That’s A Awful Lot Of Grinding: How Desto Dubb Became A Self-Made Millionaire

Desto Dubb
Image via Press

Desto Dubb has always been focused on the small picture. When he was selling hoodies out of a parking lot in downtown Los Angeles, he couldn’t see past the next day. Ten minutes into our conversation, Desto recalls, “My small picture is reaching a certain quota every day.” Back then, he was taking an awful lot of risks to make ends meet. But that’s not to say his efforts were in vain. 

At first, he wasn’t turning a profit. One might even say that Desto was the face of his brand – That’s A Awful Lot Of Cough Syrup – and its biggest supporter, wearing the clothes he made so much that it became impossible to ignore. And for the most part, it worked out for him.

His first break came from being consistent, a turn that helped establish Desto as a notable influence within streetwear. Long before he made his first million dollars (which took about 10 months to accomplish), he had been a fixture in the hip-hop community, developing a reputation for his resourcefulness. Years of relationship-building made it clear that he was a real people person, quietly becoming your favorite rappers’ favorite designer. He went on to befriend Young Thug, showering him with samples and unreleased drip “at no cost” to build rapport, and the rest is history. 

From paid collaborations to influencer marketing, the self-made millionaire remembers reinvesting money back into his brand as a key turning point towards creating a sustainable business. “As soon as I make it, I throw it back in,” explains Desto. He even admits to spending upwards of $20,000 for a single placement. 

Payola may be unethical to others, but for Desto, the pay-to-play model is essential to brand positioning. These days, he’d rather spend time with family than plan his next pop-up, but his inner hustler remains intact.

He just opened a shoe store next to his clothing store on Melrose Avenue. He’s collaborated with everyone from French Montana and Quavo to Coi Leray and the late Drakeo The Ruler. Now, he’s not trying to be “overly successful” or make more money than he did last year – Desto wants to be present in his daughter’s life.

For our interview, Desto was seated in his walk-in closet, smoking a LooseLeaf stuffed to the brim with some exotic strain. When the smoke clears, his pearly whites reveal a radiant smile that glistens in the light like his custom Drakeo The Ruler chain. And, you guessed it, he’s wearing a That’s A Awful Lot Of Cough Syrup t-shirt.

Image via Press

For starters, you’re a successful businessman. How did you transition from selling hoodies out of a parking lot to being the face of LooseLeaf?

Another brand partnership. A lot of people always want these big deals or other things,  but these big things come from little ass grinds. Me, grinding every day. And people that are grinding every day – they see me and I see them. And then a lot of people will look over and go, ‘I love the way you’re running your program,’ or ‘I see where you’re going,’ or ‘I’d like to attach my company to yours.’ And then I’ll look back like, ‘Is this guy working as hard as me.’ ‘Does this guy have as much work ethic as me.’ If he do, fuck it, let’s do it. I can at least hear you out. This is all while we’re both running to this race. It just so happens that if I won the race, then they won the race (too) because we’re on the same team. And then it just takes off from there. 

How do you know which kind of collaboration is right for you? I imagine you get an awful lot of requests. 

I’m a God-fearing man. I’m a Christian. My name is Joshua, and if you read the book of Joshua, a lot of the stuff he accomplished was God willing. I don’t read emails like that, honestly. I don’t read texts like that. I don’t read DMs like that. Unless you have some enormous following, I probably won’t see it. The best way for someone to get my attention is in my face ‘cause I do these pop-ups. If I see you purchasing an item from me, instantly my ear opens up. If you purchase something from me, you get the VIP pass. Now, if I see your bag empty and I just see you there, and I’m not doing nothing, then I might (talk to you), but if I’m busy doing stuff, I might just say “Hello.” I don’t really turn down anybody. But if you got that bag in your hand and you made a purchase, and you’re supporting me, I might retain some of that information or at least you give you my number for when I’m not that busy and you can approach me again. Nowadays, my new shit is, if someone comes to me and they’re telling me something of value, I’ma send ‘em to the right team member. If it’s something as far as retail, I’ma send you to my manager. If it’s a business proposition, I’ma send you to my business manager. If it’s a video or photo, I’ma send you to my production manager.

Talk to me about becoming Desto Dubb, the fashion designer.  

I got LooseLeaf, that’s the tobacco industry. I got That’s A Awful Lot Of Cough Syrup, that’s the clothing line, fashion, merchandising, whatever you want it to be. Bruh, I was just grinding. Me before was just waking up everyday and not looking at the big picture. I look at the very small picture and I focus on that. My small picture is reaching a certain quota every day. Sometimes it might’ve been, ‘Okay, rent is due in five days. For these next five days, all I’m focusing on every day is if my rent is $2,000, then I need to make $400 every day for these next five days to make that rent up.’ Now, I go into that mode: ‘It’s morning, I need to sell a hoodie. How can I sell a hoodie this morning? Okay, let me hit up some people. I’ma put that hoodie on today and let people see me wear it. Now, when these people see me wear it, they wanna buy it.’ Just me focusing little by little, by the end of the week, I done made $2,000. Plus, I done did a photoshoot every day, and I been marketing. Now, me focusing little by little every day… it’s people out there looking at (my grind) overall – they don’t know I was tryna make $2,000 for rent. 

In a past interview, you talked about how Instagram helped you become successful. During that time, what were you doing on a daily basis?

I was checking my comments and DMs at that time. I wasn’t getting thousands of likes – maybe a couple hundred or a thousand at that. Out of a thousand likes you’re probably getting ten, twenty comments. You can read that many comments, especially if you’re sitting in a parking lot for eight hours not doing shit. With that one post and ten comments, I probably can find that $400 I need. Of course, it’s people that’s on Instagram that know, ‘Dubb is out today. That’s where he at.’ 

Did you know that fashion would work out for you in the end or did you ever have second thoughts? 

No, no, no. Bro, I didn’t see past the week. I couldn’t see that far. When I said I needed to make that $400, it’s like in the beginning, in that parking lot, it’s two, three ways I can make that money. I got this shit niggas wanna sip. I got this shit niggas wanna wear. I got this shit niggas wanna smoke. As these months, weeks, and days go by, I’m looking at which one makes the biggest profit margin without putting me at risk. The smoke can make a lot of money, but it’s putting you in a predicament where it’s not super legal. Then you got the clothes: the clothes are making a great turnaround, and it’s making me look good on top of that. In the beginning, you got your three sources of income. You’re just pushing it out, tryna get the most out of ‘em. The one that stands out the most is the clothes, so slowly but surely I started cutting out the other sources and just focusing on one. 

Image via Facebook

Was there a specific moment that made you realize selling clothes was the way to go? 

When I went to jail. I went to jail before all of this. When I went to court and my lawyer was like, ‘Look, this is what they’re offering. You might be going to jail. The only way we can beat you going to jail is a miracle, but it looks like you might be going to jail.’ At that point in time, I told myself, ‘God is not going to bless me if I’m continuously doing illegal stuff.’ If (God) says that he likes these clothes and he likes what I’m doing with these clothes, this what I’ma do. I made a promise (to God) that I’ma just sell these clothes and not do none of this other shit if he can get me out of this situation. And once I started focusing on that, that’s when it really started cracking. 

How did you make your first million dollars? 

When I realized I made my first million, it was probably after I made it. I got my production people – the people I buy my garments from. Now, it’s getting towards a year and I gotta file taxes and shit. In probably the first six months in that parking lot, I started realizing how much I was making in a day. Some days I would make two, three thousand. Some days I would make four (thousand). Some days I would walk home with like ten thousand dollars, just sitting in the parking lot. You looking at a whole keyboard. You know how some niggas type like this (Desto proceeds to type using one finger). I’m using one button. After a year, it’s like damn, how many pages did I write pushing this one button? And then I started thinking, if I can make this much out of a parking lot pushing one button, what if I got a store and started using two buttons. So, that’s when I realized that I made a million. 

Did the pandemic slow down your hustle at all? 

I know during COVID, I was making five thousand a day, but then I’m spending money on merchandise. Now, I gotta make more than a million so that I can put a million up. As soon as I make it, I throw it back in. So, you can’t even count that. Yes, a million dollars has come to me, but that’s not a million dollars made because most of it is me recycling my money.

I could blow some bread, easily. And it feels good to buy. But instead of feeling good buying these designers, I started spending that money on me. If I was to feel defeated or upset and I needed to spend some money to feel better, I’m going to the production house and I’m dropping ten bands on production instead of spending ten bands on a chain that’s gon’ make me feel good. I’m going to spend ten bands at my production house and tell ‘em to put some respect on my name ‘cause y’all seen me two months ago in here tryna pay y’all $500 piece by piece. Just really investing all of my bread back is how I got (my first million dollars). If I made a big lump sum by the end of the week, I wouldn’t put that up or try to save that – I’d take that big lump sum and throw it all back in and be broke again. And I’ll continue to do that now. I just opened a new shoe store. I was probably crazy up, but with me just having this money, sitting up here hanging out with my friends and shit, I’ma blow it. I’ma hop on a private jet with Lil Baby or fly to Atlanta with such and such. I’ma go to Miami with (Lil) Pump and go on a shopping spree. Now, when I get money, I just reinvest it. It’s always reinvestments to go. If you got a car and your car fucked up, go and put a new engine in it. That’s gon’ save you more money than going and buying a new car. If you got a store, go and get the store painted. I just recently opened a new store. Instead of having all of this bread and living it up, I took all of that bread and threw it into another store. 

As a creative entrepreneur, how are you avoiding burnout? 

Niggas get burnout everyday. You can’t stop a nigga from burning out. I got to a point where I just stopped thinking of burnout. You look at Supreme, they will drop the same hoodie every week with a different design. They use the same red hoodie and they don’t worry about burning out because it’s a big ass world, bruh. I’m so small and I’m looking at so many other places. It’s like I’m nowhere close to them. When you think of burning out, it’s like you’re working, working, working, and your engine blows out. If my engine blows out going 60mph, then I need a new muthafuckin’ engine. I ain’t put in enough work to burn out. I ain’t got a big enough team to burnout yet. My mind is so small, and the places I’ve seen are a lot, but it’s like bruh… I can’t think about burning out. I gotta cover every fuckin’ aspect of this shit. You don’t even see me doing a lot of girl clothes like that. You don’t see me with kid clothes. They got dog clothes, stuff like that. Active wear; jeans; high designer; low fashion. When you look at the greats and shit, they don’t burn out. Oh, and the way I can’t burn out is limited availability: I don’t make a lot of shit. If I drop a collection, I’ve never dropped anything over 300 pieces. And it’s an entire world out there. I can sell most of them pieces within my network. 

What’s your stance on bots and online consumerism?

This AI shit is incredible. As a consumer, bots get in the way because you’re not able to purchase items. But from a retailer, it’s great. For myself, the bots don’t really fuck with me like that. I’m the remote control online: if I wanna turn it up, I know what to do – and if I wanna turn it down, I know what to do. The bots get on my nerves for the comments and shit. But if the website was my destiny, I would control my own website. If I wanna do a swipe up, if I wanna wear this hoodie with some crazy ass kicks and all my jewelry, and make sure these people know this is a high-end t-shirt, then that will send their ass to the website. If I really want the website to go crazy, I’ll spend some money getting it placed on somebody. And then I’ll rotate that picture through Instagram or Facebook posts and it won’t even be dropped yet. I’ll make people go to my website and look for something that’s not even out. 

What’s the most money you’ve spent on product placement? 

For a single piece, I’ve paid $20,000. This the thing, when you talk about placements, it’s a process. It’s never that simple. Let’s go back to one of my biggest advertisement people, Young Thug. I had to build that (relationship) over years of spending. Years of being around Thug, I was giving him stuff at no cost. When you do something like that, after a while, people feel like they owe you even though they don’t. If someone fuck with you, they fuck with your hustle, and they know you solid, it’s still time, energy, and money you’re pouring into this. You do shit like that to stay around so they can actually see. That’s where the real money at. People might think you just doing this and doing that, but what I’m doing is getting information. Every time I make something, I wear it around them. And I’d sit right there, chillin’. For a minute, niggas didn’t even notice it until after the fact. They just kept seeing me in my shit. All of that time and effort got me my placement. 

Once things started to pick up speed, did you struggle with operating as a sustainable business? And if so, what was the hardest part? 

Listening to other people that ain’t did the shit you did. That’s the hardest part. Let’s say I’ma mechanic right now and I fixed every car in the muthafuckin’ hood. Every car that came to me in the hood I fixed. They out here rolling, I got jewelry, I got a house, the best car, they know that. So now, you’re tired of being a nigga fixing cars. Now, you got someone that’s never fixed a car in their life but they know business. Now, they tryna tell you how to run your own business. It’s hard taking that because it’s like how you telling me something and you ain’t done half the shit I did. You don’t got the money I got… nigga, you not even as old as me, you ain’t been in the field, but you tryna tell me something that’s gon’ make my business better – and I’m supposed to listen to it. As a Black man, you lose more money not listening.

How do you drown out the noise and know what advice is worth listening to?

I won’t listen to the noise. It’s a lot of people making noise, but I won’t listen to it unless you’re up close and personal. If you can get that close to me, God must’ve put you right here in front of my face for a reason. If I see somebody around me that’s determined, that’s not asking me for nothing but steadily trying to help me, and they’re in my space, then you must be here for a reason. I’ma trust you a little bit. Just because like shit, you ain’t winning nothing by me making money. So, I lowkey believe you a little bit. I can see if you tryna help me make you some money, that’s what everybody tryna do. I came up with a lot of people that didn’t get nothing out of helping me, and those are the people that’re on my team right now. 

Pyer Moss was determined, too. Unfortunately, things took a turn for the worst. 

Honestly, it’s multiple situations like that. That’s just the one you see – I see a lot of mufuckas. It’s really all about being solid and keeping your word, even if you don’t make no money. Let’s say that one year I’m running around doing all of this shit. Next year, I don’t do all of the stuff that I was doing. I could decrease. If I do 12 pop-ups in a year and only six of them make money – am I gon’ do another 12 pop-ups next year? Yes, I am, because even though I didn’t make money, it brought recognition to my brand and it kept my brand afloat. Even though I went to this city and I didn’t make bread this time, I did give out clothes and meet all of the poppin’ people. Nex year, I’m gonna make money. I’ma bet back and it’s gonna be better. Plus, I keep all business good with anybody I deal with. I’m probably the only Black man that’s putting money into these artist’s hands. I probably gave out $400,000 in collabs last year. I’m giving people a percentage of something that I’m already selling. Instead of me pocketing these 300 pieces, I’ma give you a percentage of these 300 pieces. And I feel like that’s why I keep on growing because I’m attaching myself to these brands and companies. The world is big. Last year, let’s say I shipped out 3,000 orders. This year, I shipped out 7,000 orders. That’s all because I’m going around to these cities. I’m controlling online by being in these cities selling that shit. Even if I didn’t make money on the pop-up, I made money online and I found somebody else that wanna invest in the pop-up. I’m looking at the numbers and I’m looking at the engagement. If you look at the overall, sometimes you don’t make money – you make engagements. 

Long term, could you see yourself as a creative director? Considering what Pharell has accomplished, there are no limits with this fashion shit. 

He did that, and the KidSuper dude did (Louis Vuitton’s) whole line. That’s the other shit that inspires me, bro. This year, I ain’t tryna make more money than I did last year. And I know that sounds crazy, but if last year I won 10 races, this year I wanna win all the races and I wanna make sure I capitalize off of every opportunity that I have. Now, that doesn’t have to bring me more money. If I wanted to make more money, I’d just open more stores and take $50,000 from everybody that wanna do a collab. That’s gon’ make me more money, but it’s gon’ depreciate my brand. I wanna strengthen my brand first. I wanna make sure that this vehicle is equipped before we go off the road again. So now when we going, we killing it. I wanna make sure I have a video guy, a photographer. I wanna make sure the security is super tight to where we gon’ limit how many people can come into the store at one time. I’m not just tryna do what I did last year and multiply it. I’m tryna take what I did last year and make it better. Let’s get the foundation as strong as possible – even if it’s not making me no money. I’m spending more money than I’m making, but in the long run, I’ma have a diesel engine that can go way more miles than one of these fast ass cars that’ll burn out. I’m not tryna go the fastest. I’m tryna go the speed limit, maybe a little bit more. And on my way, I’m tryna get as much information so when I’m switching gears, I can really hit it and not have to worry about shit. 

What is that next level of success for your streetwear brand?

Right now, I’d love to be in that space to where I’m big on fashion, but I’m not there. I’m really a hustler. This is just another craft of mine. The biggest thing I’m focused on right now is my daughter. I wanna make sure that I see every day of her fucking life. When you’re tryna be overly successful, you miss a lot of time with (your family) and that’s not something I’m tryna barter. I got it to where I don’t have to work. I don’t have to go to the store or I don’t have to do this – I’m spending time with my daughter. I feel like that’s gon’ turn into my next big chapter. Like this clothing line, I had it way before I was even selling clothes. I would go every place and give a person a hoodie here and there, that way when it was time for me to drop, everybody knew about it. Every bit of time I have free, I’m putting that into my daughter, putting it into my family. For a long time I was chasing the bag. I got the bag now. What I’ma do, chase a bigger bag? Nah, I want my family to be better. 

About the Author

Derrius Edwards
Derrius is a music industry professional with experience in content strategy and editorial writing, sharing relevant and resonating stories as a conduit for hip-hop culture advancement.

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