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. Highlights: How a YouTube video led to Ryan’s first $13M sale and changed his career Why he bet his entire future on social media long before agents believed in it The balance between going viral and preserving luxury brand credibility The power of authenticity online—and why the internet detects B.S. instantly How Season 2 of Owning Manhattan became his most raw and emotional year on TV The behind-the-scenes reality of office fights, breakdowns, and $60M deals Why vulnerability drives more business than perfection ever could The moment he realized he had to evolve from broker-friend to CEO-leader What broke at SERHANT. as the company scaled from 500 to 1,500 agents The difference between respect vs. trust—and why employees must earn both Ryan’s four rules for every new hire, including “perform magic” Why culture is defined by the behaviors you allow, not what you write on paper The future of content: micro-dramas, interactive media, and 5-minute emotional arcs How SERHANT. is building a screenless, AI-powered real estate transaction Advice for new agents: join a team, do the work no one wants to do, and get reps Guest Bio: Ryan Serhant is one of the most recognized and successful real estate brokers on the planet. He is the founder and CEO of SERHANT., a modern multidimensional real estate brokerage operating at the intersection of media, entertainment, education, and technology. Ryan has closed nearly $10 billion in sales and has represented clients in some of the most record-breaking transactions across New York and South Florida. Before launching his firm, he became a global personality as the star of Bravo’s Million Dollar Listing New York and now serves as Executive Producer and lead star of Netflix’s Owning Manhattan. Beyond real estate, Ryan is an entrepreneur, creator, bestselling author, and philanthropist whose content reaches over six million people. SERHANT. has grown rapidly under his leadership, expanding across multiple states and pioneering LISTED, a dedicated YouTube network focused on real estate and lifestyle. Ryan actively supports organizations including City Harvest, Feeding America, the Ali Forney Center, the NYC Sanitation Foundation, the American Cancer Society, and Project Sunshine. He lives in Brooklyn with his wife, Emilia, and their daughter, Zena. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com . Stay Connected with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/ ###Stay Connected with Ryan Serhant: LinkedIn: https://www.linkedin.com/in/ryanserhant/ Website: https://serhant.com/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com . Disclaimer: This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions. (0:00) Preview (1:12) Selling a $13 million home via YouTube and the impact of social media (5:40) Authenticity, vulnerability, and balancing content in luxury real estate (12:02) High and low moments, scaling challenges, and leadership (22:29) Special guest insights on season two highlights (24:38) Real-time CEO moments and a major deal gone wrong (27:02) Season two highlights: Miami, Mercedes Benz, and narrative arcs (29:08) Learning from mistakes across seasons one and two (32:06) Discussing the future of content creation and media convergence (34:08) Ryan Serhant's vision for the future of his company (35:53) Advice for new real estate agents and industry insights (37:26) Closing remarks