Exclusive Interview: Pop Culturalist Chats with Million Dollar Listing’s Tyler Whitman

Tyler Whitman moved to the Big Apple with dreams of becoming an entrepreneur. After a disappointing experience working with a broker to find his first Manhattan home, he knew that this was an area where he could make a positive impact on a large scale. Since then, he’s racked up a decade’s worth of experience as one of the top real estate professionals in the city.

Pop Culturalist was lucky enough to speak with Tyler about his journey from waiting tables at Planet Hollywood to joining the cast of Million Dollar Listing New York.

PC: How did you get started in real estate and entrepreneurship?
Tyler: Good question. I don’t get asked that that often. I had humble beginnings. When I moved to New York, I started out as a waitress at Planet Hollywood in Times Square. I had gotten a roommate off of Craigslist. That roommate was a rental agent who had a decent little rental business that he had built for himself. I remember seeing what he was doing while I was hustling in this restaurant making pennies. After six months of seeing him earn a living, I was like, “Maybe I should get my license and do some rentals.” That was 2006.

I got my license and became a rental agent. I was a rental agent for a long time. I didn’t even dabble in sales. I was doing rentals until 2011. But for five years, I specialized in moving college students into their starter apartments in New York City and didn’t make very much money. In between showing apartments, I also worked in Times Square selling Broadway tickets to tourists. My family loves me very much, but they don’t have any extra money, so I never had any help. I always had that inner hustler in me.

That’s when entrepreneurship really started to grow inside of me even though I wasn’t aware of it at the time. It was like, “I can do all these things to make money.” I wasn’t making that much money, but at least I was able to pay my bills and have a tiny, sh-tty apartment. I was able to stay in New York, and that was really how it all began for me.

PC: Who or what has had the biggest influence on your career?
Tyler: I don’t like to hang my hat on it as much anymore, but the truth of the matter is I learned so much through my weight-loss journey that forever shaped how I treat myself, how I treat other people, how I show up in the world. That will always go down as the big game-changer for me. In that moment, I saw that I don’t need to listen to all the outside opinions. I can focus on what I want, listen to my own soul, and go for it. That happened when I was thirty. It was the first time in thirty years that I was able to shut off all the demons, all the voices, all the “You can’t do it” that I created inside my head. I proved to myself that I’m capable of monumental things. Once that light switch turned on, I became pretty fearless.

One of my coaches always told me that whenever I was thinking about going to the next level of my business or if I was going to go out for a big listing that I needed to make peace with the worst possible outcome and then go for it. He was like, “Make peace with whatever that fear is in your head. Just go ahead and make peace with it. Then go for it with everything you’ve got.”

It’s easy to say, but of course, doubt crept in, especially when I first started going for big listings. Worst case scenario, they call me an idiot, say no, and tell me to get out of their house. That’s literally the worst-case scenario. I was like, “Now I need to go in and make it happen.”

But on a bigger scale, there’s a part of me that’s like, “Now I’m not afraid to go for anything that I want.” Because the truth of the matter is I’ve been very poor. I’ve been obese. I’ve had no friends. I’ve proven to myself that I can survive that. While I have zero desire to go back to it, I’m not afraid of it. I’m like, “If I lost everything, I know I’d be okay. I know I’d figure it out because I proved to myself that I can do that.” I really, really treasure—even though it seems like the worst curse of my life to be an obese gay man in New York City—the gifts that the journey gave me. That will forever go down as the most important thing that has happened to me.

PC: You’ve had a lot of success already in your career. When you look back, is there a moment that stands out to you?
Tyler: It sounds like small potatoes, but I had these three clients when I was a rental agent. This was in 2008. The market had just crashed and I wasn’t making any money. I was like, “It’s time for me to pack up my bags and move home. I gave it my best shot.” I posted a Craigslist ad for a three-bedroom rental—and I remember it was a $6,000 a month rental (at the time, I had never closed a rental that big). The commission on that was $3,500. I was like, “Oh, whatever,” but I posted it for fun. I was like, “You never know.”

I got phone calls from these three guys who had graduated from college and wanted to come look at it. They didn’t take the apartment, but I really hit it off with them. I worked really hard and ended up finding them their dream apartment. Little did I know, they had just graduated from Princeton. I didn’t realize how well connected they were at Princeton. The next year, I did 80 deals with Princeton grads.

The ivy league network (and this is ironic because I didn’t go to college) quickly became my network. The next thing I knew, I was basically handling almost all of the colleges. It wasn’t a formal relationship, but I was handling Princeton, Harvard, and Yale. They were my bread and butter. Those are the kids I was moving to the city.

The reason this was so monumental is that the co-founders of my current company Triplemint, which I helped start back in 2013, were two guys who had graduated from Yale and reached out to me to talk to them about starting a company because of this ivy league network. In 2013, we started Triplemint, and now there are hundreds of us. Now we’re working on our series B right now. I always think back and realize this really all started because of a Craigslist ad. That’s how I got here. You really never know.

PC: You’re now a part of the Million Dollar Listing franchise. How did that come about? What do you think is resonating most with audiences?
Tyler: To be honest, it all happened so fast. The opportunity fell in my lap. I had been posting a lot of quirky marketing videos on my social media, and I’ve been doing that for years, since way before I was on the show. The right person saw it and I got a phone call. It was very shortly thereafter that I got a second phone call that they wanted me to be the new cast member. I was like, “I didn’t think getting on TV would be like this.” I thought it would be months and months and months and callbacks and tests and whatever. That was not the experience at all. It was “Tell us a little bit about yourself,” and “Great, got it.”

I’m definitely the underdog of the cast. Everybody else is much more seasoned. They make a lot more money than I do. They sell a lot more homes than I do. It’s almost like audiences are watching pop stars and I’m the up-and-coming singer. People watching me see something that makes them feel like they can do it too. They’re like, “Oh wait, here’s this guy who didn’t come from money, didn’t grow up in some real estate empire, and didn’t have a dollar to his name. He was overweight. He lost this weight and started putting himself out there. He took some risks and it happened for him. So, why not me?” I love that.

That’s honestly been my favorite part of being on the show: connecting with people on that level. I get DMs all day, every day about people who are on their own weight-loss journey, and have these dreams and aspirations for what they want to do. Because it’s not like you lose weight and then life happens. In my experience, I found confidence. I found happiness. I found new energy and a new zest for life. That’s what created the success. It was all the things that I learned along the way that created the success. I think people connect with that.

PC: This season, in particular, has been really different just given the ongoing pandemic. What has the filming experience been like for you?
Tyler: Regulated. [laughs] It’s a lot more work. I was really thankful because health and safety were really important to everybody involved with the show. These are real clients of mine. The show is not fake. These are people that have trusted me to sell their homes and to work on their behalf. I want them to feel comfortable with the experience too. I have to give hats off to the production team. If we were going to film an apartment, they would get there three hours earlier and disinfect the apartment.

They were doing all the work with a fraction of the crew because we couldn’t have as many people around. The people who were there were doing triple the amount of work that they’ve had to do in previous seasons. People worked their asses off so we could tell the story of the real estate pandemic.

PC: As part of your brand, you started Whitman Wisdom. How did that come to fruition? What advice would you give somebody that wants to follow in your footsteps?
Tyler: Whitman Wisdom was a very happy accident. I went to a real estate seminar with Tom Ferry. He’s a big real estate coach. He’s been preaching forever that real estate agents need to be doing videos. Nobody cares about your emails. Nobody cares about your newsletters. Nobody cares about that bullsh-t. Get in front of a camera, connect with people, show your personality, and give them information. I came back and I was like, “Oh, well I fu-king love attention.” I was like, “I will definitely be making videos.”

My first video was homemade. I made it on my cell phone. I didn’t edit it. It was me talking to the phone. I sent it out in an email, and my phone blew up. I got so many phone calls from people that I hadn’t heard from in forever. I got a lot of really positive feedback and a lot of sales from people who were like, “I forgot you were a real estate agent. I’m looking for a place right now. I’d love to work with you.” I was like, “That was from one video?”

I hired a team. I remember I was kind of embarrassed when I called it Whitman Wisdom. I couldn’t think of anything else. I was like, “Whatever.” It went well. I became pretty known for it. I started that a couple of years before I was on Million Dollar Listing. I felt like I went from a no-name in the industry to being known in the New York City real estate community. Every showing I went on, the other agent would be like, “We haven’t met, but I love your videos. I’m going to start doing videos like yours.” It felt so good. I had other people come up to me and they were like, “I hope you don’t feel like I’m copying you.” I’m like, “I don’t feel like you’re copying me. I’m flattered. I hope it does for you what it did for me.”

My advice to people is get out of your head and do it. The amount of people who reach out to me are so afraid that they’re going to sound stupid or look like an idiot. The biggest excuse I get is “I’m so awkward on camera.” I’m like, “You know what I’m awkward at? Ice skating. But I bet if I went ice skating fifty times this year, I’d get better at it.” Of course, you’re going to be awkward on camera. You haven’t been on camera before. Practice. If it’s easy, everybody would do it.

Pop Culturalist Speed Round

PC: Guilty pleasure TV show?
Tyler: Schitt’s Creek is literally the only TV show I watch. But I watch it every single night as I fall asleep. There’s a chance I’ve never finished an episode because it’s almost like my lullaby.

PC: Guilty pleasure movie?
Tyler: The River Wild.

PC: Favorite play or musical?
Tyler: My favorite play was August: Osage County. I saw it nine times on Broadway. And my favorite musical forever and always will be Hairspray. It’s such a funny feel-good musical. It’s everything I like about musical theater.

PC: A band or artist that fans would be surprised to learn is on your playlist?
Tyler: I’ve been to 120 Phish concerts.

PC: Hidden talent?
Tyler: It’s not a hidden talent, but I’m a competitive horse rider.

To keep up with Tyler, follow him on Twitter and Instagram.

Photo Credit: Jami Saunders