Ryan Serhant

I think I'm living a dream that in hindsight will be my dream. And it's definitely not the dream I thought I was gonna be living at all, in any way, shape, or form. I never thought I would be in real estate, let alone start my own company. Like, so much work. It's so hard. Ugh. Because the only way out is through. That is the quote that I go back to time and time again. No one ever got anywhere by going backwards. [upbeat music] Welcome to Office Of, a clubhouse for sharp takes on confidence, drive, and being a solid man. This is a place for unfiltered stories, questions get answered, and new ones get asked with some of today's most fascinating guys. This is your space, your story, your rules. Come on in. The door is open.

Ryan Serhant is impossible to miss. He's tall, has great hair, relentless energy, and ambition at a volume most people can't comprehend. Long before becoming the breakout star of Million Dollar Listing New York and the founder of Serhant, Ryan was a broke actor in New York surviving on little sleep, saying yes to absolutely everything, and betting on himself with almost irrational confidence. In this episode of Office Of, Ryan steps into the office and talks about the psychology of ambition, building a personal brand in public, and the pressure of constantly performing at a high level. We talk about fatherhood, burnout, ego, reinvention, and what really happens when someone believes in themselves so deeply that eventually the world has no choice but to believe, too.

Welcome to the Office Of the impeccable Ryan Serhant. I wanna know what your morning routine is. I have a perception of what I think your morning routine is. My morning routine. Okay. I bet you ... I feel like you're up between 5:00 and 5:30. Uh-huh. You hit some form of workout. Mm-hmm. Probably Peloton maybe. Mm-hmm. And then weight training. Mm-hmm. And then I don't know what happens after, but that's what time I think you wake up. Okay. When I'm in New York- Okay ... so if I do this from, like, a standard day. Yeah. The thing I knew that I could always control was my time, 'cause in my business, 'cause I'm in, I'm in sales. You know, now I run a company and this, that, the other, and we have all this stuff, but at least at the beginning of my career, it's in sales. Eat what you kill. The number one thing you can control is your time. Everything else is out of your control, so why worry about it? You can't control the weather, the traffic, everything we were just talking about, but you control your time and what you do with it.

And I wanted to maximize the amount of time that I had because I wasn't the smartest, I wasn't the best look. I'm not from New York City. I don't, I didn't have, like, a golden spoon. I didn't go to these schools. It's by myself in the city and like, okay, so I have 1,440 minutes a day. How do I squeeze as much out of it as I possibly can? That's your mindset every day? Every day for a long time. So I was like, okay, I have 400 and ... let's just round, 440 minutes a day to eat, sleep, do something that's not productive. Yeah. I have about 1,000 minutes a day as myself. If you're a single parent with five kids, you have a lot less. If you are 21 and you have no responsibility, you know what? You have more. [laughs] Yeah. [laughs] Um, and so I start my day at 4:30. [clears throat] You start your day at 4:30 in the morning? Yes. So I start my day at 4:30. Um- Alarm clock? Alarm, yeah, the, my whoop, uh, it's- And you need it?

Yeah, because I'm married, and so when the alarm clock goes off, that's real bad. This just vibrates. It, it's, it, it electrocutes me in the morning. Every day- [laughs] ... my day s- my first impression of my day is, "I'm being electrocuted." [laughs] And it, 'cause it vibrates. Uh, so that's how I wake up, 4:30. Saves the marriage. I then go through, [laughs] I then go through email that came in the night before and just honestly just, like, the news, TikTok, like, what, what was the tea last night? Anything dumb just to, like, get, you know, the, the base of my, my brain, just to like warm it up a little bit. You know, I like history, so especially with the Artemis II- Yeah ... like, really, really cool listening to a lot of the- Yeah ... podcasts about- Yeah ... kind of the history of NASA and where we go as a civilization, stuff like that. Anyway, and then I work out. What do you do? Depends on the day. Okay. So today was a push day, so push and just on weights.

Okay. So I'll do push and pull, right? So I'll do kind of like a bodybuilding split. It's what I've always done. It's just what I know. I've now, since I turned 40, started to two days a week, to your point, I'll Peloton. I have a gym at my house as well. I'll Peloton, and then I'll do a Peloton, uh, Pilates class- Good. Stretch ... which is the worst. No, it's the best. It is so terrible. [laughs] But I'll do that. And when I'm in New York, I work out every day, and that's my schedule, except for Saturdays. I don't wake up at 4:30 on a Saturday. I'm not a psycho. And that's Dadder Day 'cause I have a seven-year-old, and she is, she is ready for Dadder Day- She's ready ... every week. When I travel, I try to maintain the best routine I possibly can, but it does get thrown off. [exhales] That's my response. All right. I think that's great. I think Pilates and stretching is good. I mean, do you wake up in the morning full of energy, or does it take you a little bit to get there?

The last thing I wanna do is wake up at 4:30 in the morning. I try to make that point with the people who work for me. Yeah. Like, do you think I want to wake up that early and go to work? Do you think I don't want to roll out of bed when my eyes open and go on vacation and, like, go see a movie and hang out? Like, do you think I don't want to abuse substances? Like, I see people who drink and do drugs. I'm like, man, I wish I didn't have the level of responsibility I do because I would so ... Like, I get it. [laughs] I totally get it. I would be deep in that shit. I would be so, I would be such a d- I would be s- I would be a professional degenerate if I could, but I can't. Like, the job and kinda choosing success requires that I maximize my day as much as I possibly can, and that's, that's what I do.

You know? All right. Now I know your morning. N- and I know if I text you, you're up at 4:30. Yeah. Tell me, I know Andy Cohen famously said that you could sell milk to a cow. Yes. Do you believe that to be true? Yeah. I met that cow once, and I did sell it its own milk, and it was gross. [laughs] And I felt bad about it. I also sold his apartment for him- You did? ... a few months ago. Yeah. Do you think being in sales is inherent? Like, can you learn it- Yes ... or is it ... You can learn it? Yeah. You can absolutely learn it. It's just a muscle. It's a muscle. It's hard to teach confidence. Yeah. It's hard to teach the ability to walk into a room and make eye contact. Yeah. But anything, anything is possible. You know? Did you always have that? Did you always have the ability to walk into a room- No ... and like connect with somebody? No, not at all. Or are you like... Really? I don't now. Everything I do is just a game. I walk into a room, and I have the...

You know, I knew I was coming to see you- Yeah ... but if you were a stranger- Yeah ... you know, the first thing that I would do is probably, I use the two Cs. So I'll give you a compliment because everyone likes a compliment. It's the first way to generate a little bit of trust. Yeah. And so you have a hat that says, "Office of," and it's like, "That's so cool. I feel like I've heard of that before." And you'd say, "Oh, uh, this podcast," and now we're talking, and I'm asking you questions. Totally. And you're talking about yourself, and people love hearing the sound of their own voice. Yep. And then I would find something that we have in common, and then I just ask you questions and then show curiosity as much as possible. Compliment and commonality- Yeah ... are those the two Cs? In any room, any party, any first date, anything you go on, like the secret sauce, especially for me, like I grew up, and I just did theater because I was very shy and very introverted, and the last thing I wanted to do was be the loud one, is, um, uh, uh, is just ask questions, you know, and, and be curious.

Like what is it from Ted Lasso? "Don't be judgmental. Be curious." I also think asking questions is a way to deflect the conversation onto you. You're just talking about other people without having the opportunity to speak about yourself. You're just deflecting. I guess that's true in some cases when you're talking to somebody who is not curious. Right. Like I have conversations with people all the time, and they just answer with "Yes," "No." Brutal. And they don't ask questions back. But when someone asks questions back, then you get to respond, you know, and then you get to open up and talk about yourself as well. It depends on the person. You spoke very briefly, you said the word theater. Yeah. You were an actor. Yes. Or you, you tried your hand at acting. It's not like it was entirely unsuccessful. No, it was like the foundation of this career I didn't know I was going to have.

I thank God I went to theater school and practiced at The Globe in London and did all that stuff and did a soap opera and died and- Weren't you in a Noah Baumbach film too? I was, yeah, randomly. So I was a theater major in school. I moved to New York City in 2006. I had a little bit of money saved. My grandfather died, and, you know, he left all of us like 20 grand, and that was gonna last me 10 years. Oh, yeah. And it lasted me with some other odd jobs and things like two years in the city. It did? Yeah. My rent was, you know, 1,000 bucks a month, and food not that expensive when you just eat the same thing all day, every day. Yep. And then I did some odd jobs, and then I totally ran out of money in the summer of '08 and got into real estate because a friend said improv classes, theater, on stage is the same thing as doing sales. You meet people you don't know. You play the question game, right? And you are confident in the room just like you do in an audition, except if they don't take an apartment, they're not taking it because of your hair or your face or your nose or your voice.

They're taking it because they already took one or because they wanted to go with somebody else- Right ... you know, or whatever it might be. The rejection's not as strong. Yeah. It's not personal. The rejection in acting is only personal. In real estate, it's business. It's whatever. Sometimes it's personal but very, very, very rarely. And they said it's the same skill set. Just use the same... And you can memorize information really, really quick, which I could do. So if someone says, like, "How many apartments are in that building?" You can just, just look it up beforehand. 352, there's 27 floors, the architect, all that stuff. And so it became very, very foundationally important to me, and I tell every salesperson now, whatever you're selling, like go take improv classes. Get comfortable being outside your skin. Be weird. That's how you create relationships, let alone sell product. Do you feel as if there's a performative nature to what you do? Like you own rooms.

I see what you do. I'm talking to you now. You command people's attention, and you take up space. Do you give a lot of credit to your theatrical upbringing? Yeah, it's in the voice. It's in the eye contact. It's, you know, the soap opera taught me to talk with smiling, which is something that I couldn't do before, like holding a smile and talking all the... That's really hard for people to do. [laughs] Things like that. It's also hard to watch for a prolonged period of time. Well, when you think about it and you're like, "Wait, are they smiling the entire time? Is this a horror movie?" Um, but it's that- Are you gonna kill me? Yeah, you're, listen, you're mirroring a customer's enthusiasm or their disappointment. Like if you're selling ads on a podcast, if you're selling yourself to a, a brand, right? You're a creator. They're enthusiastic in email or in front of you in person. You don't wanna just be however you're feeling that day.

Right. You wanna be... You wanna match their enthusiasm, but you gotta be careful that you're not fake about it, like you're excited to be in the moment. You're excited to be in the conversation. You're a optimist by strategy, not by personality. I was with a friend the other day, and I was talking about the podcast, and I said, "I have somebody coming on from the world of real estate." I didn't give your name. I said, "Somebody from the world of real estate's coming on. Who do you think it is?" And without missing a beat, not one beat, they said, "Ryan Serhant." And I was like, "Yeah, absolutely." And I thought that was pretty awesome- Oh ... that you are, you have- That guy does podcasts. [laughs] Yeah, that, yeah, exactly. Yeah. That guy does too many. [laughs] That guy doesn't shut up. Definitely him. Like get rid of him. But I thought that was pretty cool that out of everybody in the real estate, he didn't know I was just in New York, anybody, he selected you without missing a single beat, and I was like, "That's a pretty big compliment to what you have built for yourself."

Thanks. That's super cool to hear. It's been part of the design, right? Ever since I kinda did the first season of Million Dollar Listing New York- Yeah ... and I saw, I saw what could happen when you do cable TV. Obviously, the world has changed since then. How did that even happen? Did you audition for it? Oh, yeah, it was... I went to, uh... I got out of theater in 2008, kinda 2008, 2009. I did my first year of real estate. I made nine grand, and then March of 2010, the production company World of Wonder in LA- Yeah ... put a casting notice out saying they were looking for the top three agents who are power brokers in New York City to audition for a New York franchise of what was Million Dollar Listing at the time. That was just based in LA. And 3,000 realtors went to a hotel in Times Square, and I was one of them, and I knew how to audition, but I didn't know how to do real estate 'cause it had only been 18 months, give or take.

But I knew how to sell myself in the room. And then they called me back, and, you know, they whittled it down to 1,500, and then 800, and slowly but surely, they, they kinda took it all down. And I think it was in October, November of that year, they said, "We've cast you as one of the final four to do the first season of Million Dollar Listing New York on Bravo. All four of you will film. Only three of you will make the cut." Okay. Okay. Like, if you think TV is- [laughs] Like, it is cutthroat. [laughs] Like, I, if I... I thought real estate was cutthroat, but that was spend the next six months of your life making a TV show. Good luck. Let's see if it airs. Um- Wow. And there was. There was four of us, and one of the people that was on it, we filmed all six months with that person, and they got cut. And you were only 18 months into the real estate game? By the time the casting happened, yeah, I was about two years into the real estate game by the time we started shooting.

It was terrifying. And what drove you towards that show? What-- Why did you even say yes to the audition? Theater was such a huge part of my life. Acting, I wanted to be on stage, let alone in- Can you sing? Film. It's no. And which is a hard thing in New York. [laughs] Like, if you don't have a triple threat, if you can't at least carry a tune. I'm in the cho- I can be the baritone in the choir. Yeah. But you're not gonna pick me out of a crowd. [laughs] I'm not off-tune. And then the dancing, I'm just like a banana, so it just doesn't work. [laughs] Which was tough. You're just, like, tall and all over the place. Yeah, just sort of, like, just lots happening. [laughs] So anyway, so all of that muscle memory kinda stuck with. And then it... I don't know, it was just weird and a random opportunity that they were looking for people, and I-- what I was, was I did a reality show on the internet in 2009, one of the first things that I booked, uh, a competition program called In Turn on cbs.com to find the next As the World Turns star, and it was the second season 'cause As the World Turns- Yeah ...

was a soap opera for 50 years. For sure. Daytime TV, and they were trying to figure out how do you get a younger audience to watch daytime TV 'cause they weren't. Right. And people were on Facebook and Twitter and soon to be Instagram. It didn't exist then. So they said, "Well, we gotta meet the audience. Where's, where's the audience? On the interwebs." [laughs] "Let's do a TV show on the internet." And it was a competition show, just the way you'd imagine. Every day was a new audition, and they would fire one of us, and I won it. [laughs] And so I won the second season. Is that how you got on the show? So I got on As the World Turns. I became Evan Walsh IV because I won a live internet reality TV show. And so I'd gone through that interview process before, and that was also traumatizing, and I knew kind of how to show people what they wanted to see to m-move the situation forward. And so I knew when I met with these casting directors, they were all from LA, they had no idea what New York was like, and I knew that they were looking at a lot of people who were much better salespeople.

Yeah. But everybody else that was in the room and in that line that wrapped around the block, oh my God, they didn't know how to be on camera, really, or they had ego, and it's the worst thing you can bring into any audition is, is yourself, right? Your ego. You know, you wanna come in and you want everyone just to want you. Yeah. You don't want to be the person wanting yourself. [laughs] That doesn't bode well. And I kind of positioned, you know, future me, like a year from today, if I got cast on that show, who would be on that show? I'd have a driver by then. I'd have $20 million penthouses. I'd live in a cool apartment. None of those things were true. I had none of them at that time. And I told them that's who I was. And then when they cast me, it was like, "Fuck, I have to figure out how to be that guy now." And so then I quickly figured out how to be that guy, and that's been the course of my life ever since. [laughs] Whoever I think I'm gonna be a year from now, be that guy right now, and I will just figure it out.

How much of Ryan Serhant is performative, a character, versus who you really are? Or is it hard to sort of extrapolate? I think it's hard. I think you-- Like, if you were to come to my office- Yeah ... and you sit in my office, you're gonna see me do email for two hours. Yeah. And sit on Zooms. Right. And be quiet. Yeah. And, like, when I go home, my dream is just, like, ordering in food in the dark- Yeah. [laughs] ... and not talk. Like, I talk for a living. [laughs] You know, I talk, I negotiate, I'm on the phone. There are some days where I get home, and, like, my jaw hurts, um- From talking ... and yeah. Yeah. And like your hands from, like, I type, like it's just- Yeah ... you're the work. Yeah. And you're dealing with people who are highly emotional all day. I've got angry sellers, angry buyers, angry developers. You know, the world moves in crazy... The war in Iran.

H-how come you haven't fixed this building yet? I'm like, just, there's only so much I can control. You placate to everybody as you move processes forward, and it can be really, really, really, really, really exhausting if you wanna do volume. If you don't wanna do volume and you wanna bet all of your chips on one potential client, you could do that. That would be a bad idea, though. But I think I'm myself. Anyone who's ever met me over the past, how long has it been now since I've been on TV? S-four-14 years. The first thing they say is, "You're so much taller." The second thing they say, "Is your hair real?" And the third thing they say is, "You're just like you are on TV. That's so weird." That's a compliment. Those are the three things I get. [laughs] That's like- Those are all good things ... in a row. In all different languages. Height, hair, and authenticity. Yeah, that's it. Take it. That's all you need in life, really. I think knowing you a little bit and talking to you now- [laughs] ...

you seem like somebody who says yes to life. Yeah. Do you? Are you a yes guy? I think my 20s and 30s, I was, "Yes, and..." That's an improv game. Yeah. You say yes, and I'll figure it out. As long as you don't die or go to jail, everything else is kind of figureoutable. Mm-hmm. And like, yes, and I'll audition for a reality competition soap opera show, sure. Like, yes, and I'll go to New York and figure out how to live with roommates who can actually afford to pay the rent because I won't really have a job at the time. Like, what's-- Again, what's the worst that can happen? As I've gotten older and since I started the company, I've had to force myself to change, which has been really hard to go from yes and to yes, but. Mm. Right? Yes- Is that protective? It's protective. Yeah. Yes, but, and even now, what I'm trying more this year than ever before is no, but, right?

No, I can't do that, but I'm gonna introduce you to this person. We're gonna get this done. Or no, it's not a great use of everyone's time or resources or money or allocations, but... You know, and you're kinda giving people the positive sandwich- Yeah ... th-that way. Yeah. I'm doing my best. But yeah, I do, I've tried to say yes as much as possible and also switch my mindset from what's the worst that can happen to what's the best that could happen. Do you sort of sit as a more optimistic or pessimistic guy? I'm a professional optimist. I think I'm authentically- Annoyingly so? No, I think I'm, uh, authentically nervous and generally anxious. I don't like losing, so I think like most people, I probably overestimate risk and underestimate opportunity. Yeah. But I will take huge bets when I can predict the outcome. Like, I knew when we started our own company in 2020, it was the depths of COVID.

Everyone said, "Don't do it. No one should start a new real estate company. They've all been started. They're all out." Like, "What are you gonna do that's any different, especially if you want to build a big national media technology broker? I don't even know what that means. I am so confident I'm gonna figure it out. Let's just do it anyway." Most people have no idea what they're doing. Some people just do it anyway. So like, what's the best that could happen? And here we are, like six years later. And you did it. It's crazy. And when your company started in 2020- Yeah ... what was the original mission of it? Well, the original mission was to survive. [laughs] It was just myself and a couple people. [laughs] Um, you know, I was in real estate for 12 years, had a huge sales team. Chase, our mutual friend- Yeah. Yeah ... was, was on my team. Yeah. I needed to continue to do my business to earn the living that I was used to earning and, and stand up on my own. Yeah. Like, could the value proposition for myself exist?

If I can make it exist, and if anybody wants to come work with us, then yeah, let's, let's look at that. But the initial goal wasn't to have this huge conglomerate of different businesses. It was just, I work in real estate. I think about this business very differently from the rest of my competition. I wish I could go to another firm 'cause I really tried, and they all suck, and so I blame every single one of them for forcing me to do this. [laughs] And so I started our own company in September in COVID and SWAT on the street, you know, pre-vaccine cards, all that crazy stuff. Yeah. And then the initial mission was, let's become the number one real estate firm in the world.As long as we earn the right to be so. Mm-hmm. So if we're gonna go to a different market, we've gotta earn the right to be there, not pay for the right to be there, right? I don't wanna go and try to collect customers who don't even know us.

So, like, going to California- Yeah ... right? We're, we're- Yeah ... announcing that. You know, a lot of people were like, "Well, you know, I used to have a team there with all the TV stuff. I could go to California five years ago." And it's like, I didn't earn the right to be there yet. Hmm. We didn't earn the right to open up California the way that I wanna open it up until tomorrow. Then we did it. Hopefully, it works out. [chuckles] Was the initial idea to also be a media company? Yes. You had that idea in twenty-twenty. You were like- Yeah ... I wanna be a media company as well, which has never really been done in the real estate world before. Not in real estate. I mean, I had a leg up because I had experience from- Yeah ... you know, and I had Million Dollar Listing, I had a wedding show, I had a renovation show, I had a sales show- Yeah ... Sell It Like Serhant, based on my first book, all on Bravo. So, like, at least I wasn't doing it from scratch. I think that would be, uh, probably much scarier. Yeah. Although, today, I would just start a YouTube show, and I would never wait on a stream or anybody else. Just own the IP all day long.

One hundred percent. Even if it's smaller, right, your engagement is so much better for your business and your lifestyle. I knew that my value proposition was in distribution. Hmm. So whereas all of my competitors have to pay to distribute their product or their messaging or their marketing or their brand, um, my distribution was bulletproof, and it was almost for profit. And I could not explain that to any other real estate company that I was talking to, and I spoke to all of them, and no one got it, and no one cared. And then I was also like, "Do you think the way we buy and sell homes is gonna be any different in twenty-thirty?" Mm-hmm. And no one cared. It wasn't that they didn't know, it's that they didn't care enough to give me an intelligent answer. And I was like, "I can't attach myself then to you people." Wow. I think I'm gonna build a media and technology company that sells real estate. And if it works, great.

If it doesn't work, at least I did it for myself, at least I tried it. At least you tried. At least you tried. And we are not for everybody, but for the people we're for, like, we are the only place to be. And it's been really, really great watching other people's success and our clients' success and our developers' success. It's been insane to watch it unfold. We've carved this path now, we're not even carving it anymore, at the intersection of media, AI, and real estate that no other firm in our category has even attempted to touch- Mm-hmm ... because it's too disruptive to their status quo. Right. And we've had the benefit of building foundationally from zero in COVID, which I think is one of the benefits of starting a startup. Like, you don't have to turn a Titanic, you know- No ... you can build a speedboat. You just figure it out as you go. Yeah. Looking back, twenty-twenty, who was the first person who really believed in you as you ventured out on your own?

My wife, for one, for sure. My entire team, for two. Yeah. They're like, "You should've done this ten years ago." They all believed in you. They all do. And then our clients really did. Yeah. You know, I called up all of our big developer clients. Yeah. These are, you know, multi-billion dollar deals, and if they had all said no, I don't know if I would've done it. That initial backing from some of the biggest developers in the country. Not financial backing, just- Yeah ... if you start your own thing. Emotional. Yeah. We're still gonna, we're still gonna work with you. Nice. Right? We hire you. We understand your process, your system. Was really, really helpful, so I, I do thank a lot of them all the time. Does it ever feel, I don't know if the word is tricky, but your last name is also the name of your brand. Yeah. I didn't want it to be. We sat in branding meetings for a long time during COVID, and I really, really, really wanted to create something that I could detach myself from. That's what I was gonna say.

Like flowersrealty.com- [chuckles] ... or something else that could've been a fun idea, and we just kept coming back to the, what I said before, like the power of distribution. If we create a new entity, that is, no matter what it's gonna be, it's gonna be much harder on SEO at the time- Yeah, yeah ... than Serhant. Right. Which there are twelve of. Right. Then I'll have to start from scratch, which is fine, but we have such incredible lead flow and organic discovery with this weird last name that I was given. That's kinda the thing. For sure. And people know that name. It's been around for a long time now. Even if they pronounce it Serhant or whatever, just lean in on it and just make sure I remain a good person forever. [both laughing] Like, don't, don't screw it up.

That's why we ended up doing it. It must be sort of interesting as you hire people, attaching your name to them as well. It f- it must feel a little bit more personal than flowersrealty.com. Sure. It definitely is, and I do hold that over everybody. I just, I hold them all accountable, and I let them know, like, "Just so you know, this is my life. Just FYI." Same thing with our investors. Like, I think one of the things I said to them at the beginning, 'cause there's also key man risk here, um, was, "There's no Serhant two." Like, there's no other comp-- like, this is my- Right ... the entirety of what I do and what I've attached my identity to, I would take a bet on the guy whose whole life is attached to it. For sure. What would I do? Leave it behind and go do something else? I don't know. Maybe when I'm much, much, much older, possibly, but for now, I get too much joy from putting the puzzle together every day.

Are you addicted to momentum and dopamine hits? Like, what gets you off? [chuckles] Well, how much time do you have? [laughs] Um, I really, really enjoy winning. I think I am a product of my deal environment that I've now grown up in, and I was like a kid, for what it's worth, coming into the city, and getting into real estate and having your income and your lifestyle and your mood attached to wins or losses- Yeah ... all day, every day- Yeah ... not just twelve a year- Right ... like a sport or anything, is probably not great, but it is what it is at this point. I really hate losing more than I like winning, that is for sure. But it's also transitioned since I've started the company. I think people look at me and they see a lot of high energy, and they see clear, unbridled ambition.

And it's like, if people knew how many other people win- Yeah ... when I win- Yeah ... now, they'd understand it's not ambition, it's responsibility. I cannot not wake up tomorrow- At four thirty ... and go and kill it and do my absolute best. There's so much responsibility now that I have to everyone that has taken a chance on me, on us, on our brand, on our process, on how weird we do things, that I just- You know what? One more day, and then I'll sleep. Yeah, you guys aren't afraid to get weird. Yes. You guys are weird over there at Sirhan HQ- Yeah ... but it works, and I think- It's weird over there. It's weird over there. But I think what's really cool in the content space, in the media space, which you guys really fundamentally are, if you're not weird, then you're not cutting through, and I think you just do things in a very atypical fashion.

It's very exciting to me. Yeah. I think, um, authenticity is a real big part of that. I think I am probably just authentically weird, and so it seeps into the DNA of the business and everybody who works with me. No one who comes to work at Sirhan is uncomfortable, whether it's our April Fools' jokes, or the way we market, or the process in which we operate, everyone who joins is like, "I need this in my life." We've definitely interviewed lots of people who are like, "Nope, this is too weird for me." [laughs] And then I'm like, "Thank you for knowing that now- Yeah ... and not making it a pros- a problem for us as we've grown." Our customers also get it, you know, and they understand the importance of attention. You know, like I hate using that phrase attention economy, but it truly, truly is a currency now. Like, you have data, capital, and attention. Mm-hmm. Like, if you can put those three together, you can build any defensible business today.

Have you always been comfortable putting yourself front and center? In the content space, in the TV space, it's one thing to be an actor or perform or whatever it is. It's another thing to put yourself front and center to sell a product which is you. I mean, not as a little kid I wasn't, but it sort of is my tool. Mm-hmm. Like, what else do I have to offer? [laughs] Like, I, I have the entirety of my human body and being. [laughs] It's, it's that, it's that thing. I try- Your banana body. Yeah. [laughs] I try to stay as, as credible as I possibly can and put myself out there, but then you ride that roller coaster, right? When things work well, it's because of everybody else. When they don't work well, it is 100% because of me. Mm-hmm. Yeah? And that's how... Yeah, I mean, that's, that's, that's the deal you sign up for when you build a personal brand and you start a company that you are the founder and CEO of, whether it's your name or not.

Like, when everything works out, it's because of the team. When it doesn't work out, it's 'cause of you. Hey, guys. Quick pause before we keep going. This episode is brought to you by Rail. I live a pretty active life. I train, I go to the gym, I sweat, and I'm moving all day around New York City. And if I'm being completely honest, I shower two, maybe three times a day. Please hold the feedback. I don't have the attention span or the patience for anything really complicated. For me, I find what works, and I stick with it. Rail's Supreme Sport Cleansing Body Wash actually feels different. It's thick, it's rich, it's premium, and it has this clean, cooling mint that hits after a workout without being overpowering. It cleans really hard but never leaves your skin feeling dry or stripped. For me, it feels like a reset, more like a recovery ritual than just another shower, and it's easily one of the best-smelling things in my bathroom.

Use code OFFICE15 for 15% off. Rail, it's simple, effective, and no fluff. Now, back to our guest. I fully understand you appreciate and love the wins more than you do the losses. Yeah. When you lose or you fail, however you deem that, how does that manifest with you? How do you deal with the losses, the hits? So a long time ago, I had to go through, like I said, in the actor world, like you audition all day long- Yeah ... and you get none of them, and you have to, one, build up thick skin to move through it, but the big ones hurt the most. And what I learned is that over time you don't care as much, right? Time heals all wounds for the most part. Yeah, yeah. Yeah, yeah. Definitely. Definitely. And so when I got an iPhone the first time, and I could have my calendar in there, one of the first things I did was to start doing little diary notes to myself 30 days out from anything awful that happens.

Any deal that dies or you get fired on this, even good things too, it's important to do both. A great thing happens today or a bad thing happens today that is affecting you, 30 days out you do a calendar invite and you type in "Read me," and then in the notes section you unload. Can be 10 sentences, can be two sentences, can be a whole paragraph, right? About how you're feeling in relation to that- About how you feel in that moment ... life event. Like, this deal just died. I hate this fucking guy. [laughs] You know? And then you let go. What happens is every time 30 days goes by, you open it up, you have no idea what's in there, 'cause you write these all the time, and you read it, and if it's bad, one, maybe you fixed it. Two, you just don't care anymore. Right. Or three, something better happened. Huh. Right? And so what it does now for me is the minute something good or bad happens, and this...

Unfortunately, it's like burning calories. You can't spot adjust. You know? [laughs] If you just wanna lose belly fat but not arm fat, you can't. Right. Right? So you just have to- Doesn't that suck? It does suck. [laughs] It also sucks because when you do this, this is a trick to building muscle memory to quickly get over loss, but it also stops you from really experiencing great joy, because now just the act of writing down what's really great or really bad, 60 seconds later I just don't care- It's amazing ... because it's gonna go away. It's not amazing, though. When great things happen, awesome things, I remind myself, and then I'm onto the next one, and you just don't care. It's, it's, it's by protecting myself so much, because the tough times as an independent contractor are so tough, and most people in my business, 92% of us quit in four years.

92% of you quit within four years? Even worse now. Even worse now. It is so much harder now to build a career in this business. Why? Because there's no salary. You can't afford to pay your rent- Yeah ... or your bills. There's no insurance. There's no benefits. There's no days off whatsoever. You wanna have a life. And because we are probably off nationally by 50%, the volume that we need in this country- Yeah ... to maintain- Yeah ... where we were- Yeah ... while pre-COVID, and so it's just hard. Guess I'm telling you I just feel nothing. [laughs] You feel empty? I feel, I feel, yeah. That's why I drink Updates. [laughs] You feel empty inside? Mm. You've sold billions, but my interpretation is what you're really selling is a belief. When you're closing, what do you read in that person? Oh, fear all the time.

[laughs]It's the number one thing to look for- Fear? ... in a negotiation, always. You wanna find what they're afraid of, and then you play to the fears. If it's a seller and the deal doesn't go through, what would spark any fear? If it's a buyer, right, and they don't get the deal, if there's no fear there, then it's, it's almost not gonna matter. For example, we're in New York City, land of the wealthy. Yeah. Right? Also, land of divorce. So you have a lot of divorce here. And, you know, you'll work with a divorced guy, let's say, and he's got kids. The kids are now, it's 50/50, you know, luckily anyway. If he's looking to buy a new place, the fear- Mm. ... if he buys the wrong place is his kids won't come, and the kids have to love it more than mom's place. So when you're working with a divorced dad in buying a new home, that's the fear you're playing to, and then you gotta make sure the kids' rooms have great closets, great views, high ceilings.

And he'll never admit it, but subconsciously, it's what every divorced dad is looking for. And so every situation is the same way. If you're dealing with an older couple, the fear is one of them is gonna die, and one of them is gonna be left holding the bag on this property, this apartment. Is it... Does it have stairs? Like things that you have to think through. You always, in any negotiation, you play to fear. It's the same thing like dating. If you're in your thirties and dating, biological clock is ticking. She's had 10 terrible dates, right? Her fear is that you're gonna ruin her life or not be the one. Right. It's a balance, right? Same thing with guys. Like fear is that they're gonna use you for what, you know- For sure. So you always figure out what the fear is, and you play to the fear. Will you talk about the fear in the close, or do you just sort of allude to it? I'm sure you do it in a really- You allude, you allude to it. I... You never say, "I know what you're afraid of, Bob."

Right? But you allude to it by saying, "Here's what I love about this home. One, it's a great deal, right? I mean, it's a great deal. It's a great location. Uh, that kitchen's incredible. I know you were taking up cooking classes. You're trying to find yourself now. Four, let's skip the primary. It's awesome." So like the master, right? "Um, I need to take you upstairs to the kids' rooms. You just gotta see them." And he'll be like, "No, I don't, no, no, no." He has to see them, and you lead that way. And so you allude to the fact that the kids' rooms are incredible and awesome. Like when you sell on the oceanfront in the Hamptons, you know you're selling to a divorced dad because all kids' rooms are on the water. Sold me. There you go. Sold me. Are you divorced? Honestly, basically. [laughs] Single. Very single. [laughs] Um, you touched on it briefly, but California is launching soon. Yes. You're taking Cali, baby. Yes.

When and why is now the right time to sort of take over California? I wanted to wait until we had earned the right to be there. Our process of opening new markets or opening new states is we don't buy revenue. We never buy our way in. We work with people who understand our value proposition and who come for the opportunity. No one comes to us for, for a check, right? The way all of our competitors do. They come to us for the opportunity, they stay for the results, and they understand our mission is to help the world move forward. And California, more than any other state that I'm in, forget politics, the markets, you know, natural disasters, the billionaire tax, all that stuff. California understands the intersection between media, technology, and real estate better than any other market we're in, and it's literally the ethos of our business.

Yeah, it is. The, it's the DNA of Serhant. It is in the DNA, and so I've known agents in and around California forever. We have a big education company called sellit.com- Mm-hmm ... which we started in twenty nineteen. Mm-hmm. And so we've been building those brand advocates for, for seven years now almost. Oh my gosh. And now it is the right time because the opportunity's there because no one is going. I'm like on a zombie movie where like everyone's on one side of the freeway, and then there's another guy going the other way, you know? Or like in Independence Day, it's like Jeff Goldblum like going back in the other way. That's me. [laughs] And we have, you know, over two billion dollars in committed- Damn ... signed up already. It's our biggest launch ever, and we have a wait list. Like we don't take everybody. Every market we go into, as we start meeting agents, we let them know we have a certain number of spots to fill- Wow ... and we'd like to meet you and see if you're the right spot. Every other firm takes everybody if they have a heartbeat, and that's, uh, that dilutes quality.

It also dilutes access to resources for the people who are actually in this all day, every day. And so we have a great group, and it's gonna be tons of fun. How has your relationship to money changed? I mean, you started out this conversation saying you had a buck to your name and a slice of pizza, and now you obviously have a lot more than that. Yeah. How has your relationship to income changed over the years? I really don't try to connect money to worth. Yeah. I think a lot of people connect money to self-worth. Yeah. And I don't think you can do that. I think money is a tool, right? At the beginning, money was my survival. It was two thousand bucks a month. Yeah. If I could make two thousand dollars a month, I could survive and stay in New York and not have to move home. Yeah. Today it is a resource and a tool. How can I turn one dollar into twenty dollars? And I only want to do that, not even to make it, it's to turn the twenty dollars into two hundred dollars, and it's more of a game.

I meet a lot of founders who talk about money in the same way. It is, it is a tool to play the game, and you wanna continue to play the game, so don't run out of it. But you gotta make sure that you can multiply it, you can play it, you can move it around, and that's really the way I, I look at it now. But I know that's also easy to say because you have it. I hated when I was in my early twenties listening to people talk about like, "You know, you never, you never-- If you follow your passion, you never work a day in your life." I'm like, "Dude, you, you say that 'cause you're rich, man. Like, I need a job." [laughs] Like I, I hate that kind of stuff. I think, um, your job is to get to a place where you can be work optional, and then from there, the possibilities are endless. How's your beautiful wife and daughter? They're great. My wife is somewhere right now working probably. How long have you been together? It's our 10-year anniversary this July.

Oh, no way. Yeah. What was your first date like? My first date with her-- Well, one, we met at a Hanukkah party. You did? Yep, we are not Jewish. She's Greek Orthodox. I went to a open house at a townhouse, 16 East 95th Street, to meet a Greek Jewish developer, of which there are seven. Yeah. [laughs] And he was there- I was gonna say- Yeah ... I'm Jewish. I don't, I don't know many of those. Yeah, yeah, yeah. So he was there, and he was raising money for the Greek Jewish Museum back in Athens, and there was a girl that was, I guess, visiting him at the time and just working the front desk for donation receipts, and that was her. I went so I could meet the developer and potentially because at that point, it was 2010, it's like I need to, I really wanna get... It's actually in 11. I'm sorry. I really wanna get into real estate, and I wanna take this seriously, and if I'm gonna be in real estate in New York City, I either have to be Jewish or I need to marry a Jew, and that's the advice that I got from real estate attorneys.

They're like, "Dude, you need to find a Jewish girl, and you're gonna convert, and it's gonna solve all of your problems." [laughs] That was the advice that was given to me. I was like, "Okay, no problem." And so I saw her. I thought she was beautiful. I'm like, there we go, and she's... No, she's Greek. So she has, she has c- she has dark complexion, and she has darker hair. I'm like, "Perfect." She saw me, and I walked in with this guy, and I, I didn't-- I don't speak Hebrew, and I don't speak Greek. So I just stood by this one guy the entire time, and she was like, "Oh, that guy's gay." And then so she talked to me because I was unassuming and then got her information, and then we went and had a glass of wine at Stone Street a couple nights later and- Did she think she was going on a friend date with a gay guy? No. At that point she didn't because I had followed up with her 'cause I'd got her-- She had sent me a donation receipt email, you know, 'cause I donated $50. Yeah. And I wrote back, "That's all I get?"

And I think she, at that point she was like, "What else do you want?" And I was like, "Dinner, drinks." And she agreed because she was only visiting for a week to see her brother who was here. And- She didn't even live here? She didn't even live here. She lives in Athens. She's, she-- They're Greek from Greece. And so she had a job waiting for her back in Athens, um, she had just gotten her law degree in London and was here. And so then she extended a week, and then a week and a week and a week, and she's still, she's still here. That's crazy timing. That's crazy. Imagine what your li-- Your life would be so d-Had you not gone- Gone to that event ... gone to that- It's every, that's, man, that's the power of anywhere, but it's also the power of New York City. Like, anytime I go out, you know, I try to make sure even if I don't feel like I want it, go and talk to strangers. Like, you never know. Imagine what could happen if you hadn't met that one person and a great pickup line, and I used to use this dating, um, which I don't do anymore- I can use it.

Tell me ... now it's talking to people and just going up to them and being super sincere and saying, "Hey, my name's Ryan, and I hate that I don't know you." It works- Wow ... all the time. Yeah? It works. Because people, they have that reaction. [laughs] Of like, what? What am I supposed to do with that? And then you give them a compliment. You find something in common. Now I've just given away all my secrets. No one's gonna talk to me ever again. [laughs] Like, "Oh, you, you really hate that you don't know me? You're just trying to sell me a condo." And I'm like, "Maybe I am, but maybe I love you." Wait, that's a good one. Yeah. It's a, I, I like the pickup line, and then I like the two Cs. Yeah. Use them. I'm g- dude, I'm going to. You spoke a little bit about tapping into people's inner fear as the sale. What are you scared of? What scares you? I guess two things. Other than, like, the normal stuff of, like, I'm scared that I, you know, won't provide the greatest life for my daughter, I won't be the best dad, all that kind of stuff.

I think I'm scared at times that I've turned myself into such a robot to survive in New York doing this job, that I don't know if I'll ever understand what it means to be truly happy and not happy because I think I'm supposed to be. I think that's a fear that I actually have. Hmm. Like, am I happy because I'm winning or we're doing well, or am I happy because I actually feel joy? Did I calendar trick myself into numbness? Like, that's a real fear that I have that, like an ER doctor, you protect yourself to survive, to be the best you can in the ER, which is impossible to get through. Spot training, fat loss, you can't turn it off at home. It is forever. So you're either training your brain to survive eight hours a day or to survive two hours a day. Which one are you gonna choose?

Probably the one that you're doing eight hours a day- Wow ... at a minimum. And then my big, big picture is making sure that, you know, myself and, you know, my family, like, just live the life to its fullest. Like, general, general, like, fear of, man, are we, are we taking as much of advantage of being alive in 2026 as we possibly can be? Like- Do you do that? And we do this now and, like, okay, we could take the weekend off and just, like, hang out or, like, let's go somewhere crazy. It's just money at the end of the day or credit card reward points. Like, let's live a little bit. Like, at any point in time, everything can just turn off- Mm-hmm ... and we are on a floating space rock. And I do think about that probably the older I get to make use that I'm ma- you know, to make sure I'm maximizing time and, and living a big life. Um, I think so. What metric matters to you most right now in life?

Gross revenue. [laughs] [laughs] Like, uh, you know, I should say EBITDA, but I don't. We're in build mode. We're profitable. One of our problems is, like, figuring out what to do with the pro- it's like, ah, investing fast enough without investing the wrong way. You know, we're, we're a seed stage business, and I'm tracking the metric of revenue and, you know, as much as I can. I also track a retention metric, you know, and making sure that we don't wanna build a leaky bucket, you know, as much as possible. I don't have any, like, personal metrics. Yeah, you must. Not really. You've built something incredible, not only as a, a leader, as a cultural figure, but you employ a lot of people. I mean, that's also pretty powerful to me. What do you want your legacy to be? I wanna create an environment where luck is easy to find for those that I surround myself with.

I want all of our agents, all of our customers, all of our employees, my kids/future kids to know that I've created an environment where, man, I, I was, I was so lucky. I was so... I got lucky. But it wasn't really them. It was because of me, and they should all fucking thank me. [laughs] All you people- [laughs] ... you're all here 'cause I have provided an environment of luck. [laughs] Do you consider yourself lucky? For sure, man. Like, I mean, it's just like that. Had I not gone to that Hanukkah party, had I not put away acting and all of those years of building up that muscle, but then also had I not gone to that open casting call for Million Dollar Listing. Like, I, I think hard work definitely beats luck when luck doesn't work hard, but it all does come together, just never when you want it to.

It's never the way you think it's gonna happen, and it's never the way you thought it was gonna be. It's all a different place, and I think a lot of people, especially who come to the, the city or who have a dream, you know, they hit a speed bump, and they think it's a brick wall, and so they retreat- Hmm ... because, ah, it's a wall, when really it was, you know, I got on that soap opera, As the World Turns- [laughs] ... by doing an internet reality competition show. I beat out 12 other people. I won when the people who watched that show voted for me. I was down to three. They voted, and I found out on the CBS Early Show on Fifth Avenue, and then they killed me. They killed off- Because the write, the writers strike of 2007 happened. Oh, yeah. [laughs] And so if you remember, like, The Daily Show went off the air. Yeah, I do. You know, it was, it was the original writers strike. Soap operas are too expensive. All soap operas, uh, other than, like, three of them were basically shut down, and so Evan Walsh IV was a good guy, and then I murdered everyone and died- [laughs] ...

including myself. And so I was like, "Oh, brick wall. Nope, speed bump. I just gotta keep going, like, keep paddling. Figure out what's next, and this tool kit will somehow be of use for me in something else. Maybe it's in, I don't know." You know, I was gonna go back to school. This real estate thing happened. Yes, and. I think there's just never been a better time to be alive, every day. I do feel that. [upbeat music] Like, we get nostalgic for the, I don't know how old you are, but you know, you get nostalgic when you see movies and videos about the '90s and the early 2000s and no cell phones. But at the same time, how crazy is it that you can have the power of the entire world in the palm of everybody's hand? Like, that's just, we've never had that before. How crazy is it that you can do any job you want, and you can have six streams of income, and you can just live your life if that's what you wanna do, or if you wanna have a normal job, nine to five, and you can also do that.

There's no rules anymore. There's no, the, the dream is now literally what you make of it, and we've never had that opportunity before, and it's like, it's, I think it's super, super, super cool. It's a great time to be out there, to be working, to be making something of yourself, as long as you make it so. Do you feel like you're living your dream? I think I'm living a dream that in hindsight will be my dream. And it's definitely not the dream I thought I was gonna be living at all, in any way, shape, or form. I never thought I would be in real estate, let alone start my own company. Like, so much work. It's so hard. Ugh. But you're doing it. I am, because the only way out is through. That is the quote that I go back to- Me too ... time and time again. Me too. The only way out is just through. No one ever got anywhere by going backwards. [upbeat music]