What Caitlyn Jenner Taught Kim Kardashian About Fame

The trans community’s reluctant poster child showed up to support Tangerine’s historic Oscar campaign—and told us what she told Kim in her early days of fame.

01.05.16 9:20 PM ET

The same advice that helped a young Kim Kardashian through the early days of fame also helped power Caitlyn Jenner during her explosive and emotional landmark year as the trans community’s reluctant poster child.

“What I always taught my kids was, ‘The ability to grow is directly related to the amount of insecurity you can take into your life,’” Jenner told The Daily Beast on Monday night in Los Angeles after a screening of Tangerine, the critically acclaimed transgender-themed dramedy she’s helping boost through a historic Oscar campaign.

Exchanging warm kudos with Tangerine breakout and fellow trans activist Mya Taylor, Jenner recalled imparting that line of wisdom to her Kardashian brood long before Kim, Khloé, Kourtney, Kendall, and Kylie became household names.

“I would tell the girls that every time they were feeling insecure,” she said. “I remember Kimberly one day came downstairs, years and years ago, and said, ‘I couldn’t sleep last night, I was so nervous.’ I said, ‘Why?’ She said, ‘I have to do an on-camera [appearance] and I have to talk right to a camera—I’ve never done that before.’”

“It is very weird! I get it,” Jenner laughed, Taylor nodding in agreement. “So I told her, ‘This is it: Once you do it, you’ll go and do a fine job. You’ll be better next time, but that will be your new norm. And the next time will be much easier. So will the next time after that, and then you go to the next one. Live in that uncomfortable zone.’”

The former Olympian and reality TV star knows a thing or two about embracing challenges. Only nine months ago she came out publicly as transgender by declaring to Diane Sawyer, “For all intents and purposes, I’m a woman” on national television. Her landmark Vanity Fair cover landed in June featuring a stunning boudoir glamour shot by Annie Leibovitz. Halfway through 2015, Jenner already owned the year.

The ensuing media frenzy drew everything from global support to intense criticism from without and within the trans community, earned Jenner high praise and high-profile awards for her bravery, and even managed to overpower negative attention on the fatal February car crash in which she was involved. In July she premiered her own E! reality docuseries, I Am Cait, which has been renewed for a second season. By year’s end, ‘Caitlyn Jenner’ was the second most-Googled name of 2015.

But being seen as a de facto representative of an entire community hasn’t been easy, Jenner said. “I always feel an obligation to speak up, although I am not the spokesperson for the trans community,” she smiled. “I say that ten thousand times! I’m only a spokesperson for my own experience. But I like exposing other people and listening to their stories and what they’ve gone through, and doing whatever I can to help bring this conversation forward.”

Jenner kicked off 2016 by throwing her support behind Tangerine, a vibrantly entertaining independent film shot on iPhones that’s nominated for four Independent Spirit Awards, including nods for director Sean Baker and stars Taylor and Kitana Kiki Rodriguez.

Taylor has already won the Gotham Independent Spirit Award for Best Breakthrough performance as trans sex worker Alexandra, who joins her trans BFF Sin-Dee Rella (Rodriguez) on a wild Christmas Eve odyssey through Hollywood. With celebrity champions like Jenner and Orange Is the New Black’s Laverne Cox, Tangerine is now taking aim at getting Oscar voters onboard.

“They did a wonderful job,” Jenner raved, smiling admiringly at Baker and Taylor. “It’s got great acting, powerful performances, it’s funny—and it’s tough to be funny when you’re dealing with such a sensitive subject. There are some very serious issues in our community, especially for trans women of color, and we need to spotlight them.”

She listened intently as Taylor recalled filming Tangerine’s most emotional scene, in which Sin-Dee and Alexandra shed their wigs in a rare moment of brutal vulnerability. As difficult it is for the characters to deconstruct their fierce veneers and expose themselves in that moment, it was equally tough for Taylor and Rodriguez, who are receiving the first-ever bona fide Oscar push for transgender actresses for their work in the film.

“At first, Kiki and I didn’t want to do that scene. We were like, ‘Girl, I do not come out of my wig,’” said Taylor. “But then I thought about it. I think I actually had to convince her—because I had hair, of course, so I didn’t have as hard a time taking off my wig, but she had a hard time with that. Then she said, ‘You know what? Acting is what I love to do, and sometimes you have to step out of your comfort zone.’ So that’s what we did, and it turned out to be beautiful.”

Taylor revealed that even exposing herself to the scrutiny of transphobic strangers during the shoot was daunting. “I had just started my transition,” she explained. “Sometimes people can say mean things when they figure out that you’re transgender. It’s really hurtful, some of the things that people can say. So I did have to come out of my comfort zone, just to film.”

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Heading into 2016 after a breakthrough year in trans awareness, Jenner says the LGBT movement still has a lot of work to do. “I’m very happy for where this community is at right now. We have a long ways to go, but people are talking about it,” said Jenner. “After the first season of I Am Cait, I was sitting down with Chandi [Moore] and Candis [Cayne] and we were having dinner. I said, ‘What did we accomplish in Season 1?’”

“We came to the conclusion that we opened up the conversation,” she said. “Movies like this open up the conversation, make it OK to talk about these issues. And when you can talk about them and bring them to the forefront, then you can start to come up with solutions.”