Office Hours: How Theater Helped SERHANT Founder Ryan Serhant Build a Real Estate Empire

Spencer Rascoff

Spencer Rascoff serves as executive chairman of dot.LA. He is an entrepreneur and company leader who co-founded Zillow, Hotwire, dot.LA, Pacaso and Supernova, and who served as Zillow's CEO for a decade. During Spencer's time as CEO, Zillow won dozens of "best places to work" awards as it grew to over 4,500 employees, $3 billion in revenue, and $10 billion in market capitalization. Prior to Zillow, Spencer co-founded and was VP Corporate Development of Hotwire, which was sold to Expedia for $685 million in 2003. Through his startup studio and venture capital firm, 75 & Sunny, Spencer is an active angel investor in over 100 companies and is incubating several more.

SERHANT Founder Ryan Serhant
Photo courtesy of SERHANT

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Real estate mogul Ryan Serhant joined this episode of Office Hours to talk about how his background in theater prepared him for the world of real estate.

As the founder of SERHANT., his eponymous brokerage firm, Serhant has become one of the most well-known real estate brokers in the world. He and his team have closed over $4 billion in sales across New York, Los Angeles and Miami. The firm has also expanded into other industries.


Serhant developed a passion for theater in Texas, where he was born and raised. After graduating college, he moved to New York to pursue his dream, thinking to himself, as he put it, “‘I'm going to see if I can make this Broadway dream and movies and television actually work.”

"Turns out it's really, really hard to do. There's a significant amount of rejection," he added.

The money he had saved lasted him just nine months. New York was expensive and he had no job. Refusing to go back to school or become a bartender, he turned to a friend who had a background in real estate.

Serhant's friend told him the job was no different than theater – like an improv game all day, as long as you adapt to clients and meet new people.

"I didn't take a day off for the first three years and just said, ‘I'm going to figure out how to build a network and actually do this in the city, or I have to move’. And that's a wall to be backed up against," said Serhant.

After years of dedication, Serhant opened his own firm and built a sales team of 65 agents.

As he was considering where to take his firm next, he realized there was a market for in-house film production, a skill he’d developed organically through social media, where he’d developed a strong following.

"Every other firm just kind of laughed it off. It's like, ‘you know what, when I'm ready, I think that's what I'm going to do, you know: bring real estate to the intersection of media technology’," said Serhant.

Serhant also decided to make educational content for his sales staff in order to help them earn their real estate agent licenses and sell homes.

“And sales is pretty ubiquitous,” he said. “If you learn how to sell or how to train your salespeople to sell real estate, you can train salespeople in any industry.”

Serhant said that the brand he's created will always come down to the people as the firm has grown.

‘"No matter what technology is invented, he added, “until you [Spencer Rascoff] or Bezos or Musk invents a way for a house to sell itself to another house, there will always be the need for a mediator between a buyer and a seller, a tenant or landlord."

Want to hear more episodes? Subscribe to Office Hours on Stitcher, Apple Podcasts, Spotify, iHeart Radio or wherever you get your podcasts.

dot.LA Engagement Fellow Joshua Letona contributed to this post.

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Spencer Rascoff serves as executive chairman of dot.LA. He is an entrepreneur and company leader who co-founded Zillow, Hotwire, dot.LA, Pacaso and Supernova, and who served as Zillow's CEO for a decade. During Spencer's time as CEO, Zillow won dozens of "best places to work" awards as it grew to over 4,500 employees, $3 billion in revenue, and $10 billion in market capitalization. Prior to Zillow, Spencer co-founded and was VP Corporate Development of Hotwire, which was sold to Expedia for $685 million in 2003. Through his startup studio and venture capital firm, 75 & Sunny, Spencer is an active angel investor in over 100 companies and is incubating several more.

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