Stacking Businesses: Brokerage, Media, Education, AI

Most people think sales is about talking. Ryan Serhant knows better — it's about translating. After closing over $20 billion in real estate deals and building one of the fastest-growing brokerages in America, the star of Netflix's Owning Manhattan has cracked the code on how to get anyone to say yes. From selling homes to billionaires to building a media empire on the back of reality TV, Ryan reveals the brutal truth about what it actually takes to win at the highest level.

In this raw conversation, Ryan breaks down the orchid trick (he's sent 2,000 of them), why silence is violence in negotiations, and how a fake Rolex changed his entire life. We dive into why wealthy people don't pay for information or access, but instead pay for confidence; how to get a stranger to trust you with real money; and why the best negotiators throw the first punch. But this isn't just about closing deals — it's about building an empire. Ryan reveals how he's stacking businesses under one holding company (brokerage, media, education, and AI), why his LTV to CAC ratio is 6x while the industry averages 1x, and how he's building real estate brokerage 3.0 with no physical offices.

If you've ever wondered how to sell to the ultra-wealthy without sucking up, how to build unshakeable confidence when you're broke, or why setbacks are just speed bumps and not brick walls, this episode will change how you think about sales, negotiation, and what it takes to become the best in the world at what you do.

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00:00:00 Introduction 00:01:22 The Fake Rolex That Changed Everything 00:04:35 From Soap Opera Star to Real Estate Mogul 00:06:36 Speed Bumps vs Brick Walls: Handling Setbacks 00:09:26 Building in Public: The Netflix Experiment 00:16:29 Gray Hair Don't Care: Dealing with Haters 00:18:24 The Orchid Trick: Turning Rejection into Power 00:21:06 Selling to Billionaires: The Two C's and the Pull Strategy 00:25:27 Confidence is Currency: What Rich People Really Pay For 00:34:11 The Thousand Minute Rule: Time as Money 00:31:38 Hiring A-Players: Intelligence Over Experience 00:39:32 Leader vs Manager: Standing at the Front Lines 00:41:11 Building Identity and Future Memoir Exercise 00:42:54 The Four Business Flywheel Strategy 00:52:07 Negotiation Mastery: Translate Don't Talk 00:54:36 Owning Manhattan Season 2 and the Evolution of Reality TV

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