BigDeal Podcast #106 — Sales Expert: 3 Ways To Get A YES Every Time | Ryan Serhant

Host: Codie Sanchez
Guest: Ryan Serhant (Top real estate broker, star of "Owning Manhattan")
Date: December 10, 2025

Episode Overview

This episode dives deep into the art and psychology of sales and negotiation, spotlighting the tactics, mindset, and resilience required to close high-stakes deals with top-tier clients. Ryan Serhant, renowned broker and reality TV star, shares his unfiltered journey from broke actor to industry leader, the strategies he uses to earn trust (especially from ultra-wealthy clients), and the rules that underpin his relentless drive for excellence. The conversation balances raw vulnerability with actionable advice for anyone wanting to break through barriers and get more "yeses"—whether in business or life.

Key Discussion Points & Insights

1. Transforming Setbacks and Building Unbreakable Confidence

• Setbacks as Speed Bumps, Not Brick Walls

  • Ryan Serhant:
    • “Setbacks are just speed bumps. They are not brick walls. … All the other issues that I've had through my career... most people would treat them like brick walls. But success is like right over there—past that corner.” (01:01, 06:57)
    • His mindset is fiercely future-focused—he draws motivation from painful memories of being broke, using them as fuel to never go back.

• The Fake Rolex Story: Crafting Identity and Confidence

  • Serhant bought a fake Rolex early in his sales career to boost self-belief and create the identity he aimed for, rather than simply “faking it.”
    • “It wasn’t fake it till you make it. It was, how do I give myself the confidence when I'm 24 to be future me? … That fake Rolex wasn’t about the watch. It was about identity.” (01:49)
    • He eventually bought a real Rolex 18 months later—a symbol of personal growth.

• Advice for Those Feeling Lost

  • “You have to determine one—what's your core identity? What do you actually want in life? … Am I okay being dead broke when I'm 70 as long as I’m performing? The answer was just no. I want to be as successful as I possibly can be. … Endurance for the win.” (06:57-08:24)

2. The Psychology of High-Performance and Obsession

• Why the Relentless Drive?

  • “Why not go the distance? I almost feel like it’s a divine duty. … I'd rather you regret the things you did than the things you never tried. And that plays a huge role in my DNA today.” (10:09)
  • Codie reflects, "You seem like a man on a mission," to which Ryan responds with his father's philosophy on trying, failure, and regret.

• Not Motivated by Money

  • “No, I’m not motivated by money. … Money is a tool and a resource to create lasting impact. … I’m motivated by goals, and the lives of the people we change.” (12:05)
  • Discipline is about doing what you don’t want to: “I woke up at 4:30 this morning. I did not want to. … But it’s the job.” (13:35)

3. Sales Tactics and Negotiation Secrets

• The Two Cs—Compliment & Commonality (21:40)

  • Ryan’s foundational technique for building trust:
    • “You immediately give the person a compliment, and it has to be authentic… Then you find something in common. … And then you’re talking.”

• Say "No"—Earning Real Trust with the Wealthy

  • Rich clients respect boundaries and candor.
    • “People don’t trust yes men or yes women. … I said, no, I’m sorry I took you here. It’s far outside your budget. … The trust was built there because I was willing to walk away.” (22:48)

• The Three Ps of Negotiation: Push, Pull, Persist

  • “Every sale has three Ps. … Sometimes it’s an amalgamation of the three. … Wealthy people—their number one asset is their time. Most of the time, the number one thing to do is just to pull.” (23:41)

• The Orchid Trick: Reframing Rejection

  • When Ryan loses a deal, he “sends an orchid with a note that says, ‘Thank you so much for the opportunity and I’m sorry for your loss.’” (18:48)
  • Memorable Quote: “My number one job is to fail. The more I’m pitching, the more I lose. So I want to take as many swings as bad as possible.” (18:48)

• Negotiation Power Moves

  • “The best negotiators… don’t talk—they translate. … You always throw the first punch. You ask the first question. … People love hearing themselves talk, especially grown men.” (53:48-55:47)
  • “If this were to go forward, what does winning look like to you? … They tell you their number one fear and give you the in to go and fix the fear.” (54:30)

4. How to Sell to the Rich—and Get to the Bullseye

• It’s About Confidence, Not Access

  • “Wealthy people want to know that when you tell them to do something or not to do something, they’re going to believe it. … Confidence is currency, and they’ll be loyal to you for the rest of your career.” (25:56)

• Cracking the Sphere of Influence

  • “The billionaire class is that bullseye. But they are protected by six rings … advisors, family, friends, assistants, bankers, vendors. … Who already has the trust? It’s interior designers, contractors, attorneys… Get share of trust to get share of wallet.” (26:40)

5. Relentlessness, Time Management, and Building Legacy

• Top 1% Salespeople Just Don’t Quit

  • “Hard work trumps luck when luck doesn’t work hard. … They understand their job is to lose. … The number one negotiation tactic is silence. Silence is violence.” (28:19)

• The Thousand Minute Rule

  • “You have a thousand minutes every day to be productive. … If you look at those thousand minutes as a thousand dollars … it’ll really start to affect the way you give someone 15 minutes, or value your commute.” (33:57, 34:26)
  • “If the call was only five minutes, would I throw away $995 because of five bucks? Probably not.” (34:24)

• Building Through Media and Public Transparency

  • “I built the number one real estate sales team … on the back of a Bravo TV show. … Selling real estate through YouTube in 2015 when it was stupid. … Now we're building on the back of Netflix. … People do get to really watch the journey.” (13:58)

6. Handling Haters, Hiring, and Leadership

• On Handling Critics

  • “There are three buckets of my audience: super fans, people who don’t care, and people who hate me. … It’s jealousy. … When people talk about me, they do it because when they talk about themselves, no one listens.” (15:52, 17:24)
  • “What other people think affects no part of my working minutes.” (17:24)

• Hiring for Intelligence & the Three E’s

  • “I hire first and foremost for intelligence. … I also test for energy, empathy, and enthusiasm. … Our three key metrics are speed, quality, and experience.” (32:12)

• Leadership vs. Management

  • “A manager does things right; a leader does the right things … The leader picks vision and stands at the front of the line.” (41:10-41:14)

• Showmanship and Branding

  • “A friend of mine told me to get into real estate—‘it’s theater, it’s the same thing.’ … You put on a performance, you put on your suit… and help them make a decision they were going to make anyway.” (38:08)

7. The Business Stack & Vision

• Multiple Business Segments Under Sirhant Technologies (44:31)

  • Cloud real estate brokerage (“we operate in the phone”)
  • Sirhant Studios (media and lead gen)
  • SellIt.com (education)
  • Simple (AI workflow for agents)
  • “Our LTV to CAC is 6.6 as a ratio … we don’t buy revenue, our lead flow is organic through content.” (46:22)

• On Scale vs. Quality

  • “I don’t want it to be big. I just want it to be the best. … If I could have 10 agents and sell more than any other firm, I would do it.” (48:11)

• Money is a Tool, Not the Goal

  • “Money is just a tool. And when you treat it like a tool and not like the be-all-end-all, then you don’t put dollars on a pedestal. You just put the potential for greatness up there.” (49:33)

8. Wild Sales Stories & Dealing With Con Artists

• The Ungoogleable Buyer
  • “He DHL’d me a photo of someone in an African headdress…on the back it just said that the purchaser’s name is good for it and does not commit to things he does not commit to. … That guy actually did one day wire the $830,000 deposit ... I asked him why he even bought it. He said, ‘To be honest, I felt bad for you.’” (50:59-53:14)
  • “Superpower number one: make people feel so bad for me, they just buy the damn thing anyway.” (53:14)

Notable Quotes & Moments

• On Confidence:
  “Setbacks are just speed bumps. They are not brick walls.” (01:01, 06:57)
• On Identity:
  “That fake Rolex wasn’t about the watch. It was about identity.” (01:49)
• On Motivation:
  “Discipline is defined by doing the things you don’t want to do.” (12:05, 13:35)
• On the Art of the Deal:
  “People don’t trust yes men or yes women. … Say no, pull the deal away.” (22:48)
• On Rejection:
  “My number one job is to fail. The more I’m pitching, the more I lose.” (18:48)
• On Leadership:
  “A manager does things right; a leader does the right things.” (41:14)
• On Building a Business:
  “I don’t want it to be big. I just want it to be the best.” (48:11)
• On Negotiation:
  “The best negotiators… don’t talk—they translate.” (53:48)

Timestamps for Key Segments

• Setbacks and Mindset: 01:01; 06:57; 08:24
• Fake Rolex and Confidence Story: 01:49
• The Orchid Trick (Rejection): 18:48
• Sales Tactics—2Cs, 3Ps, Trust: 21:40; 22:48; 23:41
• Negotiation Strategies: 53:48; 54:30
• Thousand Minute Rule: 33:57; 34:26
• Sphere of Influence/Wealthy Clients: 25:56; 26:40
• Business Operations/Stack: 44:31; 46:22
• Leadership vs. Management: 41:10-41:14
• Con Artist Sales Story: 50:59
• Showmanship in Business: 38:08

Final Takeaways

Ryan Serhant’s sales approach is a blend of relentless work ethic, self-crafted identity, emotional intelligence, and showmanship. He outlines a systematic process—from compliment and commonality to knowing when (and why) to pull away—to build trust and close deals at the highest levels. At the core is his belief that confidence, discipline, and willingness to lose are what ultimately create lasting success. The episode is packed with both philosophy and practical tactics, applicable to salespeople, entrepreneurs, and ambitious individuals looking to break into bigger arenas.