Success Secrets of 30-Something Moguls

Dream of quitting your ho-hum day job and starting your own company? Meet three women who made fortunes doing just that. Here, they reveal what it really takes to make it big in business.
Ready to strike out on your own? Top businesswomen fill you in on what they wish they knew when starting out.

By Lea Goldman

Kerry O'Brien, 39

CEO, Her Look Enterprises


AGE AT TIME COMPANY WAS FOUNDED: 31

INITIAL INVESTMENT: $3,000

CURRENT NUMBER OF FULL-TIME EMPLOYEES: 15

"I'VE MADE IT BIG" SPLURGE: "Expensive shoes. My ultimate extravagance was a pair of limited-edition Christian Louboutins I bought before an appearance on The View."

O'Brien presides over a Burlington, Vermont-based undergarments empire that includes seamless "Commando" panties and silicone-filled bra inserts ("Takeouts"). Her line is sold in some 1,200 stores, including Neiman Marcus, Nordstrom, and Saks Fifth Avenue.

SECRET #1

Be honest — do you even want your boss's job?

"At 28 years old, I was already very successful — a senior vice president at a big PR firm in New York City. Then September 11th happened, which made me re-evaluate everything. The next day, I quit my job. How did I go from PR to underwear? I love to wear summer dresses, but I'm not a small-chested woman, and I hate wearing strapless bras. I used to MacGyver support using duct tape. It wasn't pretty, but it worked. Then all my girlfriends started coming to me for advice about undergarments. That's when I started toying with the idea of selling my own line."

SECRET #2

If it hasn't been done, doesn't mean it can't be done.

"My first product was Takeouts: The Better Boob Job, silicone inserts for your bra that are sold in Chinese food containers. It was a crazy idea, and people were saying it would never work. So I did a very small amount at the beginning, partly because if it didn't work, I didn't want those takeout containers filling up my closet. But it took on a life of its own. Even today, every time I come up with an idea, the immediate answer is, 'No, it will never work.' But I always say, 'We're going to try it anyway. Prove to me that it can't be done.' I usually won't take no for an answer."

SECRET #3

Have no shame when selling your product.

"I walked in unannounced to just about every boutique and lingerie store between Los Angeles and San Francisco and tried to sell Takeouts to managers. It was an easy product to sell because it was so cute and fun. Still, I was pregnant at the time, and tried to be as fashionable as possible. You have to be able to walk in there and just sell the hell out of it, be a true believer. Because if you're not, no one else is going to be."

SECRET #4

Business decisions shouldn't be big bets.

"I never took big risks. I'm not going to play lottery with my career and my life. I didn't have any outside investors telling me what to do. I never ordered huge quantities of my products. The only thing I took a risk on was the Takeout packaging: I had to have it custom-made. Most people would have bought tens of thousands of units to keep the costs low. But I ordered only a small amount at the beginning, even though I knew that would mean higher costs. It minimized my risk of getting stuck with too much inventory."

SECRET #5

Find seasoned mentors — and use them often.

"In 2003, I moved the business to Vermont, where there's a wealth of talent, a lot of independent spirits and entrepreneurs. I have an informal brain trust here. Every time I need to check something, I call on my marketing friends from Ben & Jerry's, Seventh Generation, and Green Mountain Coffee, all of whom are based in Vermont. We sit around and hash out ideas. They're very accessible to me, and I call them often."

SECRET #6

Even successful entrepreneurs work around the clock.

"I have three kids. Running a business is probably no more difficult than working full time. The difference is that I have flexibility. But the flip side is that I work constantly, making phone calls, reading e-mails whenever I'm not doing the mommy thing. I am always available to my business, night or day. So while I don't have to punch a time clock or tell people when I'm coming and going, I still work all the time."

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