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.