Changing Lives & Feeding Thousands: Dion Dawson's Inspirational Story On Leadership, Food Insecurity, Impact & Purpose (Inspirational)

What happens when a young man who once experienced hunger decides to dedicate his life to feeding thousands of families every single week?

In this powerful motivational and inspirational episode, Reginald D sits down with entrepreneur, visionary leader, and social impact innovator Dion Dawson, founder of Dion’s Chicago Dream and CEO of Cosmic Crate.

Raised on Chicago’s South Side by a single mother, Dion experienced homelessness, food insecurity, shelters, and hardship firsthand. Instead of allowing pain to break him, he turned his experiences into purpose — building a movement that now delivers fresh fruits and vegetables directly to thousands of families every week.

Dion also shares powerful wisdom about purpose, resilience, legacy, mentorship, entrepreneurship, social impact, and what it means to choose your assignment every single day.

This episode reminds you that where you start does not determine where you finish. Through consistency, service, vision, resilience, and self-belief, Dion transformed personal hardship into a movement impacting entire communities.

This motivational and inspirational conversation helps listeners understand:

• Purpose often grows through struggle
• Impact matters more than image
• Leadership requires consistency
• Success is built through choices and discipline
• Your pain can become someone else’s healing
• Service creates lasting influence

Press play now to hear this powerful motivational and inspirational conversation with Dion Dawson and discover how purpose, resilience, and service can completely transform your life and the lives of others.

Dion's Contact Info:

Website: https://www.diondawson.com

Instagram: https://www.instagram.com/diondawson

YouTube: https://www.youtube.com/@ChiefDreamerDion

TikTok: https://www.tiktok.com/@chiefdreamerdion

Transcript

Reginald D: Welcome to Real Talk with Reginald D. I'm your host, Reginald D.

On today's episode, I have Dion Dawson.

Dion Dawson is the founder and chief dreamer of Dion's Cargo dream and the CEO of Cosmic Crate.

Dion turned a vision on Chicago south side into a movement that's feeding thousands of families every single week. Welcome to the show. Dion.

Dion Dawson: How you doing, man?

Reginald D: I'm doing good, man. Doing good. Thank you for coming on the show with me.

Dion Dawson: Absolutely.

Reginald D: Thank you for having me.

Dion Dawson: Thank you.

Reginald D: Yes, sir. Absolutely. So, Dan, tell us a little bit about where you grew up and what your childhood was like.

Dion Dawson: Childhood was amazing. I think when you think about childhood, I think how you experience it is different than kind of how you reflect on it. So while I was in it, I think, you know, it was amazing.

I think it was random at times.

But being the youngest of four boys, being raised by a single mom, you know, it was different.

And when I got older, I started learning about some of the things that I didn't have growing up, you know what I mean? So I realized it wasn't so common, moving from place to place and having to stay at a shelter from time to time and, you know, not really having things to eat when you want it and different like that.

So, you know, now I look back, and I'm able to kind of hold that balance, and, you know, the duality of having a mom and brothers that loved me and being lucky to have that love, but also growing up without a lot of the things that I should have been able to have access to.

Reginald D: Yeah, absolutely. I can relate to the stories. You know, the single mom store, man. Been there, done that, you know? Absolutely. We kind of built different.

Dion Dawson: Absolutely.

Reginald D: Come up, you know?

Dion Dawson: Absolutely.

Reginald D: Dion, you're called a Chief Dreamer. What does that title mean to you beyond just business?

Dion Dawson: Well, Chief Dreamer. You know,

when my team and I,

we were discussing titles and creating roles,

I understood that, you know, no matter what, I am the founder.

That's not gonna change.

And when it came to the role that I played was going to be the CEO role.

But the name is something that is important,

unique, and also, you know, it illuminates whatever your approach is.

So for me, I said, Chief Dream of his dreams can be as small or as big as we make them. And with my team, I'm tasked with making sure that not only is my team always dreaming, but always we're trying to go after it.

We're always trying to make sure that in Achie,

whatever the goal is or whatever mission we're fighting we're making sure that, you know, I'm leading that from the front, from the back, from the middle, with everybody by myself.

And so it just felt right.

Reginald D: Yeah. And the thing about it, people don't understand. A lot of times when you trying to achieve something, there's levels to this thing.

You reach one level you have, there's another level you got to go, and there's another level you got to go. So it's levels to it.

Dion Dawson: Absolutely.

Reginald D: Dion, can you tell us about your two companies? You got Dion's Chicago Dream, and you're the CEO of Cosmic Craig.

Dion Dawson: The Unchicago Dream is a nonprofit social enterprise that we created almost six years ago where we fight food insecurity through last mile delivery and logistics. So it's just a lot of word salad to really say that we're the opposite of the pantry.

Instead of people coming to us, we go to them. Instead of us hoping that they can receive donated food. We only provide what we purchase. We purchase fresh fruits and vegetables, and instead of leaning and relying on volunteerism, we actually create jobs in the community.

And so when you look at it as a whole, we utilize last mile delivery of a week's worth of brand new fruits and vegetables are delivered right to the doorstep of recipients all over Cook County.

Here in Illinois, which is the second largest county in America, that is something that we started from nothing grown to almost a $7 million organization and social enterprise. And then it allowed us to then create the for profit that is owned and managed by the nonprofit, which is Cosmic Grade,

and what Cosmic Crate really is. Cosmic Grade is a software and a platform that allows small and medium businesses to utilize everything that we learned with Dion Chicago Dream by creating a platform where they can connect CRM and touchpoints,

last mile delivery and fleet management and inventory and procurement. And so when you're thinking through that, Cosmic Crate is the system for small and medium businesses to be able to not say, I don't know.

So you're connecting what you're procuring to who your customer is and then being able to dispatch the last mile delivery routes. All of these talking together,

all of these connected together.

And so instead of, you know, purchasing eight different tech pieces or products,

you have this one thing that can tell you so much about your business and allow you to scale and grow it organically.

Reginald D: Wow, that's amazing, man. Appreciate it. That's amazing.

Dion Dawson: Thank you.

Reginald D: So let me ask you this. Was there a defining moment where you realized your life was about more than just success, but about impact?

Dion Dawson: Well, I Think the beautiful thing about that question is,

up until this point, my life was never about success as a black man, as a professional,

you know, you're not successful until you're deemed successful.

I was never treated as if I would be something.

And so for me, this unlocked when I realized it was about happiness.

And I realized that instead of trying to prove to everyone that I am special or that I can do it, this was the first time where I didn't try to do that.

It was really out of blind ignorance and wanting to serve something outside of myself. And so I was just so lucky that that moment really lined up with having the opportunity to, like, find my passion and my gift.

But, you know, it's crazy. Like, do I feel like I'm successful sometimes?

You know, it depends on who's watching. But I done things, and do I feel like I put it all on the line? Absolutely. I think that is what success really is, is, did you do everything you could?

Sometimes you're not going to decide how it's received, but did you do everything on your side? That's what it's about.

Reginald D: Yeah, absolutely. Because that's the thing.

You can't say like this. I don't think you can label somebody as successful or call something a success unless you put it all on the line, like you said. You know what I mean?

You stepped with it, you played with it,

and it is what it is. It's not.

That's not successful.

So what problem did you see in your community that most people were ignoring but you couldn't unsee?

Dion Dawson: I'll start by saying I don't think this problem of feeding the community or just making sure people have access to fresh and healthy options is something that anybody ignored. I think that's why we lack innovation.

I think we've tried to focus on this, but we're not asking ourselves the difficult questions.

We're not asking ourselves. Like you asked me, what is success when it comes to feeding our communities?

What is success when we treat food insecurity like it's hunger, when they're two different things?

You know what I mean? Food insecurity, by definition, is the lack of consistent access to healthy options.

So if we use a pantry model approach,

if we use a hunger approach,

we're not solving the issue because it's not fresh and it's not consistent access.

And so when we talk about what I saw, if anything, it was the opposite. I saw everybody focusing on it, but outside of the focus and the intent, we weren't judging the execution.

We want to do it, but we want to be great at it. I didn't see people wanting to be efficient and effective and getting it right and being great and scaling amazing operations.

I saw the opposite. I saw people who wanted the pat on the back to be the currency.

And as a result, I asked myself, I said, you know, what is success?

And if it's feeding people,

then we have to be judged by how many people we feed. And if it's feeding people healthy food, we have to be judged by how many people we feed healthy food.

And if it's consistently, then we have to be judged by how consistently we do.

Wasn't complicated. It was actually quite simple.

Reginald D: Yeah, it was. That's real simple. Because if you judge each category, that's how you put everything together. Yeah, that all comes together.

Absolutely.

You could have all these dreams, you could have the want to.

You know, it's more than just showing up.

Like you said, you gotta execute.

Yeah. That's what life, you know, at a whole. You know what I'm saying?

Dion Dawson: Absolutely.

Reginald D: So you built something incredible. But what did the struggle look like in the beginning that people don't talk about?

Dion Dawson: I'm gonna go a little different here.

It wasn't really a struggle.

You know, I think the framing of it is important. I think there's difficulty in everything.

But I'm lucky in that before this happened,

I walked in a room and in 2017, I believe 2017ish,

and they told me my mom had kidney cancer.

And if you've ever been affected or afflicted by cancer or by someone with cancer,

you realize that's what a bad day is.

You realize that's what hardship is.

You realize that's what difficulty is. That's what the hard thing is.

I can't take on trying to fight a problem that needs to be evolved and innovated in and think that my hardship is harder than the people I'm trying to serve.

And so in the beginning, at the time, and still I'm having a time of my life,

were there days when we didn't understand how we were going to purchase the food? Absolutely.

Were there, you know, deliveries early on? What was it? I'm rocking and I'm doing a lot of different things. Absolutely. But,

you know, even with your podcast,

there's difficult moments that people don't see.

Who's to say they're meant to see them or know about them? You know what I mean? Sometimes we have to accept that those things may never come to light.

But it's because this thing is bigger than those moments.

And if we put too much focus in on that framing, I just. I cannot remember more of the difficult days because my life has been so difficult already.

So I'm lucky and I'm blessed with perspective.

A difficult day is not knowing how you're going to eat.

Difficult day is sleeping on a bus. A difficult day is going from one person's couch to the next.

You know what I mean?

So early on, this was the first thing in my life that I ever fought for.

And I woke up every day and I kept choosing it.

And that's the beauty of the choice.

Like, we have a choice.

So is it really difficult if we keep coming back? Is it really difficult if we decide that we're going to slay this dragon now? It wasn't.

There's way too many.

Too many good days and way too many moments. I've been lucky enough to be uplifted and protected and having a village and having mentors and having all of these things to even.

Even keep it. Because sometimes, you know this, sometimes you don't want to remember.

You know what I mean? The things we remember to find who we become,

some things will be difficult. That's fine. I don't mean it's worth remembering.

Reginald D: Yeah, you hit that right on the head, man. You hit that right on the head. And like I say,

a lot of people get so wrapped up in themselves and every little thing that doesn't work right.

It's like the biggest setback in the world, and it's really not that serious. You try to look at somebody else's life, and they say, man, that could have been me.

I know a lot of people, I'm like, man, I'm blessed, man. Even though I have some days I look at somebody else's day, I'm like, man, hey, I'm blessed regardless.

Dion Dawson: Absolutely.

Reginald D: A lot of people believe that food insecurity is just the way it is. Why do you believe it's actually solvable?

Dion Dawson: Well, I think, you know, I'll tell you,

I think it's manageable.

I think that what we see is the need to eat will never change.

Something as simple as eating will always be required for life.

Then it's safe to say and, you know, conclude that there will be people for the most part, until this next big jump, you know, hopefully into the next iteration of whatever society is,

that there will be people who will not be fed or nourished as much as others because of the system that we're in.

And so if we change the framing to saying, you know, we can help manage it because you need that consistency. Remember, consistent access to healthy options.

So if we build in that consistency,

then we can talk about managing because it's a relationship.

And so, you know, I don't have to think it's solvable to know that it has to be manageable, and it has to be managed and has to be sustained and consistent.

And through that,

you know, it then becomes a challenge of meeting the moment and answering the call consistently.

And as a result, it is not this big thing, because I don't feel that they're being truthful when they say they want to solve hunger.

How can you want to solve hunger when you fed somebody one time in a month?

How can you say you want to solve hunger when you're spending more to talk about the little you're spending on feeding people? And so I just think that framing and definitions and guidelines are extremely important in this work.

And I think that I've been successful,

my team has been amazing and successful and impactful because we make sure that we understand language holds weight.

The words that we use will be the things that we're judged by. And we don't want to,

you know, tell people, hey, we're going to solve hunger. No, we're going to manage food security so that, you know, through that word, manage that we're not going anywhere and we're taking responsibility.

Reginald D: Yes.

And the thing about it, you know, I've always battled with this in my mind,

you know, now you'd ask for that.

But I was battling this ago, man. I was like, man, how can, like, people just be hungry in the United States? Just say the United States.

Dion Dawson: Yes.

Reginald D: So we can do everything else, you know, but pee, pee that's hungry and throw money at everything else.

Dion Dawson: But that's because I think even if we take away,

you know,

how things are going right now, if you really ask yourself, we've never been set up to feed everybody.

If we said, today we got the money to feed everybody,

we don't have the infrastructure to actually do it,

because we saw it in the early days of the pandemic.

We're one bad day away from our food system being overexposed and completely shocked again.

And so that's where Dion Chicago Dream and Cosmic Crate comes in. Is that. No, like, we're going to solve the problem with whatever we have, and not the problem of hunger, but this problem of having a disconnected and dark food system so that as resources come in, they can flow to the people that need it.

But right now, we don't have that. And that's the issue that I'm really trying to get to.

Reginald D: Yeah, man. ****, man. I love your vision.

Dion Dawson: I appreciate it, man.

Reginald D: Yes, sir. So what separates someone like you and your vision from someone who can execute on a high level?

Dion Dawson: Nothing.

I don't see any difference between anybody else and myself. I think it's actually,

you know,

J. Cole lyric that always. You know, one of my favorite is he say, I'm just a man of the people. Not above, but equal and for the greater good, I'll walk amongst evil.

And it reminds me of me being no better or no worse.

You know what I mean? And so, you know,

I have my flaws, and I have my things I

Reginald D: have to work on.

Dion Dawson: I also have the things that I make me, me.

And so it's not seeing myself as different. It's actually seeing myself and everybody else and that humanness, that humanity part of it that I don't have to lose because everybody else wants to put it down because it's so difficult,

so difficult to fight social issues while being faced with social trauma.

So, you know, a lot of leaders ignore it or they stay away from it because it doesn't feel good. You know what I mean? But it's the opposite for me.

It allows me to still feel human.

It allows me to remember that, you know, this thing is gonna go fast sometimes and super slow. But the thing that I control is what I put into it. But it's because I'm actually just a regular guy that loves to instill in people the belief that, you know, they're greater beyond their wildest dreams.

And if you can inspire people, if you can motivate people, if you can get them to believe that tomorrow will still come and they'll be able to figure it out, you'd be surprised at what we could do.

Reginald D: Yes.

Influential leadership, man. That's what it's all about. That's what it's all about.

So you advise Fortune 500 companies now? Yeah. What do big organizations get wrong about? Impact?

Dion Dawson: I think, you know, I'll tell you this, and I want you, you know, you can take this, and I want you to think about it after our interview. And kind of, as you do your great job of having conversations and having your platform entrepreneurs and traditional business focus too much on execution and not intent and social entrepreneurs and nonprofit and charity focus too much on intent and not execution.

So I think what they're getting wrong and why there's this civil war between the business and social sectors is that we have to understand is that because of the system that we are on top of, the foundation is capitalism.

Where the money ends up is extremely important.

When we think about all of the models that have, you know, lasted the test of time,

a lot of it has boiled down to the good and values of that person.

Until further down the line, it was able to be codified. And what I mean by that, and an example of that is,

you know, the having free breakfast across the country was preempted by free breakfast from the Black Panthers.

So through the good and through the social focus of an entity or a person,

until it can be codified and scaled and spread,

it is dependent upon who created it to keep it alive. And so when I think about that, I think that we just have this situation where there's so much ambiguity because one side only focuses on making money and the other side only focuses about doing good,

not understanding that the foundation both of them operate under is capitalism. So if time is money and we want to change it, we cannot change it without living inside of the system,

extracting the value from the system, and then maintaining our core values until it becomes codified and stale.

Reginald D: Yes, as well. But, you know,

I like that. I like the way you put that, because it all has to come together, man. I mean, as long as it's divided, it's never going to bring the impact that it should, you know, at the end of the day.

So we talk about faith, purpose, and resilience.

What keeps you grounded when the weight of impact gets heavy on you?

Dion Dawson: Sometimes I think for me, I just. I try to stay even. You. You know what I mean? There's going to be hard days. There's going to be,

you know, great days. But I think finding the joy when I don't need to be told that something should give me joy,

trying to just have that natural level of appreciation in spite of everybody's work is difficult, you know, but that doesn't define the work.

The work is actually beautiful. The work is actually worth it. The work is actually,

you know, for people other than myself.

And so I have to make sure. And I have to remind myself, like, man, okay,

it's not the best day,

man. It ain't the worst.

And I think on the flip side, I'm like, man, it's a pretty cool moment,

but also, it'll be okay.

Reginald D: Have you ever doubted your assignment?

Dion Dawson: I don't think there's doubt in an assignment. I don't think we're taught to understand how to look for our assignment. I think you can't tell me and, you know, you let me know regardless.

Like, has there ever been a time where you were sure of something beautiful and refuted it?

No.

It was only when you weren't sure if it was beautiful.

So I think that when we talk about the assignment, I don't think anybody wants to doubt their divine purpose.

But when you're not taught and you're not cultivated and you're not trained to see value in yourself,

to see value in something outside of yourself,

then how could you then be confronted with your assignment and be able to translate it, you know?

Reginald D: Yes. So then what's something you had to unlearn about success to step fully into your purpose?

Dion Dawson: I think the biggest thing that I had to. Well, I won't even say unlearn. You know, I think just I had to choose and keep choosing and understanding that it's always this recommitment.

It's just a cycle of recommitting.

I think we expect it to be one choice,

but the assignment is a consistent choice. You're always having to choose.

You never stop choosing.

Reginald D: You choose so much throughout the day. People don't even know how many. How many times they choose. I mean, thousands of times throughout the

Dion Dawson: day,

every single day. You know, it's in your actions, it's in your feelings, it's in your emotions. It's in, you know,

everything you do. And so that's the choice you always have to keep choosing.

Reginald D: Yes, sir. Absolutely. So if you work with major organizations like the Chicago Bulls and GoFundMe, how do you stay authentic while scaling partnerships?

Dion Dawson: I think that you have to know who you are.

Being authentic is being authentic to you. And you can't be authentic to you or what you're doing if you don't know who you are and what your true north is.

And so understanding that when you're scaling partnerships, partnerships have to be valuable to both sides.

So I'm really good at partnership because I start partnerships by asking, how can I give you value?

So many partnerships we always want to take,

but instead it's obvious. How do we give value?

Reginald D: Yes. And that gives it direction.

Dion Dawson: Yeah.

Reginald D: When you first start out. Because I tell people, when you try to partner with somebody or try to do something with somebody,

if you don't have direction coming at the gate, it's not going to make. It's not, because everybody will be thinking one way and thinking another.

You know, this is what I got for you. This is what I can help you with, or you just help me,

blah, blah, blah, that it all comes together that you know what you're going.

So you shared stages with major leaders.

What's one lesson that stuck with you, that changed how you move?

Dion Dawson: Tell people all the time I've been able and, you know, lucky and blessed to be in the same room, share a stage with President Barack Obama.

And what I always walk away from or from him with is appreciating time,

you know,

and understanding, like, you know, being patient with how we experience a room, how we interact with the room. I remember the first time a few years ago, and I got a chance to speak and introduce him.

So I was able to, you know, speak for, do a five minute talk and then introduce him. And I'll never forget, just be like, man, I okay, kind of thinking I'm pretty good, you know.

And then he spoke and I said, oh, I got some work to do.

That's the lesson. The lesson is always understanding that, you know,

things could be better, things could be worse, you know, but intentionality is important. How you experience time, how you appreciate time, how you show up as yourself, but demand to be better, you know?

Reginald D: Yes, yes. Always got to grow, man. Always got to grow.

So, Deon, if you could sit down with someone who feels stuck,

broke, and overlooked right now,

what would you tell them about turning pain into purpose?

Dion Dawson: I would just tell them that I love them.

And I would tell them I would want them to love themselves and that they matter.

And even when they don't think they have a purpose, they still do,

and they've always had one.

And I know how it feels for the phone to not ring.

I know how it feels to feel like you're on that island,

but also being there,

it saved me.

It allowed me to be okay with being alone. It allowed me to be okay to be lost in thought.

And as a result, it allowed me to appreciate presence and share space and understand that, okay, I can do this.

And if they feel stuck, it's okay, because we've all been stuck.

I don't mean you go stay stuck.

If you've been lost, it's okay, because you will be found.

But just understanding that all of these things are temporary.

So as long as you can save and kill, you'll understand that I may be lost in the battle, but I won't stay lost.

I may feel like it's not worth it now, but it will be.

Reginald D: Yes, sir. Yes, sir. It's all part of the process sometimes. Absolutely. All part of the process. So what's next for you and how big are you really thinking?

Dion Dawson: Oh, I mean, I'll tell you this, I don't think big or small.

I remember when my mom had cancer, just recording her voice so that hopefully I can have memories.

And now I look up and my mom is still here.

And,

you know,

not having to have a five or ten year plan,

just knowing that if I'm alive, I'm going hard.

That's the beautiful thing, Reggie is wherever I'm at, I'm going after it. And I don't care whether it's leading two companies or babysitting or cutting grass or working at a library or driving a bus, I don't care.

You know what I mean? Like, that's the beautiful thing about it, is understanding that, you know, the position doesn't really define,

you know, the dream is you can be whatever. I just know that as long as I got breath in my body, I'm gonna give it 110 every single day.

Reginald D: Yes, sir. That's what it's all about.

That's what it's all about.

So then what I have is I call them quick fire questions,

you know, no right or wrong answer. I'm just gonna throw some stuff at you.

Dion Dawson: Throw it at me.

Reginald D: All right. The biggest lesson, failure has taught you

Dion Dawson: that failure is subjective to the mood that you're in.

Reginald D: All right, finish this sentence. I knew I was walking in my purpose when I would receive the worst

Dion Dawson: possible news, and it didn't crush me.

Reginald D: Got it. What's something people misunderstand about you?

Dion Dawson: That my power comes from being around other people, when in our actuality, it comes from being by myself at times.

Reginald D: Got it. Legacy. What is that in one sentence or two? It doesn't matter.

Dion Dawson: Oh, that's easy. Legacy is something that I have no control over, and so I don't even bother thinking about it.

Reginald D: I like that. Finish this sentence. If you were waiting for the perfect moment, here's the truth.

Dion Dawson: The only perfect moment is whenever you start doing what you're supposed to be doing.

Reginald D: Got it. Now, Les, how can my listeners learn more about your confidence, follow you on social media and follow your journey? Dion.

Dion Dawson: Oh, absolutely. On every social media platform at Dion Dawson dionchicagodream D I O N S Chicago Dream at Cosmic Crate app on Every platform on YouTube websites. CosmicRate app dionchicagodream.com Dion Dawson.com and yeah, engage.

You know, I try to be a tangible and present leader. So I think it's important that our leaders, you know, are present online too and responding to people and talking to people.

But, yeah, you know, supporting is Something as simple as, you know, becoming a 5, 10, 20, $30 a month donor on our website. You know what I mean? Whatever. I think that's the beautiful thing of it and seeing those dollars in action,

you know, those dollars buying food and creating jobs and feeding people, so. But other than that, they can also support me by making sure they're okay. It's really, really hard to live right now.

So, you know, even them making it to hear this interview may have been a lot. So, you know, hopefully this can inspire or allow someone to know that they can keep going.

Reginald D: Yes, sir. Yes, sir. There you have it. Dion Dawson. Dion. Thank you so much, man. You incredible work, man, and appreciate it, brother. Keep pushing and keep going, man.

Dion Dawson: You know what I'm saying?

Reginald D: God got absolutely. You know, it's gonna keep on elevating you, man. You know, tussle your heart.

Dion Dawson: Absolutely. I appreciate that, man. Likewise. Thank you for allowing me on your platform. Thank you to all of your listeners. And I'm always around, man. You know, if you ever have me back, I'll be happy to be back.

Reginald D: Absolutely. We need to work that out.

Dion Dawson: Absolutely, brother. Okay.

Reginald D: All right, brother. Appreciate it. All right, man.

Dion Dawson: You have a good one.

Reginald D: All right.

Thanks for listening to Real Talk with Reginald D. If you enjoy listen to Real Talk with Reginald D, please rate and review on Apple Podcast. See you next time.