E258: Ryan Serhant: Why Leaders Who Don’t Evolve Get Left Behind

How do you build a $10B real estate empire by turning yourself into a media company—and why is vulnerability the ultimate competitive advantage? In this episode, I talk with Ryan Serhant, founder and CEO of SERHANT., one of the most influential real estate brokerages in the world and a pioneer at the intersection of real estate, media, entertainment, and technology. Ryan breaks down the turning points that shaped his career—from selling a $13M townhouse through YouTube a decade ago, to betting everything on social media before anyone believed in it, to building a fast-growing real estate ecosystem powered by content, authenticity, and scale. We dive into Season 2 of Netflix’s Owning Manhattan, the biggest highs and lows of his year, the reality of leading a thousand-agent organization, and why the future of real estate is screenless, human-centric, and powered by creators.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Speaker 00

  Season two of this show is probably the most raw season of reality television I've ever seen and I've ever been a part of. It'll be uncomfortable for people to watch. It takes a lot. It goes through addiction. There's so much in this show that I've just never seen before in the space. There was an altercation in the office. They were shot in real time. There was a fight. Not staged. Not staged, no, not staged. I wish. It'd make my life so much easier. There's a deal we did, Peter did, he's a new cast member this year, that he sold for $60 million. I have a buyer and he [bleep] me over in real time. We're in the car filming. $25 million, all cash.

• 0:44Speaker 00

  And he hangs up the phone on me and we do a U-turn and we drive back to the office and the cameras just followed. We go up into the office and I call him out. I go into the cell phone booth, I try to put the deal together and I lose it and he sells it to somebody else in real time as it's happening. And then I had a mental breakdown and broke a whole vase on our first floor. And then the episode just ends. We're not doing the deal. Take me back when you sold your first $13 million home on YouTube. How did that happen? It was on West 18th Street and 7th.

• 1:24Speaker 00

  So between basically 7th and 8th, which is not where everyone decides they want to live. We were broker number two and the seller was very frustrated that it hadn't sold because in the West Village, this house is $40 million. This is 10 years ago. If you're gonna sell real estate in today's world, you can't just take pretty photos and stick them on the internet or run ads. You're just, you're fishing with blind bait in the dark and maybe you get lucky and that's how every other real estate agent operated. So we created a video, started with me at the top of the house and then cut through the house like an elevator. And this is 10 years ago. Today, this would be boring. Then on YouTube, like this was like, how did they do that? And you just dropped it on YouTube?

• 2:07Speaker 00

  Just dropped it on YouTube and then it had a pool in the basement. And I convinced my wife to be in the video too. And so it ended with the two of us falling in the pool in all of our clothes. A 13 year old girl, she sees it, shows it to her mom, who's looking for a townhouse on the east side. And says, this is what you want. You want a house with a pool in it that's modern. She sees the house. She loves the house. She used to be sold on location a little bit. But she just cared about it. They offered us 12 million. We countered, it came up to 13, we did the deal. So the deal didn't happen in youtube.com. But that buyer was sourced through the kid through YouTube.

• 2:45David Weisburd?

  What was your commission on that deal?

• 2:47Speaker 00

  Probably two and a half percent.

• 2:49David Weisburd?

  So roughly 350K.

• 2:51Speaker 00

  Yeah, about.

• 2:52David Weisburd?

  Is that the moment you realized that social was the future and the traditional real estate was a dying thing?

• 2:59Speaker 00

  It was a proof point for me because I started Million Dollar List in New York in 2012. I saw the power of content to commerce for luxury items. Which until that point had really been done, let's say like for cars. But everything then below market. So makeup, right? Consumer goods, anything you can.

• 3:18David Weisburd?

  Follow the credit cards.

• 3:19Speaker 00

  Yeah, you can buy with a credit card. A house really can't buy with a credit card, even today. There's just too many different spokes in that deal wheel. And so I'd been putting things on social and we've been finding buyers and brokers through Instagram. You know, which kind of had come out in 2013, but it was the first time I'd created my own version of what I did on Bravo. Shot it, put it on YouTube the next day to millions of people who sourced it and find it. Really targeted a marketplace and then actually sold it. And I used that house as my case study for like five years. And then obviously they started rolling it from there.

• 4:04David Weisburd?

  And even back from there, 2010, you really bet your career on social. Were you sure that that was the right thing to do? Or was it just kind of an inkling, I hope I'm right?

• 4:15Speaker 00

  I didn't really have another choice. Like, I'm not from New York. I didn't have family here helping me out. It wasn't like I was best friends with a lot of rich people. Like, I looked at the top agents in New York City, the top agents in the country, and they all came or had some sort of hook that enabled them to leapfrog over the competition. And I had zero. The only thing I had was, was I understood my audience on social better than I think anyone else in sales at the time. And I understood reach. And so if everyone else went to a schwanky Upper East Side private school, I had YouTube, you know?

• 4:59Speaker 00

  If everybody else like had a rich family that was going to give them their first listings and deals and connections at Shabbat, like, I had Instagram. And I just really, really, really created this media enterprise to create deal flow. Even today, like, studios at the company like is top of funnel organic lead gen in our pyramid. Like, the company is an upside down pyramid. Starts with studios, then goes into sell it, right? And then so on and so forth. To get down to the bottom, everybody creates deal flow, creates content. Round and round and round we go, back to the top of the pyramid.

• 5:39Speaker 00

  And those were the early days.

• 5:40David Weisburd?

  You've built a rare combo of really viral things and also luxury brand. How do you balance those two things? And how do you know that you're not hurting your brand by doing something too crazy?

• 5:54Speaker 00

  Any desire to be a quiet, under the radar salesperson, I definitely hurt.

• 6:03Speaker 00

  But the world is really big, relatively speaking. And all of the business I've received that's inbound from people who don't know me, where I've been able to create a relationship with them while I sleep, because I'm engaging with them through platforms in a way that compounds over and over and over and over and over and over and over again, outweighs any potential deal I could have done.

• 6:31Speaker 00

  If I had been the quiet, under the radar, very traditional, oh, I don't do that kind of goofy stuff broker.

• 6:38David Weisburd?

  This goes back to your philosophy on not being a secret agent.

• 6:42Speaker 00

  People don't know what you sell if you don't tell them what you sell.

• 6:46David Weisburd?

  Why is there such a disconnect with people and so few people actually talk about what they do?

• 6:51Speaker 00

  I think there's a confusion between bragging and being confident in your abilities to help people. Like, when I talk about success, I never, and I think the reason my audience connects with me so much, and the reason so many people come to this company and they buy the books and they watch the shows, is I don't give myself my own trophy, ever. Most people who talk about themselves and their own business, they do it because they award themselves their own trophies. I, I talk about the business because I'm so excited about the wins and the deal my buyer got and like the deal my seller got and, you know, I talk about our agents now

• 7:34Speaker 00

  more than I talk about myself ever. I still do a significant amount of transactions and I never talk about them anymore.

• 7:40David Weisburd?

  So that's the subtlety in that you're passionate about what you're talking about, but you're really talking about the client, the opportunity, the property, not Ryan this, Ryan that.

• 7:49Speaker 00

  The Ryan this, Ryan that comes in somewhat of a self-deprecating tone, which I think is, is helpful.

• 7:59Speaker 00

  You know, and I, and I learned that in the million dollar listing years. Like, there was an episode during Hurricane Sandy in New York City where like, it was a rough time to be in New York City because we had no power south of 42nd Street and they filmed the whole thing and I was by myself, you know, I was like alone. My parents, like, you know, were busy and I didn't know what to do and people really connected with me, with me at that point and I was, I was hard on myself and I was like, wait, but that's how I always am? I'll just be vulnerable. Like, if you, if you elect to put yourself out there into the world, you can't go one toe in the water. And I'm like, I tell everybody I meet now, like, the internet calls bullshit more than the person sitting in front of you.

• 8:43Speaker 00

  Because the person sitting in front of you, oh, we're here, we made this effort, you're going to give me the benefit of the doubt because you're sitting in that chair.

• 8:49David Weisburd?

  I'm not going to scroll.

• 8:50Speaker 00

  You're not going to, you can't. I mean, you could, it would be weird. But on the internet. I can scroll from you this minute I sense any bullshit. And so you have to be more authentic online than you are even in front of your own family now. And I think people connect to that, right? They connect to the failures. You'll see season two of this show is probably the most raw season of reality television. I think, one, I've ever seen and two, I've ever been a part of. Like it, it'll be uncomfortable for people to watch. It tackles like, I mean, it tackles a lot. I mean, it goes through addiction.

• 9:30Speaker 00

  Like it, it, I mean, like there's, there's so much in the show that like, I've just never seen before in the space. I'm excited for people to see, but I think it might be a hard watch for some people.

• 9:42David Weisburd?

  We'll get to some spoilers in a bit, but I want to double click on this vulnerability, especially in real estate. It's such a traditional market.

• 9:52David Weisburd?

  When did you decide to be vulnerable and did you have to calibrate that over time? Did you become too vulnerable and then you had to step it back? Talk to me about that.

• 10:01Speaker 00

  No, I think, I mean, for what it's worth, I get more business the more vulnerable I am.

• 10:09David Weisburd?

  Has it ever backfired?

• 10:11Speaker 00

  Probably. I don't know of a specific example. I mean, I'm also just myself and I do a lot of weird goofy things. And that's backfired because agents, my competition will use it against me. And I have these moments where I'll freak out on studios here and there. I'm like, people aren't taking me seriously anymore. Like, why am I chasing ping pong balls down the street? Why am I, you know, running in an inflatable tube through Soho to push, you know, our courses? You know, because our, my competition can't do what we do online. They don't have the audience we do. So they do exactly what they know how to do, which is to talk poorly about it and say, it doesn't mean anything. It's stupid and it's goofy.

• 10:53Speaker 00

  So, you know, a lot of times, especially early in my career, I would go to a pitch with a client. Client would say, listen, I love you. I totally get it, but I met with five other brokers and they told me everything that you do will hurt me and hurt the house. That it's all stupid. The social media thing isn't real. And in 2013 to 2018.

• 11:17Speaker 00

  Maybe there was some honesty to that, but it was, it was, you know, I had to really educate people. Which is why that deal, that townhouse deal in 2015 was so, was so helpful for me. Cause I could use it and they could use the clients as case studies too, as testimonials. I'm like, all right, call them.

• 11:34David Weisburd?

  What, I know there's always this collaboration between social and real life, but what's the largest property you've ever sold through social media?

• 11:41Speaker 00

  A hundred and sixty million dollars.

• 11:43David Weisburd?

  And what was, what property was that?

• 11:45Speaker 00

  It was a property in Palm Beach. It was this year and the kid

• 11:51Speaker 00

  found me, introduced me to the banker of the family. The banker called me, interviewed me, introduced me to the family, family bought the property over the phone.

• 12:02David Weisburd?

  So I know you've said that season one changed your life, changed the trajectory of your life. In the last year, there was a lot of highs and a lot of lows. What's one really high moment that a lot of people don't know about?

• 12:16Speaker 00

  I went, I invested so hard during the tariff fallout. That was like the best weekend of my year. It's where, you know, I don't talk about investments ever. I don't talk about money ever. It's not really my lane. It's not my niche. When I do, it doesn't really perform well because people are like, show us real estate, real estate clown. They swipe away. But I had like, I had been waiting for a reset and resets now happen so fast, right?

• 12:47David Weisburd?

  V shape.

• 12:47Speaker 00

  Yeah. You're in a bear market on Friday, you're a bull market by Tuesday. And every time there's a correction, it's the worst it's ever been. And every time things are hot, it's never been better and it never changes. Whether it's COVID, a terrorist attack, global pandemic, a hurricane, right? It never, ever, ever changes.

• 13:06David Weisburd?

  Thirty-three year old TikTok mayor?

• 13:08Speaker 00

  Yeah, exactly. When Mam Dadi won, we had 48 hours of the Mam Dadi discount. And then it went away because nothing changed. But we pushed hard, right? What was I talking about before then?

• 13:22David Weisburd?

  You're talking about the Trump tariff.

• 13:24Speaker 00

  Oh, yeah, yeah.

• 13:25David Weisburd?

  What did you invest in?

• 13:27Speaker 00

  Just put money into the markets. Like I, because I'm, you know, when, when, when COVID hit and the market fell 10,000 points, I, like a lot of people, was in, nervous, especially because we were about to start the business. And we were about to start the company. I thought we were going to announce Serhant on July 1st. That was going to be July 4th week. My birthday was July 2nd. All these pieces of paper in this hallway say, announcement by July 1st. And then COVID hits, throws us off, things got pretty dark, and then we pushed until September. But I was like, man, if there's ever a big market correction ever again, it never lasts, and I'm going to double down.

• 14:07Speaker 00

  And I waited, and it never happened until Trump announces tariffs with that poster, and the market sold off so fast, up until that one moment, right? Where he came back out and was like, ah, I'm going to figure it out. 30 days. The day before that, I mean, I put a lot of money, just generally into the marketplace. And that was great. That was a good, that was a great one.

• 14:31David Weisburd?

  Last time we chatted, you were just growing really quick. I know this, the past year, you grew another 50%. What has had to change in you as the CEO in order to scale Serhant?

• 14:43Speaker 00

  Oh.

• 14:46Speaker 00

  Everything. I think I've had to learn to become incredibly clear about what I want in people. I've always given people the benefit of the doubt, like hire for intelligence, hire for energy, enthusiasm, empathy, get good people, make sure they're uniquely qualified, and they'll figure it out. And when they don't do that, it then builds resentment. And so I've really had to learn to be very, very, very clear on this is exactly what I want. If I'm going to pay you, and you're going to be here, and if you don't do this, then I've made it very clear what I want, and then I'm not going to pay you anymore. And then we don't have to work together. It's totally fine. There's other companies. That was hard. Oh, that was a low moment this year. It's firing our president.

• 15:33David Weisburd?

  Tell me about that.

• 15:34Speaker 00

  Yeah, it was hard, man. Like with every employee you hire, and every agent too, but I think you have, no one's perfect. I'm not perfect at all. And I, I kind of have this like cost.

• 15:51Speaker 00

  I'd say I have this benefit and risk seesaw with everybody. And for everybody who is currently here and working, the benefits outweigh the risk. And the risk can be personal, they can be cultural, they can be, they can, you know, they can be about the work, right? They can be about the work product sometimes. And sometimes the risk then starts to outweigh the benefit and you have to make difficult decisions. So I don't want to go into details because I can't. But that was a moment where like, I don't know, like it felt like such a failure on my part. Like anytime you have to let someone go.

• 16:29David Weisburd?

  And it is the failure of the CEO because he hired him.

• 16:32Speaker 00

  Exactly. And for, you know, for, for the rest of the company too. Like for somebody, you know, at the C suite level, you know, who has a leadership role. They're only effective if they work with everybody. So it's not like you're letting go of somebody who's doing, you know, one action and then they don't do that action anymore.

• 16:53Speaker 00

  And that was, that was a brutal, brutal low moment to go through. And it was time after time after time again, because I kept vouching and vouching and the company, everybody kept coming to me and I like, you know, I think culture is defined by the behaviors you allow, right? So.

• 17:12David Weisburd?

  The implied culture, not the stated culture.

• 17:15Speaker 00

  The way everybody understands how this business moves is defined by what you allow to happen. If you allow laughter, right? There's humor. If you allow innovation, right? There's, there's, there's excitement and there's growth. If you allow bad behavior, if you allow lying, right? If you allow harassment, you know, all the things. Even if that person's work product is really, really, really great, you've set the tone that bad behavior is worth it. If the work is there and it becomes incredibly unhealthy.

• 17:47David Weisburd?

  It's this double edged part of empathy.

• 17:50Speaker 00

  Yeah.

• 17:50David Weisburd?

  Taken to the extreme, every action someone does could be explained by some, some reason that some childhood trauma. So if you just chase the reasoning back, you could, you could excuse anything. You can excuse murder, you know, his parents, his father might've beaten his mother and he went to bad school, but that doesn't make it right. And as a CEO, you have to balance that empathy with pragmatism and how to build a great organization.

• 18:13Speaker 00

  Yeah, pink flags or red flags in disguise, you know. Like I've had, it's also hard on the hiring side, like it takes, it takes time to hire the right person. And I've gotten close on a handful of different executives this year. And then there's just something that doesn't click and I'd rather, I'd rather not take the risk, right? I don't, for their life too, uproot their life, sometimes these people have to move and like if I'm just gonna, if it's not gonna work, I'm just gonna make sure it just doesn't work.

• 18:41David Weisburd?

  Have you ever thought about sitting down and etching the Serhant cultural values? This is what we stand for, this is what we don't stand for.

• 18:48Speaker 00

  Yes.

• 18:49David Weisburd?

  And, and making it really explicit.

• 18:51Speaker 00

  Yeah, we have a success at Serhant doc that goes to employees.

• 18:56David Weisburd?

  And what are some of those core values?

• 18:57Speaker 00

  For employees, you know, I say first and foremost is just brutal, brutal, brutal transparent honesty. Like you have to be honest, two, you have to perform magic. You just have to.

• 19:10David Weisburd?

  What do you mean by that?

• 19:11Speaker 00

  Like you have to do something that your department or other people don't know how to do. Otherwise, how are you being additive?

• 19:20David Weisburd?

  And to be a one of one.

• 19:21Speaker 00

  To the culture, yeah, be a one of one in the company you're in. Like every new employee who starts here, I sit down with them, say, here's the four things I care about. First thing, okay, you have to establish credibility, right? Like why, why are you here? Make sure everybody knows that you're credible, you're hired for a reason. Second thing you have to do is you have to gain respect. And third thing you have to do is you have to earn trust. Respect and trust are not created equal, very different. And the fourth thing you have to do is you have to perform a magic trick, right? Be a one of one and let people know that, oh, you know how to do that thing over here that we didn't know how to do. Thank God you're here and everyone will be able to move much, much faster that way.

• 20:05David Weisburd?

  Cause I've never really thought about the difference between respect and trust. What's, what's the difference?

• 20:10Speaker 00

  I mean, you might trust a family member, but you also might not respect them too much. You know, like I have friends, I trust them with my life. I don't really respect them.

• 20:21David Weisburd?

  So you don't respect their life choices, but you might trust them to do.

• 20:24Speaker 00

  Look at the biggest names, you know, in lights these days. Really respect them. You respect what they've been able to do. Prob don't trust them, you know, because you know they're going to be out for themselves. So you've got to be able to walk that fine line when you're playing a team sport, which is what it is to be a company.

• 20:44David Weisburd?

  What's one thing that broke over the last year that you had to fix internally to really get to the next level?

• 20:50Speaker 00

  Every system we have. Like, we crossed 1,000 agents earlier this year, which I think when people look at a brokerage and they say 1,000 agents, that's not a lot. You remember, 1,000 agents is 1,000 LLCs for the most part. It is 1,000 businesses that we then have to support, right? In the back end and in the front end. So it's a significant amount of work. We're at about 1,500 now, but it was like, it was a lot. So the way we set up the business was for, you know, a startup company. And so as you scale, everything breaks. You know, there's that classic phrase of building an airplane while you're flying it.

• 21:35Speaker 00

  Yeah, that's not so awesome when you're in the middle of it.

• 21:38David Weisburd?

  Making your parachute while you jump out of the plane.

• 21:40Speaker 00

  Exactly, right? Somewhat scary. Yeah, this year, I mean, in specific, like our payment system just was not up to par with where we needed it to be to be national. And we decided to move west this year. So we started in Arizona. We just opened up in Las Vegas, right? So we're starting to fill in the United States. And the way you do things in every state in this business is so different. So a lot of those systems of protocols and processes really were put to the test. And there's like a phrase I had most of this year, which was just like, we'll got you here, won't get you there. From systems to the tech to the people.

• 22:19David Weisburd?

  So before we move on, I have a surprise. I want to bring my wife and your co-star Jessica Markowski to talk about season two. Let's do it. Let's bring on Jessica. Jessica.

• 22:30Speaker 02

  Hi.

• 22:30David Weisburd?

  Well, one thing that I've learned from talking to hundreds of investors, founders, and business leaders is that planning for the future isn't just about growing assets. It's also about protecting the people who matter most. Life comes with a lot of important milestones. Maybe you're buying a home, starting a family, planning for college, or simply thinking more intentionally about your financial future. As those responsibilities grow, it's worth making sure you protect those you love. Not sure what kind of life insurance you may need? Concerned about how much it may cost? Think life insurance is too complicated? Your local State Farm agent can help answer those questions. They can help you explore your options for life insurance and choose coverage that you can adjust as your family's needs change over time. Financial protection for your loved ones when it matters most. Learn more about life insurance at statefarm.com. Like a good neighbor, State Farm is there. Come.

• 23:15Speaker 02

  Thank you so much for having me on your podcast.

• 23:18David Weisburd?

  So, season two. What was the most difficult part in season two for you?

• 23:26Speaker 02

  The most difficult part for me, honestly, from season one, I think just the podcast alone that I did was something I was not really proud of. And just overcoming that was very, very difficult for me. So it always just like played in the back of my head that I knew that I had so much to really still prove at the company. So that was always difficult for me.

• 23:50David Weisburd?

  Another hand, what was your biggest highlight from season two?

• 23:54Speaker 02

  I think the biggest highlight for me was I managed to get a big listing in Tribeca. And I wanted to do it quickly, effectively, efficiently, to really prove that I could really do my job well. And I think we'll see that on season two. Just like managing, like representing both sides and navigating that was just something I've never done before. So, learning as I was doing it was really fun.

• 24:19David Weisburd?

  Well, thank you, Jessica.

• 24:21Speaker 02

  Okay, bye. Enjoy your podcast.

• 24:22David Weisburd?

  Oh, that was it? You're leaving now?

• 24:23Speaker 02

  Yeah.

• 24:24David Weisburd?

  Oh, okay. What's one scene in season two that made you...

• 24:28Speaker 00

  You think, holy shit, I can't believe this is happening. There are so many, man, honestly, like.

• 24:35Speaker 00

  First of all, I love that Netflix gives us a lot of freedom to make a show no one's ever seen before. To your point, like the purple cow, like no one, no one wants to sit down and watch something they've seen 10,000 times, even with different people. So the show has like a real narrative thread with voiceover. You know, you're really watching the show through the eyes, like an entrepreneurial lens. Very cinematic. Yeah, it's incredibly cinematic. Um, which is unique. We break the fourth wall this season. And so there's multiple times where I talk directly to the camera and it is very jarring. I think the audience, like I remember when I first showed first clips to people just to see like, hey, is this gonna work? We even showed it to Danny and his fiance, they like rewound and they're like, I don't know what just happened. That was, that was kind of weird.

• 25:18Speaker 00

  But then you're like, okay, now I gotta, I have to watch more. Um, so I think that's really, really cool. There was an altercation in the office. They're shot in real time. There was a fight that. Not staged. That's no, not staged, dude. I wish. It'd make my life so much easier. And then I had to really have like a CEO boss moment again with Nile. And that scene though. Is probably one of the strongest scenes I've seen ever in reality TV.

• 25:51Speaker 00

  There is a fight between me and Jordan Marsh that's completely insane. There's a deal we did, Peter did, he's a new cast member this year.

• 26:02Speaker 00

  That he sold for $60 million and I had a buyer. And I was excited because we were filming, you know, we filmed for six, seven months and Netflix just films in real time. Obviously, so like it deals happen, they catch them. If they don't happen, they don't catch them. And there's not a lot of like pressure to make sure things happen, but they just want to see what's going on. And it's like, it's a blink of time. And so I have a buyer that I've been working for a long time. Peter joins the company and then we put him on the show and he's got this deal. I'm like, oh, this is awesome. This is like, what a great story, right? We can film this. I got a $60 million deal and put it together and he [bleep] me over in real time. As the. Eye camera. So I'm, we're in the car filming $55 million cash I present to him and he hangs up the phone on me.

• 26:49Speaker 00

  And we do a U-turn and we drive back to the office. And the cameras just followed like you.

• 26:56David Weisburd?

  An old school reality.

• 26:57Speaker 00

  Yeah, it's like, it's like, yeah, it's like the real world. They're shaky. They're like, what's happening? We go up into the office and I call him out and he's like taken aback. You see a lot of people on camera that usually aren't because they were just working on the second floor. I go into the cell phone booth. I try to put the deal together and I lose it and he sells it to somebody else in real time as it's happening. And then I had a mental breakdown and broke a whole vase on our first floor. And then the episode just ends. So that seems insane. I also, I put together another deal at 111th Avenue. And the entire negotiation happens from when I'm in the shower to when I get my shirt on.

• 27:39Speaker 00

  In real time, it was really weird, but it's like cool to also watch that.

• 27:44David Weisburd?

  It's your, it's your real life.

• 27:45Speaker 00

  Yeah, real life. Like we got to go to Miami this year. We got to like the executive team from Mercedes Benz flew in from Stuttgart, Germany. We got the silver arrow car, you know? So like, how do you launch a $1.5 billion skyscraper? You know, an interviewer asked me the other day, it's like, define season two in two words. And all I could think of was an emotional skyscraper. That's what the show is.

• 28:12David Weisburd?

  A lot of people look at you as the real estate agent, but you're also a character. It's your real life, but you're also building this cinematic experience. Talk to me about how you build a narrative arc around a season for something like an owning Manhattan that's based on real life.

• 28:28Speaker 00

  You, you create the world to then improv. So, you know, we sit with the team of producers. And we say, okay, like, what are the properties that we think we can get access to? Because you need location releases, appearance releases, like it's, you can't just roll around, you know, and open people's doors with a Netflix camera. It doesn't work that way. So you have to have approvals, right? You have to be able to get into places. But then we kind of look at like, what's, what's the arc of the company? You know, we, you know, season one, we went from, you know, we were a couple hundred agents. We added a couple hundred during filming and we were under attack. You know, people were quitting. Maggie on the show quit. I had to fire two people, right?

• 29:10Speaker 00

  It was like, it was just a lot. Season two, we're on the offense. And so that was really the theme, right? So what's the theme of the season? Season one is defense. Season two is offense. So, okay, we're on the attack. So we're going to go from 500 people to a thousand people. And we're going to watch that happen in real time. We're going to go from New York to start spreading down the East Coast. We're going to watch that happen in real time. And I'm going to go from, really, in season one, I was broker slash CEO. This season, I really moved from being everyone's buddy to being the boss, moving from broker, moving to CEO, and really trying to determine what's really important for me. And then we see what happens with the cast, with deals, like your wife,

• 29:52Speaker 00

  I mean, had an amazing deal happen in real time, you know, that we were able to film and put on camera to show people how that's done, which is really cool. And then there's a lot of deals that don't, that help get done. So you see a lot of things dies.

• 30:03David Weisburd?

  What are some mistakes you made on season one and then also on season two?

• 30:08Speaker 00

  On season one, the biggest mistake I made was probably not selling the penthouse at Central Park Tower. That will, that will haunt.

• 30:15David Weisburd?

  Everyone asks about that. People ask me, did he ever sell it?

• 30:19Speaker 00

  Yeah, thanks. One day, one day I will. There's only so many people spending $200 million out there.

• 30:26David Weisburd?

  Although to your credit, you, you say on the show, there's 1,800 billionaires or something. You only have to find one, which is a good framing. But to buy a penthouse for $250 million, you need a lot more than a billion dollars.

• 30:37Speaker 00

  Correct, correct.

• 30:39David Weisburd?

  It's a very difficult sale.

• 30:40Speaker 00

  Yeah, so there's only so many people that have that kind of money. That said, more and more people are making nine-figure real estate purchases now than in the history of time. So it will sell. So, I mean, I say it's a mistake that I didn't sell it, but, but I also. I think it's one of the things that's so special about this show. It's 100% real in an uncomfortable way. Like, if you want to watch a real deal show, watch a business being built, a business being hurt, deals dying, deals happening, and not have any bullshit served to you, like, that's what this show is. Nothing is fake, none of the people are fake. And that's really, really important because I did a Bravo TV show for 10 years. I did four of them. It's like, if I'm gonna do TV again, I'm gonna do it my way, and it's going to be visceral.

• 31:25Speaker 00

  And so I regret putting a listing on TV that large that was gonna create that much commotion, that much noise, and that much press. And it had billions of impressions around the world that I then couldn't execute. Season two, the biggest mistake that I made.

• 31:47Speaker 00

  I don't know, I think the, it's a lot to follow, you know? I think, I think some viewers like it because there's so much. The cast is large, you know, there's 12 people, 11, 12 people. That's a lot. Like, Friends, totally different, but it's a classic example of like, how many stories you can follow. All right, it's six people. And you kind of go back and forth between their lives, and that's still a lot of people. But eight 40-minute episodes to follow the lives of 12 people, plus New York City, plus a company, it's a, it's a lot.

• 32:26Speaker 00

  So I think I probably would have narrowed in on some storylines, maybe a little bit stronger, and maybe lighten the load on some others, maybe. But I'm super proud of season two. I think it's the coolest season of docu-TV that I've ever seen. And I think it's a lot of fun, too. It's also funny.

• 32:50David Weisburd?

  You called the real estate and media convergence almost a decade before anyone else. So you're really cutting edge. Where do you see just the future of content in general? You see the different platforms, TikTok, Netflix, Instagram. What do you think's gonna still hold true in five to 10 years? And what's gonna evolve?

• 33:08Speaker 00

  I think it's getting more and more and more honest, which is why you see so much of the younger generation moving away from content that's fully produced to content that is just fully streamed, right? Because it's hard to produce, stream, because it's right now. It's just live. And so, which is kind of like the old school days of original TV. It was live in front of a studio audience, right? And there's a real talent to being able to do that. And so I think you're going to see that. I think you're also going to see more interactive media and content. So like, listen, last year, season one, we had our premiere party, but a lot of our promotion was produced. This year, we have the premiere party, but we have, I think, we have Only Manhattan Live

• 33:53Speaker 00

  that's happening, where fans get to come and interact with us. They come to Serhant House in Soho. We have the Ryan meetup, which is a group of people only named Ryan. So we have 600 Ryans coming and flying in to New York as a premiere event, right? It's interactive with the show. I also think what we're also seeing is a reaction just to ADD, right? Adult, you know, adult attention deficit disorder. And even 40 minutes is a long time for people. And so you see it now, right? You see TV shows that move incredibly fast. And you can't breathe, but because you gotta keep attention or people will switch platforms. And so I think you're going to see the rise of the microdrama. You're seeing it now.

• 34:38Speaker 00

  You're seeing brands create it. And you're seeing entire storylines being told in a way that people feel emotionally satisfied in under five minutes. I don't know if it's good, but it's definitely going to happen more and more and more now over the next couple of years.

• 34:52David Weisburd?

  What would people be surprised to hear? Your vision for the future for Serhant? And where do you want to take the company that other people might think it's a little bit contrary?

• 35:04Speaker 00

  I believe that

• 35:09Speaker 00

  our ecosystem is built to help people move forward. And we do that by helping buyers, sellers, developers, and salespeople in real estate move faster, better, and where we can, cheaper.

• 35:27Speaker 00

  And we do that in part because we're a media and technology company. It also happens to sell real estate.

• 35:35Speaker 00

  And so we're building out that ecosystem. And we have a major AI component to that that really, really automates back office. So that I can basically make the entire real estate experience and transaction experience screenless. And I think that's a contrarian point of view. And I think we are also making, therefore, the agent and consumer relationship that much stronger because we're creating tools and features that force greater connection instead of dividing it. And a lot of our competitors are just focused on the division and focused also on the property.

• 36:20Speaker 00

  Right? We, for some reason, maybe because I'm crazy, are like 1,000% focused on the people. Empower the people, empower the property. And we're the only ones who do that. And therefore, we are the resistance.

• 36:37David Weisburd?

  For people starting out in real estate as agents, what's the number one piece of advice you give them today?

• 36:45Speaker 00

  Go follow Jessica Markowski online.

• 36:49Speaker 00

  Do those first two things. I, you know, I tell everyone, you've got a, your first three years in the business are grad school. If you make money, you're lucky. You're here to learn and you want to leapfrog. So join a team, do all the work no one else will do. So then three years, you have the opportunity to do the work no one else can do. And that's it. It's not that hard. Most people are unwilling to do that and that's why they tap out.

• 37:18David Weisburd?

  And also get reps and get on deals. Make sure, even if you're getting 5%, make sure you're on a deal.

• 37:23Speaker 00

  Always learn, have the conversations. The biggest agents of anything, whether it's finance, cars, real estate, were number 11 in an organization, but they did all the work. And so as people age out, or they tap out, or they get fired, they want to go do different things. You just, it's not even a ladder. It's like an inverted slide. Like your future is just defined for you because you're the one the customers are going to have the connection to. Because you did the work other people didn't want to do. It's really not that complicated, but people want micro dramas, right? They want success in two minutes. They want to swipe for money, swipe for dollars. There's a lot of places to make money now, you know?

• 38:07Speaker 00

  You can make a lot of money on your phone.

• 38:10David Weisburd?

  Well, Ryan, thanks so much for taking the time and love the season two and looking forward to season 10. That's it for today's episode of How I Invest. If this conversation gave you new insights or ideas, do me a quick favor. Share with one person in your network who'd find it valuable or leave a short review wherever you listen. This helps more investors discover the show and keeps us bringing you these conversations week after week. Thank you for your continued support.