How Jason Cheperdak Built the #1 Real Estate Team in the DMV

Host2 00:00

I made a million bucks for the first time at 30 years old.

Host 00:03

What do you think it is about you that makes all of these people want to stay?

Host2 00:06

Like, no for sure. Being a salesperson is a really bad idea in our industry.

Host 00:10

How do you know how to partner client A with agent A?

Host2 00:14

Every conversation that I have, I try to have an unbelievably clear intention.

Host 00:19

You've got to be all in or all out.

Host2 00:20

Yeah, but don't you want people all in on you around you? We don't have time for people that are like, just want to be in because they want a piece of me. I mean, come on, that's horrible.

Host 00:28

What's up, everybody? Welcome back to the Partner Profit Podcast. I am very excited for my conversation today. I've got somebody on I've worked very closely with that has just skyrocketed in business, is absolutely crushing it. And I'm excited for you guys to hear more. I've got Jashant. Of course I would do that. Jason Shepherd is correct. Before we got live, so I went to Jay Sh uh Jason Shepherdak or Shepherdak. Goodness gracious.

Host2 00:53

Nailing it. Once you get it, you never forget it, Grant. Come on now.

Host 00:56

I am crushing it. So good. Man, thanks for spending some time with me, even though I am absolutely butchering your name.

Host2 01:02

That's fine. Always, always have to spend time with you, Grant.

Host 01:05

Yeah, yeah. Well, for people that are listening to this and maybe don't know much about Jason Sheppardak. Give us a little bit a little bit of the backstory, man. How do you get to where you are today?

Host2 01:16

Oh man, um, I am a crazy backstory. So we'll skip the whole fleer skating spandex ice dance part of my life and we'll get right into the business part. Does that sound okay? Okay, that's story for another day. Um, I was a store manager during COVID. I bought my first house and it like didn't go well. And my wife was like, you know, you've always been in real estate. My parents flipped homes when I was younger, you know, it's always been in my blood. And I was like, you know what? I will get licensed. So I got licensed with an intention to make $3,500 and make back the cost of my licensing and sold nothing for six months, but then sold nine homes in the back six months of the year, and I netted like 48 grand. And at the time, my wife was in law school. I was making about 120 grand a year. It was tight because, like, you know, law school is expensive. And that was a really like life-changing amount of money. But at the same time, I recognized that I became the person that I didn't want, which is like the uneducated realtor that didn't know what they were doing. And I just helped nine people do things really bad. So, shout out to my clients who were my first nine clients. And I just realized, wow, if I'm gonna do this, I gotta be really good at it. And I felt really called to be really good at and make a change and a difference. So I changed teams and joined the absolute best team I could and learned to become a really good realtor my second year. And then I started interviewing all of the teams in the marketplace and kind of realized there was a niche missing in my market of how teams could operate. And I got a bigger vision of what I wanted to create, and that's where Shepard Holmes Group came from. And very quickly it kind of blew up and had my first 150 million plus year. I made a million bucks for the first time at 30 years old, 750 grand in real estate, 250 grand at Target, and was like, I should probably quit my job next. That's awesome. And um, I lived a double life because people at Target didn't know I did real estate, and people in real estate didn't know Target. So it was like a really weird mix. And we had started to get to know each other at the time. I was going through all these like midlife crises and trying to figure out how do I grow this, what do I do? And so went all in, quit near the tail end of uh COVID, and started the Shepherd Homes Group and rode those kind of like last big waves of those COVID years. And now we just became the number one real estate team in the DMV, Maryland, DC, and Virginia officially in 2025. So we're very blessed to be where we are today.

Host 03:44

That's absolutely amazing. Yeah, so many questions that are unrelated to this, but I'm gonna try to stick to the topic. Um so you know, the point of the show here is like teaching people how do you turn your relationships into revenue. And something that I admired when I worked with you and and still do is you're not a team leader in like a traditional sense where you you still sell houses, like you are still out there doing business all the time. Your relationships are really important to you. And so I guess just kind of kicking it off, answering that first question is like, dude, how do I turn my relationships into revenue? You've obviously done a fantastic job of this.

Host2 04:19

I have a phrase that I talk to all my team about, which is how we talk to people. And that's where we set the tone of our business at the same time at the same time simultaneously. And so for me, every conversation that I have, I try to have an unbelievably clear intention that has a very unbelievably clear purpose. And if your intention and purpose is clear in every conversation that you have, the way that you do business, the conversations you have, and how the person on the other side feels dramatically changes everything. And so I always say my intention is to help others or create abundance for others. Okay. And my purpose is to create solutions that no one else has to create that in their lives. And so, whoa, by having clear intention and purpose, every single conversation I have automatically forces the relationship to really have a more abundant basis to it. And it's transformed the way that we do business and the way that my life is and how my personal business is.

Host 05:15

How did you stumble into this philosophy? Is this something you just have always had, or is it after making some mistakes? Or how did you get into it?

Host2 05:23

No, no, no, no, no, no, no. I think we all start out as salespeople because we're told to be salespeople in our business. And what I know for sure, like, know for sure, being a salesperson is a really bad idea in our industry. Okay. The idea of selling people on things is so archaic. It is gone. The consumer today knows when they're being sold and they don't want it. You know what we want? We want authentic relationships that create trust and create consistency in our lives where we know we can count on others. That's what I believe. And when you're buying a home and building a relationship with someone, having authenticity and transparency is even more important. I think everything's magnified when you have something so significant. And that didn't really hit me until about two years ago in my business. Cause when I said, when am I totally crushing the game, right? In my sales, it's when I just I'm so busy, I don't have time to not be just me. And whoever wants to work with just me loves me. And those are super authentic relationships and conversations. That's when my business was exploding the most. And so we reframed the way that we taught our team how to do business all about being your authentic self. And if you look at my team's website, it's a very diverse group of people. And now we throw leads and do lead distribution all by that authentic human connection of who people are. So I think it goes very deep in my life.

Host 06:51

How do you know? I've heard of another team doing something along the lines of their inside sales agents were taught how to ask specific questions to decipher what somebody's archetype is. So it's like, okay, no, we know that you're gonna be really good to work with this agent, which is not necessarily saying that's what you're doing, but how do you know how to partner client A with agent A? Like, how do you put those two pieces together?

Host2 07:17

No oneself is key. It's not about knowing the other person, it's about knowing you and your team more, I think. So, for example, a lot of teams struggle where you've got a huge group of people, you don't know them tremendously well, and they're not all like the competency level isn't always there. There's a lot of diversity in your own team. It's your team that's inconsistent, it's your business that's the variable. I think one thing that's eraning about us is our agent base has been with us for so long. Everyone stayed with us for a very long period of time. We know them so intimately as humans and as salespeople that that intimacy allows us to understand who can be malleable to meet a broader sect of who this person might be, that we can fit people in easier to the needs of that client. Okay. So I think that's more of the reverse psychology of it all than trying to like perfectly identify who the consumer is. Does that make sense?

Host 08:13

It does. So your team, you know, from an operational standpoint, spends an enormous amount of time, I would imagine, getting to know or has had an enormous amount of time getting to know the agents in the organization to know you're gonna be good for you, you're gonna be good for you, you're gonna be good.

Host2 08:27

Yeah, but I'm also like in the business with them. So I sold 97.7 million in individual production last year.

Host 08:35

I don't think people, I don't think people realize how difficult that is to sell almost a hundred houses a year by yourself and to have a team that is doing the volume that you guys are doing, like that is crazy, ridiculously challenging.

Host2 08:50

Crazy. So, like when I think about how that operates, I do business in the team with the team, and that gets to know the team completely differently, right? Like I signed 68 listings with my team last year where I went on the payment with the agent. So that kind of involvement in the business with the person also gives you lots of drive time conversations, problem solving, winning and losing together that build deeper relationships. And then the rest is like time. You know, a lot of agents have been with us for a couple of years, and it takes time to get to know someone.

Host 09:27

A thousand percent.

Host2 09:28

Yeah.

Host 09:29

How do you get to know somebody? Is it through the practice of selling real estate, or do you are you doing other things?

Host2 09:34

I take the business so seriously. So I think my problem as a leader is that I am so business and so personal, they're very separated. So for me, I'm like, no team events, none of this frou fru stuff's going on. Like, no one cares about that stuff unless you're totally winning. So for me, I'm like, well, if I'm gonna spend time with you initially, let's go spend time winning in your business first. Because if you're winning and you're economically prosperous, everything else is easier. Conversations are better, you're serving your clients better, advice is better, everything's easy. Okay. And for me, I want to spend time with people where I'm helping them strategize and grow, not like do the basics of the business. So I have found by focusing on business first, production first, client first, serving first, that putting us in that environment allows me to understand my team as an agent in their environment first. And then naturally you understand who they are as a person because you identify their weaknesses and strengths in their business. And then we peel those out. And we're like, oh, when you grew up, your parents told you this, and this is how you formed your opinions and ideas. Well, let's smash that because you're way better than that now, and you open up all these different conversations. But for me, it always started with the lens of real estate sales and business.

Host 10:47

Yeah. I'm sitting here knowing what I know about you, and I'm like, wait a second. One of the most productive real estate teams in the DMV, you just told me that you started a property management company, you've got a thousand doors. I know you clip properties all the time.

Host1 11:01

I do.

Host 11:01

I'm sitting here like, there's only 24 hours in a day. Like, how on earth do you have so much time? And you sold a hundred houses by yourself, so it's like, yeah, so this math isn't mathing. Like, help help help me understand like how how do you get the time to also go deep in these relationships? It sounds insane to me. And I think it probably sounds insane to the average person, too. So that's why I'm asking.

Host2 11:24

The whole 80-20 rule thing, you have to take to heart because if you're not reassessing your time commitments constantly, it won't work. I also think that people just don't understand how much I work and what I'm willing to do right now, and that's a personal choice. But like seven days a week, the only time I'm really checking out is uh Sunday mornings. I have a slow Sunday morning, I go to church with my wife, we have some time together. But like I think the regular day for me, I mean, I'm up early, I work out, take care of myself in the morning, but like nine to nine thirty is a normal day for me every day. So a lot of hard work is the answer. But then you got to scale through people. And scaling through people is the big miss because there's a financial and time commitment that is a drag on the business initially. Okay. So like I hired my first personal assistant in addition to transaction coordination, TC, operational support, and all of that, just a personal assistant of like four years ago. And that position's evolved and evolved and evolved and evolved over time. But like that was a big initial investment. Like having somebody manage your email during the day for the first time, it's not a productivity win.

Host 12:43

It's the least the least efficient thing in the world.

Host2 12:47

It's like every email that goes out, they're like, How do I respond for the first 90 days? Like they have to memorize everything about you and your schedule. So it's like it's six months of pain for future gain as long as they survive. And then they're also, you know, at the performance level that meets the expectations of the role. So that's what prevents people from really growing at mass, is like not being able to like have the grit to push through those 90 days, those six months of investments and the growth cycle of new people. But without it, you can't end up growing and having the leverage to all the things you really need to do.

Host 13:25

What do you think it is about you that makes all of these people want to stay? Because your retention is also admirable. You don't think you don't think people like me, Griant? Well, I know I'm saying people must. Like people must really like you a lot. Like I think you know, one of the things that I've always observed about human behavior is the greatest way to facilitate behavior modification is modeling. If I see you doing something that I admire, respect, want to do myself, I will just do whatever you're doing. And I think what uh I go back to like what I admire about you is like you are always, always, always, always practicing what you preach, you're working. Like I said, I can count on one hand the number of team leaders I know, maybe even like less than three fingers, like the number of team leaders I know that are also personally selling 100 houses a year. And to me, I feel like that's the answer. But I'm curious, what do you think it is?

Host2 14:24

Consistency. Consistency. I think uh, you know, I you can look back at the backstory. I I've had a difficult rising. I haven't always won. I've had so many losses along the way. But uh the consistency in what I call the core three are what I think make us really successful. So consistency in the business vision and expectations is number one. So the vision of where the business is going and the expectations of being in the business, the standard that's set is like the first category. The second category is the consistency I hold myself to. Because if your business is consistent and you're not consistent, well, nobody can follow either. Those are the foundational two. And then the third is a cultural consistency. So we have four core principles in the company. Zero dramas allowed. Dramas a meaning that you're more important than others, not tolerated in my world. Number two is zero assumptions can be made on anything. Zero. You can only assume one thing, which is good of others on the team, period. Prevents a lot of drama from happening. The third one is to be your authentic self and speak truthfully always. There's any bullshit answers, we call them out publicly. There's no private conversations in my world whatsoever. Um, and then you have to solve problems positively. If you complain, you're out. If you complain, I immediately say, go find the solution, come back to me. There's like no tolerance for that. And so that cultural aspect has been glued to everything else. Because I think naturally, if you kind of describe those four things to people, that's naturally what everybody's always wanted in a work environment. And that's what I I absolutely allow. I had to let someone go last week because they couldn't model those behaviors. That's how strong uh they are to us. So I think those are the three pillars that uh allowed us to be where we are today. It's so good.

Host 16:22

Yeah, letting people go. It's hard. Having tough conversations.

Host2 16:28

I really struggle with it like anyone, but I joke I know I've never fired anybody. I believe in a three-step firing process, which allows the individual to decide whether they should stay or not. You want to talk about it? So three steps. Three step number one is self-realization. Okay. And what you're gonna recognize is not everybody has the ability to self-realize that they're in a position where they are not performing. And so if they don't know they're not performing, you gotta start there. Because have you ever been fired or let go or given feedback or totally just side-blazed you? I have. Like at Target, I thought I was like hot stuff assistant store manager, like no one had the pillow aisle like I did. Oh my god, you should see my color-coded pillows. My boss was like, no, the whole thing's backwards. I was like, oh damn. You know, there's so many examples where you're like blindsided. So self-realization is number one, and that takes some time for people, and you have to really coach them and have really authentic culture to make sure that they understand what the expectation is and if they're there or not, right? Then number two is you have to gut check yourself and say, am I giving everything that I can to the individual or am I giving up on them first? And then you have to have a public, public and transparent declaration that the environment is there for that person to get whatever they need from you and that you confirming that you are giving it to them. Then the third step is you ask them whether they should be meeting expectations, whether they're meeting expectations or not. And they need to be able to articulate to you whether they are or not. And then you ask them, well, if you're not meeting expectations, would you keep you employed? Now you can't get there unless one and two are done really, really well. And that usually takes about a month and a half to do it a really high level. But at that point, they fire themselves the majority of the time. And ironically, when you take them through those processes, everybody else feels it. And by the time they're let go, the whole organization understands it, sees that all the opportunity that you've given that individual. Other people have gotten coaching moments simultaneously, and everyone's like think thankful that that person is now gone. And often those people that have left us are thankful for the time that we gave them, but we have great long-lasting relationships with them too.

Host 18:46

I would imagine there's enormous amounts of trust in your organization because it sounds like there's an enormous amount of transparency and communication and insight.

Host2 18:53

Yeah. Yes, but with that comes a very volatile in and out. So I am unbelievably trusting, like almost too trusting, but the moment that the trust is broken, it's an instant firing. There's no grace, there's none. I always say that you're all in or you're all out in my world. There's no balance. You're either like extreme in or you're extreme out, one or the other.

Host 19:19

Obviously, it works.

Host2 19:20

People that want to be enter in. And people that want to be inner in. It's like a merry-go-round going really fast. If you don't lean in, you naturally fall out.

Host 19:31

Yeah, that's a really good analogy. It is. But it leads to an enormous amount of success. It's not something that happens overnight, but you know, you've built an incredible, incredible set of companies in a relatively short time based on these animals. I guess.

Host2 19:47

Yeah.

Host 19:47

Yeah, but don't you want people all in on you around you? Without question. Without question.

Host2 19:53

You don't have time for people that are like just want to be in because they want a piece of me. I mean, come on, that's horrible.

Host 19:58

I think we have when you have too much going on, and I I think that that would be a principle even if you didn't, but when you have so much going on, any any little bit of a drag. I was in a conversation, I got to interview the gentleman that uh was the founder of Magnum Nutraceuticals, which is one of the larger supplement companies in the US and Canada. He had this analogy talking about like, well, I I could have a bunch of grants on my calendar that are just amazing and the best, and then I could have some Dugs on my calendar that are just time sucks and energy sucks. And he's like, one of the things that I noticed is if I have one Doug on my calendar, even if I only have to meet them for 15 to 20 minutes, it takes three to four hours of my energy. And then if I have you know 10 grants on my calendar, it gives me energy. I can go all day, I can be around, I can. And so I would I would wholeheartedly agree. You've got to be all in or all out. I love all in people. Like they're merry-go-round going really fast. Yeah, like what are those little spinny things on the playground, right?

Host2 20:54

That you used to have when you're younger, like, oh, I'm barely holding on. You're like, get leaning harder.

Host 21:00

Let's go. This has been one of my favorite conversations. I really appreciate you sitting down and spending some time with me. I want to respect your time. And I think the last question I always like to ask is how can we partner with you? What's the number one way that we as listeners of the podcast can support you, help you grow? What's important to you right now?

Host2 21:17

Man, you can always refer people to us in the DMV. That's always great. I would say follow me on Instagram. I love sharing. I'm really trying to share a lot of value to the real estate community on tips and tricks uh for anybody who's a realtor. And I have a real estate course that I offer to the whole brokerage. If you're locally for free, you can buy it online if you want to take that course. Unbelievably helpful. But if you're an agent that is like struggling with production, you're in the same place for a long time, I'll give you the course for free just to help you. I didn't make the course to make money, I made the course to help people. And I'm going to be redoing that course at the end of the year. And once that course is redone, it's tripling in price to $2,400 for the course. So you can, you know, capture that free course option from me now if your agent's struggling. Uh, and I'm happy to help.

Host 22:02

That's awesome. I really appreciate you doing that. Appreciate your contributions, appreciate the conversation. As always, think highly of you and everything that you do. So thanks again for spending some time with me today.

Host2 22:12

Yes, sir.

Host 22:14

Awesome, awesome. And thank you all for continuing to listen to the Partner Profit Podcast. This has been another absolutely amazing conversation. I'll see you on the next one. Peace.