E258: Ryan Serhant: Why Leaders Who Don’t Evolve Get Left Behind
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Podcast Summary
In this episode of How I Invest, host interviews Ryan Serhant, founder and CEO of SERHANT., who shares how he built a billion-dollar real estate empire by transforming himself into a media company. (03:20) Ryan discusses his journey from selling a $13 million townhouse through YouTube a decade ago to growing his brokerage to over 1,500 agents across multiple states. (44:45) The conversation covers the highs and lows of his year, including making strategic investments during market corrections and navigating difficult leadership decisions like firing his company president. (15:33) Ryan also provides insights into Season 2 of Netflix's "Owning Manhattan," which he describes as the most raw and authentic reality TV he's ever experienced, featuring real-time deal negotiations, office confrontations, and genuine business challenges.
- Core Theme: How authenticity, vulnerability, and media convergence can transform traditional industries and create unprecedented business growth through genuine human connection
Speakers
Ryan Serhant
Ryan Serhant is the founder and CEO of SERHANT., one of the most influential real estate brokerages in the world with over 1,500 agents across multiple states. He pioneered the intersection of real estate, media, entertainment, and technology, transforming from a traditional broker into a media empire. Serhant starred on Bravo's Million Dollar Listing New York for ten years and currently stars in Netflix's "Owning Manhattan," which showcases his innovative approach to luxury real estate sales and business building.
Jessica Markowski
Jessica Markowski is a real estate agent at SERHANT. and cast member on Netflix's "Owning Manhattan." She specializes in luxury properties and has experience representing both buyers and sellers in complex transactions. Jessica has worked to establish her credibility within the company and overcome challenges from her first season appearance on the show.
Key Takeaways
Vulnerability Is Your Ultimate Competitive Advantage
Ryan emphasizes that being vulnerable online and in business actually generates more clients and deeper connections. (10:01) He explains that the internet calls out bullshit faster than face-to-face interactions, requiring complete authenticity in digital spaces. Rather than hurting his luxury brand, his willingness to show failures, struggles, and genuine moments has become his greatest differentiator in an industry known for polished facades. This approach has helped him close deals worth up to $160 million through social media connections alone.
Turn Media Creation Into Your Primary Lead Generation Engine
Serhant built his entire business model around content creation as the top of his sales funnel. (05:15) He describes his company structure as an "upside down pyramid" that starts with studios and content creation, then flows down to actual real estate transactions. This media-first approach allowed him to compete against established agents who had family connections and elite school networks. By consistently creating engaging content, he built relationships with potential clients while sleeping, creating a compound effect that generates inbound business at scale.
Culture Is Defined By The Behaviors You Allow
As CEO of a rapidly scaling company, Ryan learned that culture isn't defined by stated values but by the implied behaviors leadership tolerates. (17:06) He had to make the difficult decision to fire his company president when performance issues began affecting the entire organization. Ryan emphasizes the importance of being brutally clear about expectations and following through on consequences, even when it means letting go of talented individuals whose behavior doesn't align with company standards.
Master The Balance Between Respect And Trust In Leadership
Ryan distinguishes between earning respect and building trust as separate but equally important leadership skills. (20:09) He explains that you might trust a family member but not respect their choices, while you might respect a celebrity's achievements without trusting their character. In business leadership, both elements are essential for effective team management. This insight helped him better evaluate employees and understand why some relationships weren't working despite good intentions from both parties.
Embrace Real-Time Transparency In Business Operations
Season 2 of "Owning Manhattan" showcases Ryan's commitment to showing business exactly as it happens, including failures and uncomfortable moments. (26:15) When a $60 million deal fell through in real time on camera, rather than editing it out, he used it as authentic content that resonated with audiences. This approach extends beyond entertainment - his willingness to show the messy reality of business building, including failed deals and difficult conversations, has become a powerful differentiator that builds deeper trust with clients and employees.
Statistics & Facts
- Ryan's company SERHANT. crossed 1,000 agents earlier this year and has grown to approximately 1,500 agents currently, representing 1,500 individual LLCs that require full back-end and front-end support. (20:54)
- The largest property Ryan has sold through social media was worth $160 million, sold to a family in Palm Beach where the buyer found him online, connected through their banker, and purchased the property over the phone. (11:43)
- Ryan's commission on his breakthrough $13 million YouTube house sale was approximately 2.5%, earning him roughly $350,000 and proving the viability of social media for luxury real estate. (02:47)
