Jonathan Moore

Fearless Five | Baltimore

Jonathan in fearless BLM mask and hoodie in front of shelves


  • Educator
  • Survivor
  • Leader


We can either go over, around, or under. Or we can just start chipping away and get to the other side.


Founder of Rowdy

Jonathan’s tech company is training people with criminal backgrounds or arrest records to become manual/automated QA Testers.

“I like working with people who’ve been through some stuff. Because their stress level is different. The way they troubleshoot and problem-solve is different. It’s a different conversation. It’s a different way that we interact. And no barrier is too great. It’s just like, OK, well then, we can either go over, around, or under. Or we can just start chipping away and get to the other side.”

The only thing I can be is me.

Jonathan has dedicated his life to “locally focused digital connectivity” and he is boldly bridging the digital gap that affects


of homes in Baltimore.

After completion of 16 months of training, participants become qualified candidates who are placed into entry-level positions with a tech company or tech-focused department.

We met with Jonathan to understand the motivation that fuels his fearless life and gain his insight on how others can become fearless, too.

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In their own words

Once I went through that process, I began to work on myself. I went to therapy, and I was honest, which allowed me to gain a better understanding of myself. There was this clarity. Then, I was just like, “Fuck it. I ain’t got nothing to lose.” I had lost it all. I’m going for everything.

His Fearless Story

The sun is beaming and the cloudless sky is offering no shade from the 90-plus-degree heat. The Fearless team arrives at City of Refuge Baltimore, a nonprofit located in the middle of Brooklyn and Curtis Bay on the south side of Baltimore City. The neighborhoods are not too far from the Inner Harbor, but it’s far enough to have it’s own unique culture and style.

It’s Thursday, just before noon and there is a long line of families taking advantage of the program’s weekly food drive.

The residential community is struggling, with nearly 35 percent of the residents living below the federal poverty level.

Members of the South Baltimore community receive bags of groceries, toiletries, and baby essentials, in addition to free access to Wi-Fi internet, thanks to our Fearless Five model, Jonathan Moore and his company Rowdy

Jonathan, originally from Baltimore County, has dedicated his life to “locally focused digital connectivity” and he is boldly bridging the digital gap that affects 40 percent of homes in Baltimore.

Jonathan Moore talking to his team

What do you say to the people who see the system is broken, but don’t feel as though they can make an impact?

The first thing I would say to someone is understand your comfort level. Because you need to know, if you are coming to the table with no resources, you will have to sacrifice something to make your greatest impact. And sometimes it’s your mental health. Sometimes it’s your friends. It’s your family. It’s loved ones. Sometimes it’s free time…sleep. (He laughs.) But Black people started out with nothing, so this is nothing new.

Fearless Hero Team against Brick wall

It’s just taking small, incremental steps, and realizing that you are not alone. You’re one of many. Probably one of thousands. You all just haven’t met yet. The shit you’re going through, there’s another counterpart in another county, another side of the city, in another state, in the country, that’s feeling the exact same pain you are. You are not alone but the system is set up to have you fighting amongst each other for a small slice of the pie. We have to work together and look at how we fill in each other’s gaps.

Jonathan Moore on computer

Where does your focus come from?

My focus is all about how do I leave this blueprint for the generation behind me? Because it’s not about me. The focus is trying to figure it out against a system that’s fighting against me. It’s the challenge. People say you can’t do it. It’s like, “Yeah. We’re going to do it.”

What is motivating you?

For me, hitting rock bottom allowed me to hit the reset button. I had lost everything. I lost my money. I lost a family that I was nurturing, and I was drinking like nobody’s business. I was in this deep sunken place. I was hospitalized for severe depression. Once I went through that process, I began to work on myself. I went to therapy, and I was honest, which allowed me to gain a better understanding of myself. There was this clarity. Then, I was just like, “Fuck it. I ain’t got nothing to lose.” I had lost it all. I’m going for everything.

Before, I was trying to play the game and be a form-fitting piece. The light bulb went off when I started to like the sound of my name again. I was a Black man surrounded by institutional and structural racism and not holding anything back. It was on after that. The people that helped save my life were Damion Cooper, Damien Myers and Jamie McDonald [Baltimore innovators and social entrepreneurs]. It was during this time that I was doing a year-long fellowship at Bunting Neighborhood Leadership Program, Johns Hopkins Institute. It gave me structure and a place to be. It was my North Star.

Jonathan Moore listening with team at table

Can you explain your approach to fearlessness?

I just stopped giving the fuck what people thought about me. Straight up. Friends, family, whomever. I just stopped caring. The only thing I can be is me. So, now that I like being me, I don’t really care what you say about me. I look forward, and I recognize that it’s going to be a snaky road. You’re going to get your butt kicked but you’re going to learn something along the way… Keep moving forward. Also, listen to your trusted sources and be able to pivot while absorbing the knowledge of the lesson. Because whatever you put on paper ain’t always going to pan out.

You’re going to get your butt kicked but you’re going to learn something along the way… Keep moving forward.

Jonathan Moore
On not giving up
Jonathan Moore with mask with industrial background

When was the moment in your life when you looked to your left and your right, and you just leaped forward?

Oh, that’s actually a good one. It was…here. (He pulls out his wallet.) It was when the work that I was doing allowed me to cancel my Independence Card. I keep this in my wallet all the time and it never leaves my wallet. Because it’s just one of those things, it’s a humbling experience when you’re going through the same thing as the people you serve. Because I used to, when I was going through this process and there’s no money, I used to have to stand in line in food pantries.

I remember I was in line. I had 40 bucks on this card, and I gave it to a woman in front of me. I said, “You know what?” This is when I look left, look right. I was like, “I don’t need this anymore. I can go to the grocery store, and I can buy some groceries.” That’s when that happened for me.

Jonathan Moore behind camera

How does your life experience color your view of business?

I think that the trials and tribulations that a lot of people have been through, our people have been through, have set us up to go down this road, this pathway, and deal with stress and deal with the way we look at optimism. Deal with a whole bunch of things differently. I look at it as a transferable trait.

Because if I take someone from a privileged neighborhood and put them in the situations that I’ve been in or put them in situations that other people have been in, or say we’re troubleshooting, they may freak out. Where a boy or girl will be like, “Okay. Well, it’s cool. We’re going to get through this. Somehow we’re going to make this work for us.” Those are the people I like to surround myself with because we look past the barriers.

How do I make this easier for the generation behind me, and how do I be their next step or the next two stairs? I didn’t want this company to be set up to be a billion-dollar company. It’s how do we set the blueprint so other people can achieve what we’ve done? Because I’m here because of somebody else.

Walking the Walk

Around Town

 A lot of people put everything they have in, if they see the value in it.

I’ve heard you say that human good is a community asset. How does doing good give people paper?

Sometimes it does, sometimes it doesn’t, to be honest. There’s an actual study that I’m reading where it says the good you do is more of a priority in life than how much money you make. [The study asked work-from-home employees] would you go back to work for a $30,000 increase? Most people said, “I’d rather work from home because of the quality of life.”

A lot of nonprofits think that the first place to go get money is through the philanthropic machine. I would encourage people to look at strategic partners rather than just funding mechanisms. If you start looking at your idea and who’s the strategic partner involved in this, now that’s long-term money. That’s a long-term relationship, and it’s more resources. That increases your valuation. It makes you look bigger. Now when you go ask for money from someplace else, now they see the relationships that you’ve built.

It’s really starting to tactically stack your team, so that way, they fill in gaps where you can provide multiple types of value to organizations. Because eventually, these people will help you get the money that you need to sustain your operations or organization. Not only are they giving you capital resources and knowledge, that’s the triple bottom line that you want for your organization in order to grow, but they’re also talking to you about how you organizationally manage your cash flow and stuff like that. I am a big fan of strategic relationships.

Can you tell me about a time when you had the best intentions to impact change, but the wrong approach?

I just learned about this recently. Best intention was to hire youth, but how I went about it [taught me that] you can’t treat youth like adults. I had to put a team leader in and team supervisor managers who are caring, as simple as that sounds.

We had somebody on the team today who’s having a rough day, who showed up a half an hour late. Old me would’ve been like, “You know what? Yo, you’re half an hour late. Take that…” There’s no chance for forgiveness — now that’s an old corporation. The team leader approached me and said, “Hey, I’m taking him out for a walk. He came to me. I want to talk.” I’m like, “Cool. Take as much time as you want.” Now when he comes back in, he’s smiling.

Now we’re being proactive versus reactive. Reactive would have been just like, “Okay. You’re fired.” Now, I sent another young man back to the hamster wheel. Proactive is “OK, let’s create space.” Now, I guarantee, he’s going to be a loyal employee like nobody’s business because he feels safe here.

As an employer, you have engaged and communed with men who have spent their lives in the prison system. What do you think people can learn from the people you’ve reached?

The one thing they can learn is just persistence. There’s a different type of grit. That could be an asset. If you’re used to…managing people, well you can manage teams. It’s just a different language. It’s the same process.

A lot of people with criminal backgrounds are very observant about their environment. If I’m used to coming into an environment like this seven days a week, if these things are out of place or out of character, I’m going to pick up on that real quick. It’s the power of observation. Being able to read people is amazing. They know when you walk into a room, in five minutes, are you that person or are you not?

When you start to look at all those traits, you have to look at them from an asset-driven narrative versus a deficit-driven narrative.

What’s the difference? What is that?

The deficit narrative is like, such and such spent time in prison: They’re still a thug, criminal and he’s living in that type of neighborhood. Blah, blah, blah.

I’m like, “No, man. They’ve been through some stuff. They’re not interested in going back.” A lot of people put everything they have in, if they see the value in it. Once I prove the value to you, then I know you’re going to take 18 steps towards me. Well now, I got to be on a level with you about everything. You need that level of honesty, but you’ve got to create that space where they can have that honest conversation about what’s going on. If you don’t create that space and that trust, you’re never going to have that.

Jonathan Moore roundtable with team

We would like for you to be honest about the narrative of the Black experience, from the perspective of someone who has a vision of moving forward.

The Black experience, among other Black people who are like-minded, is refreshing. I’m very hopeful about Black people moving forward. Big time. Because I see that there’s a switch: They call this the next civil rights movement, where there are a lot of Black people focused on the economics of who we are. The beauty of it is, Black women are killing it. Straight up. You all have taken being Black to a completely different level, because you all get stuff done. Black men are not that far behind. More Black men are going to college now and educating themselves. At some point, it’s going to become the perfect mix of togetherness in the level of equal playing field.

It gives me hope for the next generation, because now when I look at the youth, the Black male youth that I’m working with, I’m like, “Yo, somebody just needs to put you in the position where you understand you’re a genius. Straight up. You’re not going to work at a McDonald’s. That’s not good enough for you. This is where you should be over here.” [If they say] “Well, I don’t know how to get there…” [we should say] “Well, here’s a roadmap on how to get there.”

I think that we need to stop looking at our Black youth as disposable. Well, what does it take to see the genius in them and cultivate that out of nobody’s business. With adults as well.

Anytime I do any consulting, I’m like, “We need to be deliberate.” They’re like, “Well, what do you mean by being deliberate?” I’m like, “There’s certain things we need to really think through. Let’s be as methodical and detailed as possible so that we’re all speaking the same language and we’re all on the same page. Because what’s “better” to you means “different” to me, based on your socioeconomic background.

Interviewed by Dionne Joyner-Weems, Director of Brand and Social Impact, Fearless Sports

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