How to Get Out of Production & 2X Sales Every Year | Outliers

Have you ever asked yourself, why is it that some people seem to constantly outperform their potential? Call them an outlier. While other people with the best of intentions fall dramatically below or just below their expectations. And listen, they're not bad people. They set big goals, but they don't align their behaviors with what it is they want to accomplish. The next 7 shows, this quick little series I'm doing where I'm interviewing the outliers. What's the psychology? What's the mindset? What do they do that cause them to outperform their potential. Enjoy the show. Hey, so coming off the success of the Outliers shows, we decided we would take it one step further and talk to some outliers who happen to be team leaders and brokers that are experiencing tremendous success. Now, whether you're a brand new agent or you're an owner of a company, you're gonna get a lot of value out of this Outliers show. Hey, so coming off the success of the Outliers shows, We decided we would take it one step further and talk to some outliers who happen to be team leaders and brokers that are experiencing tremendous success. Now, whether you're a brand new agent or you're an owner of a company, you're gonna get a lot of value out of this Outlier Show. Well, Kyle, it's about time I get you on this show.

Yes, it is. Thank you for having me.

I was busting your chops. I'm like, what do I got to do to get on your podcast? You're like, you've been on my podcast. But I— okay, so Kyle, for the person that doesn't know who you are, where you're from. Give them like a little— I mean, 12 years in the business. Give them a little backstory. You know, why'd you get into real estate? How old are you? Where are you from? And then we'll get into the nuts and bolts of everything you're doing now.

Understood. So I'm 33 years old, born and raised in Boston, Massachusetts. And I got into real estate honestly because I was, I was in college and I was looking for what was going to be that next thing. I thought I was going to be an electrical engineer and I realized like it's a lot of school. Yeah. And lo and behold, I actually seen a piece of content on social media and it talked about the benefits and opportunities in real estate.

Yes.

And I seen what it did for my family and how my mom purchased a piece of real estate and it changed the trajectory of our lives.

Right.

So I kind of delved into it a little bit more. I wanted to get some more insight. And after doing the research, I was like, okay, I'm sold. Let me make this happen. And then, you know, time goes forward. Obviously, I had, I had to mature. I experienced some success, but I had to mature and understand that I was going to make this a career. And that's where becoming a broker, opening the brokerage, and kind of trying to build something that's bigger than myself, right, was born.

But you weren't— you opened the brokerage at 27 years old. You were 6 years in as an agent. Were you successful as an agent?

I was. You know what it was? It was success, but it was belief. I got to a point— I was the top producer in my office. I was with a big franchise brokerage. I became the top producer within my first year. But it got to a point where the other agents in the office were more comfortable coming to me and asking me questions that they should have kind of been going to the broker for. Um, so, and at the time I had my broker's license. As soon as I could get it, I was eligible, I went to go do it because I knew I wanted to at some point. I just didn't have the confidence, if you will.

Yes.

But it was when the team around me showed me that they seen it in me, it was kind of like, all right, let me take this, let me take a step back. If they see it in me, I need to see it in me, and I need to take this leap of faith.

I love that. So, so you get in the bit like 21, right?

Yeah, I got my license at 21.

So 21 years old, you go into real estate, you have some success, And, and I love that backstory. By the way, if I went to your website, if I couldn't read the story of how your mom buying that house changed the trajectory of you, and right, like, that should be on there.

You know what's funny? I need to put it on there, but every time I talk to somebody, they're just like, so when's the book coming out?

I, I agree. Well, hey, this is the beginning. You heard it here first, ladies and gentlemen. Here we go. So today, walk us through the trajectory. So you start your brokerage 6 years ago, you're 6 years in, you're 27 years old. You start to have a little faith, start to have a little belief, a little positivity around maybe I could do this. So, so tell us about the first couple of years, because if I'm correct, you may have been there. We went straight into the pandemic.

I was just getting ready to say, so I got the license approval February 20th, 2020.

Oh man, it was your fault. You did this.

Yeah. And at that time I thought I was going to go take over the world. I was prepared to hit the ground running. I knew how to sell real estate. Team believed in me. Let me make this happen. And then COVID hit and it was basically like, all right, that's cute, but sit down, figure it out and get your feet under you. And it gave me the time to really put the systems in place, really put the structure around the business because I had an idea. I knew how to sell real estate, but I didn't think all of the things that I needed to put in place. And to be honest with you, had I gone and done it the way that I wanted to, no COVID, I would have went out and generated a ton of business, but I probably would have failed because I wouldn't have been able to sustain and support all of it. Yeah, so it gave me the time to actually slow down and put the right systems in place, put the right people in place, and honestly learn that I needed coaching. It got to a point where obviously now I'm leading people, so I had to go find information, um, and just put into perspective, hey, you got to do it right.

I love that. And, uh, it's interesting that you figured out the demand side, but like in business, we know it's demand and capacity, right? If you generate too many leads and you don't have the right people in place, or you don't generate enough leads, you got too many people in place. It's always the balance between those two. So, so year one as a broker, give us like a sense how many agents, how many transactions. And we're gonna get into, as we always do, outliers. We want to know what's going on in here. So if you're listening, you, you know, you know I'm going there.

Year one, so funny, when I opened the brokerage, I was like, I know how much I'm making, I can keep the doors open. Yeah, I don't need anybody. I opened up with 2 agents. I ran into an agent that was at my last brokerage. She heard I was opening an office, she was like, I'm coming.

Yeah.

So I started with an agent. I didn't even plan on it.

Yeah.

Um, but we finished that year— I want to say we finished that year with about 4 agents. We probably did maybe 20 transactions or something like that. Nothing—

any of those were yours?

Probably all of them.

There's a reason why they call me a broker.

Yes, yes. Um, and at that time, you know, again, just getting started, we were heavily in rentals too. We were doing a lot, just kind of whatever was going to bring in a check.

So, so the next year is 2021. We jokingly call that the champagne and cocaine of real estate, right? Everybody was going crazy. The Massachusetts market, the New York market, some of those markets weren't the same.

Yeah.

How did you do in year 2?

So I'm proud to say every year we've doubled in business. So year 2, we got to 40 transactions.

Okay. Okay.

And then so on and so forth.

Right. So, so part of the, part of the game of this Outlier Show is to look at people that you know, did something last year, in this case talking 2025, and from, you know, 98 transactions, right? Which is— is that you? Is that the whole company? Is that a team?

So now, fortunately enough, I'm out of production, so that is now the, the company running. And my director of operations is fortunately out of production as well. Um, so now the team's carrying the bag.

I love it. I love it. So this year, the numbers show 38 closed, 31 pending.

Yes, sir.

So that is a I mean, you're basically two-thirds of the way to what you did all of last year.

Yeah.

So one of the things that I observe, and I want your input on this before we get into all the psychology stuff, is it takes time for agents to mature. It takes time for leaders to mature, to not be so snappy and fast and, oh, I gave you a lead, you didn't sell it, you're fired, right? So, so have you seen a maturation? Is that part of it? Is it, is it the marketing and lead generation? Is it the market? Like, why are you now— we're only 2 months and 23 days in and you've already done two-thirds of what you did all last year.

I would say it's definitely a maturation. Um, so it's funny, there's, there's the, uh, the saying that Jeff May says, the leads get better when you do. The agents get better when I do. Yes, the agents get better when I do. And I, and I say that all the time to my director of operations. Because don't get me wrong, as you know, there, there are always things that happen that we can get frustrated about and we can get upset, but it's like, hey, we're running the show.

Like, right.

If they don't know it or they're, they're expressing or exhibiting behavior that is showing that they haven't retained the information or learned it, we got to put the stuff forth to make sure that they're getting it or holding them accountable. So definitely a maturation and just becoming a better leader.

Yes, I love it. Okay, so let's get into the psychology. This whole, this whole outliers conversation. You know, January, we're in San Diego, we're talking about, hey, we, you know, we basically looked at Revy, our AI tool, 230,000 coaching sessions, completely anonymized. And what we're now mapping is like basically within 6 coaching sessions, we know if a client's an outlier, right? Or they're going to underperform their potential. That doesn't mean they're bad. Doesn't mean they're all great people. They all sell a lot of houses. Jill Biggs, who you know, says, ah, I'm an outlier. I'm an underperformer, right? She's like 546.

I was going to say, I don't know where the underperformer is in her.

Right. So, so, but we know the reasons why and we've broken that down on the show. So we won't go in detail on that. But I want to, I want to start with this question. Walk me through the last time you and your team missed a goal and then what did you personally have to adjust to get yourself back on track?

Oh, okay. I would say the last time. So we are a Zillow preferred team. And with that, obviously there are certain metrics that we need to hit. Recently, we actually did not hit one of our goals, and we've since then recovered, but it put us into an interesting perspective to where we were facing elimination or disengagement, if you will, from the program. So what did I change? I had to sit back and reexamine the entire system, really, and I had to look and see, was it me? And a lot of it leads to me as a leader making sure that I'm putting the right things in place, but just examining the entire system. Did we have the right people? Did we have the right systems in place? I think in that it exposed a lot for us. There were a lot that we thought we had control over or we thought we had buttoned up and we really didn't. And having that program or at least being put in that position gave us an opportunity to really stress test our system and see where are the leaks, what can we adjust and how can we make it better?

We literally were just in this conversation like, where is the sales friction I need to remove? Where are the gaps in? So, hey, I know I'm interrupting the show, but check this out. You know, when I built my business back in 2004, I was very clear. Whoever gives away the most high-value content for free is going to win the game. And I think it's one of the big reasons why my company and my 193 coaches have been named the number one coaching and training company in real estate for 12 years going. But my question is, like, we do all this stuff on content and, you know, video, podcasts. But have you ever been to tomferry.com/tools? tomferry.com/tools, T-O-O-L-S. If you've never been, you should check that out today because there is so many playbooks, systems, strategies, marketing hacks, tactics from top agents, from coaches. There's so much there. If you thought the podcast is good, tomferry.com/tools, check it out, and then send me a DM on your favorite social channel and let me know what you think. All right. Let's get back to the show. So in that exercise, this is helpful for everyone listening. Um, what was it? Was it, was there multiple things or was it one or two things? And if so, what were those specifics? And then how did you then solve it at scale for the size of your business?

So it was, I would say I narrowed it down to two things. One, it was leadership because as leadership, we needed to make sure that we were putting the right things forth, or at least I needed to examine that. And we did. We realized, okay, well, we have the trainings in place. But what was missing or where the disconnect was, was the accountability in the team to live up to the things that they were taught and execute the way that they were shown. So leadership for sure, but then the accountability that we placed on them, or maybe it's holding both leadership accountable and the agents accountable, but we had to address or identify it, talk about it, and then bring it to the team.

So was it CRM audits? Was it like, like when you get to the tactics, like for even for a solo agent, like Have you ever taken the time to, like, look into your CRM and go back, like, to September of 2022 when the rates went to 8%? Mm-hmm. If you just started there and you looked at every lead you had in your, in your funnel and how many of them have now bought a house from somebody else 'cause we didn't follow up, right? We both know it's a startling number. So, so what did you do? Was it the CRM audit? Was it, you know, monitoring a little bit closely? What, what did you do better?

It was, it was a, I would say a mixture of both. We did a lot more CRM auditing, but we did it— obviously now we're in 2026 and, and at tail end of 2025, it was a lot more AI-focused. So we were utilizing AI to examine our business, dive deeper into the numbers, and really help us focus on the things that we should be focused on. Because, you know, we— again, we thought we had everything. So it was really focusing on that, but also looking at what the agents were doing.

Yes, yes.

And we were able to now have conversations. We got better with our pipeline reviews, our one-on-one meetings. We were already doing weekly trainings and weekly office meetings, but the accountability side to it of, okay, hey, we talked about this, you said you were going to do this, you didn't, how do we adjust this, right?

So, so just for my friend watching or listening, we're in Miami right now in Coral Gables, and we got, you know, a couple hundred extraordinary team leaders in a room, and we're having all these interesting conversations. I'm just curious, what was your take on Carolyn Young today talking about having virtual assistants though they don't call them that, as basically the agent interface to make sure the agents are doing everything they're supposed to do inside of their CRM and more. What was your takeaway on that? Well, or how did you share with the listener? What did you hear? And then give them the insight.

I heard better leverage. I heard a, a way to grow the capacity of leadership without growing the funds exponentially, or at least growing the cost exponentially.

Cost in Massachusetts versus a virtual assistant doing the same thing.

1,000%. And it's funny, on the way up here, I actually had a conversation with Carolyn about that, and we set up a call. So shout out to you, Carolyn. She said she was going to watch too. So, um, but it was, it was great. It was, it was— I have 5 or 6 VAs already, but to think— I didn't think to put them in that position and, and leverage it that way, because that is something, like she said, 8 hours a day. Now we can have somebody focused on it rather than system we tried. We tried, we did, we still have a mentorship program, but we tried implementing different mentors and it didn't necessarily work out. Um, but I loved the virtual assistant idea.

We don't want to call them virtual assistants, but you never want to call them a virtual assistant. They're a teammate, right? You call them a VA, it's like it might be degrading to them. And, and then others in the organization might know these are rock stars that just have to live someplace else in the world and work virtually.

1000%.

So I loved that insight. And maybe that's— I think there's gonna be a lot of people coming out of this meeting that are like Oh, I'm doing that amongst everything else.

I told her I was stealing that.

So, so a big question that you and I as, as CEOs, as leaders have to face is like, how do you decide whether a strategy, if it's not working, what do you do? You got something in your place, it's not working, and maybe I'll go deeper. Is it a people issue or is it a systems issue? How do you analyze when things aren't working?

Well, we certainly look at, we look at the entire system. First off, and sometimes I try to lean on it's not the systems because we have a lot of the best systems. It may be that we don't know how to fully work the systems or interpret the data. Exactly. So I think it starts there, but a lot of times we examine the entire system and we try to, like I was saying earlier, see where the leaks are, and then we can address it there. So sometimes it may be a people issue, and we've all been there. We've all either needed more people, we've needed better people, or we've had to get rid of some people. And unfortunately, I've experienced all three. Um, and same things with systems. We've had a great, we have a great tech stack now, but we've had to change things. We've had to add things. We've had to prune things away. Um, so I don't know if there's one answer on how we decide, but it's really, we stress test the system where we look at what are the issues that we're facing? Where are the leaks at? And how do we solve that?

Hey, I'm interrupting my own show with a little PSA. What are you doing August 3rd through the 5th? Well, it's going to be my 23rd, maybe my 24th. I should probably know that. Annual Success Summit, where thousands of the best agents from around the world gather for networking, idea exchange, and making strong commitments so September through December are better than they were the year before. So I'd love for you to write down those dates, and if you're interested, check out tomferry.com/success. That's tomferry.com/success to find out the best ticket rate, 'cause I can't wait to see you face-to-face in August. Do not miss this. Mark your calendars, get it in there, and I'll see you at the summit. Now back to the show. So I'll tell you how we, we attempt to do it amongst my management team. Consensus-based, data-driven meritocracy. Right? So we want consensus, right? Because if I just walk in and say, we're doing this, then my management team's like, ah, Tom Ferry seminars. You come back with too many ideas.

The Tom bombs.

You with me? Like, That there's actually a Slack channel called Tom Bombs and I don't follow it, um, because I create the bombs. But consensus-based, like getting consensus on is, do you find that that's important as a leader? It is like getting everybody on the same page. Everybody's voice gets heard, then we like decide and commit.

It is, it definitely is because you have to have buy-in from the people that are gonna be executing.

Right.

So it's definitely important.

Right. How do you balance the data-driven decisions, the reality of the numbers and the numbers and the numbers don't lie. Um, versus the people side, cuz you know, oh yeah, but you know, Phyllis, man, we, we can't cut Phyllis, right? Like, you know what I mean? Like there's that side using the worst case scenario, which is having to terminate somebody because you created a strategy, you built up a person around the strategy, the strategy goes away. What do we do with the person now?

To be honest with you, coaching has helped me with that a lot because I am very much the, I think I can fix, I think I can help everybody.

You're a bug and a fixer.

Yeah. And, and, and I think I can fix everything and I think I can help, but To be honest with you, um, sitting down with my coach, sitting down with my team, my director of ops, he's a huge numbers guy, and I'll be the one that says, oh, maybe we can help. And it's like, no, this is what the data says.

Yeah, the math says no.

Exactly. And, and, you know, a saying, a quote that we always use all the time is, if you're doing the same thing expecting a different result, you know what you are.

So, you know, it's interesting, I, uh, with Jill Biggs and, and one of my mastermind groups, I had Robert Refkin right? Because he was in town, we had dinner the night before, we're in New York City. I'm like, hey, why don't you come over this little mastermind? I got all these like rockstar agents there. And he was like, yeah. And one of the things he said that really stuck with the group was just that exact thing, Kyle. He said, I said, what, you know, what's as for you as a leader, 13 years building this company, now you've acquired Anywhere, and now you're like this monster behemoth. And he said, you know, every 18 months, if I'm doing the same thing today that I was doing 18 months ago, I have failed as a leader. Yeah, I've got to continually evolve. Which leads nicely to my next question, which was, as you grew your team, what was hard for you to let go of, but once you did, everything changed?

Control.

Unpack that.

Um, so again, in starting the company, like we talked about earlier, I was the top producer. And starting the company, a lot of the business was done through me. And normally I would think that in that type of scenario, you always think that you are the best person for the job.

Of course.

Not that I don't believe in my team and I don't think that they can handle it, but it's, it's just easier if I do it.

Yeah.

I had to get out of that. I had to give up control. I had to stop trying to do everything, have everything go through me and one, empower the team, but also really empower my director of operations. It was the leverage that I was able to get in hiring him. We were able to scale and grow the team. Um, but also it got me out of production so I could focus on the actual company. Growing the company, making sure that we had the things in place that our team needed. Because if I'm selling houses, I can't necessarily be everywhere at once, right?

So, but how do you give up the control? I mean, you know, again, even as a top producer and as a young CEO, it's your paycheck. You with me? It's your checkbook. Your name is on the lease. You know what I mean? Like all that pressure, I see it as a way, like it consumes people. And they basically screw themselves because they try to control, the photo's gotta be taken this way, this is how I want the people's bios to be. Did anybody look at the Google business page? And like, you know, like my team's over listening like, all right, control is maximus. Like I look at everything and I'm like, right, I'm always pretty like, oh, we can make this better. How do you, or do you try and mitigate some of that by empowering the people around you?

1000%. And that's the only way that you can execute that at scale is you have to empower the people around you and make sure that you have the right people in the right place. Right. Um, it's funny, it's a saying that we have in our market: gotta have the aces in their places, right?

And aces in their places.

Yeah, um, so aces. No, definitely. And, and I was going to say, you have a good team. I mean, yes, you may be controlius maximus, if you will, but in talking to my kids, I have. But, but in that, um, it, it's— you still make sure you put the right people in place and trust that Trust them to make decisions, have input and things like that so it can continue to scale. Because if we're stuck with just your ideas or my team is stuck with just my ideas, it might get stale.

Yeah. The founder's dilemma. We get so many data points and so much insight. You know, it's like, so, so you get the same, you got the same issue I got. I got a thousand things coming at me and I do a pretty good job sorting through what's important and what's not important. Um, how do you do that? How do you make sure that you're, you know, you're keeping the ship going the right direction? And not missing mega trends happening around you, or, and not overreacting to things that maybe don't need any overreacting? Like, how do you do that?

A lot of it is I slow down. I slow down. I try to make sure that I'm not misinterpreting things, but I talk— again, this is where I guess the consistency comes in. Consensus. That's where that comes in, because I speak to my director of operations and I talk to my coach a lot. I'm throwing stuff at him all the time, like, hey, this is what I'm getting, this is what the data says, this is what I'm thinking. Am I on base here? Is there something that I'm missing? What should What should I be doing? And Coach helps me all the time.

My mentor, which I really wish, you know, you and all my friends could have met this guy, is Mike Vance, right? Worked for Disney, mentored Steve Jobs. Like, it's just— hey, it creates a lot of pressure for me, right? But I can imagine one of the things he would always say, Kyle, is the problem that most leaders have is the arc of perspective. And what he would say is, you know, if you kind of imagine an arc, right, like a triangle if you will, if you're down at the end of it You don't see the whole picture. You have to step back and see the whole thing. And he's like, that was Walt Disney's superpower. That was Steve Jobs' superpower. That was Jack Welch's superpower. He said even Mother Teresa, who he worked with, that was the superpower, the arc of perspective. So you say slow down, and I love it because then it's like you get a minute to rethink about it, right? To really examine and reexamine like, what is the right move? But let me ask you this, because one of the outlier things that we observed When you look at like all of you that I put in the outlier category, you hop off a session with your coach, how fast do you take action?

Immediately.

That's the key.

Okay, and I love that. You know, it's funny, I think that's why I said slow down is because I know I make decisions quickly.

I'm—

I believe in what you say. Hey, if, if you can do it quickly, it can be reversed without messing everything up. Yeah, go for it. Yeah, and I do that. I eat, sleep, and breathe that. Yeah, so sometimes when I have to examine things and see what the issues are, I have to slow down and like you said, see the whole picture because I know if I got enough information, I'm making a decision.

Right, right. All right, I got another question. When results stall, because they always do for all of us whether we like it or not, because right now you're sitting at, call it, what is that, uh, 69 closed and pending, which puts you on pace for, because in Massachusetts you don't close deals in like 3 weeks, Right? Takes a little, takes a little more time, probably between 160 and 190 closings, right? For the year, which is, you know, puts you at double what you did last year. So you're keeping your trend going. The question is when results stall, what's the first thing you examine?

First thing that we examine would be the output. What is our team doing? Where, where are the leaks? And then if the output is good, then I'm checking with the team. I'm checking their mentals. I'm trying to see what's going on with the distribution. What— where are the bottleneck issues and how can we address those?

So, so if a home's not selling, the rule is like, hey, if you're not getting 3 showings a week, right, then there's something wrong. If you get 3 showings a week and it happens for a month and you don't get an offer, something's wrong. Do you have some, some data that you look at that way? Because It is sometimes easy to examine the number side, the funnel side with a real estate salesperson. Um, but then that other side is you just brought up, it's the mental side, which is far more interesting, far more challenging, never seems to ever go away.

Ever.

You with me? Like we're therapists, psychologists, psychiatrists, slash, you know, helping people sell houses. So, so like the example of the, the listing, 3 showings in a week, 3 showings, 4 weeks back to back. No offers. Houston, we got a problem. What are some of the data points you're examining on that end? I mean, is it just contacts, leads, appointments, conversion? Like, is it that simple?

Well, yeah, we're looking at conversations. We're looking at how many people are actually writing offers. We're looking at how many appointments they're going on.

Offer to accepted.

Yeah, we're tracking everything. So we— again, this is back to becoming better leaders. We weren't getting that granular with the data. Then I had to go and upgrade the tech stack. So now we have a CISO.

So we're tracking everything.

And now it's sitting down with my coach and saying, okay, this is what the data is giving me. What do you see that I'm missing?

Yeah, yeah, yeah. And then it's like non-anecdotal, it's precise. And it's not the team, it's Phil and Mary. You know what I mean? Versus getting in front of your whole team and going, listen everybody, you gotta follow up more. But really what I mean is Phil and Mary, just you two, you know what I mean? But that's a mistake that a lot of leaders make. This is a problem we have. But it's actually those two people. Just have a conversation with them and then celebrate everybody else.

1,000%.

Any other— like, when results stall, what else do you look at on the mental side? What do you do there?

Well, we talk with the team. I mean, a lot of stuff we focus— we're big on culture. So if we have to, we'll take everybody out. Like, a couple weeks ago, I took the entire team out to steakhouse and was like, order what you want. Yeah, you know, it's different things. We're very big on camaraderie. We do a lot of team events. We do a lot of things in the office. So I mean, and of course it's not a one shoe fits all and fixes everything, but it's just trying to make sure that we relate to people on a humane level and understand really where they're at. Even when I start my one-on-ones, the first question I ask is, how are you?

Yeah.

Is there anything that I can help you with? Where are you? And whether it's monetarily, whether it's physically or anything, if there's— if you just need somebody to talk to. Yeah, I start there.

Yeah. So you do one-on-ones with everybody?

I do one-on-ones with the—

you got a group? All right, okay, so it's divided. Um, am I the only one that goes with your face-to-face? Hold on, let me grab the tissue.

Right?

Do you have some of those moments? All the time, of course.

But that's because they're real conversations. They're real conversations, whether it's talking about something that's going on in their life, whether it's talking about real bottleneck issues, or just them knowing that they got to get out of their own way. Um, It happens a lot, but one, it makes our relationship stronger. It makes them stronger. It makes me a better leader because we can have those conversations and they know that they can talk to me.

Yeah.

Um, but 1000%, I keep the tissues close for sure.

For sure. It's automatic, right? Uh, so what does coaching do for you that if you reflect back, it would just be harder and harder to do it on your own?

It shortens