What's your life like when you assist one of the most recognizable names in the world? Arianna Davis finds out.
As we drive to West Hollywood for a meeting, Shepherd tells me her career story from the beginning. After dancing for the Cleveland Cavaliers at 18, she moved to LA in 2009 to try for bigger gigs — and she got them, but they were assisting, not dancing ones. Choreographer Mikey Minden hired her as an assistant to help him and his main client, Erika Girardi (then an international nightclub performer, now a cast member of The Real Housewives of Beverly Hills), saving Shepherd from her part-time job at the front desk of Gold's gym.
When I say I came from a small town, I mean that I would pass cows driving to school. It was country life: bonfires and football games. Our nicest restaurant was Olive Garden. So when I came out here, it was a whole different thing. I had never seen a Range Rover. I hadn't really traveled, I didn't know what Givenchy was or how to pronounce it. Mikey and Erika took me under their wing and taught me everything. We traveled the world together. They both opened my eyes to so much, about being a hard-working, meticulous assistant, yes, but also just all the things life can offer.
And then, after a few years working for Minden and Girardi and a few freelance backup dance gigs for artists like Pitbull, Minden's business partner and former Pussycat Doll Robin Antin asked Shepherd if she might be interested in an assistant job with a friend of hers: Kim Kardashian. And just like that, dancing became a distant memory.
On a Monday morning in April 2013, Shepherd — fresh off a trip from Coachella — drove to Jenner Communications in Woodland Hills to interview with Kris Jenner's then-assistant. The next step, she was surprised to learn, was a meeting with her potential boss herself, at Kim's home in Beverly Hills.
She had no makeup on and was in her sweats, super pregnant with North. She was just like, 'Look, I need help, Robin loves you and says great things about you; this is what I need. Can you do it?' And I was like, 'Okay, sure, I can do that — and if I can’t, I’ll figure it out!' Meanwhile in my head, I was so nervous. Coincidentally we were both wearing French braidsKim later told me she was thinking 'This girl has good vibes and a braid, I'm into her!'
Shepherd started the very next day. She dove right in, often staying at Kardashian's home until 10 p.m., learning on the fly.
I was doing her whole schedule, doing her laundry, booking travel, putting the stroller together and all of these things. But I wasn’t nervous. I was just excited, always staying longer than I needed because I was trying to prove myself — and then North came early! I was a brand new assistant who had no idea what to do with a baby, but we all moved into Kris' house, and she was the one who made it all feel okay and moved mountains for us. Four years later, Kim now also has a personal assistant, a house assistant, two kids, two nannies, and I was recently promoted to COO of Kardashian West Brands, so we're looking for someone to fill my executive assistant position. Sometimes we look at each other like, wow, remember when it was just me and you?
Even as the newly minted COO, though, Shepherd is still in assistant mode, constantly checking her iPhone and revealing a trunk fully stocked with Kimoji paraphernalia. With Kim, you never know when you might need to gift some merch!
Shepherd is a master multi-tasker, checking texts and emails and sending voice notes throughout our day together. Somehow she never seems distracted, or like she's only half paying attention.
The first thing I do every morning is read my email. Then I'll check in with her personal assistant, Michael, who I also brought on to the team — he used to work with me and Erika. I knew I could trust him because when we worked together before, he saved my ass so many times! We used to have a Jenner Communications office where I would work out of sometimes, but now I just kind of work from home or with Kim at her house, or sometimes at Kris' house in Calabasas.
I'm not surprised when Shepherd mentions who, in the family, is her biggest career inspiration.
Kris Jenner is a fucking G. The biggest lesson she's taught me is to not procrastinate. When you want something done, get it done. If you're a procrastinator, this is not the world for you. If someone tells her no, she has no problem standing her ground and saying, 'We're not accepting that, get someone on the phone and make it happen.' That woman can literally get on the phone and change the world. And somehow, she juggles all of these kids, all of their careers, and still makes sure that every assistant, every staff member, has a Christmas present, delivered to us by Christmas, with a thoughtful card. And it’s a nice ass Christmas present. That’s the kind of person I aspire to be one day.
As a former assistant myself, I've long noticed Shepherd in the background of episodes of Keeping Up With the Kardashians. But she's never been a starring player, like Kardashian's BFFs Jonathan Cheban or Simon Huck, have. I ask her if that's by design.
I've never really wanted to be front-and-center on the show. But the thing is, the girls really don't stop living their lives for the camera, so the reality is I'm often there, because I'm actually working. Sometimes the camera will catch that, but usually I look like shit because they'll always come when we're traveling somewhere, and I have on no makeup or just woke up! I think everyone thinks this job is super glamorous — and I can't lie, it is. Truly, this family is so much fun, and we go to some amazing places and do some incredible things. But don't forget that when you're an assistant, with all of that glamour comes schlepping the bags and the suitcases and taking the fall when the car doesn't show up or the flight is delayed or something goes wrong.
Despite her more behind-the-scenes role on the show, with nearly 700,000 Instagram followers, she's clearly built up her own cult following.
Sometimes I think about how it’s such a weird thing that people want to know or even care about me, just because I work for Kim. But then it's like, well, she is one of the most recognizable celebrities in the world. I don't get recognized a lot unless I'm with her, though there are some places that I know Kardashian fans will be. Like Sephora: Our fan base loves some Sephora, so I have to stay clear of Sephora stores if I'm trying to be lowkey!
And though it seems she has the assistant thing down, Shepherd admits she's struggled now and again.
I’ve fucked up a lot. I’m only human. I get a lot of young girls asking me how to be a great assistant. I tell them three things. One is if you mess up, take responsibility and own it. I've fucked up, I'm human. But I will just say, 'I am so sorry, and I will fix this.' Second, I say be resourceful. If your boss wants or needs something, you gotta do whatever it takes to make it happen. Don’t ask questions, just make it happen.
Once, we were in San Francisco, and Kanye was obsessed with that game Cards Against Humanity. I didn't ask questions, I just figured out where the hell to find the game in San Francisco. Lastly, I say take notes. Write. Shit. Down. Even if you think you’re gonna remember it in your head, you're not. We have interns through Jenner communications, and every time I see an intern not taking notes when they're getting instructions, I’m like, you’re gonna fuck this up! Just write it down — it's not that hard!
En route to the Kimoji meeting, Shepherd bangs her hands on the steering wheel and yells, Fuck me! I need to get gas! We cross our fingers and ride on E through a red light to the nearest gas station. (Sorry, LAPD.)
Shepherd exudes style even while pumping gas. She credits her Japanese father, who's always lived in Japan, for her waist-length hair, and then clarifies — on the record — with a laugh, that it's not a weave. Unlike her beauty-loving boss, Shepherd doesn't have a hardcore routine: just Jen Atkins' Ouai shampoo, Sally Hershberger's 24K gold hair oil, and air drying, no heat.
I'm not that fussy about all that stuff, she says. But whenever Kim's makeup artist Mario Dedivanovic offers to do hers, too: I'm not gonna tell him no! (And who would?)
As for fashion, her all-black everything aesthetic is as influenced by Kim as it has been improved upon by Kanye. Those snakeskin boots that I caught multiple people, myself included, eyeing all day? My Christmas present from Kanye, she says. The Yeezy boots. They’re everything.
Over tuna bowls back at her house, Stephanie and I bond over several similarities. We're both in our late 20s, both biracial, both grew up in smaller towns and ended up as assistants in big, glamorous cities. We're both driven and career-minded, and yet we both often field those When are you having kids? questions.
Growing up where I grew up, that’s what you’re programmed to do: Go to high school, maybe college, get married as soon as possible and have kids. Many of my friends are already on their second kid by now. But I’ve never really wanted kids, I’ve never really seen that for myself. When I picture my life, like, 20 years from now, I don’t picture myself as a mother.
I was an only child without any cousins or a huge family, like Kim's, so I don't have a ton of baby experience. My only true example is North. She is the sweetest child, truly, she’s so smart and so charismatic — and she looooves mommy and daddy. So when I look at their little family, it’s cool because it takes two people, and their love, to create this person, and this bond, and it’s so dope. You create a life! So sometimes I think, well, maybe. But then again, when we all travel together with, like, four kids, it's tough! So, I don't know. I think I just have a lot more left to do before I’m ready for that kind of responsibility, but it's insane that people think that it's just okay to ask that, just because we're women.
When Kardashian and her family took some time off after the Paris incident, that also meant time off for Shepherd, who's lately making sure she gives herself space to chill, more, too.
Kim's never really taken a break, you know? She's the hardest working person, both her and Kanye. So at the end of last year, we all kind of just took some time and regrouped. There was a period last year, I remember, when we literally went from New York to Miami to New York to Iceland to Los Angeles to CubaCannes was in there somewhere. So we needed those four months to just really reflect on what's important. Now I'll text Kim and her assistant Michael to say, 'Hey guys, I'm off the grid in yoga for the next hour,' just so they know where I am in case the world ends in those 60 minutes. But that one hour is me time.
She also likes to indulge in Netflix and chill sessions with Jackson, whom she's been dating since last fall. (On the mantel in their kitchen is his Grammy, for producing Jennifer Hudson's 2008 Best R&B album.) Shepherd says she actually first met Jackson a few years ago, because he used to manage West, but it was at The Life of Pablo tour stop in Miami in September that the pair really connected.
It's hard, because he's busy, and I'm busy, but you make time for the things that are important. He's been in the business way longer than I have, so he knows everything and really pushes me, truly. But like anyone else, we need to decompress. For New Year's we went to this really romantic resort in Cabo. That was probably the first proper vacation I've had since I started working!
I ask if he's also the first proper boyfriend she's had since she started working; I imagine traveling the world with Kim Kardashian doesn't leave much time for Bumble. (Not to mention, how can you possibly suss out a person's intentions when you're close to a Kardashian?)
I didn't date anyone at all for, like, the first two years working with Kim, because there just wasn't time, she says. And then I did meet a DJ who worked with Kanye, but it just didn't work out — we were too busy. But man, that probably sounds so bad. I really should stop dating Kanye's friends!
There are two more things that take up the rest of Shepherd's time when she's not working: Slowly moving her clothes from her apartment in Little Armenia, which she stills rents, to her new bedroom closet, and working out, a hobby she reluctantly got into thanks to her boss' family.
Being around Kim and Kourtney and Khloe, I’m always working out. I never was a big exercise person before, but they work out religiously. So I’ll drive to Calabasas and work out with Kourtney or with Kim here and there, and now I'm on Class Pass so I can take classes, like yoga or Barry's Bootcamp and Pilates and Spin. Sometimes I’ll jump in on my boyfriend’s training sessions, which he doesn’t love, because I think I slow him down.
Though she's closest with Kim, of course — I don't think it's possible for any person to talk to anyone more than I talk to Kim — she also has a unique bond with each of the Kardashian-Jenner sisters, which she says is probably the result of being one of the few employees who've been around this long.
Kendall and Kylie, we have some of the same friends, so we'll go out together and have that relationship. Khloe is just like everybody’s friend, you can talk to her about anything, she’s just a down ass girl, truly. And then Kourtney and I weren’t really close at all when I first started working — I don’t think she really liked me at first to be honest! But I think when we were doing that world tour of Miami and Iceland and all those places, with so much travel time, we bonded. Now we talk all the time and we'll go to dinner, or I’ll spend the night at her house. People always think we're either lesbians, because we're always together or holding hands, or that I am Kourtney, I guess because we look alike and have a similar style.
While the trunk of Shepherd's closet is full of Kimoji items, her bedroom is all about The Life Of Pablo and Yeezy merch.
I think people would be surprised to know how funny Kanye is. Do people know that he’s funny? I know everyone thinks he's so deep and serious, but he’s also so funny, like he has me rolling laughing, and sometimes I’m like, Is this inappropriate that I’m laughing so hard? But he’s just so fucking hilarious, he has these one-liners, and he’s just so unfiltered. He makes me laugh so hard, but he's also truly the hardest-working man I've ever met.
Kanye and Kim's 2014 wedding, Shepherd recalls as she organizes some merch in her closet, was her most challenging task on the job thus far. While Shepherd says the Kardashian Wests did have a wedding planner, obviously, they only had two assistants on-site for the nuptials, which started with a bachelorette party, rehearsal dinner, and other events in Paris before the couple surprised the family and flew them all to Florence for the actual ceremony. For Shepherd, that meant a lot of planning, logistics, and travel arrangements.
I didn’t even get to watch the ceremony because I was also filming — I often producer-cam the more personal moments for the show, when they don't want full-on cameras around — so I was filming everyone getting ready. And then Caitlyn lost her suit, so I had to locate it; all the girls are getting ready, we're getting Kim together, we’re in this castle; Kanye is down rearranging the floral arrangements and all this stuff, all while I’m trying to film. I was in Adidas sweatpants and a T-shirt and hadn’t showered that day! And then I walked her down to the elevator so she could walk down that really long stone aisle, and then I ran back up and started filming her from the roof! That was the money shot for the show. Meanwhile, there was some security guy yelling at me, 'You can't film here!'
I was still relatively new back then. I remember just not sleeping that whole week, and then I came home and I got pulled over on Hollywood Boulevard and I just started crying to the police officer, like, 'Please, I'm just exhausted, I gotta go home; you don’t understand!' Truly. I went to bed at, like, 5 in the afternoon and woke up the next day at, like, 11 a.m. But it was all worth it, because it was the most beautiful day.
Shepherd has a few other producer credits to her name, including many of their travels and the most recent episodes in Paris. Executive assistant, television producer, brand COO — the possibilities seem endless for Shepherd. Except for dancing, she says. I don’t have it anymore! I think once it goes, it goes. I always tell my friends who are still dancers, 'Can I come to class with you?' And then I see a video of them and I’m like, just kidding.
What will she do next?
I think when you're an assistant everyone wants to know that, like: 'What the heck are you gonna do after this?' And I'm just like, what do you mean? And then that starts to put the pressure on me and makes me freak out a little and start to wonder, where is this going? Oh God, how will I ever leave this family? But I've realized that I just need to utilize this position and learn as much from all of these experiences and grow as much as I can. Honestly, I'm just going to see where it takes me. I'm learning. I'm helping Kim Kardashian run her empire. I'm also building something for myself. I think that's a pretty fucking great gig.
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Kim Kardashian Parts Ways with Assistant Stephanie Shepherd
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Kim Kardashian's ex-best friend Stephanie Shepherd takes Kourtney
Stephanie Shepherd's Instagram, Twitter & Facebook on IDCrawl
