A lot of people think the heavens opened for your family and dropped fame and fortune into your laps.
I wish it were that easy. I’ve been working nonstop for 20 years. When I married Bruce, it was sort of hit the ground running. I married a guy who was really talented and had been doing motivational speeches for Fortune 500 companies—and this is a guy who didn’t have a business card or a press kit. People who were in his business had all these marketing tools, and Bruce was just winging it. I knew he could be much bigger.
In his book Finding the Champion Within, he says that when he met you, he was $500,000 in debt and living in a one-room apartment.
He was at a place where he had really low self-esteem and thought, Now what do I do with my life? I think I was probably a breath of fresh air. But he brought the goods. Managing isn’t a magic show. You don’t work with somebody and instill talent in them. I am blessed to have these children who have the most amazing work ethic. I have a 13-year-old and a 15-year-old [Kylie and Kendall Jenner], who were at a meeting at 8:30 this morning with Ryan Seacrest Productions to talk about their careers. They were at this crazy-long conference table with executives, who are fascinated by what the girls have to say. That’s better than any education I could offer them.
You started as a flight attendant and then became a housewife. Were you prepared to become a business manager?
I was the Brownie leader and the soccer coach and room mother and car pool driver. Being a mom gave me great knowledge of how to be a professional multitasker. I see a problem, and I fix it. To me, Bruce was a problem that needed to be fixed.
Did you have professional ambitions during your first marriage?
Oh God, no. I was working 24 hours a day trying to raise four babies. I didn’t want to be anything but a mom for a very long time.
So after you married Bruce Jenner, how did you know the right way to package and market him?
I just figured it all out. [I used] gorgeous folders for his press kits. I made stickers of him crossing the finish line, and that was his logo. To me, it’s all about the details. I think everything wrapped in a beautiful bow makes it that much more attractive.
When I wanted to get Bruce into the Sherwood Country Club [with the idea of making business contacts], I had his press kits on everybody’s deskalong with little Hasbro Bruce Jenner dolls and his Wheaties boxes. I had thrown the most amazing parties for so many years [while married to Robert Kardashian]. It’s like, “OK, these are your party favors.” You have to figure out a way to communicate with people.
What’s the secret to becoming self-made?
If someone says no, you’re asking the wrong person. Don’t get discouraged, and don’t be afraid to try new things. Get organized.
What’s been your biggest success since you became an entrepreneur?
The thing I’m most proud of right now is our relationship with Sears. I’ve been working on getting the girls a lifestyle line—apparel, shoes, bags—for the last three years. When I came upon the Sears opportunity, it was perfect. My grandmother took me there all the time; it’s one of my favorite memories. Who knew that all these years later, my girls would have their own line at Sears?
How do you know a business opportunity is right for the brand?
I use my intuition. When something starts to feel really forced or not natural or doesn’t resonate with my family, I know it’s time to walk away.