Kendra Wilkinson On Kendra Sells Hollywood And Her Career Journey - Exclusive Interview

You may remember Kendra Wilkinson from her time in the Playboy mansion and her role on "The Girls Next Door," a reality show that documented the lives of Hugh Hefner's girlfriends. However, she's been through many life changes since then, and after her divorce from football star Hank Baskett, Wilkinson decided it was time for a serious career shift into real estate. According to Wilkinson, real estate was something she's always had an interest in, so when she needed a job to support herself and her two children, it was an obvious choice. Now, you can watch Wilkinson take her first steps into the new field on the discovery+ series, "Kendra Sells Hollywood."

Between tackling a new career, being a mother to two, and re-entering the world of reality TV, it's fair to say Wilkinson has a lot going on. In this exclusive interview with The List, she discussed the challenges of making her way in real estate, what it's like being in the public eye, and her journey to finding herself.

Kendra Wilkinson is serious about her new career in real estate

"Kendra Sells Hollywood" follows you building a new career. What was it about real estate that drew you to it?

I've always been really into the real estate game. I invested in a few properties while I was living at the Playboy mansion, and I just always loved the idea of being in it in some way, shape, or form. I just never had the time because TV ended up being a 14-year career. So when that all came to an end one day and I found myself years out of work, I just realized that real estate was a perfect fit for me. I studied, and I worked hard, and I ended up passing the test, and then I was asked to film and document the start of my real estate career, and I agreed. I'm really excited to be back with the new show on discovery+.

That's interesting that now you get to combine your TV work with real estate, which you've always been interested in.

Yes, exactly. I never really had an actual job on camera or on TV, so this is my first time filming a show [and] having an actual job.

What would you say that you've learned throughout the show?

I'm really truly learning real estate with the best real estate company out there, Douglas Elliman. They are training me. They have the best real estate agents on me, making sure that everything is professional and making sure that we win. This is a real career move for me, and it could be a big win for everyone.

So, do you think you're going to continue in real estate going forward now?

I signed up for real estate to provide for my children. This is a real job for me, this is what I have, and this is what I'm committing myself to, with or without cameras.

So during your time when you were on reality TV for years, did you ever picture that this is where you would end up working as a real estate agent?

No, no, no. No, not at all. I had no idea what was coming my way. I found myself in a three-year depression, very, very depressed, and I lost everything pretty much, everything except for my children. It was just me and the kids, and I had to get back up and fight for my life, and I chose real estate, and it's bringing me back to life. It's a really exciting time.

Kendra Wilkinson's advice for others going through career changes

If you could give yourself any advice during those times [on reality TV], what would you have told yourself?

Oh man, just keep having fun, just enjoy life, and I did! I did! That's the thing — I enjoy every stage of my life, but with every stage comes pros and cons. I mean, nothing's perfect. No stage is perfect. I would like to know who's perfect out there. Tell me your ingredients of a perfect stage of life, please. No, I'm enjoying every stage of my life.

What would you say is the biggest challenge you've overcome to get to this stage you're at now?

The biggest challenge was getting to know myself for three years alone. I've been alone and in silence for three years, so it was very important for me to get to know myself without the world telling me who I am. So I got to know who I am, and that's the biggest challenge of my life.

Like you said, with the world telling you who you are. Obviously, you're in the public eye. What do you feel is the biggest misconception about the way the media and people see you?

People have gotten to know me. That's the thing; people have gotten to know me through the years. So, my fan base who have followed me, they know. The people that don't really know me and they see me, they have this label on my forehead, which does not even equal, is not equivalent to who I am. I'm a tomboy dork mom. I'm such a dork mom. I'm in the grocery stores every couple days a week figuring out what recipe to make and at soccer practices four days a week. That's pretty much it. I mean, I'm just such a dork mom, but I'm now creating space to really focus on this real estate career and making sure that this works.

If you could give advice to anyone who's going through a career shift or just a big change in their life, what would it be?

The biggest advice I would give someone who's going through a transition is to focus on only your own self. Focus on yourself, do not reflect, [and] do not look at someone else on what they're doing. You're on your own path. You need to take your own small steps, whatever they are. You're the only one that knows what those small steps are to achieve the bigger picture. No one else can tell you that but yourself. 

So you have to really create your own way and not look at someone else's way, because me jumping in the real estate game ... there's this and that. It's so easy to like, "Oh my God, how can I ... ?" There's no competition; the only competition is with yourself. That's it. Focus on yourself, focus on your own, and you might create your own way. You might create your own little thing and believe in yourself. That's how I'm doing it.

The highs and lows of starting a new show

What were the best and worst parts of filming the show for you?

The best part about filming "Kendra Sells Hollywood" is just really getting to know the few real estate agents that are around me and knowing that they all have a story. They all have a heart, they all have a story, they all have families that they're providing for. They're not just salespeople; they're real people, and that's what my show is going to show you as well. The worst parts are exposing my weaknesses and my blond moments. Sometimes I'm like, "Oh my God, the world's going to now see how blond I really am."

At least that's real, though.

Yeah, I'm having fun. Again, I'm not ashamed. I'm having fun.

What can viewers look forward to in Season 2? Is there going to be a Season 2?

Oh, we don't know that yet. We don't know. We are hoping, please subscribe to this show. It's on discovery+. Make sure to watch because it's really gold, gold TV, and I couldn't be more proud of it and the people that are on it. The cast is so amazing, and the agents I'm with and Douglas Elliman — I mean, everyone was just so amazing, and it's so important to watch this because you're not only supporting a single mom, you're supporting hundreds of families and people. So that's important to know too, how you're not just tuning in to support me; you're supporting hundreds of families and people just by subscribing to the show.

Right. A lot more goes into it than the one person.


So, you're entering a new phase of your life, and you're documenting it on the show. What pieces that you learned from your time on reality TV are you taking with you going forward?

I've been preparing, I think, for this real estate business for longer than I thought. I started working at 16. I never stopped working. It doesn't look like I'm working, but I'm working.

Yeah. You make it look fun.

Yeah, so it's just having a thick skin and building up that thick skin through the years is what prepared me for this, because already I've experienced some real let-down already in this business. All the depressions and all the little things I went through in my past career and TV, and all this prepared me to get back up and stand strong again.

What would you say was the biggest challenge learning real estate and starting out at a run like that?

The biggest challenge starting real estate is just really admitting that I need to really earn this. I need to work hard and put the time and effort into this job. Celebrity is only going to get you so far. You have to earn it, you have to earn it. Earning it takes time. It takes patience, a lot of patience. So yeah, that's the hardest part.

I guess that comes with any new job you're starting out. 

Yeah, exactly.

How Kendra Wilkinson balances her career and motherhood

What's it been like balancing having this whole new career along with being a single mom?

Ooh. Yeah, I mean, it's a challenge. It's a challenge being a single mom and balancing a new career, and even being open to love again. The most important thing are the kids, but the most important thing to them is me, so you have to remember that too. So, we're all sitting here saying that, "Oh, the kids come first," but in their minds, mama comes first. So, it's really important that I show them what I have and what I can do right now and the time. It's really important to commit to this business, and they are rooting for me as well.

Yeah, you don't want to forget yourself while you're looking out for them.

No. No, putting your kids first is putting yourself first.

Like you said, you have this whole new career, you're a single mom, so it's got to be stressful. What's your go-to way to relax after a long day?

My favorite thing nowadays is just a straight whiskey with one cube in it and a cigar and some golf.

You said a cigar too? 

Cigar. I love cigars now.

Oh, wow.

Yeah, I love cigars, whiskey, and some golf. I'm like a guy, I'm like an old guy. That is my happiness; that's my ultimate. You want me in heaven, then you give me a cigar, some whiskey, and some golf.

So as you've been going through these changes and these challenges, who are the people in your life that you've been able to lean on?

I have a few amazing friends that have really stuck by my side through challenging times. They're always asking me how I am, but no one's there holding my hand through anything. That's up to me. So yeah.

What it's like being in the public eye, according to Kendra Wilkinson

You're kind of showing different sides to yourself on the show that maybe people who haven't followed you the whole time won't know about.


What aspect of your personality do you think maybe new viewers will be most surprised by?

Well, I'm still me, so they're going to discover Kendra selling Hollywood. I'm just kidding. No, they're going to show me in a very professional setting, being Kendra in a professional setting.

It's still you, just a new environment, right?

Yeah, but I'm really taking it serious. It's very important.

Yeah, I think maybe when people are just first seeing your name on a new reality TV show, they might not realize how seriously you're taking it, but you had to take the test and everything, the estate agent test.

The test is the test, but the business is the business — two completely, very different things. I learned that really fast.

Have there been any times in your life since you've been in the limelight so long where you've wished you could not have so many eyes on you and not have people paying attention?

Yeah, that's why I took a step back these last few years. These last few years, I chose to not fight to be famous anymore. I just chose to accept it and accept myself and learn who I really am. I came up with a lot of answers, and it was very challenging few years, but I stepped away, and it was really amazing. I really took the time to really discover who I really am, and it took a lot, a lot.

Since you've gone through that self-discovery, do you feel like you're more prepared now and feel more like yourself as you're entering back into having a TV show again?

Yeah, I mean, I didn't even know if I could film TV again. The cameras turned on that first day, I'm like, "What do I do again?" But no. It came right back to me. The thing about me is I guess [we're] more powerful than we think. It's almost like I was chosen to do this or something. I don't go chasing it or anything; it's almost like it's choosing me or something. It's almost like I, I don't know. I feel like I have messages [that are sent] from God or something. I'm just kidding. I'm just kidding. But it is. It's very unique, very different, and I'm very, very, very thankful and grateful for it all. I think that it's really cool.

What inspires Kendra Wilkinson

So, do you have a favorite reality TV show to watch this year?

I've been into black and white movies lately because I'm trying to get my love thing back. So I've been watching "The Masked Singer." That's been really fun to watch lately. So it's between "The Masked Singer" and black and white movies. Black and white movies, like very romantic. I'm trying to get that side of me back [and] pumping. ... This is my heart. Yeah. And being a single mom, you don't really have a lot of time. I don't even have any help cleaning or anything. I don't really have a lot of time.

Right. There's not that much time to be watching TV.

Oh my God.

Do you have any favorites of those older, romantic movies you've been watching?

You know who I've really fallen in love with is Audrey Hepburn. I know she's an icon, but I've just now started to get to really know her as an actress. And she's just ... what a light, what a light. She really did so much [with] the messages she sends through her movies and just the power she had. And she was just a beautiful person. And that's who inspires me.

Are those the kind of messages you feel like you want to put into the world as well?

Yeah. Yeah, definitely. Audrey Hepburn definitely, definitely was here to change the world for the better, and that's what I want. I see myself a lot in her. A lot of the messages I want to send, even when it comes to my real estate journey, I definitely 100% want to figure out a nonprofit and really, really put that kind of work into the world too.

That's amazing. Do you have any ideas of kind of the area you'd want to work in with that?

Yeah, there are so many ideas. I want to change the world [in] every way. Like, I love animals, and you know, but you know the homelessness is such a heartbreaking thing to see every day. I was on my way to film, or I was on my way to an open house in Venice Beach, like this gorgeous mansion. And, and I saw this, like this homeless family on the side of the street, and it just crushed me, absolutely crushed me. And I'm like, it just feels weird, like going to this mansion and, on my way, seeing this homeless family. Just really heartbreaking for me, and how can we change that? How can we change that? I mean, there has to be a way, there has to be, and I want to try to find the way too.

Kendra Wilkinson adores this royal's style

What is your favorite celeb look of the year? 

My favorite celebrity look of the year. Who do we have? Oh, you know who? I really love Kate, the princess. What's her name? Kate, the princess ...

Kate Middleton?

Kate Middleton's style is my favorite. So if I were to have a real estate agent look, it would be hers. I really love [her look]. I mean, any chance I scrolled, I'm like, "How am I going to look as a real estate agent?" She's it. Yeah, she's it. I love her style. I love her.

She has that classic Audrey Hepburn feel too.

I love her. She's so just down to earth, real. I just love her. I love, I love her.

"Kendra Sells Hollywood" starring Kendra Wilkinson airs Wednesdays exclusively on discovery+.