnson:
You’re all in with this, Will? 

Will Keeps
Oh, I’m all in. 

Jeff Johnson:
Yeah. 

Will Keeps
Yeah. 

Jeff Johnson:
One last question, and I so appreciate your transparency. I appreciate how honest you’ve been with all of these questions and just our discussion here. But one last question. I’ll let you go. What would you say? And before I ask this question, I’m thinking that you say this to the kids, probably that you have. It starts right here all the time. But what kind of encouragement would you give somebody to. To have the courage to say no or to have the courage to walk through some fear or something like that? Somebody that’s facing a difficult decision right now. What would you say to them doing. 

Will Keeps
I’ll tell them this story. It was one day I was at a club. It was before I became Will Keeps of helping the community. I was at a club and I came out this club and. And it was like three guys. And one of the guys was sitting on my car. And in my mind, I’m thinking to myself, I know this fool ain’t sitting on my car. Like, I’m getting mad, you know what I’m saying? Like, wanting to fight. But I tell this guy, I said, hey, man, this my car. He’s sitting on my car, and he says, okay, my fault, my bad. And then as I’m about to get in the car, he wanted to show off to his friends and start cursing me out, you know what I’m saying? Saying, so what? I’m sitting on your car. 

Will Keeps
This car is whack anyway, you know what I’m saying? I can sit on your car. It was talking to me all crazy and then showed me his car and said, my car better than yours. And I’m thinking to myself, why are you doing all this, man? If your car is better than mine, why aren’t you over there on your car? But he’s cursing me out, talking crazy, trying to punk me out. The old me would have probably fought, you know what I’m saying? Got in his face. This new me decided to think and say, what if he has a gun? Because he’s showing off right now. Everything was all cool. He’s showing off right now. Maybe he has a gun or maybe he don’t have a gun. And. And I fight him and something happens where I hurt him. 

Will Keeps
So I decided to just get in my car. As I’m in my car going home, I’m screaming and I’m crying because I’m so angry that I felt like he pumped me out that I felt like he was trying to make me look like some weak person in front of everybody. And it was making me so mad. And I’m in there crying, screaming, hitting the car, everything. I was that angry. I came home and my wife was like, what was wrong? I told her what happened, and she said to me, she said, you gotta understand the bigger picture. And I said, what’s the big picture? She said, you made it home. You’re home. And I looked at her and I was like. She said, what if you would have did something else and you never made it home? 

Will Keeps
So those are one things that I want to help with these kids, to remember before you make a decision or maybe before you do something that can cause an issue, your main goal is to get home, to be able to. Because there is a. Because maybe they might talk about it for a couple of days, they might talk about that for a week, but at one point, they ain’t going to talk about it no more. But if you react, you might be dead forever. You might be in jail for a long time or anything that can last forever in your life. But by walking away screaming in your. 

Jeff Johnson:
Car. 

Will Keeps
Yeah, I made it home. 

Jeff Johnson:
Thank you for visiting with me today. 

Will Keeps
Thank you for having me, man. 

Outro:

Thank you for joining us today on Courageous. If you’d like to hear more about the work and ministry being done at Crossroads Apologetics, please visit our home on the web at crossroadsapologetics.org Would you or someone you know like to be featured on Courageous? Send us an email at info@crossroadsapologetics.com or info@crossroadsapologetics.org telling us about the most courageous thing you’ve ever done.