Bootstrapped and Proud

Illustration by Nate Otto

I first learned about boot jacks a couple weeks ago, when I reported this story about Alcala’s Western Wear, a 41-year-old retailer in Chicago. Illinois is not a place where you see a lot of cowboy boots — not like, say, Texas or Montana, where airport security checkpoints come with boot jacks to help flyers take off their boots.

Yet even in this urban metropolis, Alcala’s Western Wear has flourished, offering a massive selection of cowboy hats, boots, shirts, belt buckles and more. Western wear has been far more than a fashion fad for the Alcala family, now in its second generation of ownership. The Alcalas know what it’s like to bootstrap a business in every sense of the word.


Transcript

WAILIN: Richard Alcala has been selling clothing for a long time, long enough that you can track his career by the width of men’s pants. When Richard was starting out, bell bottoms were all the rage, thanks to Saturday Night Fever.

RICHARD: They were really tight in the thigh and they were really wide as soon as it got to the knee. From the knee down, they were like a big, big V. And they covered — they were so wide that they covered your shoes. Everybody wanted to be like that guy in the movie.

WAILIN: That guy, of course, being John Travolta. Saturday Night Fever came out in 1977. And men’s pants have gotten a lot slimmer since then, surprising even Richard, who’s been in the retail business for more than four decades.

RICHARD: Guys’ skinny jeans. I never saw that coming. And it’s still coming strong, my gosh. I don’t think those tapered jeans are going anywhere. I think people really really love them and they love the way they fit.

WAILIN: Richard’s business isn’t going anywhere either. He’s the president of Alcala’s Western Wear, a Chicago store that sells cowboy hats, boots, shirts, belt buckles, and more. Here, east of the Mississippi River, you’ll find more apartment dwellers with cats and dogs than grizzled ranchers with cows and horses. And yet Alcala’s Western Wear has endured, outlasting disco and many other fashion fads. You’ll hear the story of this urban cowboy outfitter on The Distance, a podcast about long-running businesses. I’m Wailin Wong. The Distance is a production of Basecamp. Introducing the new Basecamp Three. Basecamp is everything any team needs to stay on the same page about whatever they’re working on. Tasks, spur of the moment conversations with coworkers, status updates, reports, documents and files all share one home. And now your first basecamp is completely free forever. Sign up at basecamp.com/thedistance.

RICHARD: I’m wearing some brown alligator boots by Old Gringo and I’m wearing a Stetson hat and it’s a white color because good guys wear white, supposedly, from the movies, okay, and I’m wearing a bolo tie. It’s made out of stone. And this is how I dress every day. You know, it’s who I am.

WAILIN: Richard Alcala is the fifth of ten children who were born into a family of salesmen. His great-grandfather sold cars at one of Ford’s first dealerships in Mexico, and he was also the first taxi cab driver in the city of Durango.

RICHARD: He had the first license for a taxi and he would go up and down the boulevard giving people rides. And my father said there were so many people they would stand on the outside of the car on the running boards and just hold on because they couldn’t fit into this car because they could only fit so many people in this car, right? And he loved selling cars. My great-grandfather loved selling cars, and so I think it’s just in our blood.

WAILIN: Richard’s father, Luis, came to the US and landed in Chicago, where among other jobs, he had a table at the Maxwell Street market. This was an open-air bazaar on the city’s near west side that was known as a bargain hunters’ paradise for over a hundred years, until the mid nineties. It was where Richard learned how to make a sale from watching his father.

RICHARD: He would go to Maxwell Street every Sunday and set up his own little booth there on the street and he would sell things. He would sell clothing. He did brooms. He sold lawn mowers. Basically whatever he could get, he would sell. And since we had a large family, you know, the sons would go with him and help.

We weren’t allowed to keep our hands in our pockets. That was a big no-no. Never put your hands in your pocket because you’re telling the customer that you really don’t care. So you could never put—even if it was below zero, you could not put your hands in your pocket.

It was neat to sell something. That was like the pat on the back. When you sold something, you felt like, “Wow, I did this. I did this and I did this on my own.”

WAILIN: Luis Alcala eventually opened a brick and mortar store on the south side of Chicago, selling men’s clothing. Many of his customers worked at a nearby US Steel plant, and business declined when that factory closed. So he opened a second menswear store in 1975, this time further north, in a neighborhood populated with Polish, Mexican and Puerto Rican residents. Five years later, another John Travolta movie — Urban Cowboy — sparked interest in western wear.

RICHARD: They wanted to wear his hat. They wanted the same shirt that he wore in the movie. All of a sudden, every guy in Chicago wanted a big pickup truck. Now, was it practical to have a pickup truck in Chicago? Probably not. Did anybody care? No. Nobody cared that they didn’t need a pickup truck, but they wanted a pickup truck because that’s what he drove in this movie and they wanted the hat that he wore and it really really brought western wear, like—it made the whole industry, like, really really popular.

WAILIN: At Alcala’s, customers were coming in asking for shirts with snaps, and boots, and hats. Richard, who had worked at the store since the eighth grade, thought the family business could distinguish itself from other menswear stores in the neighborhood by focusing on western wear. But his father took some convincing.

RICHARD: He wasn’t very fond of the idea because we had been carrying menswear for a long time, and to all of a sudden stop carrying it and switching over to something new was like a real big change. It was a real big change but I told him, I says, “Dad, we have to do this. We can’t be — we can’t be both. You know, we can’t be western wear and we can’t be menswear. We have to be one or the other because we don’t want to confuse customers.”

WAILIN: Not only did Alcala’s make the switch, but it grew into an enormous one-stop shop for everything western, and expanded to women and children’s apparel. The store is 10,000 square feet and carries 8,000 pairs of boots, 3,000 pairs of jeans, three thousand shirts and 4,000 hats. There’s also belt buckles, bootstraps, leather duster jackets, bolo ties, blankets and jewelry.

RICHARD: We’ve always believed that the customers should get a good selection. Customers don’t want to come in and look at a shirt and have ten shirts to decide from. I think it’s better if they can look at 200 shirts and decide from 200 which ones they like.

WAILIN: Alcala’s prides itself on its large inventory and customer service. There’s a tailor on staff who will alter jeans and shirts for free, usually while you wait. There’s also a specialist in the hat department.

ENRIQUE,: Hi, my name is Enrique Mendoza and I’m working at Alcala’s, shaping and cleaning hats for a very very long time.

WAILIN: How long? Since 1988, when Enrique came to the US from Mexico. His brother-in-law worked at Alcala’s as a tailor and got him a job in the hat department, where he’s been ever since. If you want the brim on your Stetson to frame your face just so, Enrique’s your man. He uses a foot-operated steamer and his hand to mold hats into the right shape. Enrique estimates he works on 200 hats a week. Sometimes it’s a quick spot clean, other times it’s trimming a brim and shaping the crown. You can get the cattleman crease, which has three creases, or the pinch front crease, which creates a triangular shape, or the telescope, which is a circular crown with a crease that goes all the way around. There are a lot of choices — straw, felt, leather, different colors and band styles and brim sizes — and Enrique has 27 years of experience helping customers make sense of it all.

ENRIQUE: I’m asking, “Okay, where are you going?” If you going to a wedding, you need a nice and elegant hat, right? If you go to a rodeo on an open field, you need a different hat, so it depends on where you going, is the hat you have to buy.

WAILIN: Enrique’s secret weapon is a spray bottle of Windex. He discovered by accident many years ago that it’s a good cleaner for hats and dries faster than water.

ENRIQUE: You gotta do the brush, you see? The clock go this way; you have to do the other way. That’s the way that finish the hat, look.

(Sound of brushing)

And the Windex, it helps you clean it, look. See?

(Sound of brushing)

WAILIN: The kind of personal attention that Enrique and other staff members provide is more important than ever, now that Alcala’s is facing so much competition — both from online-only retailers and its own suppliers like Levi’s, who have started selling directly to consumers. The store sells merchandise online, but Richard thinks of the website as more of a big, Google-friendly business card than a source of revenue.

RICHARD: I don’t understand how people can buy boots and shirts and jeans online without trying them on. I guess you gotta order them and return them if they don’t fit, and do it all over again, you know, I think it’s easier if you just come to a store and try them on.

WAILIN: And if you come to Alcala’s in person, you can try on merchandise while your kids ride one of the store’s two mechanical ponies. You can feel the difference between rattlesnake and eel skin and stingray boots, or ask Enrique Mendoza how your hat should look.

RICHARD: If we close our store tomorrow and we depended online business, we would be closed in 30 days. There’s so much competition out there. There’s so many non stores. There’s so many people out there selling the same product that we do who don’t have a store. They have a garage. They’re working out of their basement. They don’t have 30 employees. We have 30 employees here.

WAILIN: A lot of those employees are family members. Remember when I told you Richard is the fifth of ten kids? Five of his siblings work at the store too, along with other relatives.

RICHARD: My brother Robert, he’s the accounting. I have a sister, Lupi, she’s accounts payable. I have a brother John who is in charge of shipping and receiving. And I have another brother Louie, who’s a cashier. My wife Elia, she’s a cashier. And then we have nieces and nephews working here and I’ve got a brother-in-law working here, so there’s a lot of family members working here.

Everybody has their own responsibility. You don’t have two or three people doing the same job, so I think it’s important that everybody kind of like has their own position. They have their own responsibilities, and I think that really helps when you’re in a family business. So this way, not everybody’s meddling into everybody else’s job.

WAILIN: Richard’s job is president, a position he’s had since 1982, when his father picked him as his successor after a year of observing him and his siblings.

RICHARD: Since I was number five out of ten, I thought I would never be able to run this company because I have four brothers who are older than me. And so one day, my dad had a family meeting and he called us over and he says, “I want someone to run this company. One of you’s are going to run this company and I’m not gonna base it on age.” And I was like, “Yes, that’s great, I’m so happy, wow. So now I have a chance.” And so I really really worked hard and I proved to my father that I wanna be the one who runs this company. He picked me and he told my brothers — he told my older brothers, he said, “Look, even though he’s younger than you, you have to respect his decisions. You can’t look at him like he’s your little brother and now your little brother is bossing you around.” He said, “Everybody had the same opportunity that he did, but none of you’s showed the same interest that he did. So now this is how it’s gonna be. Your brother’s going to be in charge and if he says go right, we’re gonna have to go right.”

WAILIN: Richard’s father, Luis, passed away in 2014 at the age of 92. Portraits of Luis Alcala and his wife of more than 60 years, Carmen, hang side by side at the front of the store. Hand-lettered signs above each painting say “El Rey” — the king — and “La Reina” — the queen. In Luis’ portrait, he’s wearing tinted aviator glasses and looks every bit the patriarch, watching over the business he founded. Richard is 57 and starting to think about stepping back in a few years. He plans to search for a successor the same way his father did, by finding someone who really loves the business and will take care of it, someone who’s a natural salesperson.

RICHARD: I’m a real firm believer that you have to wear what you sell. I would feel ridiculous if I’m helping a customer, showing him cowboy boots, and I’m wearing gym shoes. It’s important that you wear what you sell and that you love what you sell. You have to believe in it.

WAILIN: Over four decades in the business, Richard’s tastes have evolved a bit. But he’s still very much a believer in the appeal of a sharp-looking pair of boots and a hat — in white, of course, because he’s one of the good guys.

RICHARD: I used to wear, like, real loud fancy shirts with a lot of embroidery in them, and I’ve noticed that I really don’t anymore. So yeah, you know, your tastebuds kind of change. Your tastebuds kind of change over the years, but you know, I still love what I’m doing and it’s been 43 years and I’m still here.

WAILIN: The Distance is produced by Shaun Hildner and me, Wailin Wong. Our illustrations are done by Nate Otto. We’ll be back next week with a mini episode where Shaun shops for a pair of cowboy boots at Alcala’s, so stay tuned for that. In the meantime, if you could leave us a review on iTunes, we would be so grateful. It helps our show gets discovered by new listeners. The Distance is a production of Basecamp, the leading app for keeping teams on the same page about whatever they’re working on. Your first Basecamp is completely free forever. Try the brand new Basecamp Three for yourself at basecamp.com/thedistance.

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