Kendra Wilkinson On Proving Her Real Estate Chops And Smashing Stigmas - Exclusive Interview

Kendra Wilkinson became a household name in the mid-2000s when she began her career in reality TV starring on "The Girls Next Door" on E! while living at the Playboy Mansion as one of Hugh Hefner's girlfriends alongside Holly Madison and Bridget Marquardt. She became known for her vivacious, authentic, and funny personality and soon landed her own spinoff series on E! called "Kendra" after moving out of the Playboy Mansion, living on her own, and becoming engaged to now-retired NFL player Hank Baskett. "Kendra" ran from 2009 to 2011 and was followed by "Kendra on Top," which ran for six seasons; both shows showcased her navigating life as a wife and mom to her and Hank's two children.


After a number of years away from the spotlight, Kendra returned to the small screen in 2021 in "Kendra Sells Hollywood," which explores her life navigating single motherhood (she and Hank divorced in 2018) and reinventing herself as she starts a new career in real estate.

With "Kendra Sells Hollywood" back for Season 2, we sat down with the star to talk all about the new season and her life today as a real estate agent and single mom.

What's next for Kendra in Season 2?

At the end of Season 1 of "Kendra Sells Hollywood," you begin seeing some success in real estate and have to make a choice between Ernie's team or going to Lisa's team. What can you tell us about what viewers can expect from Season 2?


Season 2 is a completely different vibe than Season 1 because this [was my] year one of real estate versus year two of real estate. Year one — I was just breaking into the business. I wasn't ready to sell my first house, or I couldn't find anyone to do that with me or convince anyone. Being new and famous doesn't help. ... In Season 2, I'm finally understanding the business, getting knowledge, [and] learning. I found my first seller who ... listed their property with me, and I had never known a feeling like that in my entire life. This was real, this was on camera, and it was so cool. ... 

I've captured so many ... moments of my life on camera. I've captured the births of my two kids, my marriage, my wedding — golden moments of my life have been filmed. The first sale in my real estate career was filmed, and I was over the top. It was a feeling I've never felt before. Accomplishment. I know that I've succeeded a long time in Hollywood, and it's been one long, awesome career. But ... I had never in a million years thought I would ever accomplish something more than that, more than just being Kendra ... 


I was able to learn something and earn something, and it felt so powerful and so good. It took so much work, [and you're just] seeing touches of it, but it took a lot of work to accomplish. To sell a house and to list a house isn't easy.

This season is a whole different vibe. It's down to the nitty-gritty. It's down to real business. It's down to getting into the trenches of real estate, and it got really heavy this year. It's not all fun and games. It's challenging. It takes a toll on your mental health. I started getting extreme anxiety because it's not just me in a room. It's the world watching and a company watching and production in the room. Here I am trying to focus on how to make my clients happy, how to sell this [house], how to achieve my goals, and can you imagine the world watching you during that time? You're like, "Oh my God."

On working hard, being real, and overcoming stigma

It's great for people to see that you are being yourself and this is your authentic journey and that it's not so-called "easy" for you.

There's no such thing as easy. Nothing's just given to you. Nothing's just been given to me. I've created it from my blood, sweat, and tears. It's been more of a challenge than easy in my life. And I'm more alone — I don't have a nanny, no housekeeping. I have to manage all the time. It's a lot to manage, and nothing comes easy, so I have to push so hard. I see I'm an innovative thinker, and I try to keep pushing and keeping myself up. It's about staying focused day to day on what you really want because there are so many distractions. 


Being in Hollywood, everybody wants to hang out with you, and it's so easy to be like, "I want to do 10 things this week" and [then] lose track of your own life. It's so important to stay focused on what you truly want. There are so many distractions all around ... Social media ... There's 20 people asking to go out in one week, and then you're going to find yourself not doing anything. Then it's like, "I just partied 20 times a day, and I didn't even do anything." It's so important to put yourself first, take care of myself, and put my kids first as well, and the rest is on God. It's all about knowing who you are and not allowing the past to define who you are.

It wasn't going to [be easy]. The thing about me is I'm so real. I can't fake anything, so you're getting a real experience through my journey. For instance, I wasn't going to fake-sell a house. If I wasn't able to sell a real house or sell anything, then that's how we're going to stay. We're going to stay there because I'm not going to fake it. 


I sold my first house, and in that moment, it wasn't for anybody else but me and my children. We were able to capture it for the camera, for the show, for you. That sale was for me and my children. We could have easily faked it like other shows do, but nope. I was so proud of myself. I don't remember the last time I felt proud of myself like that. It was strength I've never known before. 

This is unlike any other show. This is so raw. It's not the glamorous thing you're all used to. It's raw, and it's part of a real journey. I have this label on my head, which is "celebrity," "Playboy," and all that stuff, which doesn't help at all. You have to break down more stigma and walls than anything else because it's very challenging to approach the sales world with a public history. I have to work extra hard to make sure that people trust that I'm really doing this for them and doing it for real life.

Her move to real estate

How did you decide to make that leap into real estate?

I was down and depressed and in a dark place for a very long time. For about four to five years, I was in a dark place. I was raising my kids — that's the only thing that was keeping me alive, but I was spiraling downward. I had nothing to do. I had no job, because my only job was just being me, Kendra. How do you make that a job moving forward? You can't, so I'm like, "God, what am I supposed to do now?" I didn't think fame was coming back. I didn't think I was going to be on camera, on a show again, so I had to figure it out fast and figure out how to make money again and to try and start a new career.


I had already invested in some properties before, and I enjoyed real estate, so I entered the real estate world in real life. And because I chose that path, I was able to have a show again. It's amazing how it all came back, and everything is working, moving forward with the past trailing along. It is what it is. It's a part of it.

It's so important to me. Real estate has become my life. That's all I talk about, dream about. It makes me really happy to do it, but it's not easy. I'm probably turned down 50 times a day. It's not easy for a celebrity to do, either, so I have to work extra hard. I have to work so hard because people are like, "Aren't you that Playboy girl?" And it's like, "No, I'm now a mother of two and a real estate agent. Thanks so much. I'm really in real estate, and I'm here to do the best job, to sell your house, to help you find a house." It makes me happy. It all works hand-in-hand together. 


I am so beyond grateful for this chance in my life. I didn't think it was possible to even have this chance, but here I am having this chance, and it's a blessing. It's nothing less than a blessing. It's amazing.

What's coming up next for you and the show?

This is a journey. I love doing the show. I love filming my journey, but this process I want to take over. I want to be the best real estate agent in the world, and I'm not there yet. We need to get there, and I want to show you guys that I can do it. My goal is to truly get to that point. I'm working so hard every day to get to that point. If there's a Season 3, you're going to see a whole other ballgame. You're seeing the process, but I'm telling you I'm about to knock down some walls and take it all.

In Season 2 of "Kendra Sells Hollywood," Kendra Wilkinson is back, and this time, the stakes are higher than ever. The first two episodes of the six-episode season debut on Max today, May 26, followed by two episodes weekly through June 9.