"If you start limiting yourself at the beginning, you can't reach the magical solution at the end."

Let's start with the things you don't already know about Carlos Segura: He likes Judge Judy. He's insecure. He loves his dog Yuki. Only eight people work at Segura, Inc. And despite being in the ranks of graphic-design's elite, his career isn't the result of a master plan. This is more of an artist's story than a 10-step formula for success as a graphic designer. Talent, luck, curiosity and drive all factor into the equation.

It doesn't take long to get the feeling that Segura is one those people you either love or you hate. Perhaps this is where Judge Judy factors in. He likes the TV personality's no-nonsense, straight-talking style. She says what needs to be said and doesn't stop to ponder what other people might think about it. With that kind of philosophy, it would be easy to ruffle a few feathers.

Difficult, however, isn't really the right label for Segura. A more accurate adjective would be determined. He's someone who decides on a goal and makes it happen. Not a bad trait for an entrepreneur, especially one who runs five ventures under the banner Segura, Inc. From his graphic design studio to his digital type foundry, he cares deeply about his work and the people who work for him.

The Early Days
Segura didn't follow the typical path to running his own firm. With no formal training, he's largely a self-taught designer. "I don't know how I learned what I know," he says. "Other than that I'm extremely curious. I think sometimes that curiosity is the best educator." Segura came to the U.S. from Cuba when he was just 8 years old, but he says his heritage hasn't really influenced his work. His design roots really began forming while he was pursuing music in and around Miami. Segura joined a band at age 12 as the drummer's roadie, but he practiced so much that he soon found himself with his boss's job. The band played a mix of Latin, jazz and disco music on the nightclub circuit six nights a week. "They used to sneak me around the back door because I was underage," he says. After gigs the band would grab breakfast at Denny's before dropping Segura off for a sleepy day at high school.

In addition to playing, Segura created all the band's fliers by hand and became known for these works. This was 30 years ago, however, and music posters had yet to achieve a widely recognized status in art and design circles. Eventually, his godfather convinced him those posters represented talent, and Segura set his sites on becoming an art director. Despite his scant experience, the aspiring graphic designer landed a job doing charts and graphs at an engineering company in New Orleans. "I think that I was lucky in the sense that I met a person who acts very much like I act," Segura says about getting the position. "He took the opportunity to see my potential not my current ability."

By 19 he was an art director at an ad agency in New Orleans and six or seven years later he moved to Chicago for another agency job. He stayed in the city's advertising world until 1991, when he made a rather abrupt move. It was one of those harried times before a new business pitch when the creative staff works nearly 24 hours a day. Segura spent his entire weekend editing a TV spot, and when Monday morning rolled around the company's president strolled in and decided he didn't like the piece enough to show it to the client. Segura quit on the spot—even his wife didn't know until she picked him up at the end of the day.

When he left his job, Segura had no clients and no concrete plans. But within a week he found himself with a big project from another agency, and he's never looked back. "One of my biggest regrets is that I didn't do it earlier," he says about going out on his own. He describes working for himself as a selfish move: The limitations advertising placed on him were simply more than he wanted to accept.

Art vs. Commerce
The atmosphere at Segura's design studio is more like an artist's studio than a traditional design firm. He makes a point to keep his staff small, so he can turn down projects or clients that aren't a good fit. "Carlos is all about fun and inspiration," says Susana Rodriguez de Tembleque, an executive creative director at Stone Yamashita Partners in San Francisco, who worked for Segura in 1996. "His great strength is getting the best out of people and making it seem seamless. People who work there don't see it as a job. It's about art. Sure, we worked very hard; but it was always fun."

In part, this rich creative atmosphere stems from the staff's freedom to embrace any possibility. When the boutique firm's team starts thinking about a particular project, they toss the limitations—perhaps a low budget, tight timeframe or strict branding guidelines—out the window. "If you start limiting yourself at the beginning, you can't reach the magical solution at the end," Segura says. It doesn't mean there aren't limitations, he points out, but during the problem-solving process, it can be beneficial to start without them.

It's the work and office culture—rather than big agency salaries—that draw people to the company, and employee satisfaction is a high priority for Segura. Kari Merrill, who works on the business side of the company as an assistant manager, says if they don't have a meeting, Segura stops by to check in with her at least once a day. "He isn't at all how the world views him," Merrill says. "He doesn't have his head high in the air." She describes Segura and his wife, Sun—who is the firm's managing director—as humble and down to earth. Before landing her current position, Merrill worked in the mortgage business, but she was always interested in the creative world. She says Segura hired her more on potential and capability than her past work experience.

A Different Kind of Strategy
It's tempting to call Segura a renaissance man, if only because there are so many ventures under the umbrella Segura, Inc. He runs a design firm, the digital type foundry T-26, an independent record label, and an online venture called 5inch that sells blank, silk-screened CDs and DVDs. Then there's his newest baby: www.cartype.com. The website allows Segura, who owns four German cars, to indulge his interest in automobiles, type and motorcycles with extensive entries on different car models and logos.

While this may seem like an odd assortment, these businesses are all driven by one unifying factor: Segura's creativity. He isn't a jack-of-all-trade as much as he's figured out how to apply his artistic talent to whatever piques his interest. Some might say it would be easier to run a more strictly defined business—a firm specializing in environmental graphics or Web design—but for Segura it would be harder not to follow his creative impulses. "I've heard comments about Carlos not being strategic," Rodriguez says. "Well, Carlos is an artist, and great strategy is in him, in his subconscious, as he works. His work often hits all the sweet strategic spots but it gets driven from instinct and art versus frameworks and PowerPoints."

One of the biggest testaments to this gut-level strategy is the fact that Segura's non-client driven projects often garner him the most attention. 5inch, for example, has appeared in glossy magazines ranging from Real Simple and Wallpaper to Wired. He also made a big splash in the design world for his type work during the '90s. The inevitable ebb and flow of popularity, however, isn't a driving force behind his work. "It definitely doesn't affect what I do," he says. "I care as much as any human cares." When asked what other articles about him haven't captured, Segura says his insecurity. He's a confident and knowledgeable designer, but he still suffers from the same moments of self-doubt all creative people do—the fear of making something from scratch and wondering what's going to happen when you put it out in the world.

Give and Take
Like many designers, Segura struggles to find what can seem like an endangered species: good clients. His definition is someone who lets you do what you were hired to do, and he's only run across four or five in his entire career. Too often politics, worries about job security or a focus on short-term returns get in the way of a project's true goals. Even though he turns down projects that don't seem like a good fit, there are still comprises. He worked on a project, for example, where he had to use red, because it's the favorite color of the president's wife.

Segura compares client relationships to dating. He gets a sense of a client during a first meeting, just like you form an impression on a first date. While he works to educate his clients about design and help them make the best decisions for the target audience, he knows getting into occasional confrontations with clients is why he's sometimes labeled as difficult or having a short fuse. "I definitely try to be diplomatic about it," he says about disagreeing over projects. In fact, he names being more diplomatic as one of his biggest ongoing goals and describes his efforts to do so as a growth process.

Merrill sheds a little more light on the subject. While she would never describe Segura as difficult, she does says he's committed to using his knowledge to help clients avoid potential mistakes. "He's just been doing this so long he can see things others can't," she says.

Man's Best Friend
When asked if there's anything else he wants to add to the interview, Segura's answer is simple: "I love my dog." Yuki is his golden lab and the office mascot. She also seems to by a symbol of the laid-back creative atmosphere at the company. Rodriguez lists walking Yuki as one of her favorite memories at the firm, and in a roundabout way, the dog helped Merrill land her job. She met Segura through her sister, who met him at the park while he was walking Yuki. Be sure to look up the dog's official staff bio at www.segurainc.com. It's probably as a good of window as any into Carlos Segura.