Business Besties: Slobby Robby and J.R. of Generation Cool

Vintage aficionado, Slobby Robby, and local Tucson deejay, J.R., became business partners back in 2013 to create one of the most unique vintage stores, Generation Cool. An '80s/'90s culture boutique that caters to the retired, the millennial, and the youth with toys, collectables, jerseys, jewelry and more - these two have created not just an atmosphere you want to hang out in down the historic Fourth Avenue but have created an experience of nostalgia like none other.

As business besties, friends, and movers and shakers of Tucson, let alone the vintage market as a whole, both Slobby Robby and J.R. share their insight with us by sharing what you should look for in a business partner, where they were taken off-guard when opening up shop, why they're different, the biggest lessons they've learned, and more! 

How did you two meet?

Slobby Robby: We met at a Tucson nightlife club scene in the mid-2000s. I was a promoter at Vaudeville and J.R. was a deejay at Vaudeville.

J.R.: When I met him he was wearing this distinct starter Pistons jacket. Real story.

Slobby Robby: J.R. liked my style. He was hitting on me.

So is style what started the conversation between you two?

Slobby Robby: Yeah, I think so!

J.R.: That and every time I hung out with Robby there was some weird adventure we’d go on and I didn’t even know him that well.

When did you start talking business?

Slobby Robby: In 2012, I was looking to open store but I didn’t have partner. I didn’t have as much direction. I didn’t have a location. By about October of 2013, I really knew what I was going to do to. I really knew I wanted to be on Fourth and the only thing I didn’t have was a partner. I knew J.R. was interested in opening up a t-shirt shop with sneakers and that was part of what I was going to do. I just hit him up and said, “Yo let’s have a meeting and see if we can do something together.”

J.R.: Exactly. Good thing I knew him then because I was just going to be doing t-shirts. I was looking at REP TUC’s old building and he was like, “Don’t be an idiot. They don’t have A/C.” (laughs)

Slobby Robby: I think I was really able to communicate to him that we could do what he was interested in which was to run a business, be creative, design things and get involved with sneakers as part of my concept. That was the key. He could meet his goals and I could meet my goals. I didn’t want to do it alone. I think I was smart enough to know that I couldn’t do it alone.

We were friends enough to know each other and trust each other but we weren’t close friends enough to where it’s like family you wouldn’t want to go into business with.
— Slobby Robby

What would you say is the dynamic between you two when doing business together? Because I feel like you guys work really well with each other.

J.R.: I think dynamic is just knowing your role and that’s a big part of every business you’re in. I’m probably more of the second guy here, which is fair. I’m a big, firm believer of not having too many cooks in the kitchen. So therefore, if you know your role the system could work. I’m never telling employees their schedules or what they need to do as much and I’m cool with that. That’s not really my strong point. I know a lot of businesses that don’t do that and they’re having trouble right now, like people getting kicked out for example.

Slobby Robby: The dynamic we have is fun! We both have so many similar interests, which makes things smooth and enjoyable. It wasn’t like he was only interested in sneakers and I was only interested in vintage. I was interested in sneakers and he learned more about jerseys/vintage. We also have a lot of the same hobbies outside of work and we have a lot of the same hobbies within work. It’s a smooth transition. Also, the fact that we weren’t old friends helped. It’s not like we grew up together and we had this huge history. We were friends enough to know each other and trust each other but we weren’t close friends enough to where it’s like family you wouldn’t want to go into business with.

What advice would you give to someone who’s seeking a business partner?

Slobby Robby: The key is to look for someone who has strengths that accommodate your weaknesses. I think the fact that J.R. was interested in the financial part  - keeping the bills, keeping the books, and being a daily Operations Manager - was really appealing to me because I was more interested in the merchandise, the marketing, and being the face of the business. I think if you know what you’re good at it’s a lot easier to admit what you’re not good at and find someone else who can fill those holes for you. His interests were things that I’m not good at. Daily organization, bills, math, finance - some of the things I’m capable of doing but are not my strength. I would’ve been overwhelmed doing everything. Someone that’s interested in doing things that I was feeling a little bit self-conscious about was a really good boost of confidence for me as far as someone who I would partner up with.

Now, could you tell me a bit more about opening up this shop itself? This place opens up and then what?

Slobby Robby: This place opens up and then you realize that there’s a lot more to it than you ever thought. You realize that there’s a lot more things that need to get worked out. There’s a lot more holes in the ship and there are creases that need to be ironed out. So both peoples roles get bigger. He probably had more on his plate than he thought he would. I probably had more on my plate. We realized we needed employees and that him and I couldn’t do anything alone. We realized that really fast. We started figuring things out like, “Hey, we can make money off of painting shoes.,” “Hey, we can make a lot of money off of refurbishing clothes that are really dirty.” We started realizing aspects of our business and places where we could make money that you wouldn’t normally have expected or that weren’t in our initial business plan. You also start realizing what you like and what you don’t like. Again, he didn’t want to worry about hiring and firing employees and that was something I’m comfortable with because I’ve been a supervisor before at other companies. Our roles grew but at the same time our roles got solidified and concentrated.

The key is to look for someone who has strengths that accommodate your weaknesses.
— Slobby Robby

How about the initial vision of the shop when you first opened?

Slobby Robby: I was really specific about my vision and I think, if anything, it was a learning curve for J.R. at the beginning of knowing what vintage is. So if someone brings in a Crooks and Castles shirt from 2004, that’s not vintage and that’s not something that’s worth that much money. It took a matter of weeks or even months for him to just know what we don’t mess with, for him to think like me. But then also for me to think like him. He knew a bit more about sneakers than me. A lot towards the beginning, he was schooling me on sneakers and what was worth money, so we were both learning.

As far as the actual vision for the shop, this is my life dream since I was a kid. I’ve been obsessed with toys and sneakers and clothes since as long as I can remember. If anything, he was in a lot of ways buying in and investing into my dreams but at the same time it was enjoyable enough for him that it was worth taking that leap because it was something fun.

J.R.: My dream was just to open a business that was working and would bring new things to the avenue which we did. We were one of the first places to have internet! It was a pretty big deal.

Slobby Robby: Yeah we had WiFi and air conditioning. We had a place where you could hang out that wasn’t just shopping. We were interested in creating a community and creating an atmosphere. My Masters is in Art Gallery Management. So a lot of the things I was doing was based on the way you would run an art gallery or an art museum where people would just come and spend time and enjoy.

J.R.: So I was buying into his vision. Like I said, my goal was to own a functional business. To find a business partner that has the drive as much as or more than you is a big deal. I know a lot of people I could’ve done business with that probably wouldn’t be here. When times got tough, they probably would’ve ran or find a thousand different reasons not to be there. We’ve never had that problem. Knock on wood. It’s tough! I mean, when we first opened he had a baby like two/three months after and you just gotta make it happen! I never heard, “I can’t do this/that.”

To find a business partner that has the drive as much as or more than you is a big deal.
— J.R.

Speaking of that, could you tell me of a time where something took you off-guard in regards to starting a business?

J.R.: The first time I was disappointed was when I saw that some employees were stealing. That kind of took me off guard. I was naive to it. Other than that, that’s really the only thing that caught me off guard. I like to think I give people everything so why would you steal from me?

Slobby Robby: I think we were caught off guard with people not understanding our concept. People still to this day are surprised that we charge sales tax, which is funny to me. Why would we be any different than the store? Circle K? The mall? Why would you expect to come in here and not be charged sales tax? I think there’s a lot of aspects of retail that are really kind of shocking. People can be really mean and combative and it’s really weird because you’re trying to provide a positive environment. People seem to take on an aggressive role sometimes when they come in and it’s probably jealousy or… I’m not sure. I was always very confused at the aggression towards the beginning.

J.R.: You were always mad at the comment about not having enough stuff either. That was your big pet peeve when we opened, there were a lot of bloggers that you knew who’d ask how we’d keep having vintage stuff.

Slobby Robby: Yeah people were always really skeptical of us being able to keep it full. We had so much cool stuff they thought that somehow I had accumulated this stuff over the course of five to ten years. There’s stuff in this world and it’s just our job to curate it and our job to process it. In fact, there’s never been a problem having enough stuff. I think there’s always naysayers in the beginning but for us, I was just never worried. I never thought twice. It’s kind of like being in love. Nobody can tell you otherwise because you love that thing or that person so much that you just keep moving everyday because you can see how good that person or thing is. Even if everyone else can’t see it. For us it was just really easy to keep it moving but I was surprised at the amount of negativity and the amount of (for the lack of a better term) hating.

If you feel comfortable sharing, can you tell me of a time where you experienced a hiccup in your business?

J.R.: There’s really never been a time where I felt the world was going to end.

Slobby Robby: I mean there’s hiccups like… recently we had our expansion and our air conditioning broke. I had to buy a whole new system. Our finances, our savings got hit. We weren’t in any kind of jeopardy or danger but but I think it would be fair to call it a hiccup in the world of business. It’s the kind of thing we’ve always been prepared for and that we should be prepared for. I think that having to fire employees and having to fire staff could be considered a hiccup with us having to work all the hours ourselves but again, nothing that we weren’t ready to do or were totally willing to do.

I think there’s always naysayers in the beginning but for us, I was just never worried. I never thought twice.
— Slobby Robby

What would you say makes you different from other vintage shops?

Slobby Robby: That’s a good question. In Tucson, we’re a lot different because most of the vintage stores here cater to women. Especially in our area, being in a vintage district. There’s How Sweet It Was and Desert Vintage. These are really prominent and famous vintage companies that have been around twenty plus years, way before us. I think we accommodate to males a lot more than both of those places. We accommodate to what you would call “millennials” (as far as a customer base) a lot more than those two. We accommodate to actual kids with the toys, too. That’s on a local level.

When I look at a broader, national level there’s a lot of vintage stores that opened around the same time as us, such as Round Two and Mr. Throwback in New York. We all opened around the same time. One thing that I’ve always been proud of that sets us apart is the toys and the collectables. So we do have a little more of a child and older, retired age vibe. Old people can come in and look at our collectables. Young kids can come in and play with our toys. I think we have a wider appeal than a lot of the vintage stores that are around.

I feel like there’s so much behind the “vintage” business. What are some things someone must know before getting into the vintage industry?

Slobby Robby: The key is knowledge. Just because you found a polo at the thrift store, doesn’t mean it’s worth money. Just because you found something that says “Tommy Hilfiger” it does not mean it’s worth money. I think it takes the right knowledge to know that. I had a pretty hardcore base knowledge of vintage and toys. J.R. had a pretty hardcore base of sneaker knowledge. The Hip Hop and music culture that he brought in was really strong on. You have to know your shit. All my employees are trained to know their shit. You should know more than the customer. Saying, “I don’t know,” is unacceptable for us. We don’t say, “I don’t know.” We don’t say, “No, we don’t have it.” Going back to my Art Gallery Management roots, my job is to teach the consumer.

At the beginning you think about money and at the end, now, I could care less about the money. All I care about is enjoying myself.
— Slobby Robby

What are three of the biggest lessons you each have learned that perhaps you’d like to remind yourself of in the future?

J.R.: I feel like patience is a big one. I wasn’t a manager and I learned there’s some sort of respect for accountability. I need to know why things happen a lot more. I can’t just turn a blind eye every now and then. So, accountability is also a big one. Patience, accountability, and… dedication? I don’t know. I don’t know what the third one is… I’ll give you two!

Slobby Robby: One thing I learned was to let my ego go to the side and realize that sometimes I needed help. While at the beginning I was willing to give J.R. a piece of the action and step aside, I didn’t realize we probably needed an accountant the whole time - which we have now and has been a really big help. I probably didn’t realize that we needed someone to run the website as a separate job too, which we also have now. Along the way, one big lesson for me was to set my ego aside and accept help and accept other people as part of the team. Let the team get a little bigger than just J.R. and I.

Second lesson is probably not to listen to anybody because at the beginning, again, there was so many people telling us a hundred different things. Everyone wants to come in and tell you what you should do. So literally, don’t listen to anybody at all. I have no desire to listen to anyone’s advice. That’s not something I learned, that’s something I already believed in but was something that was solidified and confirmed for me. I’m not interested in peoples opinions on what I should do.

The third thing I learned is that you just have to be enjoying yourself. If I was alone, if I had just me and the employees it’d be way stressful. J.R. always comes in and has a joke. J.R. always has something funny to say and it brightens my whole day no matter how shitty it was before he arrived. More than ever, I’m able to let my to-do list go and just start making jokes with J.R. because I realized that at the end of the day this shit may not last a hundred years. Maybe I’ll pass it on to my kids, maybe I don’t but at the end of the day if we have fun and we smile a bunch and we all got to eat, all of our employees got to eat and pay their bills, then all we could really ask for is to enjoy ourselves along the way. At the beginning you think about money and at the end, now, I could care less about the money. All I care about is enjoying myself.