Podcast Summary

Podcast: Creating Confidence with Heather Monahan
Episode: Confidence Classic: Master Sales and Build Unstoppable Confidence to Raise Your Goals with Ryan Serhant
Host: Heather Monahan
Guest: Ryan Serhant (Author, Star of Bravo’s Million Dollar Listing New York, Real Estate Entrepreneur)
Date: August 19, 2025
(Detailed transcript available; summary skips advertisements and technical outro)

Episode Overview

This episode brings together Heather Monahan and Ryan Serhant for a candid conversation on sales mastery, confidence, and consistently raising one’s personal and professional bar. Heather discusses real challenges in her business and podcasting journey, while Ryan shares actionable insights drawn from his spectacular rise in real estate and self-branding. The dialogue digs deep into what true confidence looks like, demystifies the sales process, and highlights the relentless personal discipline and authenticity needed to build a successful career—and life.

Key Discussion Points & Insights

1. The Reality Behind Seemingly Glamorous Careers (00:33–18:00)

• Heather recounts a professional setback—an event in NYC cancelled at the last minute—and how she turned disappointment into an opportunity by networking and seeking out new podcast guests, underscoring resilience and adaptability.
• Reflection on learning from red flags in partnerships:

  “When you see red flags in partnerships, that is an indicator to walk away, no matter what your benefit is. Letting go of that selfishness, I wish I had done that.” (12:53, Heather)

• Organization tips for entrepreneurs: build a pipeline of connections segmented by city, always be ready for face-to-face opportunities.

2. Setting, Raising & Measuring Goals in Business (16:00–19:00)

• Heather’s journey: setting podcast download goals far beyond those suggested by her team, aiming for 1M downloads in the first year, and achieving high growth via consistent hustle and strategic guest selection.
• The power of envisioning success, tracking metrics (“dashboard analytics”), and asking for support from one’s network.

3. Encountering Ryan Serhant & Navigating Energy Shifts (19:18–23:00)

• Heather describes how she found Ryan just after he had lost a multimillion-dollar deal—a real, human moment that affected his initial mindset.
• Tactics for shifting someone’s mood in a meeting: asking about emotional memories to elicit presence and openness.

4. Ryan Serhant on Confidence & Handling Low Moments (20:18–22:13)

• Ryan’s lowest confidence moment wasn’t business-related—it was high school heartbreak, demonstrating vulnerability and universality of insecurity.

  “My confidence was at its lowest… probably when I was like a sophomore in high school and I was like nice and chubby, riddled with acne… broke up with by a girl in front of all the lacrosse players.” (20:45, Ryan)

5. Sales is Human Connection, Not Manipulation (23:00–29:42)

• Sales compared to dating:

  "Every time I meet somebody and I want to sell them something, it's really just a first date… People love shopping with friends but they hate being sold." (23:00, Ryan)

• Sales is “assuring people” of choices they were going to make—facilitating action, not “taking” from them.

  “Selling is just assuring people. All you're doing is you're assuring them of the choice they were going to make anyway.” (27:08 & 00:00, Ryan)

• The “wow moment” tactic: show clients something aspirational to anchor their perception of value, then lead them to a more suitable middle option.

  “People don’t know what they want until you show it to them. When you show them exactly what they say they want, they never want it.” (25:44, Ryan)

6. Handling Objections & Power Dynamics in Sales and Relationships (28:39–36:39)

• How to respond when clients stall (“I need to think about it”): ask authentic questions to identify real objections; connect as a friend would.
• The person who “cares least” holds power in any negotiation or relationship.

  “The person in the relationship who has all the power is the one who cares the least.” (34:07, Ryan)

• Recognition that this dynamic permeates all relationships, not just business, but needs to be handled with authenticity and empathy.

7. Resilience, Rejection, and Building Confidence (40:41–44:08)

• Ryan’s “make it in New York or go home” moment forced him to shed shyness and fear of rejection: “Go out there and just hustle or it’s literally go home to Colorado… I wouldn’t come back.” (40:41, Ryan)
• Influence of family, especially a tough father, in building grit and resourcefulness.

  “My dad…marching us down the street…knock on everyone's door and say, 'Hi, my name is Ryan. My name is Jack. We just moved in across the street. Would you like to be our friend?'” (42:34, Ryan)

• Connecting with strangers—still one of the most effective ways to create opportunity, even for established agents.

8. Social Media, Branding, and Consistency (46:10–54:18)

• Social media as double-edged sword: pressure for visibility versus the necessity of self-promotion in today’s market.
• Building a personal brand by consistently associating your name with your expertise (“I want everyone to see Serhant and think real estate”).
• Positive impact of vision boards and public commitment to goals:

  “If you wake up every day with goals in your mind and you put it out there, it's going to change the way you talk to people… and make those dreams realities…” (53:15, Ryan)

• Heather notes that while Ryan wants his brand to be about real estate, it is broader: he is known for sales, not just property.

9. Serhant’s Path: Luck, Preparation, and the Power of ‘Inception’ (56:28–58:16)

• Ryan’s big break—being cast on Million Dollar Listing—was about being prepared to seize an opportunity.

  “Luck is when opportunity meets preparation.” (56:32, Ryan)

• Sales as the “power of inception”: make what you want become the customer’s idea.

  “How do I make what I want to happen someone else’s idea? And how do I plant that seed so once they decide to make it happen, I can just smile.” (57:10, Ryan)

10. Continuous Self-Improvement, Family, and Passing on the Sales Mindset (59:06–end)

• Heather prizes being a present, authentic businesswoman and mother—her son learns about sales and negotiation by observing her, leading to a touching anecdote about him “selling” her on a YouTube promotion idea.
• Recognition, celebration of wins, and self-acknowledgment are crucial in both business and life.
• Instilling confidence in children (and oneself) is about reminding them of past triumphs and focusing on future positives.

Notable Quotes & Memorable Moments (with Timestamps)

• On reframing sales:

  "Selling is just assuring people… assuring them of making that choice with you today."
  — Ryan Serhant (00:00 & 27:08)

• On formative failures:

  "My confidence was at its lowest… when I was like a sophomore in high school… broke up with by a girl in front of all the lacrosse players."
  — Ryan Serhant (20:45)

• On the real secret to sales:

  "People love shopping with friends but they hate being sold."
  — Ryan Serhant (23:50)

• Power dynamics in negotiations:

  "The person in the relationship who has all the power is the one who cares the least."
  — Ryan Serhant (34:07)

• On connecting with strangers:

  "Some of the agents who do the absolute best… spend half an hour a day just talking to people on the street… There are so many people on the street who can provide opportunity to us. We just have to ask them."
  — Ryan Serhant (43:06)

• On branding:

  "I want everyone to see Serhant and think real estate… The more that happens, the better it’s going to be for my business."
  — Ryan Serhant (51:36)

• On ‘luck’ and being prepared:

  "Luck is when opportunity meets preparation… When you’re in that moment, you know what to do."
  — Ryan Serhant (56:32)

• On sales as inception:

  "How do I make what I want to happen someone else’s idea? … I just planted this seed that you’re not going to buy what you told me you wanted… but you’re going to buy my middle option because I know you want it—and it’s your idea."
  — Ryan Serhant (57:39)

• Heather’s learning as a mom and businesswoman:

  “My son watches me run my business and conduct business every day… He’s learning to be resourceful and a very good salesperson.”
  — Heather Monahan (after 59:39)

Timestamps for Key Segments

• Red flags in partnerships & event disaster: 00:33–12:53
• Setting goals & learning from analytics: 16:00–19:00
• Preparing for the Ryan Serhant interview: 19:18–20:18
• Serhant’s lowest confidence moment: 20:18–22:13
• Sales philosophy/dating analogy: 23:00–24:39
• The ‘wow moment’ in sales: 25:17–26:38
• Handling sales objections: 28:39–29:21
• Power dynamics in negotiation: 34:07–36:39
• Connecting with strangers for opportunity: 43:06–44:08
• Brand building and social media: 51:36–54:18
• Vision boards and goals: 54:56–55:17
• ‘Luck’ and opportunity: 56:28–57:10
• Sales as inception: 57:29–58:19
• Passing on sales mindset to children: after 59:39

Episode Tone

Open, candid, witty, and direct—Heather and Ryan blend humor, vulnerability, and hard-won insights. Both are unapologetically honest about the highs and lows, embracing both hustle and self-reflection.

Takeaways for Listeners

• Confidence is built by surviving—and learning from—both public failures and small wins.
• Sales is everywhere: in business, relationships, even parenting.
• Emotional intelligence, genuine connection, and the willingness to “ask” are essential sales (and life) skills.
• Brand-building is relentless self-promotion and value delivery.
• Recognize your achievements, keep setting bigger goals, and stay present for the journey.

Standout Moments

• Ryan’s vulnerable story about adolescent rejection, paralleling Gary Vee’s experience (20:45).
• The “wow moment” sales tactic revealed (25:17).
• Heather’s anecdote about her son “selling” her—proof that sales skills are transferable life lessons (after 59:39).
• Ryan’s pragmatic take: “The person…who has all the power is the one who cares the least.” (34:07)

This episode is a masterclass on the mindset and practicalities of modern sales, branding, and unstoppable self-confidence—applicable whether you’re aspiring to sell million-dollar properties or just to sell yourself on your next big leap.