04/10/2013 05:06 pm ET Updated Jun 10, 2013

What Is Working Spotlight: Margaret O'Leary

What Is Working Spotlight is an ongoing series that aims to highlight the successes, challenges and unique lessons faced by different group of entrepreneurs. This April, What Is Working: Small Businesses will be talking to female small businesses owners. Below, our editors ask Margaret O'Leary about her biggest challenges, proudest achievements and what the future looks like for women in business.

What, according to you, are the main challenges facing women small business owners today?

Convergence is a challenge for all small business owners today. For Women the challenge may be more acute as it demands more of our intuition and forces us to react more quickly than we might have twenty years ago. I define "convergence" in the fashion industry where I work as the immediate and never-ending need to satisfy the consumer. The business of fashion has changed dramatically - from being a brick and mortar business just 10 years ago to now being a universe of inputs, from runway to shopping cart, available to anyone with a mobile device. As a small business owner, my Team and I must figure out how to be engaged with the ever changing fashion retail landscape, and the desires of an infinitely informed consumer.

How are women business owners different from men? What specific strengths do they bring to the table that business owners could do well to learn from?

Women business owners often tend to be really good at multi-tasking; balancing business and family in ways that men in our society don't. I know this sounds like a cliché but I believe it is a deeply rooted social phenomenon and it leads women to learn different skills - both tactical and emotional. I know that for myself it was not natural to divide my time - and my mind - between getting the kids to bed, then coming back downstairs to reply to emails for hours. It has given me - and other women I know - a different type of agility when it comes to managing our lives. I also agree with the recently published views of Cheryl Sandberg in that women are more afraid to ask for money than their male counterparts!

What inspired you to start your own business and what is the biggest challenge you've faced to date?

I am fortunate in that Margaret O'Leary Inc grew organically from my love of fashion and my skill in designing knitwear. The business invented itself, right from my knitting needles oh so many years ago in my basement apartment in San Francisco (think = cold, fog, yummy cashmere sweaters!). Now I truly enjoy the freedom I have to orchestrate and design my own life and pursue my passion (and get paid for it!). Good entrepreneurs tend to be engaged in their business almost 24/7 as we can work any time we want... and we usually want to work because we love what we do.

As for challenges, in my industry it has become more difficult for smaller design houses to obtain financing for growth. I compete with many brands much, much larger than Margaret O'Leary - all of which seem to have gotten a pile of cash from some investor. We remain self funded, which does create limitations. Also, there is no down time in the fashion business; I am truly only as good as my last season so the challenge is to always be "on" and to keep my crystal ball polished so I can predict the next fashion trends and design into what people will want to wear a year from now. My husband tells me it's like painting the Golden Gate Bridge. You never really stop... when you get to one end, you just turn around and paint your way back to the other side! And now with on line retailing there is a constant and growing need to maintain a social media presence via blogs and the sometimes unholy cocktail of FB/Pinterest/ Tumblr/etc...

What's the one piece of advice you'd give to aspiring women business owners?

Always focus on two things; great product which begets great customers. And don't ever take your eyes off the numbers, because if you can't analyze cash flow you will one day get yourself into trouble.

What's the one achievement you're particularly proud of?

I took a crazy chance years ago to open retail stores, which is a big gamble, because you sign a lease and promise to pay your landlord for years into the future. Now we have ten stores and growing, so I couldn't be happier about having taken that risk!

How empowered do you feel by other young female business owners?

Women are becoming much more of a force in business today and it sure is great to see Cheryl Sandberg, Melissa Meyer and of course Arianna working and building as the executives they are. These women are clearly role models that are inspiring for women and will have a positive, and snowballing effect on women who are just beginning to create their own businesses.

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