Go behind the scenes with Inman’s Dani Vanderboegh to get the answers to all your burning questions on the newest releases. Stay tuned to Real Tea, the intersection of real estate and reality TV.
Tyler Whitman was about to quit real estate and head home from New York City to Alabama. In sort of a last-ditch effort, and on the very last day, a concerned co-worker took him out for a few drinks. From there, he went on a chance meeting to show a Craigslist rental that he almost didn’t post.
Those renters were Princeton grads, who introduced him to friends, who introduced him to friends. Then Princeton became Harvard, and Harvard became Yale as Whitman’s rental business spread like Facebook through the Ivies.
That’s how he met Philip Lang and David Walker, who later approached him to start a business that eventually became TripleMint. Early iterations were more like “this online, real estate Yelp website where agents could advertise their services,” but it eventually became a well-respected brokerage.
When Bravo called Whitman for Season 8 of Million Dollar Listing New York, he says he wasn’t quite sure he was what they were looking for. Ryan Serhant and Fredrik Eklund had been with the show since its first iteration. Steve Gold had been on the show since Season 6. But it turned out that Whitman was a perfect fit for the show, which was looking to feature some up-and-coming agents.
Newcomer Kirsten Jordan joined Whitman for the last two seasons before Bravo put MDLNY “on pause,” the playful way that the network says something is canceled, at least for now.
TripleMint was acquired by The Agency as the brokerage opened up in the New York City market in 2022. Now, a year after MDLNY and the acquisition, Whitman is taking The Agency into the Hamptons by launching an office with local Dana Trotter, in addition to his 5-person, 5-staff “well-oiled machine” team in NYC.
Trotter recently moved over to The Agency after a 26-year tenure at Sotheby’s International Real Estate. Trotter and Whitman are both actively doing business in the Hamptons market as they’re setting up their new office, which will open in Bridgehampton in mid-August.
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Whitman also has three seasons of Glitter and Gay, a podcast he hosts with Glennda Baker, TikTok phenomenon from Atlanta, Georgia, with 880,000+ followers and 136,000+ followers on Instagram. The dynamic duo — and real-life friends from way back — come up with a topic to guide them, and let the rest of the podcast flow naturally, based on their own life experiences.
Inman sat down with Tyler Whitman to get the Real Tea on post-Million Dollar Listing New York life, his Glitter and Gay podcast with Glennda Baker, his new Hamptons locale and upcoming projects in the works.
Million Dollar Listing New York went ‘on pause’ in 2022. How has business been since the show?
I started my team in the city six years ago, and within two years, we were on the show, and that first year we saw a huge influx. The second year, we saw a massive influx, especially because we were heading to the 2021 market when things were crazy. And now, things are just beyond my wildest dreams. It feels very surreal.
With MDLNY on pause, what reality TV do we have left in your market?
I think there’s like stuff coming out. But since the show’s been off, I’ve been involved with, as of yesterday, my fifth conceptual [TV] show, but the way TV works is it’s a lot of hurry up and wait. You film what’s called a “sizzle reel” where they put together a five-minute version of an episode that they can shop.
Then, you sit around while they shop it. I’ve had a lot get really far, and any of them could still happen at this point. But you know, I’m just kind of in this phase of my life where you don’t make much money by being on TV.
That’s a big misconception: You get paid per episode. I always said for Million Dollar Listing, it was like closing one extra sale a year. But the bulk of my income — 99 percent of it — comes from my real estate business. I was really grateful, I had two years, and it exploded my business. [But] it takes up so much time. We filmed for nine months a year.
I was really excited to get this little break to focus on my business and start this new project. And then the TV show that we started shopping yesterday looks like it actually is going to happen.
OK, I have to ask this. The Agency now has a lot of former reality TV stars. Former Million Dollar Listing LA stars James Harris and David Parnes, who have always been with The Agency; Vanessa Villela, who recently moved back to The Agency after a stint at The Oppenheim Group and on Selling Sunset; and now you. Is The Agency trying to have a nationwide reality TV show?
Everything in TV is super unpredictable, but I do think that’s definitely a goal. I think that’s something that they would really like to see happen.
It seems like Mauricio Umanksy has a good foothold over at Netflix.
That’s my understanding as well.
It’s funny because I reached out to him, and I was like, “Hey, does this [show we’re shopping] interfere with anything? And he was like, “Sounds exciting. See where it goes.”
We all keep a very open mind for what the possibilities are.
In my opinion, the best thing that could happen for us or any brand out there is to cast as wide of a net as possible … in terms of building a huge brand and a huge company, my fantasy is everything kind of rolled into The Agency. You just see us everywhere … I’m open to all the different ways that can happen.
You’ve spoken publicly about how you went from rentals to Million Dollar Listing. Can you tell us a little bit about that journey?
On the show, they kind of depicted that it was like my introduction to real estate. My introduction to real estate — I’ve been doing it in the city since 2006. And I did not make any money. I mean, I was dirt poor. That was why, by the time I was getting to the show, I was like, “I should be somewhere already that I’m not. I’ve been doing this for a long time.”
In 2008, I was about to quit the business. I was doing rentals but I was also waiting tables at Planet Hollywood in Times Square. I was triple moonlighting because outside of that, I was also one of those kids in Times Square who holds up flyers and sells tickets to Broadway shows to tourists.
I was super hustle, but also just kind of like desperate and lost and always so discouraged. I hit a point at the end of 2008 (when the market crashed) where I was like, “Oh, I’m dirt poor now. And [moving forward] I’m gonna be extra dirt poor.” So I kind of made peace with the fact that it was time to move home, go back to school, get a more real corporate job, whatever you want to call it.
The last day, I posted this ad on Craigslist, and you have to keep in mind, I was doing Craigslist ads for entry-level studios. Back then, you could get the studio for $1,300 or $1,400 a month. It will make your phone ring, but people weren’t loyal.
You’d run around showing all of these apartments that were really difficult to get people excited about. Most of them would go silent on you if they took one. By the time everything was split up, you made like $400 to $500. It was not glamorous.
I posted an ad for this $6,000-a-month, three-bedroom; I never had the courage to post an ad like that. I was like, “Today’s my last day. Let me just post this ad and see what happens.” I didn’t even expect my phone to ring.
A girl who sat next to me who I’d been kind of venting to and telling her that I was leaving the business said, “Let me go buy you a drink.” And so we go to this bar in Chelsea, and she gets me a few drinks.
My phone rings and I remember thinking, “That’s probably a debt collector,” and I almost didn’t answer. But I did answer and it was this group of guys looking for a three-bedroom and wanting to go see that apartment.
I was 23. I was almost 400 pounds. This is a much different Tyler. And so I showed them the apartment, and it wasn’t the right one for them. But we hit it off, and they decided to work with me. I ended up getting them something the next week, and little did I know, that would be the ad that changed my life forever.
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So then what happened?
I made $3,000, and it was just enough. It’s not a life-changing amount of money, but it was enough for me to be like, “OK, let me not give up quite yet.” It was enough for me to be like, “I’m gonna make this work for just another minute and see what happens.”
[Those rental clients] had all graduated from Princeton. That year I ended up doing, like, 100 deals with Princeton grads, and it changed my life. It was all rentals. It’s not like I made a million dollars. But I made enough so that all of a sudden I could stand on my own two feet. I could pay my rent. I could eat and not have to work these other two jobs at the same time.
Then, the next year, in 2009, Princeton started to become Harvard. And then Harvard became Yale. And all of a sudden I was “the Ivy League relocation guy” for all these fresh graduates from the schools who are moving to the city.
Two of the Yale grads were Philip Lang and David Walker, who are the co-founders of TripleMint.
How did TripleMint come to be?
They reached out to me, along with another one of their friends from Yale, and said “We’re thinking about starting this company. Can we pick your brain?” They were sending me so many referrals; I was like, “Sure, let’s do it.” I met up with them quite a few times over two or three years.
The concept of the business changed a million times. They opened a brokerage. They called me, and they were like, “We want you to do this with us.” I was at a spot in my life where I was like, “I’m just starting to do OK,” and I was not rich by any means. I was paying my bills, but there was no savings.
And so I originally said no. I was like, “I just don’t think I can pull this off.”
And then they reached back out a month later. I was having a really bad day at my previous office, and I was like, “You know what? Let’s do it.”
I’ve just had these moments in my life — and it’s always the story I try to share with other agents — where I just took that little risk on myself. I just posted that Craigslist ad and then met them and then took care of them. Then that led to [this TripleMint opportunity]. And then I said no, but then I took that next little risk, and I was like, “Sure. I’ll start a company at 25 [years old] and clueless.”
Did they have a real estate background at that point, or were you bringing all of the real estate background?
I was bringing all the real estate, and that really intimidated me because I did not feel like I had enough to be able to be like, “Sure, let’s build a company around my experience doing Craigslist rentals with college.”
It sounds like you’re kind of battling some impostor syndrome?
Yeah, it’s the work of my life battling impostor syndrome. I’ve gotten so much better at it, but it still shows up for me sometimes.
You’ve been very open about your weight-loss journey, from over 400 pounds to today.
This was pre-Obamacare days and pre-being required to have insurance. So I’d never had health insurance, once I was out of the house, because I couldn’t afford it … Having this salary was the first time I was in a position where there were benefits … I used to always complain about my weight. I was very self-deprecating and making fun of myself.
I think I made a mean joke about myself. [An agent, in one of our one-on-ones] said, “Can I share something with you? I used to be really overweight. I had weight loss surgery. And I know everybody has mixed feelings about it. I’m not very public about mine, but it changed my life. I highly recommend it.”
I was like, “I think you think I make more money running this company than I do. I don’t have enough money to get the surgery.” And she said that at a certain weight, insurance will cover it. So maybe see if you’re at that weight.
Turns out it was. I gave it some thought. And I just had kind of this white light moment at a Phish concert, where I passed out. I was so embarrassed, and I knew it was partially because I was dehydrated and being irresponsible. But it was largely to do with the fact that I was 400 pounds and trying to dance through a three-day music festival. My body was just like, “We can’t handle this.”
That was the moment for me. I was like, “I’m gonna do this.” Because if you meet all the requirements and you have insurance, I think my deductible at that time was like $500. I was like, “I can do that.” And I did.
So you’re about to launch a new office in the Hamptons officially. Tell us more.
It was an emotional roller coaster for me when I found out that we were becoming The Agency. There was this part of me that was so proud that we had reached this moment in our business and this next huge thing was going to happen.
And there was also like deep, deep mourning over this thing that I had spent the last decade of my life building and creating and being a part of all of a sudden being stripped away from me, in a weird way.
I had ownership equity in TripleMint. Now I have that in The Agency. And it’s strange because it’s a comparable amount in both, but I felt like an owner of TripleMint, and The Agency is so big. I don’t feel like an owner of The Agency, and I really liked that feeling of ownership.
So when all this happened, I turned around and, as part of my grieving process, bought the Hamptons franchise at The Agency.
[I thought], “This I’m gonna own.” Then I started taking some new risks, started repeating some of those old behaviors I did early in my career. Asked some very powerful people in the Hamptons market to meet with me, thinking that they wouldn’t, and they did. One of those people is now my business partner, Dana Trotter. And between the two of us, it is such a spectacular combination.
She’s pretty much been out here her entire life. She moved here when she was, like, 8. Then she started in real estate when she was 21. Her mom was in the business and so she grew up around it.
You know, she spent the first 27 years of her career at Sotheby’s and then she came over to build this and start this with me, and we’re going through all the things: We’re building out our office, we are hiring, we’re onboarding, we are doing payroll. You forget that is behind-the-scenes of the business and so I work 24/7.
And you also have this wildly popular podcast. Tell us a little bit about Glitter and Gay with the infamous, ‘oh my stars’ Glennda Baker.
So, Glennda and I have been friends for a long time, like 2015-2016, when nobody knew who either of us was. We always just kind of kept in touch here and there. I sent her a referral and we had this hysterical interaction over this referral that I sent her.
And I was like, “Oh, she could be a real friend of mine.” So after my first season of Million Dollar Listing, I was doing this online Whole 30 that a lot of people were participating in, and I went to this real estate convention. Glennda had been participating in it. [I suggested we do a] Facebook live video, where we talked about our Whole 30 experience. And to this day, I think that was the funniest video I’ve ever posted in my life.
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I posted it and everybody was like, “You guys need a show.” When the pandemic hit, I reached out to her and said, “I think we do need a show. Let’s start a podcast.” … We recorded 12 episodes in two days. All we come up with is the topic for the episode. We just kind of use that topic to loosely guide us through the conversation, but we don’t plan the conversation at all. We don’t really set any boundaries with each other. We just trust each other.
It’s my favorite thing I’ve ever done. It’s cathartic. It’s funny and our audience is so amazing … We actually don’t have a distributor, and we wanted to keep it open for a few reasons. Some of the TV opportunities that are being discussed are around us and so we didn’t want to be owned by anybody in case an opportunity came up. And we also didn’t want to be told what to say.
Did you say that there could be a show with you and Glennda Baker?
I mean, that would be the dream. Okay, those are some of the things that we’re definitely working on. That would just be that would be my absolute favorite thing to have happen. And I think it would, if somebody was smart enough to pick up that TV show. … Of all the things that I’m working on right now, that’s the thing that would be a major hit.
What are your thoughts as this Pride Month ends?
We’re learning about all the different ways that various people identify. It’s reminiscent of when being openly gay was new and taboo. And, you know, people are ridiculing it and creating walls around it and restricting drag queens from performing and all of these things. I’m just like, “How are we back here?”
Pride is always a time to be reminded of why it’s important and why the work never ends. It is very easy for me to feel comfortable today. Because I’m a gay man. I’m white. I identify, you know, as the sex I was born. And so now, I’m the privileged one. And I get that, you know what I mean?
I have to stand up for the people in my community who are fighting a real fight now. And being in the middle of Pride, it’s so great when the community comes together, and you remember just how big and giant and loud the voices are and how many people are here for us.
Because the headlines are nasty, and you start to forget that that’s still not the majority, but we’re hearing all this negative news and all of this legislation, and all of these things.
Pride is just one of those beautiful times when you come together. You remember the love, you remember why it’s important. And you remember the power. I mean, this community is so powerful, and not just powerful — so fun.
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