Chicago Real Estate Top Performer: The Art of Reading Clients to Close Bigger Deals

Summary

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.

Transcript

[Sammy Lubeck]

I captured my entrepreneurial spirit at the age of 47 that I was stuck to that steady paycheck for so many years. 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.

[Narrator]

Sammy Lubeck is a bold, self made real estate leader known as Chicago Lands real estate agent. Built on risk, reinvention and relentless drive, he's built a reputation for closing deals across more than 80 communities and leading a team with over $450 million in sales, redefining what it means to build trust, momentum and legacy in real estate.

[Ray Gutierrez]

How do you discipline yourself?

[Sammy Lubeck]

I think we can so easily get trapped on our phones. At the same time, when you're not getting that steady paycheck and you know your hustle is directly correlated to how much you're going to get paid, it fuels you.

[Ray Gutierrez]

How do you stay clever or stay ahead and stay unique?

[Sammy Lubeck]

One of the most important things that helped me become more successful in my industry is to realize it spans the globe like a super high pole.

[Guest/Interjection Voice]

Internet Elvis. Brandon I. Today, Apple is going to reinvent the phone. It's not over until I win.

[Ray Gutierrez]

The Living youg Legacy podcast.

[Guest/Interjection Voice]

For those who live to leave a legacy that's extraordinary. The impossible. Oh, that is sensational. Jordan, Open Chicago. With the lead, Usain Paul is the fastest man on the planet. You can live your dream.

[Ray Gutierrez]

Welcome back to another amazing episode of the Legacy Makers podcast. For Inside Success, I'm Ray Gutierrez. Joining me today is Sammy Luback, all the way from Gotham City, I mean, Chicago. Sammy, what brings you here to Miami?

[Sammy Lubeck]

I mean, I'm a legacy maker. Chicagoland's real estate agent, Sammy Lubeck. Ready to roll.

[Ray Gutierrez]

Let's do this. I love it. We're cutting a WWE promo. Sammy, what are we going to learn from your episode? You literally just finished filming it with Count Anton.

[Sammy Lubeck]

Yes. Shout out to Anson. Way to go. Thanks for. Thanks for dealing with my perfectionistic styles.

[Ray Gutierrez]

Shout out to Studio 3. So what are we going to learn? How was the US like, how do you feel?

[Sammy Lubeck]

Amazing. You know, I think that anytime anybody gets ready to be in front of the camera, it can be a little stressful.

[Ray Gutierrez]

Oh, sure.

[Sammy Lubeck]

You find yourself overthinking every single line. You want it to be perfect, but very confident that you guys are going to do amazing job of splicing it all together in the episode. Really? It's talking about how, at the age of 47, decided to give real estate my full efforts Right after being, you know, having the ceiling and advancement controlled by bosses in the past and finally able to be in charge of my own success.

[Ray Gutierrez]

When you are in charge of your own success, what does that truly mean? You wake up at nine and go golfing and then get to the office at 12? Or do you wake up at 4, take your ice shower and you're selling your first house at seven? What does success mean to you?

[Sammy Lubeck]

I think every day is different. And in my industry, it's dictated by our clients, for sure. You know their needs. If they want to go see a house at 9 o'.

[Guest/Interjection Voice]

Clock.

[Sammy Lubeck]

O', clock, we're going to go see a house at 9 o'.

[Guest/Interjection Voice]

Clock.

[Sammy Lubeck]

If they're not, you better believe I'm not setting that alarm to get to work. That's the beauty of being. Having your own business. I am a workaholic. But, yeah, there are days when I wake up and go for a walk and just have that pride and get some exercise and everything and then ease into my day. Right on. But then there are other days where I got to wake up at 7 o' clock and it's go time all the way to, you know, 10:30, midnight, whatever. But, you know, having that ability to be in charge of your own success, it's. It's nice to not have to answer to a boss. Of course we answer to our clients, but I do not miss bosses.

[Ray Gutierrez]

Well, you seem like a really cool, chill guy that does not miss bosses. How do you discipline yourself? How do you get out of bed knowing that just five more minutes can easily turn to five hours?

[Sammy Lubeck]

I think we can so easily get trapped on our phones. That's a gift. At the same time, when you're not getting that steady paycheck and you know, your hustle is directly correlated to how much you're going to get paid.

[Ray Gutierrez]

Yeah.

[Sammy Lubeck]

And survive, it fuels you. And I have this intrinsic motivation now after never being allowed to show initiative or being rewarded for showing initiative and in my previous positions. So I think that, that also having people you know on my team, I have to lead them, I have to motivate them. That that definitely helps. And I, of course, want to be successful.

[Ray Gutierrez]

Who?

[Sammy Lubeck]

I mean, if anybody comes in for your podcast and says, I don't want to be successful, you're going to cut. You're going to mosey on to the next person.

[Ray Gutierrez]

You never know. I'd be like, why? Why are you afraid of success? And we'll go in deep. I'll even use my.

[Sammy Lubeck]

If they are good, my creepy Voice yeah.

[Ray Gutierrez]

Right on, dude.

[Guest/Interjection Voice]

What.

[Ray Gutierrez]

How is the market back in Gotham City?

[Sammy Lubeck]

So Chicago, it's been. It's been steady for us. It's been great.

[Ray Gutierrez]

Chicago's beautiful.

[Sammy Lubeck]

We hustle well during the summers it is. During the winter, it's beautiful, but it's a different beautiful. You can respect the snow, but do you want to be driving around all over because the.

[Ray Gutierrez]

Respect the snow don't respect you?

[Sammy Lubeck]

Hell yeah, man. Hell yeah. So Chicago market's incredibly competitive. Still a seller's market. Over the last few years, coming out of COVID Chicago's been steadily increasing. Hell yeah. Which I'm very grateful for. Thank you to my clients. Shout out to you. I think in other parts of the country, like California, Arizona, Florida, you saw such a huge climb in prices coming out of COVID they couldn't keep up that pace. And that's why you're seeing some of those markets coming down a little bit. But Chicago, steady incline.

[Ray Gutierrez]

I feel like Chicago very much like Austin or Miami in many ways. San Francisco, they're very isolated. Their. Their own micro climates. No matter what's on TV or who's on tv, talking about who's on tv, how do you see the. The pulse of the country and how are they reacting to. With. With their dollar? Folks aren't buying. Folks aren't quite selling. How do you pivot that? How do you pivot the unknown?

[Sammy Lubeck]

Well, people are always going to have to move. You know, they're getting new jobs, they're getting kids into good schools, they're having babies. They need to upsize, they need to downsize. That's steady. As far as inventory goes, it's been a smaller amount of inventory across the country, which has led to it being much more of a seller's market.

[Ray Gutierrez]

Gotcha.

[Sammy Lubeck]

At the same time, from exposure standpoint, for me, you know, there's, of course, there's a reason why I was looking forward to doing this project. I think for the agents out there and in any industry, it's a different advertising style that we're seeing going from tv, print ads and everything to influencers, you know, who's ever getting the most exposures, getting the most clicks, and happy to increase my exposure to that, naturally.

[Ray Gutierrez]

Well, my friend, you do have quite a natural charisma about you. Was that something you taught yourself, or is this something you were born with?

[Sammy Lubeck]

My dad. Yeah. Dad had the gift of gab. He could talk to anybody. He could get them smiling, get them laughing. Definitely funnier than I am. But I got to tell you, I really Enjoy putting people at ease, putting my clients at ease, putting other people on the other side of the real estate deal. Other agents, attorneys, lenders, whoever. I think that it absolutely goes where, if people are comfortable, they're going to want to do business with you.

[Ray Gutierrez]

Absolutely.

[Sammy Lubeck]

And thanks to my dad. Thanks to Pops for passing along that ability to get people laughing and smiling.

[Ray Gutierrez]

Quite the legacy, my friend. Yeah, yeah, I feel quite at ease with you, my friend. I'm quite the contrary. I go into these talking about I going with the spears and looking for heads to chop off, but it's going well for me is. Anyways, speaking of, of the market, how do you stay clever or stay ahead and stay unique? Miami is very different than Chicago, obviously. Different clientele looking for a different experience in Miami versus someone in Chicago. How do you stay ahead and stay clever and stay, you know, in the. Within the imagination of that one customer that's got that extra obnoxious zero in his paycheck and is willing to go the extra mile to buy that property that's going to make him feel like a God.

[Sammy Lubeck]

One of the most important things that helped me become more successful in my industry is to realize within the luxury marketplace that those people that were buying the multimillion dollar properties, they just happen to have an extra zero in their bank account. 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. But one of the gifts that I have is being able to read people. And as far as, like, if they're going to be really intense, I know, I just have to stick to the script, make sure have results, get them to a house, see if they like it and move on, not waste their time over talking. But then there are other people that definitely need to be walked through the process.

[Ray Gutierrez]

Here's how you turn the doorknob to the door. You. You want to try it? No, I can.

[Sammy Lubeck]

Come on, let's go check it.

[Ray Gutierrez]

This is a window.

[Sammy Lubeck]

Yeah. So I think that reading all those different personalities is key. Whether or not you're a real estate agent or you're hosting a podcast, whatever industry it is, if you're in sales, if you're in customer service, you got to have that gift.

[Ray Gutierrez]

Otherwise it's stand up, you're up there, you're going to drown. I just dropped an F bomb.

[Sammy Lubeck]

What are you going to do? You're going to heard that word before, you're okay.

[Ray Gutierrez]

Drown. Oh, sure.

[Sammy Lubeck]

Yeah.

[Guest/Interjection Voice]

Yes.

[Ray Gutierrez]

But yeah, it is. It is a Lot of what we're doing right now is we don't go at home and talk like this when we're showering. You know what I mean? It's all part of survival. It is part of the gab for folks that are having difficulty finding that flow, that gap, that are struggling in sales, that are struggling picking up the phone and getting like, who are you? Click. How do you encourage those souls to keep going?

[Sammy Lubeck]

I think it's a very challenging industry right now. You have the people that have been in the industry for years that haven't been able to pivot to the new world of social media and video. And then you have the youngins, the influencing crew that saw how, quote, unquote easy it was coming out of COVID It was like fishing with dynamite because everybody wanted a new house. But now that they have to hustle with the limited inventory, it's a challenge for them. So I think it really is, is a give and take, trial and error. Online lead generation's been great for me because it provides a steady stream of leads that I can go out, meet and try and convert.

[Ray Gutierrez]

Awesome. How do you gain your leads? Is it Facebook ads? Is it clever videos where you're walking towards the camera and you deliver your why in the first 15 frames? Psychological warfare. AI. Give me the gamut, brother. How do you, how do you generate these leads?

[Sammy Lubeck]

All right, to all my competition, that's listening, get ready. Congratulations. For me, Zillow has worked advertising on Zillow and it's, it's a, it's a bad Z word in the real estate industry. But I've been, I've been advertising on there for about five years. Early on in my career, I did more Facebook ads. You know, they worked, they're, they're nice, but it's a lot of follow up and it's a lot of people that you're just not sure if they're serious about buying. Majority people that are looking on sites like Zillow, like realtor.com, like homes.com, they're looking for a house, you know, so it's a matter of, you know, navigating through the, you know, not every lead is going to be a conversion, but you better believe I'm going to find out pretty quickly how serious they are and if I can help them in any way, my team's going to do it.

[Ray Gutierrez]

Do you just quietly internally profile your clients immediately? Do you already know what they're looking for, what their, what their sensation is?

[Sammy Lubeck]

I think it's very important to get in front of your leads as quickly as possible.

[Ray Gutierrez]

Absolutely.

[Sammy Lubeck]

This industry, in most industries, you know, if you're selling, you know, a $5 product online, doesn't matter they're going to click it and order it. But when you're putting yourself in a position where you're helping people buy a million dooll property, you better believe they have to trust you.

[Ray Gutierrez]

Oh yeah.

[Sammy Lubeck]

And at the same time, trust is a two way street. So I don't want just some looky Lou. And many times I meet these looky lo who aren't serious buyers and that's okay because if I can be a resource for them, odds are if they're not ready to buy now, they will be down the road and I can provide a service and, you know, build up my reputation and I want to be as helpful as possible.

[Ray Gutierrez]

Right on. What resources do you share to be as resourceful as possible? Is it online classes? Well, PDF, like what's, what's, what's your hustle here to educate a potential customer?

[Sammy Lubeck]

I think it's all about access to the information. A lot of, you know, I, coming out of college, I actually was a teacher for five years. Right on. So I know about providing that information to clients. Sure. At the same time, you know, so many people are looking at homes online. Do they have access to like the private networks that only agents have access to? I provide that to my clients. If they're looking at comps, you know, recent sales in the area, I can get that for them in seconds. You know, it's just I, I, boom, get it. So I think that really just giving them the pulse of the market along with the information is critical. Anybody can send a website to somebody. That's a given.

[Ray Gutierrez]

Oh yeah.

[Sammy Lubeck]

But it's all about the whole package and that just provides a nice picture and makes them more knowledgeable to the point where, okay, if they're trying to figure out is this house truly worth, you know, overpaying in a multiple offer situation, we're going to help them get there.

[Ray Gutierrez]

What, what do you think makes a good you if you were to create a hamster ball because you want to get out of your business so you can help it grow. What makes a person in your field qualified to work for you or become the next user you can mentor? What does it take? Truly, not just being good at the gap, but what is it really?

[Sammy Lubeck]

The last few years I've gotten a lot of experience with people that, you know, were meant to work with me and not. And originally when I got, when I started at team, I thought, I'm going to bring in as many people as possible so that my sales volume can benefit, you know, from, from their sales. And what I realized very quickly is that these people were representing my brand as Chicagoland's real estate agent. So if they're not, if they don't have that attention to detail, if they didn't have the gift of gab, they weren't going to be good resources for our clients. It wasn't a good fit, and that's okay. And not everybody's going to be a great fit. You want to try and surround yourself with great people in every aspect of your life, but you do have a choice on who to go with. And, you know, if they weren't a fit, I wish them the best of luck and try to stay on good terms and hope to do a deal with you.

[Ray Gutierrez]

A lot of folks say it, real estate is easy, but I'm sure it's not a lot of sweat equity, a lot of time. Can you talk about your journey and how you got to where you are?

[Sammy Lubeck]

Absolutely. So I was working in sports television actually.

[Ray Gutierrez]

Right on, man.

[Sammy Lubeck]

And for many years I could definitely tell. Thanks, man. Okay, anybody want to know the score of the game? I got you. So with that being in, being a teacher and then working in sports tv, teaching, props to all your teachers out there, because when you start in that industry, you're not making any money and you are working non stop, grading papers, prep work. So to all your teachers, props. I'm glad I'm not one of you anymore because I don't miss grade in the papers and I don't miss the work. Okay. Gosh. Then I went transitioned to sports television. Same kind of thing. All the sports fans out there, they want to work in sports. The companies out there, whether it be a network or production crew, they're going to be able to bring people in and not pay them that much money because everybody wants to be involved in sports. Okay. So unless you're a big wig, you're not making a lot of money. So I started selling real estate on the side starting in 2007. And it just kind of blossomed to the point where after I was done working for the sports information company, I transitioned and gave my full effort starting in 2018 into real estate and haven't looked back since. And sure, I wish I was doing this my whole career because it's definitely just in me. I feel it, I'm very passionate about it. At the same time, those other positions I had, sure, they shaped Me. They made me appreciate the fact that, yeah, I'm making a little bit more money than I was now. I was able to buy, you know, some. Some threads for today and, you know, impress you guys with my looks.

[Ray Gutierrez]

I'm very impressed. I'm swiping right. I swiped right. What can folks learn from your episode? Give us a small preview of. Of what your Legacy Makers episode hasn't enforced.

[Sammy Lubeck]

Yeah, I talk a lot about my dad. Probably the most I've talked about him. He actually passed away a few years back. And really, the main thing is me being able to pass along information with a smile and a laugh and just really putting my clients at ease. Y. I, I think they're going to be making these huge, you know, financial decisions to the point where, yeah, they want to be relaxed. They want to be able to comfortably discuss the process and have results. But along with that, it really is about how I. I captured my entrepreneurial spirit at the age of 47 that I was stuck to that steady paycheck for so many years. I relate 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. So I would encourage everybody that has the dream, that has the financial Runway to really attack it, to really pursue their dreams.

[Guest/Interjection Voice]

Yeah.

[Ray Gutierrez]

Are you offering any sort of mentorship? Anyone that can just email you and be like, hey, but I saw you on that podcast.

[Sammy Lubeck]

I am more than happy to talk real estate with anyone and everyone Cool. They can find me at www.sammy.homes s a m m y dot homes. Yes, that is a domain.

[Ray Gutierrez]

That's easy.

[Sammy Lubeck]

More than happy to talk real estate. Sammy Homes, anybody. Buyers, sellers, agents, industry leaders. More than happy to help out in any way I can.

[Ray Gutierrez]

Sammy, such a pleasure.

[Sammy Lubeck]

Sammyhomes.com such a www.sammy.homes sammy.holmes yeah, wow.

[Ray Gutierrez]

Even better. Even cooler. I but sammy.holmes www.sammy.holmes such a great episode, my friend. That concludes yet another episode of the Legacy Makers podcast for Inside Success. I am Ray Gutierrez.