‘Million Dollar Listing New York’ star thought Kelly Bensimon was 'going to be mean': 'I had you all wrong!'

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Tyler Whitman is ready for his first full season on Million Dollar Listing New York.

The co-founder of Triplemint joined Bravo’s long-running real estate reality show midway through its eighth season, and the recently premiered ninth season pits him as the quasi-underdog when compared to his co-stars Ryan Serhant and Fredrik Eklund. But Whitman has aspirations to be just as big as them.

Tyler Whitman joined In The Know’s pop culture interview podcast, We Should Talk, this week, where he previewed what’s to come on season 9 of Million Dollar Listing New York, dished on how he got former Real Housewives of New York City star Kelly Bensimon to one of his open house events, opened up about not being defined by his headline-making weight loss journey and so much more.

“I’ve gone through a recent transformation in what that whole experience has meant to me,” he told In The Know. “Looking back on it, no, I wasn’t afraid to share it, but I was attaching all of my self-worth to that story all of a sudden. All of a sudden I was like, ‘The reason I’m good enough for the public eye is because I have this story.’ It took finally just being like, ‘No, I am me. I’m a different person. I’m more than a weight loss story.'”

Listen to Million Dollar Listing New York star Tyler Whitman’s full episode of We Should Talk below, and keep reading for highlights from the interview:

Tyler Whitman on meeting Kelly Bensimon on Million Dollar Listing this season: “I haven’t had cable in, like, five or six years, so I was early Housewives obsessed. Obsessed! Back during my obsession was in her heyday, and I think so many of those women are so interesting, but I thought she was particularly interesting. Then, obviously, when she got into real estate, everybody heard about it. It was like, ‘Kelly Bensimon is in real estate!’ I reached out to her. Obviously she’s well-connected, certainly [she] knows a lot of wealthy people, so it makes sense that she’s in the business. I didn’t think she would show up, but I invited her. Then she came! That was the first time I met her face-to-face, and I gotta tell you: She was so nice. You make up these stories about these people and you’re like, ‘They’re going to be crazy, they’re going to be mean, they’re going to be difficult.’ She knew my story when she came in, and we were talking about weight loss and what it’s like, then I was showing her the place. She’s just so playful and fun and energetic. I was like, ‘I had you all wrong! You’re a good person, at least in the way I’m experiencing you right now.’ I haven’t done a deal with her yet, though. I want to do a deal with her. […] I just learned this — not from her but from my horse trainer — that she rides at the same farm as me. I was like, ‘How have we not ridden together?’ She and I can have a horse spinoff show. Can you imagine?”

Tyler Whitman on his changing view of his weight loss journey: “I’ve gone through a recent transformation in what that whole experience has meant to me. Part of the reason that I was addicted to food and that I’ve struggled with addiction in general is because I struggle with self-worth, right? I struggled with not being good enough or feeling worthy of certain things. Looking back on it, no, I wasn’t afraid to share it, but I was attaching all of my self-worth to that story all of a sudden. All of a sudden I was like, ‘The reason I’m good enough for the public eye is because I have this story.’ It took finally just being like, ‘No, I am me. I’m a different person. I’m more than a weight loss story.’ But, I was in a mindset back then of the only way people are going to want to hear my story is if I tell them this juicy weight loss story. Which, for me, it was still such a blessing, because it did give me confidence. It did give me a new sense of self-worth.”

Tyler Whitman on his relationship with Million Dollar Listing co-star Ryan Serhant: “One of the things that Ryan and I really connect about that none of the other cast members have in common is that all the other cast members work for these huge name brokerages. They plug into someone else’s system, and they plug into all the new developments that the brokerage already has. Way before I was cast on this show, I was bound and determined to build one of those and not go through someone else’s. I started Triplemint when there were three of us and now there are 400 of us. I’ve just been on a different career path, and Ryan, similarly, did the same thing. He and I have that in common, and it’s a huge difference that he and I have compared to really all the other cast members in both cities. Nobody’s really done that. When cast members give me a hard time about Triplemint and this and that, I’m like, ‘You don’t know what it’s like. You’ve never started your own company. You’ve never built something.’ But he does. He and I just get each other based off of what our goals are, and he’s definitely further along than me, for sure. I’m humble enough [to say that], but our journeys are more aligned.”

Tyler Whitman on causing a stir by wearing sweatpants in the Million Dollar Listing cast photo: “Can I tell you? Firstly, I would like to give a shoutout to Armani for finally making me relevant in the comments section. Thank you so much. People were like, ‘What were you thinking when you bought that suit?’ I was like, ‘I was thinking I look really handsome in it!’ You know how sometimes you put on an outfit and you’re just like, ‘Wow! I feel really good in this.’ That’s how I felt in that suit. That’s all it was about. […] I thought it was fun and cheeky with the fact that we’ve all been wearing sweatpants for the last year, but these were high-end suit pants. I guess the audience had their own opinions on it! Listen, some people loved it, but a lot of people were like, ‘Who would wear joggers to a photo shoot?’ I’m like, ‘That’s the most expensive suit I’ve ever bought in my life.’ Whatever.”

Watch In The Know’s full interview with Tyler Whitman below, and tune into Million Dollar Listing New York on Thursdays at 9 p.m. EST on Bravo:

If you enjoyed this story, check out In The Know’s recent interview with Selling Sunset star Chrishell Stause.

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