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

Summary

Podcast Summary: “How I Invest with David Weisburd”
Episode 258: Ryan Serhant – Why Leaders Who Don’t Evolve Get Left Behind
Date: December 9, 2025

---

Overview

In this episode, host David Weisburd sits down with Ryan Serhant—high-profile real estate broker, entrepreneur, and star of Netflix’s "Owning Manhattan"—to explore the intersection of real estate, leadership, content creation, and business evolution. Serhant shares candid insights about leveraging social media, the power of vulnerability, scaling his brokerage, cultural values at Sirhant, and behind-the-scenes stories from reality TV. The conversation blends personal anecdotes, leadership lessons, and contrarian visions for the future of the real estate industry.

---

Key Discussion Points & Insights

The Power of Raw Content and Vulnerability

• Reality TV as Business Exposure:

  • Serhant reflects on filming "Owning Manhattan" Season 2, describing it as “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 tackles a lot. It goes through addiction… never seen before in the space.” (00:00; 08:56)
  • Real altercations, business failures, and personal breakdowns are covered with zero staging.

• Authenticity as a Business Asset:

  • Serhant’s willingness to show both professional wins and messy, emotional lows resonates with audiences and clients.
  • “I get more business the more vulnerable I am.” (10:01, Serhant)

• Being Memorable and Differentiated:

  • Compares his unconventional, attention-grabbing content to traditional, under-the-radar brokers, highlighting the outsized impact of being visible, even if the approach is “goofy.”
  • “Any desire to be a quiet under-the-radar salesperson, I definitely hurt. But the world is really big... Outweighs any potential deal I could have done if I had been the quiet broker.” (05:54)

Social Media as Lead Gen for Luxury Real Estate

• Origin Story:

  • Describes selling a $13M property via a YouTube video a decade ago. The buyer was sourced when a teenage girl found the video and alerted her mother.
  • “That buyer was sourced through the kid, through YouTube.” (02:45, Serhant)
  • Early adoption of social media was an existential choice:
    “I didn't really have another choice… The only thing I had was, I understood my audience on social better than anyone else in sales at the time.” (04:15, Serhant)

• Proof Points:

  • Largest sale via social media: $160 million Palm Beach property, initiated by a DM.
  • “The kid 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.” (11:44, Serhant)

Leading and Scaling Sirhant: Trials and Lessons

• Being Clear in Leadership:
  • Serhant was forced to become explicit about expectations as Sirhant grew:
    “I've had to learn to become incredibly clear about what I want in people… If you don't do this, … I'm not going to pay you anymore.” (14:46)
• Difficult Personnel Decisions:
  • Candid discussion about having to fire the president of his organization:
    “It felt like such a failure on my part... Culture is defined by the behaviors you allow.” (16:32, Serhant)
  • Pink flags are red flags in disguise when hiring.
• Values at Sirhant:
  • Core values include “brutal, brutal transparent honesty,” performing “magic” or unique contributions, and cultivating credibility, respect, and trust within the organization.
    “You have to perform magic. You just have to. … Be a one of one in the company you're in.” (18:58, Serhant)

Business Systems and Scaling Challenges

• Growing Pains:
  • Scaling from hundreds to over 1,500 agents meant every internal system—payments, processes, people, tech—had to be revamped.
    “Every system we have… broke. … What got you here won't get you there.” (20:50; 22:07)

Behind the Scenes: “Owning Manhattan” and Reality TV

• Realism and Cinematic Risk:

  • Season 2 features real-time negotiations, fights, and failures—not artificially orchestrated.
  • “We break the fourth wall this season. ... Very jarring. ... There was an altercation in the office. They shot in real time.” (25:35; 26:12, Serhant)

• Building a Narrative in Reality:

  • Outlines how the show is produced—by structuring the real world and improvising within constraints.
  • “You create the world to then improv... what’s the arc of the company?” (29:11)

• Growth and Mistakes:

  • Discusses overloading the show with too many characters, and the regret of publicizing massive listings without certainty they will close.
    “Biggest mistake... probably not selling the penthouse at Central Park Tower... I regret putting a listing on TV that large that was going to create that much commotion...” (30:48; 31:19, Serhant)

The Future of Content and Real Estate

• Evolving Attention Spans and New Frontiers:

  • Sees a shift toward “more and more honest” content; rise of live streaming and interactive experiences; and micro-dramas with entire story arcs under five minutes.
    “You see the rise of the micro drama... storylines being told in a way that people feel emotionally satisfied in under five minutes.” (33:48; 35:33, Serhant)

• Contrarian Company Vision:

  • Sirhant is positioning itself as a media and tech company that sells real estate, not the other way around.
  • Emphasis on people over property, and developing AI tools to make transactions “screenless.”
  • “We're a media and technology company, but also happens to sell real estate. … Empower the people, empower the property. … We are the resistance.” (35:45; 36:16; 37:17, Serhant)

Advice for New Real Estate Agents

• Learning and Grit:
  • “Your first three years in the business are grad school. If you make money, you are lucky, you're here to learn.”
  • “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.” (37:29, Serhant)
• Getting On Deals:
  • “Even if you're getting 5%, make sure you're on a deal. Always learn, have the conversations.” (37:58, Weisburd)

---

Notable Quotes & Memorable Moments

• “People don't know what you sell if you don't tell them what you sell.” (06:42, Serhant)
• “You have to be more authentic online than you are even in front of your own family now.” (08:50, Serhant)
• “Pink flags are red flags in disguise.” (18:13, Serhant)
• “Culture is defined by the behaviors you allow.” (17:12, Serhant)
• “Perform a magic trick. Be a one of one and let people know, ‘Oh, you know how to do that thing over here ... Thank God you're here.’” (19:06, Serhant)
• “We are the resistance.” (37:17, Serhant)
• “It's not even a ladder. It's like an inverted slide. … 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.” (38:03, Serhant)

---

Guest Segment: Jessica Markowski on Season 2

[24:06]–[25:00]

• Jessica shares her difficulties overcoming self-doubt following Season 1 and her triumph winning a major Tribeca listing in Season 2.
  • “Biggest highlight for me was… I managed to get a big listing in Tribeca… to really prove that I could really do my job well.” (24:35, Markowski)

---

Episode Timeline & Important Timestamps

• 00:00–02:52: The “rawness” of Season 2, origins of selling via YouTube
• 04:15–06:38: Betting his business on social media, disrupting traditional real estate norms
• 08:56–10:09: Vulnerability as a business advantage
• 11:41–12:02: Selling a $160M property via social media
• 14:46–16:30: Leadership evolution, hiring/firing challenges at Sirhant
• 18:58–20:24: Sirhant’s core values; credibility, respect vs. trust, performing “magic”
• 22:07–22:19: Scaling pains—systems breaking as the company expands
• 24:06–25:00: Jessica Markowski guest segment
• 25:11–28:19: “Owning Manhattan” behind-the-scenes, real altercations and narrative arcs
• 29:11–33:28: Structuring the show, learning from mistakes
• 33:48–35:33: The future of content—honesty, streaming, micro-dramas
• 35:45–37:17: Contrarian vision for Sirhant—people over property, media first
• 37:25–38:50: Advice for aspiring agents; the grind, getting on deals, “the inverted slide” of career progress

---

Final Takeaway

Ryan Serhant's story illustrates how authenticity, relentless visibility, and willingness to adapt are crucial for modern leaders and entrepreneurs. Whether in luxury real estate or business more broadly, those who don’t evolve—or expose their real selves—are left behind. His vision for Sirhant and the future of high-trust commerce involves not just technology, but a radical focus on humanity, culture, and storytelling.

Transcript

[A]

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 tackles a lot. It goes through addiction. There's so much in the show that I've just never seen before. In the space. There was an altercation in the office. They're shot in real time. There was a fight.

[B]

Not staged.

[A]

Not. No, not a stage. Dude, I wish. It would 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 me over in real time. We're in the car filming 5 million, all cash.

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 base on our first floor. And then the episode just ends. We're not doing the deal.

[B]

Take me back. When you sold your first $13 million home on YouTube, how did that happen?

[A]

It was. It was on West 18th street and 7th, 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 going to 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. This is 10 years ago today. This would be boring. Then on YouTube, like this was like, how did they do that?

[B]

And you just dropped it on YouTube.

[A]

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 the location a little bit, but she just cared about it. They offered us 12 million. We countered, 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.

[B]

What was your commission on that deal?

[A]

Probably two and a half percent.

[B]

So roughly 350K.

[A]

Yeah. About.

[B]

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

[A]

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 follow the credit card. 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 had been putting things on social and we'd 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 source it and find it really targeted a marketplace and then actually sold it. And I used that house as, as. As my case study for like, five years. And then obviously they started rolling it from there.

[B]

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.

[A]

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 swanky Upper east side private school, I had YouTube. You know, 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 then so on and so forth to get down to the bottom. Everybody creates deal flow, creates content. Round and round around we go back to the top of the pyramid.

And those are the early days.

[B]

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. By doing something too crazy?

[A]

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

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 if I had been the quiet under the radar, very traditional. Oh, I don't do that kind of goofy stuff. Broker.

[B]

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

[A]

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

[B]

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

[A]

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

[B]

So that's the subtlety and 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.

[A]

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

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, were busy, and I, like, didn't know what to do. And people really connected with me, with me at that point. And 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, like, I tell everybody I meet now, like, the Internet calls more than the person sitting in front of you, because the person sitting in front of you or, 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.

[B]

I'm not going to scroll.

[A]

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

[B]

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.

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.

[A]

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

[B]

Has it ever backfired?

[A]

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 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. So, you know, a lot of times, especially early in my career, I would go to a pitch where 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 2013-2018.

Maybe there was some. 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, 15 was so. Was so helpful for me because I could use it. And they could use the clients as case studies, too, as testimonials. I'm like, all right, call them.

[B]

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?

[A]

$160 million.

[B]

And what was. What property was that?

[A]

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

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.

[B]

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?

[A]

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. Swipe away. But I had, like, I. I had been waiting for a reset, and resets now happen so fast. Right, V. Shape. Yeah. You're in A bear market on Friday, you're in 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.

[B]

33 year old TikTok mayor.

[A]

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

[B]

You're talking that about the Trump tariff.

[A]

Oh, yeah, yeah, yeah.

[B]

What did you invest in?

[A]

Just, 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 Sirhant 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. And I waited and it never happened until Trump announced his 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, I'm gonna 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.

[B]

Last time we chatted you were just great, 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 certain. Oh.

[A]

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 higher for intelligence, higher 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. Is firing our president.

[B]

About that.

[A]

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.

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, and especially the failure of the.

[B]

CEO because you hired him.

[A]

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. 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?

[B]

So the implied culture, not the stated culture.

[A]

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 have set the tone that bad behavior is worth it. If the work is there and it becomes incredibly unhealthy.

[B]

It's this double edged part of empathy taken to the extreme. Every action someone does could be explained by some reason that some childhood trauma. So if you just chase the reasoning back, you could excuse anything. You could excuse murder, you know, his parents, his father might have Beaten his mother and he went to bad school.

[A]

But.

[B]

But that doesn't make it right.

[A]

Yeah.

[B]

And as a CEO, you have to balance that empathy with pragmatism and. And how to build a great organization.

[A]

Yeah. Pink flags are 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, you know, 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 want 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.

[B]

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

[A]

Yes.

[B]

And making it really explicit.

[A]

Yeah. We have a success at Sirhant Doc. That goes to employees.

[B]

And what are some of those core values for employees?

[A]

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. If you're. What do you mean by that? Like, you have to do something that your department or other people don't know how to do. Otherwise, how are you being additive and to be a 100 one 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. Third thing you have to do is you have to earn trust. Respect and trust are not created equal. Very different. Um, 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.

[B]

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

[A]

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.

[B]

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

[A]

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.

[B]

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

[A]

Every system we have, like we crossed a thousand agents earlier this year, which I think when people look at a brokerage and they say a thousand agents, that's not a lot to remember. A thousand agents is a thousand LLCs for the most part. It is a thousand 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 1500 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.

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

[B]

Making a parachute while you jump out of the plane.

[A]

Exactly. Right. Somewhat. Somewhat scary. Yeah. This year, I mean, in specific, like, our, 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 and protocols and processes.

Really were put to the test. And there was like a phrase I had most of this year, which was just like, what got you here won't get you there. From systems to the tech to the people.

[B]

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. Let's bring on Jessica. Jessica.

[C]

Hi.

[D]

Well, when you want more for your business, start with Northwest registered agent. You could build your complete business Identity in just 10 clicks and 10 minutes. Everything you need to launch and protect your business is all in one place. Your business identity is more than what your customers see. It's also legal paperwork, website security, and compliance. Behind the scenes. With Northwest, you get more more privacy, more tools, and more guidance. Northwest Registered Agent has been helping entrepreneurs for nearly 30 years. They're the largest registered agent LLC service in the US with over 1500 corporate guides who know your local laws. You can form your business for just $39 plus state fees. Get an LLC, domain name, business email, phone number, business address, registered agent, service and compliance tools again, all in 10 clicks and 10 minutes. Northwest also protects your identity by letting you use your business address on state filings. And with mail forwarding in 20 states, they'll scan your mail and upload it securely the same day. Privacy is automatic. They never sell your data. Don't wait. Protect your privacy, build your brand, and get your complete business Identity in just 10 clicks and 10 minutes. Visit www.northwestregisteredagent.com paidinvest and start building something amazing. Get more with Northwest registered [e-mail] paidinvest.

Welcome.

[C]

Thank you so much for having me on your podcast.

[B]

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

[C]

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.

[B]

On the other hand, what was your biggest highlight from season two?

[C]

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. 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.

[B]

Well, thank you, Jessica.

[C]

Okay, bye. Enjoy your podcast.

[B]

Oh, that was it?

[A]

You're leaving now? Yeah.

[B]

Oh, okay. What's one scene in season two that made you think, holy shit, I can't believe this is happening?

[A]

There are so many, man. Honestly, like.

First of all, I love that, and Netflix gives us a lot of freedom to make a show no one's ever seen before. To your point of, 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.

[B]

Very cinematic.

[A]

Yeah, it's incredibly cinematic, 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 going to work? Or even show 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. But then you're like, okay, now I got to. I have to watch more. So I think that's really, really cool. There was an altercation in the office. They shot in real time. There's a fight that.

[B]

Not staged.

[A]

Not. No, not staged. Dude, I wish it 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. 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.

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, if 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 a. 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 me over in real time as the on camera. So we're in the car filming $55 million cash. I present to him, and he hangs up the phone on me, and we do a U turn and we drive back to the office, and the camera's just followed. Like, you. You see it? Yeah, it's like. It's like. It's. Yeah, it's like the real world. They're, like, 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.

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

[B]

It's your real life.

[A]

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.

[B]

A lot of people look as 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. You.

[A]

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. Then we kind of look at, like, what's. What's the arc of the company? You know, we 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? It was like. It was just a lot. Season two, we were 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, 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 move 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, 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 don't get done. So you see a lot of things dies.

[B]

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

[A]

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

[B]

Everyone asks about that. People ask me time. Do you ever sell it? Yeah.

[A]

Thanks. One day. One day I will. There's only so many people spending $200 million out there.

[B]

Although to your credit, you, you say on the show there's 1800 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.

[A]

Correct? Correct.

[B]

It's a very difficult sale.

[A]

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 and watch a business being built, a business being hurt, deals dying, deals happening and not have any 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, I did a Bravo TV show for 10 years. I did four of them. It's like, if I'm going to do TV again, I'm, I'm gonna do it my way and it's going to be visceral. And so I, I regret putting a listing on TV that large that was going to Create that much commotion, that much noise and that much press. I mean, I had billions of impressions around the world that I then couldn't execute. Season two, the biggest mistake that I made.

I, I don't know, I think the, 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, there's 12 people.

[B]

11.

[A]

12 people. That's a lot like friends. Totally different, but it's a classic example of like how many stories you could follow. Right. It's six people and you kind of go back and forth between their lives and that's, 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, it's a lot. So I, I think I probably would have narrowed in on some, 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, of docu TV that I've ever seen.

And I think it's a lot of fun too.

[B]

It's also funny, 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 is going to still hold true in five to 10 years and what's going to evolve?

[A]

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. Right. It was full back 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, was produced this year we have the premiere party, but we have, I think we have only Manhattan Live that's happening, where fans get to come and interact with us. They come to Sirhan House in soho. We have the Ryan Meetup, which is a group of people only named Ryan. So we have 600 Ryan's coming and flying in to New York as a premier event. Right. It's interactive with the show. I also think what we're also seeing is, is a, is a reaction just to add, right? Adult, 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 gonna see the rise of the micro drama. You're seeing it now. 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.

[B]

What would people be surprised to hear? Your vision for the future for Sirhant and where, where do you want to take the company that other people might think is a little bit contrary?

[A]

I believe.

That.

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

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. Right. We, for some reason, maybe because I'm crazy, are like 1000% 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.

[B]

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

[A]

Go follow Jessica Markowski online.

Do those first two things. I, I, you know, I tell everyone, you, you've got a, your first three years in the business or grad school. If you make money, you are 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 and.

[B]

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

[A]

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, there's. 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, you can make a lot of money on your phone.

[B]

Well, Ryan, thanks so much for taking the time and love the season two and looking forward to season ten.

[D]

That's it for today's episode of how to 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.

[B]

Short review wherever you listen.

[D]

This helps more investors discover the show and keeps us bringing you these conversations week after week. Thank you for your continued support.