As a kid, Brooklyn-born Alexis Bittar was a creative schemer, always trying to make a buck: He would buy up vintage clothing and antique jewelry and sell it on the street on New York City's then-bustling St. Mark's Place. He framed and sold images cut from dusty old books. But it was years into creating his jewelry business before he ever considered himself an entrepreneur. 

"When I was starting out I was just a little punk kid, you know. I was basically a high-school dropout." Bittar says. "It wasn't even a word I would have known."

But Bittar did consider himself an artist. That fact--in the past 20 years of building his business--has never changed. His unorthodox, right-brained approach to managing has bred a particular set of challenges, which Bittar, now 46, speaks about frankly.

Alexis Bittar--the business--began in the early 1990s. It got almost immediate validations in its efforts creating beautiful punk-rock-inspired metal and Lucite pieces. A buyer at Bergdorf Goodman put in an early order in 1992 and Bittar--the man--hired two people to help him fill an initial stream of small orders. They carved the first pieces working out of his Brooklyn bedroom.

"I very slowly built the business. It grew organically for the first 10 years, out of this mission of straddling the line between art and fashion," Bittar says. "But after 10 years, I became incredibly focused and finally gained a clear vision of what I wanted to do."

Today, Alexis Bittar the jewelry company employs 450 people. Its product--three lines of jewelry retailing at $65 to $1000 a piece--sells at every major high-end department store, museum shops, online, and in 10 new Alexis Bittar boutiques. It's the go-to for Lady Gaga when her stylist wants an edgy new headpiece for a music video, or when Miley Cyrus wants an armful of clear bangles for, say, last weekend's American Music Awards. His pieces have been worn by First Lady Michelle Obama, and last month the company launched a fine jewelry collection. From a retail perspective, that's a difficult move to pull off--one that few brands, only Ralph Lauren comes to mind--have been able to execute successfully.

The new upward reach and the recent expansion in stores--the company hopes to have 25 locations globally by 2016--are helped by a private-equity investment by TSG Consumer Partners, a firm that's helped consumer brands, including Smashbox and Vitamin Water, grow.

It didn't come naturally for the designer to be a manager or executive. Nor did writing a business plan for a company without an existing model to mimic. But after 20 years, he's found solid footing on both fronts. Bittar, who is CEO and Creative Designer of his Brooklyn-based company, explained to Inc. the lessons he's learned along the way. They have been slightly condensed and edited for clarity.

Expect a steep learning curve. 
When I first started the business I didn't really understand management. I hadn't been around it, and I just wanted everyone to be happy, and that was a disaster. The whole thing wasn't natural for the first 10 to 12 years. I was a slow learner, I think because I have both the left and the right brain. There was a big learning curve for me.

Be clear about your expectations.
I've learned that people want clear deliverables and clear communication. Almost the less emotional you are, the better. I think people do mostly want to do a good job, and want to be pushed, even when they voice that they don't. People want to succeed, and feel like they've accomplished more than they thought possible. But that took me years to get to.

Don't overthink.
It took a lot of trial and error. A lot. I mean, 15 years of it. I feel like I just got there in the past few years. One of the great things about getting busier, and the speed of work, is I don't have the luxury of overthinking. I've learned to just trust myself.

Embrace your mistakes.
Back when I was young in my business, and everyone told me "you are the designer, you need to hire someone who can really build up your business." I listened. I hired this guy who had worked at a large company and turned into a complete disaster. He was a combination COO and CFO. He almost singlehandedly sunk the business. It was honestly the best lesson I could have ever had. It taught me that I needed to understand all the aspects of the business--I couldn't just be the designer. It wasn't going to work for me. I immersed myself in a way I never had. They say pain is your best teacher. It's what pushed me through to where I am now. When you hit that point where you're about to lose something, you realize what you need to do--and what you were afraid of doing comes easier. There's also something when a business contracts that's super freeing: you see where the dead weight is.

Put your plans in writing.
I was in Paris during a trade show and it occurred to me that I always had one foot in the business and one foot out. Part of it was I intuitively knew that if I put both feet in and I failed, I would feel like I failed. But if I kept one foot out, I could always say, I wasn't totally committed. It was juvenile. Then I thought, 'if I was to drop dead, what would make me feel like I succeeded?' In half an hour I wrote out what I needed to do with the business.

Find your niche. 
In terms of stores, I wanted to have a chain that was only about jewelry and accessories, that felt curated, and it felt more thoughtful. When you think of chains of jewelry, there's Claires Accessories, there Swarovski, and then you jump up to Yurman. There's nothing in between. As a business model, it's great. And it was the first on the market. When I went to bring in private equity, everyone wanted to jump on it.

Play to your strengths.
I think I'm pretty logical. My brain moves very fast, sometimes too fast for the people I work with. I've trained myself to find solutions quickly, and not get involved in the drama. I think that comes from design: I can look at a design and put it together like a puzzle in my head very quickly. And the same goes for business strategy.

Word-of-mouth is your best friend.
We are the most used jewelry line in the past three years editorially--out of everyone. We beat Cartier, Van Cleef [and Arpels], and this is before we started advertising. We just started in the U.S. literally a few months ago. During Fashion Week we'd do wild postings, but we never really advertised. We're working with Lady Gaga. We just worked with Miley Cyrus for the AMAs. We're working with everyone every day. We would get a call from the stylist, and we'll talk about the concept. Then I'll do a sketch and send it over. There will be a little bit of a back-and-forth, but it's generally easy--I think I'm super easy to work with, as long as you're definitive and concise. If you're too wishy-washy I'll lose my patience a little bit.