discovery+ is debuting a new reality TV series, Kendra Sells Hollywood, this week.
Kendra Wilkinson is no novice to reality television. Nor is she immune to deep invasions of her privacy.
So Wilkinson suffered as the press had a field day combing every detail of her divorce on very public platforms. All while having to take kids to school and make small talk with other moms and neighbors.
It was a difficult and invasive time and brought home that no one but Kendra would take care of keeping her family from financial ruin.
Before the super tough times, Wilkinson came up California golden, a beautiful Playmate who caught the eye of Hugh Hefner and became part of his trio of captivating beauties in her first TV appearance for the 2005 series, The Girls Next Door.
Curse of Oak Island and Ancient Aliens executive producer, the late Kevin Burns, and the late Hugh Hefner, founder of Playboy magazine, created this series that premiered on the E! cable network in 2005. It boasted Hef’s comely girlfriends, Holly Madison, Bridget Marquardt, and Wilkinson.
As time moved on, Wilkinson settled down and married pro athlete Hank Baskett, then had two children, Hank and Alijah. Life seemed perfect, until after another Kendra reality TV series, it suddenly wasn’t. Like a phoenix rising from the ashes, she launched another reality series, Kendra On Top, short-lived and canceled by WEtv. She took stock of her life and her children’s future.
Kendra obtained her real estate license and went to work with arguably one of the best in the house selling businesses, Doug Elliman.
Now, discovery+ has Kendra Sells Hollywood, which will follow along as Kendra joins the Douglas Elliman Los Angeles real estate firm, reinventing herself and creating a whole new world for her and the two children.
The six-part docuseries focuses on Kendra as she joins Elliman while learning how to navigate luxury real estate deals, cultivate clients, and bring home a nice slab of bacon.
Selling real estate in the upscale LA market can be a lucrative endeavor, but she has to crack the ice. Will people take her seriously and trust a multimillion-dollar listing with a girl who made her bones in a men’s magazine?
Monsters & Critics spoke to Kendra after the Television Critics Association summer tour exclusively. We found out that the gig and fears are real as this single mom uses a lot of signature humor to obfuscate some genuine nerves about doing well and making her mark.
Exclusive interview with Kendra Wilkinson
Monsters & Critic: I remember when my mom became a broker, and she did incredibly well her whole career. What was in the back of your mind about this career switch?
Kendra Wilkinson: You are bringing me luck today. My kids are so proud of me, and I’m so proud of them, and it’s just literally just the three of us in our house.
And I just made the decision one day. I was healing from my divorce, and I literally just said to myself, “Am I going to continue to cry for another year? Or am I going to get up and learn something new and start and start something?”
And I chose to start real estate with my kids there. They were so happy and gave me all the respect and the time I needed. I was juggling so much at that time, studying and passing the tests and with the pandemic and everything.
It was just a lot being a single mom too, but my kids were so amazing through it all, and they were so happy for me. Not only that, but when I passed the real estate exam, they were screaming and celebrating, and it was terrific, and to prove to my kids that you can get back up again at any point in life, hit the desktop, and learn something new and start something new.
I’m in a very vulnerable, scary position because all eyes are on me while I’m doing that. But my kids are the most important, and I don’t want to fail them. I want to succeed in this new phase of life that I’m entering right now. I need to show my kids how to live a life of no regret and pick back up again and start something new and learn. Show them how it’s done.
Not just because everyone can talk [the] talk, but this is about walking the walk right now. And this is about proving it because many parents have a lot of advice to give to their kids.
But my goal is to show them how it’s done. And so far, wow. It has been so powerful. It’s been amazing. It is just the three of us and me being a single mom. And it’s been a wild ride and exciting for the three of us.
M&C: How did you connect to Doug Elliman?
Kendra Wilkinson: Doug is one of the top real estate agencies in the country. I had a couple of my picks, but I wanted to be with Douglas Elliman’s firm once I passed my real estate exam.
And so the camera’s turned on literally the moment I stepped my first foot into his offices, and there I was, facing my boss who gave me a chance.
In the series, you’re getting the first steps into my new career. You’re getting the fear. You’re getting the failures, and you’re getting the excitement. You’re getting the truth of the journey.
You’re seeing my kids who will be on it, and so far, I’ve put so much work into learning, growing, and building. But this business, at the end of the day, it’s about money.
And so far, all these months into the business, I still have yet to find my first deal and close my first deal. And that’s been the biggest challenge so far is finding a client, finding someone who wants me to sell their house, or helping them find a home.
And, I’ve been going out and doing everything I can to get that done. So, it’s just been a challenge, but it’s taking a lot longer than I thought it was.
M&C: You’re a hard worker, and you always have been. You’ll accomplish it.
Kendra Wilkinson: I appreciate your positivity. Every day, you wake up in business, and it’s challenging because it’s up to you to get it done. It’s up to you to make it work.
I feel like I’m putting a hundred percent into it, but sometimes I feel like I’m getting nowhere, you know? My kids are watching, and they’re there every day I walk in that door. They said, “did you do it? Did you sell a house?” And I’m like, “no, not yet.”
So it’s just tiny steps, and I really hope that I can get it done to show them that all the hard work pays off. I’m here, and this business is about trust.
I get that people may or may not trust me yet, being a celebrity, but I’m here to prove it. I’m here to do whatever it takes to prove myself in the business world.
M&C: I’ve been stalking you on Twitter and Instagram, and I see lots of modern, clean, industrial, neutral palette, ultra-modern, almost Japanese design ethic reposts from you. What are your favorite homes?
Kendra Wilkinson: [Laughs] My favorite homes to show are all homes! I find it fascinating how people live. I like being in someone’s personal space and absorbing their designs, and getting ideas.
You can call me a design creep. I like to be in someone’s house and see how they live and what they use, the furniture they have and where they bought it. So maybe [I am] a little bit of a stalker.
When I walked into a home, like the other day, I was in a beautiful modern house, with all modern functionally. I’m like, this is my favorite. And then I walk into a Spanish-style house. I think, no, this is my new favorite. There are so many beautiful homes. It just depends.
It’s so funny. I’ve been in the most beautiful mansions on my show, but just yesterday, I walked into a smaller cottage-style house that was about 2000 square feet.
And out of all of the enormous houses, that one was my favorite. It was like a bit of a dollhouse. The client was a celebrity listing the home, but she has the cutest little cottage-style dollhouse. And it was my favorite one out of all the big mansions I’ve toured.
M&C: What have you found to be the biggest mistake potential sellers might make? And what would you caution in this hot market?
Kendra Wilkinson: Oh, probably listing the property wrong, you have to list it right. And, you have to make sure to list it correctly and work with the right real estate agent. And that would be me.
Kendra Sells Hollywood will premiere and stream Wednesday, Nov. 17 on discovery+