Living Your Legacy

Episode: Chicago Real Estate Top Performer: The Art of Reading Clients to Close Bigger Deals
Host: Ray Gutierrez (for Rudy Mawer)
Guest: Sammy Lubeck (Chicagoland’s Real Estate Agent)
Release Date: December 17, 2025

Episode Overview

In this candid conversation, Ray Gutierrez sits down with Sammy Lubeck, Chicago’s top-performing real estate agent, to dissect the art of closing deals by reading clients, transitioning to entrepreneurship later in life, building a trusted brand, and adapting to an ever-changing market. Sammy shares hard-won insights from his journey—leaving behind a steady paycheck, leveraging his innate charisma, and creating a team that puts client trust first. The episode is packed with practical advice for anyone wanting to build their own legacy in real estate, sales, or any entrepreneurial field.

Key Discussion Points & Insights

1. Breaking Away to Build a Legacy

• Late Start, Big Moves:
  • Sammy embraced real estate full-time at age 47, after years of “having the ceiling and advancement controlled by bosses.”
  • Quote: “Never late to start and then having to really hustle to earn money and saying goodbye to the bosses. And you know what? I’m going to be in charge of my own success.” (00:00; 02:38)
• Entrepreneurial Spirit:
  • Encourages others not to be held back by age or routine and to “attack it, to really pursue their dreams.” (18:29)

2. The Reality of Self-Motivation

• Discipline Without a Boss:
  • Success as an entrepreneur depends on self-motivation and aligning your hustle with your income.
  • Quote: “When you’re not getting that steady paycheck…your hustle is directly correlated to how much you’re going to get paid, it fuels you.” (00:39; 04:24)
• Flexibility of Schedule:
  • Days vary by client demand—sometimes long hours, sometimes a relaxed start—but always driven by a sense of ownership.
  • Quote: “That’s the beauty of…having your own business. I am a workaholic. But, yeah, there are days when I wake up and go for a walk…and then ease into my day.” (03:32)

3. Mastering the Market & Staying Relevant

• Chicago Market Insights:
  • Chicago remains a “steady incline,” functioning as a microclimate distinct from national trends.
  • Quote: “Chicago’s been steadily increasing…thank you to my clients. Shout out to you.” (05:46)
• Adaptation in Advertising:
  • The shift from traditional media to digital exposure and influencer-driven marketing changes the agent’s approach to gaining leads. (07:08)

4. The Power of Reading People

• Adapting to Clients:
  • The foundation of Sammy’s success: skillfully reading client personalities and adjusting style accordingly, whether for multimillion-dollar buyers or nervous first-timers.
  • Quote: “You can have the nicest people in the world that are rich. You can have the biggest assholes…that are poor. It doesn’t matter. But one of the gifts that I have is being able to read people.” (09:06)
  • For intense clients: “Stick to the script, make sure you have results, get them to a house, see if they like it and move on—not waste their time overtalking.” (09:06)
• Transferable Skills:
  • “Reading all those different personalities is key…whether you’re a real estate agent or…hosting a podcast.” (10:08)

5. Generating and Converting Leads

• Techniques for Lead Generation:
  • Leveraging Zillow for leads (despite its controversial reputation among agents), supplementing with Facebook ads early on.
  • Quote: “Zillow…is a bad Z word in the real estate industry. But I’ve been advertising on there for about five years.” (11:52)
• Building Trust Quickly:
  • Immediate response and resourcefulness set Sammy apart in converting leads.
  • Quote: “It’s very important to get in front of your leads as quickly as possible. When you’re helping people buy a million dollar property, you better believe they have to trust you.” (12:54)

6. Educating and Empowering Clients

• Resourceful Service:
  • Sammy’s teaching background informs his approach—he provides clients with exclusive info, comps, and market analysis, not just generic links.
  • Quote: “I provide…private networks that only agents have access to. If they’re looking at comps, I can get that for them in seconds.” (13:55)
  • Key: “It’s all about the whole package…and makes them more knowledgeable to the point where…we’re going to help them get there.” (14:41)

7. Building a Standout Team and Brand

• Choosing the Right People:
  • Learned quality > quantity the hard way; those without “attention to detail” or the “gift of gab” weren’t a fit.
  • Quote: “They were representing my brand as Chicagoland’s real estate agent. If they don’t have that attention to detail…weren’t going to be good resources for our clients.” (15:14)
• Team Culture:
  • Focus on legacy, reputation, and staying on good terms, even when moving on from team members. (15:14)

8. Backstory & Life Lessons

• Past Careers Influence Present Success:
  • From teaching to sports television to side-hustling real estate in 2007, Sammy’s varied background enhanced his skills.
  • Appreciation for former careers: “Teaching…you’re not making any money and you are working nonstop…Props to all teachers.” (16:30)
  • Transitioned full-time in 2018 and “haven’t looked back since.” (16:30)
• Legacy of Laughter and Ease:
  • Tribute to his father, who passed along the “gift of gab,” making clients comfortable—a critical skill in high-stakes deals.
  • Quote: “My dad…could talk to anybody…Definitely funnier than I am. But I gotta tell you, I really enjoy putting people at ease.” (07:44; 18:29)

9. Giving Back & Mentorship

• Open invitation for others to contact him for advice or mentorship:
  • “More than happy to talk real estate with anyone and everyone…Buyers, sellers, agents, industry leaders.” (19:39)

Memorable Moments & Notable Quotes

• On entrepreneurship at any age:
  • “Never late to start…and saying goodbye to the bosses. I’m going to be in charge of my own success.” (00:00; 18:29 — theme repeated throughout)
• On self-motivation:
  • “Your hustle is directly correlated to how much you’re going to get paid, it fuels you.” (04:24)
• On reading clients:
  • “You can have the nicest people in the world that are rich. You can have the biggest assholes in the world that are poor. It doesn’t matter.” (09:06)
• On team building:
  • “I realized very quickly…if they don’t have that attention to detail…they weren’t going to be good resources for our clients.” (15:14)
• On mentorship:
  • “More than happy to talk real estate with anyone and everyone…More than happy to help out in any way I can.” (19:39)

Important Timestamps

• 00:00–00:39: Sammy’s career pivot at age 47; mindset shift
• 03:21–04:12: Defining entrepreneurship, discipline, and daily routine
• 05:29–06:46: Chicago market climate, regional differences
• 07:44–08:20: The “gift of gab” and reading clients
• 09:06–10:08: Adapting approach for different client personalities
• 11:39–12:58: Lead generation methods; Zillow, Facebook, speed to response
• 13:55–14:41: Resources & education for clients
• 15:14–16:16: Team building, brand protection, lessons learned
• 16:24–18:16: Sammy’s professional journey: from teaching to real estate
• 18:29–19:39: His father’s influence and encouragement for dream-chasers
• 19:39–20:12: Mentorship and how to contact Sammy

Final Takeaways

• Legacy is About Impact: Whether starting late or pivoting from another field, building your legacy involves risk, hustle, and a relentless focus on people.
• Trust & Resourcefulness Win Deals: The art of real estate—and sales overall—lies in listening, adapting, and delivering value beyond what clients expect.
• Never Too Late: Age, career history, or previous “ceilings” don’t define your potential. Starting with purpose and commitment is all that matters.

Connect with Sammy:
www.sammy.homes — open to conversations, mentorship, and sharing wisdom with anyone ready to build their legacy in real estate.

This summary captures the essence and standout advice of Sammy Lubeck’s Legacy Makers episode—ideal for entrepreneurs, real estate professionals, and anyone inspired to take control of their career and legacy.