It all started with a pair of socks.
When most people hear the name Kathy Ireland, they are bound to think of the Sports Illustrated swimsuit edition. The former supermodel graced 13 consecutive issues, including three covers, and her 1989 cover led to the all-time best-selling issue of the magazine.
The story goes well beyond that neon yellow bikini. Ireland’s company, kathy ireland Worldwide (kiWW), is far from being a small passion project run by a former supermodel. It’s a multibillion-dollar worldwide brand that has made Ireland, 56, one of the richest self-made women in the world.
The chair, CEO and chief designer of kiWW is believed to be the wealthiest supermodel in history, with a net worth estimated at $500 million by Harper’s Bazaar. On top of that, she’s a major player in the licensing industry: She sells billions of dollars in licensed goods each year—more than Martha Stewart, Ralph Lauren and Tommy Bahama.
“We’re under the radar. As a private person owning a private company, I like that anonymity.”
“We’re under the radar,” says Ireland, whose voice is warm, approachable and familiar. “As a private person owning a private company, I like that anonymity. I like being under the radar.”
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Upon learning about kiWW, many people (myself included) are slightly confused. Wait a second, I found myself thinking countless times while researching for my interview with Ireland. What exactly does kiWW sell?
The list is beyond extensive. kiWW sells handbags, sunglasses, sleepwear for women and children, intimates, socks (obviously), luggage, men’s suits, men’s denim, flooring, complete bedding, diamond jewelry, acne treatments, at-home STI testing, furniture, lighting, rugs, pet accessories, adult and children’s books, wall art, and as the saying goes, much, much more.
“While recognizing our strategy might not be clear to many, it’s so intentional for us,” Ireland says.
Ireland also works in the world of destination weddings and honeymoons through resorts owned by kiWW, including three in Hawaii and two in Palm Springs. The company does payment processing, and talent management: kiWW managed Janet Jackson during the resurgence of her career, and a wholly owned subsidiary of kiWW recently signed singer Vanessa Williams as a client.
“I know you’ve dabbled in many different areas,” I tell Ireland before asking her if she has any advice for other entrepreneurs who might want to pivot their professional efforts.
“Respectfully, I don’t dabble,” she says. “I expand.”
By ’93, Ireland had been modeling for a decade and was ready to switch careers. She was asked to model a pair of socks. She had a different idea in mind: Going into business with the company to make and sell Kathy Ireland branded socks.
Now, a quarter of a century later, kiWW sells over 17,000 different products.
The growth of kiWW hasn’t always been linear, or a sure thing. In its early years, the company primarily sold women’s clothing. It had one retail partner: Kmart. When Kmart filed for bankruptcy in 2002, it was the largest retail bankruptcy in history.
“People thought we were done,” Ireland says.
Kmart’s bankruptcy taught Ireland a lot about business. She learned that it was important not to put all of her eggs in one basket, especially because she had 37 employees and their families on the payroll.
She also learned the importance of being resilient. Eventually, kiWW persisted and pivoted by entering the home furnishing business. “At that time, there weren’t people who were known for ‘other careers designing home furnishings,’ ” she says. “We were laughed at and had doors slammed in our faces.”
But her vision was spot on, as home furnishings is one of kiWW’s biggest markets today.
“When you’re betrayed by people you trust… you find your resilience.”
“To be a successful entrepreneur… if you don’t hear no every day, you’re not trying hard enough,” she says. “You have to be willing, not to gamble, but to take an educated risk. When you’re betrayed by people you trust, when you’re kicked to the curb and failure looks certain, you find your resilience.”
It has paid off. In 2015 alone, Forbes reported $2.5 billion in retail revenue for kiWW.
“From Day 1, the key for us has been listening to our customer and really learning from her,” Ireland says. “Even though we’re in our 25th year, we’re a baby brand. We’re just getting started.”
That mindset is as true for Ireland personally as it is for kiWW. In both cases, she believes there is always more to learn and experience to create growth opportunities. Ireland doesn’t have any more than a high school diploma. But that doesn’t mean she’s not well educated.
“There are no limits for the ways you can educate yourself,” says Ireland, who makes it a goal to learn one new thing each day. “The smartest people I know never stop learning.”
In 2012, Ireland was given an honorary doctorate in Humane Letters from California State University Channel Islands for using her influence to help others.
Ireland has attempted to instill her children with her philanthropic sense, as well as her streak for independence.
She lives in Santa Barbara, California, where she grew up, with her husband, ER physician Greg Olsen. They have three children: Erik, 25, Lily, 20, and Chloe, 16. She says raising her children with Olsen is her single greatest accomplishment in life.
“They’re discerning,” she says. “And when they hear something, they don’t necessarily accept it as truth just because they heard it from say a professor or an esteemed person. They really check it, vet it for themselves, and think independently.”
* * *
If kiWW has been under the radar, it is largely because Ireland prefers it that way. She always knew slow, steady progress would be the key to her success. It’s one of the reason Ireland has always intended to keep her company privately owned.
“There are a lot of decisions that I make that would not fly on Wall Street,” she says. “Wall Street wants to see results—needs to see results. Every 90 days, they’re looking for results. And oftentimes, we make decisions [that are] much more long-term.”
Though many companies the size of kiWW would have long ago opted to go public, taking on shareholder and media scrutiny, Ireland likes to play things closer to the vest.
“I’m a private person owning a private company,” she says. “If we’re a private company, I have to ask: Why would we want people to know everything? We don’t.”
One reason for the steady approach to growth has been the care Ireland pays to choosing the right business partners. She does her best to make sure she takes the time and consideration necessary to carefully vet each potential partner, ensuring they were working toward the same goals.
“There have been some who have criticized that we’ve grown too slowly,” Ireland says. “My response is we’ve grown at a pace I’m comfortable with.”
One way Ireland has been able to quietly and effectively grow her business at her own pace is by prioritizing her professional relationships over all else.
When Ireland initially launched her brand, she says most other companies in the space were buying brand awareness through advertisements. But Ireland knew independent retailers didn’t typically have large ad budgets, so she focused on building her brand by growing sustainable relationships with people she knew she wanted to work with, many of whom she still works with to this day.
Today, furniture is one of kiWW’s biggest markets. Ireland has worked closely with both furniture designer Michael Amini and Nebraska Furniture Mart CEO Irv Blumkin.
“She deals with people honestly and fairly, and she has these personal relationships where people want to help her succeed,” says Blumkin, who has known Ireland for over 20 years. “She’s involved and she’s engaged. She loves what she does, she’s passionate and she leads her team to make sure they accomplish their goals.”
Amini hasn’t known Ireland for nearly as long as Blumkin—just two years—but he agrees.
“She is the most caring, kind and likable individual that you will meet in your life,” Amini says. “I do business with many, many people. I am a very lucky and fortunate individual not only because I love what I do, but because I’m involved with such wonderful people, and one of those people I can tell stands out is Kathy Ireland. She has the touch that not everybody has.”
Her strong relationships with Amini, Blumkin and countless others have proved invaluable in growing her business.
“I don’t judge success in terms of dollars, but rather sense—common sense,” she says. “How we treat others determines our success.”
This article originally appeared in the September/October 2019 issue of SUCCESS magazine.
Jamie Friedlander is a freelance writer based in Chicago and the former features editor of SUCCESS magazine. Her work has been published in The Cut, VICE, Inc., The Chicago Tribune and Business Insider, among other publications. When she's not writing, she can usually be found drinking matcha tea into excess, traveling somewhere new with her husband or surfing Etsy late into the night.