04/10/2014 11:07 am ET Updated Jun 10, 2014

Women in Business Q&A: Kim Castellano, Founder of Fashion First Aid

Kim Castellano is a fashion malfunction expert, entrepreneur and the Founder of Fashion First Aid (Solutions That Stick Inc.), a company with 40 clever products (and counting) to provide first aid for everyone's most embarrassing and annoying beauty and fashion dilemmas. For more than a decade, her products have been helping men and women feel more confident and comfortable in their clothing. Popular among editors and stylists, Kim's Fashion First Aid Kit, including a best-of assortment of fashion fixes, is a favorite among the fashion set and has been selected twice as a New York Fashion Week favorite on NBC's The Today Show.

The former lawyer turned chief inventor left the lucrative life as an attorney to launch Fashion First Aid in 1999. Tired of her expensive white T-Shirts getting ruined by underarm stains, she introduced Garment Guard, the first disposable adhesive underarm shields. Armed with Nordstrom as her first account, Kim continued to grow the brand, securing numerous patents and trademarks and debuting dozens of new solutions to beauty & fashion faux pas like visible drool and deodorant stains (Skid Out Erasers), ripped hems (Quick Fix Sticks), visible bra straps (Strap Trap), sagging boots (Boot Stay), unattractive blisters (Wundercover) and smelly shoes (Flat Liners).

With 40 products on the market, 10 more in the works and a new upbeat book, The Dirty Side of Fashion, Kim's still following her corporate mission to save the world from fashion and beauty disasters, while helping clothes last longer. She currently lives between Laguna Beach, CA and Sun Valley Idaho, where Fashion First Aid was recently relocated. When not in her office or on her boat, Kim can be found with her new husband Andy, her dog Schooner, her costume closet and her nutty imagination.

How has your life experience made you the leader you are today?
Although I am thankful for my education, life experience, both good and bad, has been the key factor in who I am today. And while these life experiences in themselves were significant, the continuous analysis of how I handled each part and how I could improve next time was actually the most integral part. I grew up with an amazing single mother and never wanted to have to go through that myself, so I took great care in selecting a wonderful spouse. Then, very shortly after that I had to face an early widowhood and what to do with my life without my partner and when all of my friends were starting families. So, naturally, I bought a boat and started sailing around the world, which proved to provide a much better education than if I would have gone back to school for a PhD. So through all this, three principles surfaced that guide me in business: Storms will come. The key to surviving them is to stay calm and do what needs to be done, one step at a time. In choosing people, skill is important but heart is the most important. It actually IS about the journey and not the destination.

How has your previous employment experience aided your position as the Founder and Chief Inventor of Fashion First Aid?
People who know I was a lawyer tell me lawyering is a great background for running a business. And yes, I honed my research skills during that phase of my life, but it was actually all of the jobs I have ever held that are just as important. From selling clothing at a department store as a teen, to tutoring students for the SAT, to working at a logistics company, to working at a showerhead manufacturing firm, to working for an entrepreneur with a golf device that he never brought to market, all of these jobs have taught me about a different, yet important field vital to my business. In running a business, I think it is best to have enough knowledge of each aspect to know how to hire an expert in that field when you need it.

How do you maintain a work/life balance?
From someone who spent half of six years sailing around the world while running a business and who has now moved her business to Sun Valley, ID, I could talk all day about how thankful I am for technology and its ability to let me, and my employees, work from anywhere. The mantra at Fashion First Aid is "Work less, earn more." Company-wide, I encourage people to work 20 hours a week instead of 40 and make those 20 really, really good hours so that they have more time to do the things they love. Hopefully I'm setting a good example by emailing them from the slopes or from the ocean. :)

What have the highlights and challenges been during your tenure as a business owner?
Highlights: Every time a customer sends a thank you note that one of my products solved an embarrassing problem or a note that they got a big laugh from one of my joke products, it honestly makes my day and makes all my hard work worth it. I still have a photo of me with the first person to have me sign a Subtle Butt.

Challenges: In January a few years ago, one of my biggest customers declared bankruptcy right after holiday orders. Instead of getting 6 months of pay, I was actually negative because I was out the money for all that product. I ate air sandwiches and plain rice and only stayed in business to be able to pay my vendors back, because that was important to me. During that time, thankfully things turned around and I was able to be profitable AND eat.

What advice can you offer those seeking to establish their own business?
Cash is king. Make sure your cash flows are done and that you have been conservative because things always take longer and cost more than you think. If you have a product, make samples and try to sell them to actual people for actual money. Most people are too "polite" to tell you to your face that your product is just OK (or worse), and getting people to part with their money is a good way to find out if people will put their money where their mouth is. Also, by selling it yourself in person, you can get a lot of valuable instant feedback.

What do you think is the biggest issue for women in the workplace?
I think this is a double whammy. Women need flexibility in schedules so that they can have a family or get their hair done or go sailing. Most workplaces do not offer that kind of flexibility, so women accept lower compensation to get it. I have a lawyer friend who went to part-time practice (with part time pay) to be able to work from home and be a mom to her two small boys. However, she is billing full time hours and still getting the part time pay. But she does it so that she can work from home 4 out of 5 days. I think that stinks. If you perform, it shouldn't matter how, where or when.

What are your thoughts on Sheryl Sandberg's Lean In book and movement?
I haven't actually read it. It's a positive message, so it's great. However, I'm not sure about how effective it is for someone who would not lean in on her own. It's more of an innate or self-realized principle. So yes, I agree that women should be assertive about what they want (career and personal), as long as it keeps them true to themselves and who they are as a woman, but I'm not so certain how effective it is for people who have other obstacles to overcome first. It's almost as if it is just one piece of the total woman puzzle.

How has mentorship made a difference in your professional and personal life?
I was that weird, independent kid with her head in the clouds, who thought it was best to figure things out on her own. The first mentor I realized I had was when I was starting as a summer associate at a law firm. My mentor, Kelly, showed me how a grounded woman could be an amazing lawyer through intelligence, honesty(!), and discernment. She is still the person I turn to (and recommend) for anything legal and who helped me realize how powerful mentorship can be. Since then I have mentored a few young women, and although I feel like I have been a good mentor, I have certainly learned from my mentees, as well. Without mentorship, I had to learn from my own mistakes, not other people's experiences, which is usually costlier and lengthier.

Which other female leaders do you admire and why?
Aimee Christensen of Christensen Global Strategies & Sylvia Earle, Oceanographer, National Geographic explorer-in-residence. Both of these women work tirelessly to make a difference. Besides being incredibly intelligent, both of them have amazing inner strength, can give powerful speeches, and are true to themselves in practicing what they preach. Although both are extremely convincing in swaying middle-of-the-roaders to accept their position, neither forces it on others. I also like Aimee's approach that doing business and doing good aren't mutually exclusive principles and I aspire to do both.

What are your hopes for the future of Fashion First Aid?
I hope to do lots of co-branding with other amazing brands/designers/stylists. I plan to write more books and invent more useful and absurd products. I also hope to offer women the opportunity to earn extra money by showing their friends how Fashion First Aid products help them look their best and be comfortable in their clothes. Fashion First Aid is committed to making fashion emergencies a thing of the past and to helping apparel last instead of being disposable.