Kendra Wilkinson Reflects on Missed Opportunity at Playboy Mansion: “I Should’ve Started My Real Estate Career Then”

Kendra Wilkinson, former reality TV star and one of Hugh Hefner’s most recognizable girlfriends during her time at the Playboy Mansion, is opening up about a major career regret that still lingers years after her departure from the infamous estate.

In a candid moment, Wilkinson admitted that she now wishes she had launched her real estate career back when she was living in the mansion—surrounded daily by A-list celebrities, high-powered executives, and billionaires. The opportunity, she says, was hiding in plain sight.

“Looking back, I realize I was in the perfect environment to build a client list most real estate agents could only dream of,” she confessed. “I was young and focused on other things, but that time could’ve been the launchpad for something huge.”

Wilkinson, now 39, has been forging a new path as a real estate agent in Los Angeles in recent years, starring in the reality show Kendra Sells Hollywood, which chronicles her efforts to break into the competitive luxury property scene. While she’s been steadily building her portfolio, she acknowledges that she had access to elite clientele long before she ever held a license.

From lavish parties at the Mansion to intimate connections with moguls and celebrities, Wilkinson was uniquely positioned to pivot into high-end real estate—had she recognized the opportunity.

“I was literally living in one of the most iconic homes in the world, and I was meeting people every day who buy and sell $10 million homes like it’s nothing,” she said. “I had the network right there. I just didn’t see it at the time.”

Now a mother of two and embracing life beyond the Playboy spotlight, Wilkinson is focused on making up for lost time. She’s taken her career seriously, joining a top-tier agency and working to prove herself as more than just a former TV personality.

“It’s never too late to reinvent yourself,” she shared. “But sometimes I do wonder where I’d be now if I had started earlier.”

Her honesty resonates in a city full of reinventions. Los Angeles is no stranger to former entertainers carving out second acts, and Wilkinson is determined to earn respect in her new profession—not for who she used to be, but for the career she’s building now.

Still, the glamour and mystique of the Playboy Mansion continue to follow her. But this time, Kendra’s not looking to be the center of the party—she’s looking to sell the house.