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Twenty years ago, shapewear was considered taboo. It wasn’t that women weren’t wearing it—for centuries women have shimmied into corsets, girdles, and slips—but no one was talking about it. Then in 2000, Sara Blakely invented Spanx, a not-your-grandma’s take on the torsette and its ilk, and cornered this silent market. Spanx has become the generic term for shapewear, the Kleenex or Xerox of the compression fabric.
In the two decades since, shapewear has become shame-free. On Instagram the Kardashians and their minions lounge in waist cinchers; Kim has launched her own take on the garments, with Skims. And with Spanx’s success—plus Blakely’s commitment to owning 100% of her company—she’s become a self-made billionaire. The mogul, who started off as a ride operator at Disney World, is now—for lack of a better phrase—filthy rich. She’s own-a-stake-in-a-basketball-team rich (the Atlanta Hawks, which fellow billionaire Tony Ressler also owns a share of). Appear-as-a-guest-star-on-Billions rich. The kind of rich who can purchase Olivia Newton-John’s skintight black pants from her final bad-girl costume in Grease. (Newton-John also sang at Blakely’s wedding.)
For Blakely, wealth and success are things to be celebrated. “I tell women that money is fun to make, fun to spend, and fun to give away. But that money just makes you more of who you already were [to begin with],” Blakely tells Glamour. “So make sure that you’re comfortable believing that you deserve an enormous amount of money and wealth and success, because you do. And don’t feel guilty for aiming so high. Aim as high as you can, because you got one shot at life.”
As Spanx approaches its 20th anniversary, Blakely is looking back on her entrepreneurial journey for MasterClass, the online educational platform, and sharing all the wisdom she’s learned along the way. “I’m 20 years into Spanx. I did it without any outside funding, and I’ve learned a lot. Part of life is sharing both your successes and failures with others so you can help them on their own path,” says Blakely of her decision to partner with MasterClass. “There’s a moment in one of the classes where you see me get choked up and emotional. It’s funny because people have asked me for years, ‘Does your success hit you? Do you understand what you’ve done?’ And honestly it never does. But in very random moments it will, and that was a moment. Doing MasterClass made me have that moment where I could digest the journey.”
Here, Blakely previews the ups and downs of her story. From bombing the LSAT to being too short to play Disney’s Goofy to holding tight to her belief in the potential power of Spanx.
Always have a plan B—and C.
I wanted to be a lawyer, but I’m a terrible test taker, so I bombed the LSAT. When I realized that law school wasn’t a real possibility for me, I drove to Disney World and tried out to be Goofy. Unfortunately, you have to be 5'8" to play Goofy, and I’m only 5'6". So I got the part of one of the chipmunks instead. I worked at Disney for three months and put people on rides at Epcot. I was never actually the chipmunk; I left Disney before I got the chance.
Then I started selling fax machines door-to-door and did stand-up comedy at night. I was really just trying to find my path. I asked myself a lot of personal questions. Things like, What am I good at? What do I enjoy? I like to challenge myself and do things that scare me. I just have lived my life that way. If something seems really terrifying, it becomes the next thing I want to explore and find out why I’m so afraid of it and then try to do it.
Don’t be afraid of the word no.
I tell everybody, if you can cold-call once in your life, it’s one of the best life trainings you can get. It’s very humbling. It teaches you to be quick on your feet. It also teaches you not to take the word no so seriously. Face the rejection, and get back up and do it again. I would hear the word no all the time selling fax machines, so to me it just became like a numbers game.
But it was very, very hard to keep my spirits, and mind-set, in the right place. I would listen to motivational tapes all the time in my car—from people like Brian Tracy, Zig Ziglar, and Wayne Dyer—that would help me get the courage to step back into the next office building. I was getting escorted out of buildings by security, I was having people rip up my business card in my face a couple times a week. It was really intense. But it was laying the groundwork for Spanx. I didn’t know it at the time, but it was really laying the blueprint for me to be able to invent something the way that I did. Because while trying to get something made with no expertise, no background in it, and not knowing a single contact in the industry—I heard the word no a lot. But I was so trained to not let that stop me that I think that’s really part of why Spanx exists.
Own your desire for success.
Two years before I cut the feet out of my pantyhose to solve an undergarment issue [the initial inspiration for Spanx], I had literally written down in my journal, after one really bad day of selling fax machines, “I’m going to invent a product that I can sell to millions of people that will make them feel good.” I asked the universe to deliver the idea to me. And for two years after that I still sold fax machines. Then one day I cut the feet out of my pantyhose, and thought, Maybe this is my big idea. So that’s how that happened. I just thought, Okay, this might be my idea that I asked for. I'm going to explore this idea.
Then I told myself, “This is crazy, Sara.” I mean, there are billion-dollar companies where people sit around all day thinking up new products. There must be a reason they didn’t think of this one. If it’s such a good idea, why doesn’t it already exist? I played a lot of mental tag with myself, going back and forth between “You should give this a go” and “No, you're crazy, don’t bother.” But I continued to fight through the negative self-talk and the self-doubt. And I think so much of that was listening to people talk about how to control your own mind-set. But that doesn’t mean I never have moments of doubt. I’m 20 years into my Spanx journey. I still have those thoughts.
Believe in yourself, even if nobody else does.
When I started my company, I’d reach out to hosiery mills—which were all run by men—asking them to manufacture Spanx. I called them all on the phone at first, and they all pretty much gave me the runaround. So I took a week off of work and drove around to all these manufacturing plants that were all mostly concentrated in North Carolina. I had my lucky red backpack from college with me, and I would walk in, and they would always ask me the same three questions. They would always say, “And you are?” And I would say, “Sara Blakely.” And they’d say, “And you’re with?” And I’d say, “Sara Blakely.” And then they’d say, “You’re financially backed by?” And I’d say, “Sara Blakely.”
Some of them would just escort me out and say, “We’re not interested.” But the way that I handled it was that I used very definitive, confident language. If you’re only given 30 seconds or a minute to try to make your pitch, you need to also figure out how you can make it about who you’re presenting your idea to, and what’s in it for them. So I did that all along the way of my journey. I would say, “I’ve invented a product that’s going to definitively change the way women wear clothes. It’s going to end up becoming an enormous program for you. You have to give me the chance for this to happen. I have total confidence that you’ll end up getting a great amount of business from making this decision.”
This interview has been edited and condensed.
Samantha Leach is the associate culture editor at Glamour. Follow her on Twitter and Instagram @_sleach.
Originally Appeared on Glamour