81. $75K/Month Clothing Business Started From a Single Craigslist Ad

0:00A New York City streetwear brand that brought in 75k in a single month and it all started with a Craigslist ad and numbered t-shirts. Just know that anything can change at any time and keep that with the most optimistic perspective. Once you have one retail store, do it again. Like anything that H &M or Journeys or Zoomies or any of these places have done, like it's the same blueprint. So I really have narrowed it down to certain designs. Be like, yo, this is tried and true, tested. Like this is Big Mac McDonald's cheeseburger. It is so standard. It's always going to work. If you're just starting out, just make sure your intentions are correct.

0:36really marinate and get in touch with your intentions, and then check yourself on your discipline and consistency. I never went to business school, but I would just really sum it up and like, come up with something awesome, sell it, sell more of it. Done. I'm your host, Alex Freeman, and today we're joined by Doobie Duke Sims. This is how this former band guitarist with no business experience built Snow Milk. Doobie Duke Sims, welcome to the show. Thank you so much for joining us. Big blessings. Thank you for having me. So to get things started, can you just kind of give us a bit of your story and how you ended up starting Snow Milk?

1:10I answered a Craigslist ad for a t-shirt print shop business that I didn't know anything about. And I walked down the stairs of this print shop in Williamsburg. And long story short, I taught myself how to print, built a recording studio in there. COVID happened. I had a vision. Milk made from the snow in a time of many milks. We have many milks now. We have almond milks and oat milks and rice milks and soy milks and hemp milks. I said it would be great to have Snow Milk, which is just a concept for a print, like a t-shirt print or just an image. And then long story short, I became a fashion designer, started Snow Milk as a brand and came up with different ideas and just boom, just been off and running for the last real good 365 days.

1:49It's incredible because as you kind of alluded to there, you kind of accidentally became a fashion designer, but that wasn't where you started. you started as a musician. So can you talk about your experience as a musician and how that ultimately helped you as you got Snow Milk off the ground? For sure. So I have done music since I was a little kid. I first started playing saxophone in third grade, and I was really good at the saxophone. And I settled the saxophone all the way through high school, ninth grade, then I dropped out of high school. Certain circumstances in life pushed me in a certain direction.

2:18And then I started playing guitar. I got an eight track, taught myself how to record guitar, bass, started writing songs. Eventually I went to music conservatory. I graduated music conservatory, went out in the world, started as a session musician, then, you know, audio engineer, music producer. And then I started a band called Shinobi Ninja. And we had a good amount of success in the band. I toured and, you know, I had songs in video games and movies and I was on television and different magazines and played a lot of big shows and a lot of small shows, a lot of small towns, slept on a lot of floors, a lot of people's couches, you know what I mean?

2:47So I just lived the whole journey. And then when I became a fashion designer, the thing that really helped me for sure was the structure of being in a band and having your position and knowing your role and what you need to do. So being a fashion designer, I knew what my role was as far as being the visionary. And then as you build the team, the guitar player, the drummer, the DJ, the lead singer, like everybody has to have a position. So building the infrastructure of the business that was growing, that's where the band element helped me because I already know how to lead a band. Now I can lead, you know, as a fashion designer instead of the songwriter.

3:17So as you went to kind of build out the band of the business, how did you go about finding people to bring into those spots? You know, it's a slightly different process than auditioning a new drummer, I imagine. Yeah, I mean, it was just like at first I was doing all the prints and then I had sellers. People would sell. I would make the prints. And then we were doing so many sales. I couldn't make all the prints. So to hire somebody to do prints and then hire more people to sell. because now I had more prints. I had more production. I had more manufacturing, more sales, get more sellers, more production, auxiliary pieces.

3:50You know, each piece is individually numbered. So I need a heat press and that's like another position. I remember one time it was like in the business, like I've only been doing it for a year. So it's super young and I can really like reflect on it, enjoy it. It's like the taste is still in my mouth, but it's like, there was this one worker, Julio. I love Julio. He's a great worker. I hadn't met him for three weeks and everybody knew him. And then like, once I finally came to New York and to like met him and like everybody had this bond with him. I hadn't met him and I was like, oh, things are changing.

4:14This is a different animal now. Tell us more about that. What was that experience to kind of like have somebody in the business for a decent amount of time, actually, before you'd even met them? I mean, it was just trippy, man. Like this whole thing is trippy to me. Like I was just like in awe of it. I'm like, I can only be of like service to it. Like I feel like in somehow, some ways I'm like separated from it. And like my job is to like really be of service to this role because this has never been my dream in my life to be a fashion designer. I didn't even know who a fashion designer. I could not have named you a fashion designer.

4:43I didn't know how t-shirts were made. I didn't know any, right? I had to learn everything from YouTube. And the fact that I did learn it, you know, it was really to sustain my family, to be able to earn and support my family and my visions as an artist, which is really about freedom. Like I really feel very blessed to have carved out something that allows me to be free and to be as awesome and strange all at the same time. Yeah, it's like, it's trippy, man. Like I didn't meet him for three weeks. Like what's happening? But the clothes were piling up. You got to put another Craigslist ad. You got to hire somebody, you know what I'm saying?

5:11Like, or else you're going to have a bottleneck in your business. And it's just trippy, man. It's just trippy stuff. I want to take us back to that initial Craigslist ad that got you into the screen printing business and the screen printing shop. Why that ad? What attracted you to it? And why did you kind of enter into it? Because you didn't have screen printing experience before you ended up buying into a screen printing shop, right? Yeah. I mean, the thing was, it's like I answered this Craigslist ad because my dad sat me down. My dad and all his great wisdom, super stand up guy. Like he was like, listen, man, like, you know, I just didn't have any money, man.

5:41Like I had like maybe$500 in my sock draw. You know what I mean? I didn't even have a bank account. Like this wasn't prepared. And my daughter was about to be born in like three months. So it's like I had to figure it out, man. And like, you know, that's what your parents do. Like, you know, hopefully that's what your parents will do. Sit you down when it's time and be like, listen, like I've already been here and I see what needs to be done here. So let me give you a little wisdom. And he was like, bro, you need to figure it out. So I went to Craigslist, which I had done before. I mean, the whole reason I was even in a band was because I answered this Craigslist ad right when I was about to get out of college.

6:10I started working at this recording studio in basically Times Square and met all these people. And that's how I first got on the road and played with people and just like all these life experiences for this Craigslist ad. So I was like, I'm going back to Craigslist. Thank you, Craig, for making the list. And I'm going back to the. So when I saw it, it was just like I marinated on it for a second because it said like, you know, like you said, it was like T-shirt print shop, blah, blah, blah. I didn't know any of that stuff. But what I did know in my mind was I know merch because I've been on tour and I make the designs for the band merch as simple as it might be.

6:38Right. Image just on the front band rock band shirt. But I know that I'm good at Photoshop and I know people who needs who needs merch, who needs clothing, bands, singers. I have a whole like index of that because I've been doing this for a decade. And, you know, so I know a lot of people. So I'll just be a middle person. That was my concept. I'll come in, I'll be a middle person and I'll just make a certain percentage on the deals I bring in. That's how I'm going to make my money. That's why I answered that ad. And I came into that ad with nothing. I had no money and no knowledge. Like the only thing I could really bring to the table was just like fire.

7:09Do you know what I'm saying? And I told my guy, Will, I said, Will, man, if you give me the keys, like I know what to do. And I did know what to do. Like I had been recording. I'd been in many recording studios. I knew the recording studio business as an audio engineer and music producer. I knew what to charge per hour. I knew how to build a studio. And that's exactly what I did. When I first came in here, it was a dark room. And I said, no, we're going to clean out this dark room and stick it in the closet. It's big enough closet, big enough for the dark room. And I'm going to build a recording studio.

7:32And then I had two businesses. I had a t-shirt print shop slash recording studio. And I was running both of them. You know what I mean? To the point where I was like, man, I can't run both of these at the same time. And then I had to get people for that. And that was before Snow Milk. I already was like a business. Before Snow Milk, I was already doing business because I had to. I had to figure out money. Yeah. As you look back on that time, what advice, knowing what you know now, might you go back can offer to yourself in those early days? I don't know if I would have given myself any advice.

8:00I think I really have always kept like a good energy. Like I didn't make too many mistakes. The only thing was I was separated from my family. You know what I'm saying? Like I was, sometimes I was just here in New York for a long time and my family would be, you know, my girl's mom was helping us and watching the kids and, you know, all the wonderful things that grandmas do. So I would be gone for like weeks at a time, but I would just be marinated on artistness. I'd be in full artist mode for two weeks, like literally just drenched in paint and life, engineering sessions and hustling and meeting every, I tell everybody to come see me, come see me at studio.

8:31I would meet everybody. I was just like super hustler. So I wouldn't change it because like I always had the right intention. My intention was never wrong. So my decisions were based on a very positive intention, which is to support my family and to bring a certain lifestyle to the family that I, you know, have chose to start. So any advice is just like, I don't know, make sure you stay hydrated. I don't know what else. Yeah. No, I mean, that's probably the best advice anybody can give or take is to stay hydrated. Can you talk about balancing the business with your family, being a father? How did you work through that in those times when you had to be away from the family for kind of weeks at a time while you marinated in the business?

9:08And how has that balance shifted now? The balance is good now. You know what I mean? I see my kids. I've established the energy so it can sustain and live. Like I set the infrastructure. Really what I did, bro, when I came down here, like, is I just curated the energy, which sounds like a really, like, silly bunch of words. Like, if you were to put it on, like, a subject of, like, memo or something, but curation of energy is a very strong aspect to building anything on top of it, right? Same thing with martial arts. You have to have the horse stance. You have to have your foundation first. If you don't have your foundation, anything you build on top of that is going to be wobbly.

9:40So for me, it was just curation of energy. You know what I mean? Now I have a good balance. I'm with my kids, with my wife and family and I go into artist mode. And now for me, it's just a different balance of like, then all I was doing was art all the time, right? There wasn't a necessity for hundreds of pieces of manufacturing every day and thousands of sales and things like that, where it's like, maybe I spend 80 % of my time on business and or a small percentage on artistry, but I'm always thinking about art. Like I live in as an artist, you know, when I walk down the street, my thoughts are my own, you know what I'm saying?

10:09So it's a good balance. Quick reminder for our listeners that UpFlip's courses are taught by real-world business owners who share the strategies they used to grow their businesses in a step-by-step blueprint. If you're ready to start your business, UpFlip's courses will help you grow it faster. You can find those at upflip.com. I want to learn a little bit more about the business model that you're employing. Can you talk about kind of the structure of the business as it is today and kind of walk us through how you built that structure? All right. So the first thing you have is the product, right?

10:37Which is the clothing, making clothing. So you have the product and then you have the consumer, right? So if you have a product that the consumers really like, there's more demand for it. So as more demand happened, I just found more real estate to reach new consumers. And the way to fill that real estate was more salespeople. So the product, it changes and I have different ideas, but just like in music, how coming from music is like, you got your hit song, like U2 is going to play with the without if we go to the YouTube concert and they don't play that song, I feel like, you know, you got gypped a little bit.

11:11Like I got to hear one. I got to hear, you know what I mean? The hits, you know, you're going to make the hits. Once you've established that they love it, you know, you change the color, they love it. They just love it. You know what I mean? It's a great print. It's a great song. So I really have narrowed it down to certain designs. Be like, yo, this is tried and true tested. Like this is Big Mac McDonald's cheeseburger. It is so standard. It's always going to work. So sales, consumers, and I'm really just in New York. I started doing wholesale now, servicing the world, but I'm majority selling product in New York.

11:41So it's like so much more space out there to continue to just expand and just spread the goodness. You know, all the clothing I make is really about positivity, optimism, goodness, oneness, kindness, togetherness, just like love, just like really just put in a good energy. You know what I'm saying? So the world needs good energy and we just manufacture clothes and the clothes we make are upcycled. A strong amount of it is upcycled clothing, which is like, you know, thrifted vintage clothing that you print on, which then saves the earth by not manufacturing and going through all the resources of constantly manufacturing new clothing.

12:15Though we do new clothing as well. It's a balance of it. But that's pretty much the infrastructure, man. Came up with an idea. Sell it. Sell more of it. You know what I mean? I mean, I don't know what else. I never went to business school, but I would just really sum it up and like come up with something awesome. Sell it. Sell more of it. Done. I want to ask about the thrifted and upcycled clothes that you use. What are some of the pros and cons of that approach? And also, like, how do you go about sourcing those clothes for the design? So the number one thing you're looking at is price, right?

12:41So when you're dealing with sourcing, like, you really want to get your price as low as possible. So if you have, like, a used red sweatshirt or used red crew neck, whatever you want to call it, like, it's going to kind of look the same wherever you buy it, right? You know, in good condition. So you want to get that at the cheapest possible price. That's how you source it. And you just get it the most that you can. You know, the more the business has grown, the bigger the vehicles have got. Start with the, you know, duffel bag, fill up the duffel bag. That's how I started going to thrift stores, filling up my duffel bags.

13:07I'm like, I'm 42 years old. I can't be running around here with a duffel bag. You know what I mean? Build a business on the duffel bag. So then you get a car, you know, start taking lifts. And then you get to a point where you start renting trucks and you're just buying the clothes. Same things that you love. You know, I want this jumpsuit. I want this trench coat. I want t-shirts. I want hoodies, you know, but I want them in bulk. So I want to pay the cheapest possible price for them. at the same time, uplifting the earth by instead of having to buy only wholesale hoodies, only brand new manufactured hoodies, right?

13:34And the old ones, what happens to the old ones? They become landfill or they somehow, it doesn't just, it doesn't help the earth to constantly use the resources and the water and the power to manufacture new things. When there's a red crew neck right there, that's just all it needs is a good positive star on it. You know what I mean? What a cool drawing. Now you can sell it for more than it was even originally manufactured for. I mean, that's like the biggest blessing involved to be able to make something on something that was manufactured for a certain price. Now you're selling it for X amount more of it.

14:02And then the other side, the drawback is you can't go super specific with it at this level. At least I'm not able to do it at this sorting level. I can't say like, oh, I got a whole set order for red crewnecks. You know, I need 500 size medium and 500 size large. That's going to be tough. I could get 500 hoodies. I might be able to sort them by size, but I won't be able to get the exact color. So if somebody wants Walmart or Macy's and like, I want this very specific design just like this. And I need 10 ,000 of them. Now you got to shift to a wholesale. And talk to me about how you test out the different designs.

14:34How do you go about, I have this idea and then we test it and now, okay, we should make more of this idea. What does that process look like for you? If you were in the ice cream game, right? And you were testing ice cream, like say you didn't have chocolate, right? Say he just coming in the ice cream game. There's no flavors. You got to be the inventor of flavor. So you start with chocolate and you go, I got this idea. It's called chocolate ice cream. Let's see if people like it. You give it to them, you sell it to them and they go, I love this chocolate ice cream. You say, great. Hold on to that one.

14:59I got this new one. It's called vanilla ice cream. Let me see if you like this one. They say they love it. All right. So you come with the next one and you say, well, this one is a different vision. This one's going to be, you know, sardine ice cream. They say, we don't like this at all. This is terrible. You never make sardine ice cream again, ever. Do you know what I'm saying? Okay. You got chocolate, you got vanilla. What's the next one? Strawberry. And you just, once you lock it down, you're looking at people like, once I was able to see what people look like, what age they were, what sex they were, like their whole vibe, what they bought, what the design was, what the Garmin type was, then you could just really just use data.

15:29You know what I mean? My dad's a computer programmer. I just grew up with data and computers. So once you get into the analytics game and I'm doing it without a computer, I mean, I have a computer, right? But I'm not pressing the AI button that's telling me exactly what people want. Like I'm looking at pictures and I've been watching them. Like I'm the analyst of Snowmilk since day one, like watching the first person buy that trench coat and being like, wow, that's what that person looks like. So that's how I do it. I just look at them and I know and I get the feedback from the sellers. If they tell me that, bro, like nobody wants this.

15:56I did a baseball one. I did a basketball one. I did a football one. I love baseball, basketball, and football. There's millions of baseball and basketball football fans, but they didn't sell. Maybe nobody wants to wear a picture with a football that says football and some drawings of some football players. They didn't want it. I'm cool with the ego, man. Just don't make that anymore. What was that first breakthrough moment for you with Snow Milk where you really felt like, oh, this goes beyond just like a small kind of business? This is something that this could be big. I just knew I could just see the smiles on people's faces.

16:26I don't know if it's because there's not something else in the marketplace. I'm not going to say that, you know, the clothing is numbered. And I think that is also an interesting aspect. I don't see that in the marketplace. I don't see people printing on the clothes the way that I kind of like did it just because I didn't know. Like, I just didn't know. I was just like, man, I want to print on these sleeves. I want to print on the side, like I want to print everywhere. And I just got these visions, man. I just put it down. And once I put it down, it was like people really like this and they're buying it and they're buying it so consistently.

16:55You know, I'm coming from no fun. So it's like it's a constant flip, right? Just like the name of the podcast, like a constant flip. And once you flip enough times, you're like, damn, we flip this many times from like this one T-shirt. This is crazy. So I just kind of can see it. You know what I mean? Like even when I was in the band, I just knew I knew we were great. Like I knew it, you know, like did we have like millions of Taylor Swift record sales? No. But like when that super famous, most powerful people, many most powerful people in the music industry were like, oh, you guys are amazing.

17:21I love it. In my mind, I was like, I already knew this. I didn't even need external validation. I don't need external validation to understand, you know, simple things like why are the Beatles so great? Like, why does it just transcend, let it be? Like, why does a four-year-old hear it and be like, that's really great. I love that. Things just work, you know, and I draw like a kid, man. I draw like a nine-year-old or a 10-year-old. So it's like, it's just tapped into something. And outside of the ego, it's just like, nice, good job. Like, I feel really blessed. And I just got to just keep watering the plants so that they continue to grow correctly.

17:52How did you go about attracting those first few customers? How did you start making those sales? And where did your sales strategy kind of grow from there? Okay. So what happened was in 2021, I came up with Snowmobile in 2020 and the first image and the concept of it, but it wasn't until 2021. Maybe I sold one thing in 2020. I probably sold something on like Depop. You know what I mean? Something like some website like that. But in 2021, Mayor de Blasio wanted everybody to come out of the COVID thing. So during the summertime, long story short, they started doing these street festivals right outside our studio for whatever reason.

18:25It was like another circumstance. Legit, like hundred hipsters drinking tall boys right outside the studio. like, what else can you do? It's like, yo, we need to take this rack, our one rack of clothing and go upstairs. And while these bands are playing, just stand there with the rack and be like, yo, we're selling clothes, Snow Milk. Like it says it on the clothes. That's the brand. No pull up banners, no stickers, anything like that. Just the clothing that said Snow Milk on it with the designs that existed at the time. And the first day thing we made 300 bucks and it was like just eye opening, man.

18:53Like I said, I saw somebody with the clothes. I saw what they look like. And I was just like, wow. Then one day I was walking through Washington Square Park and it was like a party that I hadn't been invited to. Like, I didn't know what was happening. It was like a party, man. It was like a club. And I was like, yo, we need to be out here in Washington Square Park. And once we started selling in Washington Square Park, those$300 days became$400,$500,$600,$700. And that first year, the most we made was$900 in a day. But to make$900 in a day and see 10, 11, 12 people, you know, wearing your clothes, buying your clothes consistently, it's a wrap, man.

19:24And we've just been on it since then. And how do you now determine where you should be selling the clothes? Do you have regular spots? How are people finding you? Yeah, we do a lot of street fairs. We do a lot of pop-ups and markets, right? We're at Grand Bazaar, Brooklyn Museum, any Clearview Street Fair. We're all over the city, Queens, New York, Manhattan, and every day we're in the Chelsea market. So every single day from 11 a.m. to 7 p.m., we're in the Chelsea market, Artisan Fleas, right here in Manhattan, 16th Street and 9th Avenue, I believe it is. on 10th Avenue is Artisan Fleas. And yeah, I mean, it's just like, wow, like just keep building it out, you know, franchising, licensing, more places like retail.