Seth: Hey, everybody, how's it going? This is Seth Williams and Ajay Sharma. You're listening to the REtipster podcast.

Ajay: That's right.

Seth: Ajay is back in the co-host chair today because we're talking with Katie Desmarais. Katie has actually been on the show before with her husband, Brian. That was back in episode 241, where we talked about how they built and scaled their land business, how they structured their team, and how they made the transition into full-time land investing surprisingly fast.

Today, we're going deeper into something Katie has become especially known for in the land investing world, and that is sales, leadership, and coaching. A lot of investors think their business is mostly about pricing and data and mail and acquisitions. But if you've been around this industry long enough, you realize that two people can get the exact same lead and have completely different outcomes depending on how they handle the conversation. So Katie has spent a lot of time thinking about that process — how to communicate better, how to build trust, how to train teams, and how to create a business that doesn't completely depend on the founder doing everything themselves.

She's also one of the coaches at Land Closers Academy with Ajay, where she's helping other land investors improve not just their closing rates, but also how they think about leadership, accountability, and building a sustainable operation. So this is going to be a great conversation. Katie, welcome back. How's it going?

Katie: Seth, Ajay, thank you guys so much for having me back. Super excited to be here and dive in a little bit deeper into my experience. And hopefully I have a bunch of information that I'm able to offer out to the community.

Seth: Yeah, awesome. So last time we talked a little over a year ago, we spent a lot of time talking about the business itself that you and Brian run. Since then, is there anything you think you've become better at as an operator or leader? Has anything changed in your business about how you guys work?

Katie: Yeah, absolutely. One of the biggest changes that we have made is something that I always had really on my "vivid vision" for the business itself, which was to be as irrelevant as possible within the business without damaging the business operations, profitability, et cetera. And so a major shift that we have done really over the last year or so was to be able to slowly remove myself over time. But that came with a ton of training, coaching, and development hours for my team members. It certainly doesn't happen overnight. For myself to start to be removed from that true closer / damage control role and be able to delegate that out to my team — knowing that the deals were in great hands — that added a high level of comfortability for me as a business owner, but has certainly removed me from the day-to-day grit and grind of the sales calls.

Ajay: Is there like a pseudo leader on your team who kind of filled your shoes as the team leader? How do you remove yourself when you're such a key component of how everything works?

Katie: So no, not necessarily. Our team really functions within the EOS model. So if anybody's read Traction out there, we have a lot of pod calls on our team, and it's really based upon business area. Every person on our team is responsible for their desk and their role, and they are the leader and the expert of that seat.

Within these pod calls, we'll have, for example, a marketing pod call. We've got anybody who touches the data, the SMS marketing, really looking at the campaigns, social media marketing, all of that. All of those people are on a group call. They come to the table, present where they're at, what's happening in the business, what their bottlenecks are. And then they relay that information to me, whether there is something that should be escalated or something that does require approval. We do the same for our sales leaders, etc.

So we have these groups, and they're very, very intentional about what the agenda is, what is supposed to be accomplished, and what are you allowed to make decisions on versus what actually needs escalation and approval. And that changes over time as people become more confident and comfortable within their role. So no, there is no leader necessarily underneath me — every person is a leader in their own role.

Ajay: Katie, I want to highlight a point about that and then also ask a question. Because basically what you just described was: the way you make yourself less relevant is not by simply substituting yourself, but rather by up-leveling your team, right? So really strong leadership is not just putting leaders in place, but instead raising up everybody to almost be leaders in their own way. And from my own experience, what I know is that when you do that, there's a lot of failure along the way. Growth is hard and painful, and there's mistakes that are made, and that's really hard on the people that are making those mistakes. Could you maybe speak to your philosophy on leading the team as they're going through those mistakes, how you continue to coach them up, and maybe share an example or two of a time that's happened on the team?

Katie: Yeah, absolutely. So first things first — when you provide employees with more opportunity, sometimes you do get feedback from them that they are nervous. They may not be feeling totally comfortable. They have fear of making mistakes, or letting you down, or letting their teammates down. And I think the first and most important thing is to acknowledge that they are going to make mistakes, and that it's okay. Because if they feel supported, seen, and heard, then they'll let that guard down and give themselves the opportunity to advance, to add more skills into their toolbox, so on and so forth.

For the most part, the people that I hire — they want that. They just might have some fear lingering in the background. As an example, I hired somebody who had a pretty great background in cold calling and moved her right into a cold calling role. But I noticed over time her attention to detail, the way that she was asking questions, not totally reading off of the script, having follow-up questions, digging deeper — I thought, "I really think she's got some opportunity to grow here." We weren't necessarily in a position where we needed to have a second lead manager at the time, but we did have future plans to increase marketing. So I presented her with the opportunity, and I told her, "Listen, this is a bigger role. I know it might be scary. There's going to be more responsibility that comes along with it. I'm going to give you the opportunity to fail and to make mistakes. What I am asking in return is that when we do spend time with coaching and developing and identifying gaps, we're not seeing a pattern of those same things happening over and over again. It's okay to mess up as you're learning and growing and developing — I just don't want to identify a pattern."

And she did it. So it really has worked out really lovely so far. A plug for myself overall — I have a 0% employee-chosen exit rate on my team in almost three years, as long as they've gotten past their first week. I give them that first week, and I say, "Hey, listen, maybe you've never done this before. It might be a totally new environment, totally different skill set. Spring in. Let's see if this is going to work for you." Yes, I had somebody whose laptop broke and they physically couldn't do the job. I had somebody that had to deal with some family matters and child care and whatnot. We were as flexible as we could be. But anything past that, we have a 0% employee-chosen exit rate, which I hang my hat on.

Seth: I've got the same thing in my business. And the trick to that is you just fire them all before they have a chance to want to leave.

Katie: Oh my gosh.

Seth: Gives me a really good batting average that way.

Katie: Yeah, yeah. Really good.

Ajay: So, Katie, since you've made this transition, it sounds like you're sort of spending more time on the sales coaching and leadership coaching aspect of things. What does your typical week look like? What percentage of the pie goes to the coaching side, and how much is still in the land business?

Katie: As I mentioned, we do run through the Traction/EOS-type model. So while my team does co-run and manage their individual pod meetings, we still do have our Level 10 meeting. We still do team calls. I still do one-on-ones with anybody on the team that is basically in a sales role or has a direct correlation to moving the lead forward — once we get past the basics of what the leads coming in from marketing look like. So I still do the one-on-ones, I still do the team calls, I'm heavily involved in helping deals get across the finish line, supporting Brian on disposition management and some of those relationships. So I'm still involved, but I am not in the nitty-gritty, "have a list of people to call," day-to-day grit and grind.

Ajay: That's probably the dream for a lot of people, to kind of be where you're at — still involved, but not so tied down to where everything functions with you involved.

Katie: Exactly. And they know what decisions they are able to make on their own. They understand what they can make a decision on, but they have to tell me after. And they also are aware of what things do require an approval. That changes per person, and it changes based upon time period — how long have you been in that role, how many things have I been able to delegate to you. So I can confidently say, "Yes, we're in that secondary tier, we're in that tertiary tier of not requiring approvals," etc. That has certainly been helpful, but it takes time to build that. This never happens overnight by any means.

From a coaching perspective versus a land perspective, I would say it's split probably 50/50 on the amount of time that my brain is in either direction. But there is so much overlap, because a lot of the items that I'm coaching, training, and developing externally are the same topics I'm really honing in on internally as well. A majority of my time in general in the land space is around people, process, our systems, and sales.

Seth: So when you think about people, process, systems, sales — is leadership its own separate thing, or is that kind of built into the sales component of it? Sometimes I think, what is the difference between sales and leadership? I know they're not really the same thing, but there's definitely overlap in a lot of respects.

Katie: Absolutely. I bucket leadership into people and sales — especially depending on the org chart or accountability chart, there may be somebody who is responsible for leadership but you're not sales-focused. So there's the operational side to the business of leadership, which is really encompassing your people and your processes, and the execution of that by your team, and then utilizing the systems appropriately to their maximum capacity. Versus the sales leadership. I do see those as two separate sort of pillars from a leadership perspective.

Seth: What do you think is like the biggest need for most people that you've seen? What is the biggest pain point that they need the coaching in? Is it sales, or is there some mechanical part of the business they're not getting? Where do you find yourself helping the most?

Katie: Are you talking about individual operators or team members?

Seth: Great question. I was talking about individual operators when I said that.

Katie: Okay, perfect. For individual operators, the biggest thing that I see time and time again is, after we go through a self-reflection activity, more times than not, the business owner is identifying themselves as the bottleneck within the business.

Seth: Does it become a leadership issue then? Like, "I need to lead my way out of this, find other people, lead them so I don't have to do it." Is that the bottom line, or is there some other issue that they have to fix?

Katie: Not necessarily. Most of the time it is because of the time constraint of being a business owner and operator within this space. I see a lot of people swing back and forth like a pendulum between marketing, sales, disposition; marketing, sales, disposition; marketing, sales, disposition — when in reality, they all need to be running full cylinder at any given time to see consistency within your business. That consistency then alleviates all of the questions, the pressure, the stress, and everything else that comes along with it. And depending upon the size of operation and what their goals are, that determines: what do the people look like? What do the systems look like? What are the sales pieces of the puzzle going to look like? How do you build this out to start to remove yourself so that your team and yourself are making the highest impact possible on the business and not being a hindrance to the business? A lot of the time, it's time. It's the time vacation to it.

Seth: Of the different individual operators that you've coached, I don't know how often you're able to follow up and see what kind of progress they've made, but when you see people who make progress versus people that kind of stay stuck and don't get anywhere, are there any patterns you notice? What is it about the people who are making progress that enables them to do that, other than just listening to you?

Ajay: That's what I was going to say — they just listen and do it.

Katie: I know.

Ajay: Is that Brian's advice too? Just listen to Katie and everything will be fine. Just listen to her.

Katie: Absolutely. No, so I don't see necessarily the same thing over and over because the people that I'm working with sometimes have had absolutely no land experience whatsoever. They listen to a couple of podcasts, maybe they were in a networking group, and they learned more information about the asset class and they decided they were going to do it. And instead of fumbling through, they're like, "Hey, can you help me get this business foundation done?" That's a totally different type of coaching on my end as opposed to, "I've been doing this for three years, here's what my business looks like today, here's what my financials look like, I need help figuring out how to become profitable again," or, "I need help restructuring my team," or, "I'm drowning as an operator."

So it truly is different person by person, which is why I do individual business consulting. There is no playbook that I'm going to be able to say, "Here's how you create and run this business." Every marketing channel is different. There are tons of different acquisition strategies, tons of different disposition strategies. It depends on where that person is at. So I try to meet them where they are to then formulate a three-month, six-month, nine-month, year-long plan to be able to get their business where they want it to be. And I'm not looking for perfection — we're just looking for progress.

Ajay: Yeah, that's so good for a lot of reasons, Katie. Early on with so many investors — and I'm somebody who invested a lot of money in one-on-one coaching early on — I'm a big fan of group coaching, one-on-one masterminds, events. I've done it all, I've hosted a lot. But I think when you're in especially your first two years of land investing, you have all of this head work on how this stuff works. Even down to, if we talk about marketing channels, somebody might say, "Should I do cold call? Should I do text?" And you're like, "Well, that depends. What's your bandwidth look like? What's your budget look like? What does your list cost you based on what you're using right now? What's your goal? Are you taking the calls? Do you want to bring somebody on?" There's all these little pieces. And so what I love about people getting to work with you one-on-one is, not only do they learn skills, but they get to soundboard off of an experienced operator who helps them put together a custom playbook that serves their life.

The real value of coaching, obviously — make more money. That's everybody's goal at the beginning. But at a certain point, you have to ask yourself, "Am I coaching with somebody whose life I want some version of?" I always joke, I'm like, "Katie and Brian, that's the life you want." They're living in Costa Rica right now making beaucoup bucks with their team just running the show. I say that as if you obviously hadn't spent several years working on it — taking over a decade of experience in your past careers into this stuff. But there's a lot to be said about — when I talk to operators who want to build businesses that serve their lives, you guys are like the gold standard for a lot of that. We're like, "Hey, you get to hang out with your kids in beautiful weather with each other. Yes, you're running a business, but also your life's freaking cool." You know what I mean?

Katie: Yeah, thank you so much for that. I think that a lot of the drive for us, and the why behind why we work so hard these last couple of years — I've got to be honest, it was easy being in my W-2. I was even remote. But the freedom and financial flexibility that comes with owning your own remote business, there is nothing like it. We didn't have the financial flexibility or the financial freedom for quite a while when we started this business, because we were grinding and we were making it happen — we had a three-year plan as to what we wanted our life to look like. And we built our business to support our lifestyle.

Seth: A lot of people get into the land business because they kind of think of it as a simple real estate business, or simpler. And I think that's true, but that doesn't mean it's easy necessarily. I know for you, being sort of a sales expert in your previous career, when you were getting into the land business, did you kind of know before you even got into it, like, "My sales skills are going to be a big deal in this business"? Or did you not realize it until you got into it and realized, "Oh, I'm actually kind of a unique situation here. Not everybody is good at this, and I am"?

Katie: Thanks, Seth. I didn't realize how critical the sales conversations are within this business. I truly had no idea. And after hearing Ajay say this even more recently a couple of times, it resonates so deep with me — you truly have to be able to say the right words in the right order enough times to be able to move these conversations in a direction that's ultimately going to benefit the business, but also the seller. So there is a mutually agreed-upon process that we're moving forward with. Without that key piece, you're lost in the sauce, no matter how good you are at sales and building rapport with people.

There was a turning point within the business where I kept getting pushback from people. I felt like I was getting steamrolled. I'm like, "They like me. Why are they ghosting me? I thought we had a good relationship. They're not calling me back. They're not texting me back." And Ajay had posted something on Instagram, like, "Hey, I'm looking for one operator to do some one-on-ones with." And Brian came home and was like, "I already reached out to him." I was like, "Oh my gosh, I was going to tell you. That's crazy." And it was in that moment that I realized that yes, my background is super helpful, but I wasn't selling effectively enough to have consistency and growth in this business that we were desiring. It wasn't going to happen. That was a turning point for me. It was uncomfortable having somebody listen to your calls and provide feedback. We could be like five seconds in and he's like, "Okay, pause." I mean, five seconds!

Ajay: You need that. That is an excellent coach. You need somebody who's going to take the time and be brutally honest with you because they genuinely care about your success.

Katie: And so I said, "You know what? Screw it. Let's do this. I'm just going to put myself out there." And a couple of weeks of the consistency of the training, the repetition of it, until I saw, "Huh, okay, we really got something here." I just needed some additional tweaking and I needed some mindset adjustments from a sales perspective. And I train that a lot now.

Ajay: Which is awesome. It's really cool for me to see it multiplied through you now, Katie. Because I remember when I had posted that, it was before I had actually launched Land Closers Academy. So I was trying to get some experience on, "What are the fastest levers I can pull to get land investors quick wins?" The way to do that was to test, which is why the fee I charged you way back when was so much cheaper than anything I would charge now. I knew it would just be too easy to say yes. And gosh, I just remember — you were so coachable, which is great. But also it was nuts because you and I would text so often. You'd get a PA signed and you'd send me these fun gifs and all of a sudden, "We just got five this month. I'm at seven. Oh my gosh, I just hit eight days this month."

You guys had been like humming and hawing along at like two to four kind of in that window, which was good and profitable, but it wasn't like the breakout you needed. It's so funny too, because I think so many people hear that and they're like, "Ooh, either I don't want to sound salesy or I don't want to triple my marketing." We didn't do any of that. We just tweaked — right words, right order, enough times — with your existing pipeline, CRM leads. We even had you fire somebody the first couple weeks I think, that wasn't a good culture fit. So you had one less staff member, the same amount of lead flow, less time on your calendar because you and I were meeting for two or three hours a week. And we somehow turned that into like eight contracts within the first month, which was amazing. So that was super fun, but anyways, I just remember this because it's such a fun era for me getting to work with you guys. I'd spent some time with Brian because he came to one of the small masterminds I was in in Dallas, which was super fun getting to know him. So it's cool. I feel like I have independent relationships with you, but I've gotten to watch your business grow. But anyways, I'm just going off because this is so much fun for me. But Seth, was there a question you had or something you were going to add there?

Seth: I had this aha moment when you were part of the group that we interviewed in episode 264, Katie. We did like a roundtable thing — listeners, go check it out if you want, it was a great conversation. But I had this aha moment where we were talking about filtering lists, and you mentioned how you don't actually over-filter your list that much. You can kind of work with a lot of different types of leads. I was like, "Oh, weird." Because if that's true, that's a very monetizable, valuable skill — to be able to work with many more leads and squeeze deals out of them when otherwise you wouldn't have even bothered talking to them in the first place. It makes me wonder, is it a common thing where you're able to end up doing a deal with the lead that did not seem like they were ready to do a deal? Are you able to squeeze value out of something that kind of looks like there's nothing there, or like there's no motivation in the seller, but you're able to make it work anyway?

Katie: Yeah. I want to go back to the point of not over-filtering. The first part of the question that you had — I think now with all of the technology, tools, and resources that we do have available, I'm a huge fan, I'm all for it. We are diving deep into AI right now, like really creating some pretty awesome things. Stay tuned for that in the future. Now that we have the ability to essentially overfilter, once we do that, so does everybody else. And then you're reaching out to that same list that has great road frontage, a certain acreage size, limited slope, limited wetlands. And now there is a false complex from the seller that their property is perfect. "It's amazing. Everybody wants it. I'm getting calls all the time." And I'm like…

I kind of want the land where the person's like, "Meh, I don't know." I kind of know the land's okay because we love to do improvements. How can we add value here? What solutioning has to occur to make this land sellable, buildable, et cetera? So the first part is, we like a lot of leads to be able to look at, because we think that we can solution and look at some of these pieces of property differently than other businesses. I think that certainly gives an advantage over, you know, calling Susie Q who has 15 beautiful acres with a nice clearing and two sides of road frontage, flat with no wetlands. It gives us more opportunity to be able to do our job as salespeople, to essentially use those defects as negotiating factors. So we're all talking the same operating reality about what's the highest and best use of that land and what can we, at the highest and best, actually pay for the property in order to essentially take it off their hands at this point.

In regards to getting a seller across the finish line that had no motivation — Ajay, you and I may have a little bit of a differencing of opinions, I don't know. You tell me. You can't force anybody to sell a property.

Ajay: You're agreeable there. You can't. No, there are ways, believe me. I've explored it.

Seth: He can though. I think he can. I think he's that good that he can.

Katie: I haven't been able to really be like, "You're selling this property to me. I'm buying it. Here's my offer. You're taking it. You've got no option." No, I don't think that you can essentially force somebody to sell a property. But I think that you can evoke enough reasonable emotion for them to think that, "Hey, this actually could be a good idea for me, for my family, for my future, et cetera." And that goes through questioning, asking the right questions to have them provide you with enough information with the past story, the present, and the future status of their essential relationship with the land.

Over time — it's not going to be in that first call. That call is just going to spark some curiosity. So if somebody has no motivation, do I think that you can close them on the first call? Probably not, being realistic. But do I think that you can create and start to paint maybe a picture of reality in their mind? And they start going, "Hmm, maybe that does make sense for us. Maybe I can actually use that and put it here. Maybe I just didn't realize that I needed it at the time. Maybe I kind of forgot about it." And then their motivation can grow and change over time. But that goes through follow-up, cadence — having a very specific process in place to be able to continually reach out to those folks who basically didn't say, "Don't ever talk to me again, take me off your list, or I'm going to burn your house down." So I think you can do it over time. That's me being realistic.

Seth: I would like to drill down to — just because you mentioned the property improvements, Katie. I think you've shared some of this maybe in the first interview you did on REtipster with Brian. But just for a recap, you guys are really savvy on the engineering side. What property improvements are you typically making on a lot of your deals these days?

Katie: Yeah, so we've gotten quite a bit more into subdivides over the last year. We will typically do anything from getting (for us) a perk test done. We perk test basically all of our properties. We are not afraid of putting money out for a survey. We do wetland delineations very frequently because of the markets that we're in — whether it's you've got marsh, you've got vernal pools, you've just got some standing water here and there. So we certainly do the wetland delineations or flaggings. We'll go and get driveway permits. We'll cut driveways in. We'll do clearings. We're in a nice rural area. We have in the past done some trail cutting as well for four-wheelers, for just general hiking. So we certainly do those things as well.

And then also in regards to some subdivides, we're doing anywhere from just a mini subdivide to a multi-lot subdivide as well. We want to get the properties to a place where we feel — and our agent partner (because we disposition with agents 99% of the time) — that they feel confident that we have done everything that we can to create the vision for the next buyer, and that the funds that we are putting in we will either recoup from a financial perspective or a time perspective.

Seth: Kind of backtrack a little bit — another little sales question for you. I think you had said something earlier in this conversation about, if you say the right words in the right order enough times. Just hearing those words, it made me think, okay, does that mean you're following like a script? Are there literal, exact, canned phrases you're supposed to say that just unlock everything and make deals work? Or is it like, no, not really, but it's more of a conceptual thing?

Katie: It can be as simple as a tweak of one word. "Hey, Seth, this is Katie calling with Patriot Plots." Or, "Hey, Seth, it's Katie with Patriot Plots." That's a tweak of one word. Or, "Hey, is now a good time?" Or, as Ajay would say, "Is now a bad time to talk?" Right? So it could be a one-word tweak.

A lot of these — saying the right words in the right order enough times — a lot of that also has to do with your questioning in order to identify their objections, so that we do have the opportunity to isolate them and overcome them. And then also, as you are having any type of financial conversations when you are negotiating with them, how often are we working to loop and to anchor them to get them essentially to the point where we know that this really is their bottom line, or as close to it as much information that they will provide us, so that we can go back and say, "Hey, can we truly make this work?" So, "Hey, if I were to come back to you with anything less than 70,000 at this point, should I bother?" There's just certain things that are truly critical in the conversation.

Seth: Is part of what you do listening back to recorded calls that your clients had with potential sellers? Is that part of the work you do?

Katie: Yeah. And as I mentioned, it's different for every person depending upon where their business is at and what their bottlenecks truly are, which is why in the very beginning we typically will go through an assessment so that we can identify what that looks like and then prioritize, based upon their self-assessment, what we should focus on within our first month, second month, third month, and sort of what's future and what things will naturally improve over time by the priorities being tackled.

For me, baseline, when I do work with somebody, they also have access to my personal team's bi-weekly roleplay calls. We typically do three different offerings on there. It could be a live roleplay where two different people are roleplaying a situation and looking at a specific property and they're live. Everybody on the call — we're off camera because you're not on camera when you're having a sales call. It's kind of awkward with anywhere from five to 10 other people staring at you.

So we go off, they roleplay through, they come back on, they self-assess, and then they get feedback from the group. And then I typically go last. And we go through the whole group like, "Hey guys, what were your main takeaways?" It's just very interactive. There's a lot of support there. We also do live call reviews. We just did one yesterday for one of the gals that I'm doing some sales coaching with. She was in the hot seat for an hour going through her call. It was a seven-minute call. We went through it twice, actually, and really went super deep with that because the focus for her within my one-on-one coaching was really heavily sales-focused.

And then other times we'll go through topics — re-offers, presenting an agreement, having to have an extension conversation, so on and so forth. That is in addition to the other calls that they have with me one-on-one. And depending upon their bottlenecks, we could just be going through basic tech stack setup. We could be going through hiring profiles, or we could certainly be going through the operator's calls or the team member's calls. However, if I am reviewing people's calls, I do like them to be present, because then we're down the alley of feedback, and I don't think it's as effective.

Seth: When you listen to those, is there a common mistake that people make without realizing it? Or is it just kind of a totally different problem for everybody?

Katie: I think people tend to default to what just kind of comes naturally to them within a conversation. So if you're going to present them with a number, we know as salespeople you pause and you just kind of grin and bear it through the conversation. But as somebody who hasn't had years of practice doing that, it can be uncomfortable and you break the silence. How people do that in calls is all different. But I think that sometimes we go back and we default to what comes naturally or is most comfortable for us in some of these sometimes uncomfortable situations.

I don't want people necessarily, "Hey, stick to the script, stick to the script." But there are certain words and phrases that you do need to stick to. You can put your own twists and turns on it. But if we're not able to get the most out of that call, then we still have a ton of opportunity that's being left on the table.

Seth: I hear this phrase "building rapport" talked about a lot. It's obviously important to develop some kind of relationship with the person you're talking to. How do I know when I'm effectively building rapport? Is it like a specific phrase I'm supposed to say, and in my head I can say, "Oh, now I'm building rapport"? Or is it just like a feeling we're trying to go for? I just want to get them to like me — is that the bottom line? And is there a point where rapport building starts to feel fake or manipulative?

Katie: That is such a good question. I think Ajay and I should both answer this one. I'll go first and then you can jump in as well. I truly don't believe that I need to be best friends with a seller for them to do business with me. I don't think that they need to be like, "I really like her. She's so lovely." I think that they need to trust me and feel very confident and comfortable with who they're dealing with, and that they feel confident that we're going to be able to do what we say we're going to do and get the deal across the finish line. Because sometimes I have to come in and I need to come in from a harder angle. They might not like what they're hearing, but I want them to respect it and trust me that I've got their back and everything I'm doing is with the greatest of intentions to get them across the finish line. So rapport itself, for me, is more so built on trust and confidence than it is necessarily on likability.

Ajay: Yeah, I would echo everything Katie said there. Just to hone in on this too, because if you study the era of sales we're in, you can never make somebody feel like they're being sold or else it will turn them off so fast. And so when we talk about rapport in 2026, it's very different than rapport was in 2005. Back then, it was all about getting them to like you, and you kind of have the sleazy car salesman from '80s, '90s, early 2000s, and people are just so turned off by all of that.

So truthfully, I think the two words that I would hone in on when I think rapport are one that Katie used really well, trust. And one that goes hand in hand there is actually authority. There's this example I like to use when talking about rapport. Seth, if I were to have called you and told you, "Hey, dude, I am starting a new company and I am raising money from investors." Okay, now, if I told you it was a sales training company, your ears might perk a little bit more to at least hear me out, right? Versus if I told you it was, "I am going to start building rocket ships," you might scratch your head a little bit. Yeah, Katie made a face. I don't know if we're going to see that, but that's the perfect example. Versus somebody like Mr. Elon Musk — for his business career, we're not talking political, right? Who can build rockets. We might be more interested in investing in a company where he builds the rockets, right?

Now, the question is, why do we trust one more than another? And it comes back to authority. Somebody has a certain place of experience so they can command things a little bit differently. The way that looks in our conversations in sales, that I think Katie was hitting so well: if we can leverage past experience and ask questions that show authority, we are going to automatically instill that level of trust.

I'll just make one last point here. Let me give some examples of good questions versus bad questions. I think a bad question that people might ask sometimes — and this one's hit or miss, but it's an easy one to pick on — is, "Do you know if the property has road access?" When you ask a question like that, it communicates to the seller, "I don't know anything about your property."

The more specific I can get, however, if I say, "Hey, I'm looking at County Road 121 on the map here. I actually can't tell if this is asphalt or concrete, though. I haven't been out there yet. Do you know if it's asphalt or concrete?" — same question about the road. One was a slightly more educated question, just based on the same stuff we can all look at on Land ID or PropStream or Land Insights or Google Maps or whatever, Landglide, whatever GIS tool we want to use. In doing that, you have asked a more pointed question, which shows the seller that you understand this a little bit different. That could look different based on — on the messy title side, we'll do family tree pointed questions to show we're more researched. When we get more into development, I might ask about ag exemptions in the area to figure out rollback taxes, to show them we have bought other farmland properties before or ag-exempt properties, that I understand the tax implications on the back end and that's something we need to go negotiate on the front end. So there are things that experience leads to — more educated questions that then automatically build rapport because of trust. Sorry, that was kind of long-winded, and I think it echoes everything you said, Katie, just adding more color to it.

Katie: I think we're totally aligned on that.

Seth: On that whole note of good and bad questions to ask, is there something you think a seller can hear that immediately lowers trust? That example you gave — I don't know, it would lower trust, but it wouldn't really build authority because you're not showing that you've looked at anything. But is there something you could say where it's like, "Don't say that. That's going to totally screw this up"? Anything come to mind?

Katie: Gosh, I'm trying to think.

Ajay: Yeah, like a red flag question.

Katie: Golly, not one is coming to mind right now, but if one pops up, I'll circle back on it. I'm sure there's stuff out there.

Ajay: I would just echo — I think the less educated you sound, the worse the probability is that you sound good. So I think rather than a bad question, a misinformed one is probably a better way to think about that. Like, I've listened to calls where you accidentally screw up the acreage or the county, or you say the county name wrong. That's a big one, especially if you deal in any state, I think you've got some funky ones. One of my favorites, like Oklahoma — if you ever invest in Grady County, we've done some deals there, you've got the city of Chickasha. But if you looked at it the way it's spelled, you would read it like "Chakasha" or something. My wife's from Wisconsin, they've got some funky cities and names. She's from Waukesha County — if you were to just read it, you may say "Walk-Esha." There's cities up there, Oconomowoc, you might say "O-cona-moc," you know? So it's one of those things where, if you sound like you don't know what's going on, it would turn into a bad question. But I think the precision to answer your question, Seth, would be: the less educated you sound about either the area or the subject matter or the property, generally the worse it is. But it's hard to give you an exact example of a bad question. I hope that adds some more color.

Seth: No, that definitely helps. It helps a lot. It made me think of Alachua County, Florida. I remember the first time I saw that, I thought it was like "Alashua" or something. Yeah.

Ajay: Okeechobee down in Florida. I definitely said it, "Okeechobee," my first time.

Katie: There are some interesting ones in the New England area too. I remember Brian and I were driving up one time and he would point to signs and be like, "How do you say that? How do you pronounce that?" I'm like, "Well, now I know I'm going to do it wrong." And yeah, I got it wrong. But it was like a little fun game that we would do on our road trips up. There's one that looks like it's "Worchester." It's pronounced "Wooster." The letters aren't the same, but you know, that's just how it's pronounced there.

So I think that's a good point, Ajay. If I could add one other thing, because from a sales perspective this is interesting, especially if you're doing mass outbound from a calling perspective. I do find too that there's a fine line between trying to speed up but then also slowing down for efficiencies. Because some of the folks that I do coach — they've got the speed dialing going, but their folks are essentially reaching out to people but not having the property's information readily available and have a difficult time putting that pause in the conversation to be able to get to that point and instead just going through the questioning. And then essentially I see it on the other side where folks are over-preparing for calls without the line being answered. So there's a fine line between speed but then effectiveness — the call, and how do you balance that when you get somebody on the phone. What are your options to be able to find that balance so that you do sound like you know what you're talking about, but you're not wasting time? You're still getting the activity volume in.

Seth: Interesting question came to mind here. What do you think is harder to teach someone? Is it confidence, or is it empathy, or is it listening?

Ajay: Is it a man or a woman we're coaching? No, I'm just kidding. I'll say… but I think that's actually, it does kind of depend on the person. Because I think certain people are more receptive. And I know you're talking about how Katie was very teachable.

Seth: So why was she so teachable? Did she already have the confidence part and the empathy part, but needed to learn listening or something? It's a good question.

Ajay: I think I'm going to answer that in two chunks. And no, Seth, he was very specific about why he picked me. Well, truthfully, I think there is a piece of that. I heard Layla Hormozi talk about this concept once where when you know somebody is going to be successful regardless of your input in their life and their business, you are a lot more excited to help accelerate their career. Because you know you're going to see fruit from it. There's this thing — and Katie, I'm sure you get this — like, when you coach and mentor, watching people win is the most energizing thing, right?

Katie: Totally.

Ajay: And so I knew — because you and Brian came from our mutual friend Mike, who I have known for years and is one of my closest friends and is just this phenomenal human. So instantly I'm like, "Okay, if they come from any similar mindset, I know that these are good people." And then I watched you guys implement what Mike gave you quickly to get your business off the ground. So I was like, "Great, they're action takers." So I did know that there was some preexisting, like, "They're going to succeed whether I get to work with them or not, but I do know I can accelerate a piece of that success if we get to work together." So that was piece number one, Seth — I think coaches love getting to work with people that are already winners and taking them up to the next level. I can say confidently, from having met Brian and knowing that based on the fact that you guys are married you're probably very similar, I didn't know you very well yet, Katie, but I was confident enough that I knew y'all were going to win regardless.

The second piece of that, though — truthfully, I wasn't trying to turn it into a misogynist joke, but quite the opposite earlier when I asked if it was a man or a woman. One of my favorite things about all the gals I've had the pleasure of working with, both in a coaching capacity and also on my staff — women tend to have higher levels of natural empathy. Now, that's not to say that men don't, or that's not to say that whatever, but it's a trend, I think, where the gals are just really good with their emotional intelligence. They can just read rooms and read between lines and they just get it. Whereas I have noticed a lot of men I train sometimes are more focused on either outcomes or waiting to say the right things. It's a little different. Now, that's not to say either — like, I've seen both be extremely successful at sales. I've also seen men that are extremely empathetic, and women that, again, like — it's not to say one or the other 100% of the time, just to say there are trends.

So in that, though, I think when it came to coaching Katie, she came with no ego, which I think would be the biggest thing. It would have been really easy for her to say, "Hey, I'm already successful." But she came and like — yeah, I would stop her calls five seconds in to get feedback, and she took it. I remember one of the things we had to work on more than once — so we talk about in leadership, with patterns — was, ironically, Katie, you are a wonderful listener and you are also a wonderful talker. And sometimes your wonderful talking talks too long, or at least it did right early on, maybe not as much anymore. But I do remember that was one of the things we worked on. The cool thing about that was we identified it together. Katie carried no ego about it. And then we would catch it in a call, to the point where she would hear it before I'd say something and she would get better.

Katie: I did it again. Totally.

Ajay: And you kept getting better. So the biggest thing is to have the humility to be coachable, and then to continue to take new feedback and implement and iterate. Like we talked about at the beginning of this episode, it's knowing that we are continuously trying to get better and we're going to make mistakes, and that's okay. That's what coaching and mentorship and leadership is all about. Anyway, super long-winded. I feel like we're just gassing Katie up this whole episode, and I love it. Can we start all my days like this? Yeah. All right, guys, I'm ready. I only need five minutes today. Start me off.

Katie: Well, no, but thank you. That means so much. Because I've got to be totally honest with you guys — when Brian first approached me to co-run this business with him, I told him he was insane. And I'm like, "I don't know anything about real estate. I got my real estate license when I was bored because it was COVID and I was pregnant and I had nothing else really to do, sitting there with my flashcards, I guess."

When he approached me, I'm like, "You're nuts. Absolutely not." And he's like, "Just start consuming content. I want you to just listen to things more so on the sales side of the business." Kid you not, the first podcast I ever listened to was of you guys, Ajay. Triple dial, double dial, double dial them again for two more weeks after that. And I'm like, "I mean, I can set this up. I used to make my team members come in in my corporate job and within their first hour, they had to make a hundred dials. I didn't do this. Let's go." And that started to build my confidence — and that confidence of transferability and relativity sort of gave me the ability to go, "Okay, this is really scary. I don't know what the heck I'm doing, but I'm confident enough in myself that I can figure it out, but with the right support along the way."

So for everybody out there that's going to listen to this — Brian and I, within under three years of starting our business, have worked with five different coaches. All for very different reasons. And it was very intentional and specific with what we were trying to accomplish next within the business. So I, like you Ajay as well, have a budget for continuing development for myself and my team. That is because this business iterates so quickly. And if you're not along with it, you're stalling. You're done within this space. So certainly wanted to put it out there, but this is a very fun, like full-circle moment for me. I thought you guys were like fake people, you know, like untouchable. Here we are.

Seth: Yeah, very, very cool. It sounds like your lack of ego and teachableness has been a huge asset to you, and it's allowed you to dramatically improve through all these different coaches you've worked with. If I wanted to hire either of you as a coach, is there something I can do to self-evaluate and know whether I'm ready to learn? How can I look at myself and know, "Yeah, I can learn to listen and have confidence and empathy," versus, "Now I'm a brick wall, like nothing's going to get through to me. I shouldn't be bothered doing this." Could a person even do that if they're self-aware enough?

Ajay: Yeah, good question. And I know you mentioned it at the beginning of the episode, and we'll talk about it a little more at the end. But part of Katie's evolution, and getting to work with Land Closers Academy now, which is so exciting — transparently, I don't do a lot of one-on-one anymore. I maybe take on a handful of people a year, because there are different seasons for stuff, right? I'm in a season where I don't have capacity for a lot of one-on-one, unfortunately. So when I found out Katie was doing some one-on-one, I was like, "Hey, why don't we stack up some stuff and partner up together?" Which is where she's been able to help at the group level with her strategy calls where she's helping people with Q&A and putting together systems and all the things in our kind of group and community. But then also for folks that are wanting to move faster, we basically have like a package deal where you can work with Katie one-on-one and join Land Closers Academy, which is super fun.

So what I would say is two things. The first one would be something I think Katie and I gab on all the time, which is — you're sitting on gold right now. The things that always ate at me, and how I ended up in this kind of niche of coaching, was knowing there was money sitting in my pipeline. If you have leads — if you have a couple hundred leads in your pipeline — you've got money in there. Every deal in land, on the low end, people make like $15,000 on a pretty normal rural rec assignment or flip or whatever. On the high end, six figures plus. And so you've got money just sitting in this pipe. And if you don't know how to work with that pipeline, or don't know how to say the right words in the right order enough times, or you don't know how to lead your team, or what marketing is right for you — you're just sitting on this gold and not bringing it into your bank account.

I think we recorded an ad once that was super cheeky — I was like, "If your pipeline's full and your bank account isn't, click this link." It was very cheeky and silly, but there's a lot of truth to it. So I think, Seth, the question is basically, "Who's good to work with us?" And I think the answer would be somebody who is really — like Katie was — trying to take their business to the next level. Again, we talked about it at the beginning, you were doing two to three contracts a month, which was pretty solid. And then you guys shot up and you're doing six-figure months now, which is awesome, with this really good team in place and your marketing systems in place. So if you're somebody who has aspirations — you don't need to want the exact same business as Katie, but you can certainly desire the same lifestyle. If your goal is to make more money on your leads and build a business that you would love, I would say at least book a call with our team and see if it's a fit. So hopefully that answers your question, Seth.

Seth: Yeah. Anything you have to add, Katie?

Katie: I was just going to say, because the question was, how do you essentially know if somebody is a good fit for this type of partnership together — I can pretty quickly determine what the relationship is going to look like based upon what they have done thus far without coaching, and what is the duration of their business to date. If somebody comes to me and says, "Hey, I've been doing this for a month. I've watched and I've listened to every podcast. I've basically watched and consumed as much content as possible. I've had demo calls with a couple of different companies. I've started posting some ads" — they're showing that they are willing to put in the work in order to get desired outcomes. So I think that what they've done to date is a pretty good indication of what we can see the output be in the future. And that's different for somebody who has a zero baseline versus someone who maybe has been doing it for a couple of years.

Seth: Have you ever seen somebody become dramatically better at sales in a surprisingly short amount of time? And if so, what changed? How did that happen?

Katie: I have. Super exciting. I am working with an operator right now, and it has been about nine months that we have been partnering together. He was able to quit his W-2. He's running this business now, no prior experience in land, in real estate, et cetera. So when I think back to conversations, calls, sales tactics from essentially day one until a couple months in — once he was able to start hiring for roles because he then knew how to continue to coach and train and develop his employees, and be able to hold them accountable because he knows what great looks like, right? That's a huge turning point. To then see the business where it is now, where he's essentially just taking on those closing calls and conversations.

So in nine months, we went from zero business whatsoever to quitting a W-2 and building out an entire team around where the operator primarily focuses on tough-to-close deals and getting things resold. Huge, huge, huge success. Ajay, you said it so well — my greatest happiness outside of my family is being able to see people succeed. And it was truly because he did active listen. We worked on building that confidence. And through that, it works through ensuring that we had the stability of that empathy, but put in the time. Put in the darn time. And it was an exhausting nine-plus months. But here we are.

Ajay: Yeah, I'll answer that too. I'll brag on somebody that I don't think she'll mind me dropping her name. But it's somebody you had on for the roundtable you had mentioned earlier, Seth — Shelby Wendgreen, who is just one of my favorite people on planet Earth at this point. She's awesome. She was just in town. I met her husband a few weeks back, super fun. But I watched Shelby run in this business extremely part-time. She's a mom with a little toddler, did not have any kind of sales background. I think she joined Land Closers Academy back in May, and watched her come to every call. Every Monday when I run my group call, I see her on there. She's always smiling, which is awesome, and just watched her learn. She would upload a call every now and then, and they were spaced out enough that I'd be like, "Oh my gosh, you sound wildly different. This is so good."

So I watched her take these things in and kind of execute in private while still learning. But in like a six-month span, it was night and day. And now I'm watching her get better on the leadership side. She's hired her first AM, and she's just making these huge strides where last month in April, she had like nine transactions between both buy and sell, which is just so great because the girl only works like three or four hours a day tops. It's just really cool. To your point, Katie, of just watching operators do really cool stuff like that, and just improve and get good, and you're like, "You sound awesome and you're doing deals and you're making money." I love this. So it's very, very rewarding. It's almost selfish — I do this for me, just because I'm good about your success.

Katie: Totally.

Seth: It really fuels it. Something I learned about Shelby in the brief interactions I've had with her is the power of a smile. Just smiling — that's it. That can go a long way towards setting the tone for the communication, and probably even comes through in how you talk and everything. I haven't learned to actually do this myself, but I've just noticed it in her. She's really good at that.

Katie: Yes.

Seth: Well, Katie, I want to thank you for your time hanging out with us. If somebody wants to work with you and/or Ajay — whether it's together or just hiring you for a coach or anything like that — is there a place they should go? How can they learn more?

Ajay: If it's us together, just go to landclosuresacademy.com and book a call. You'll meet with either me or Jacob on my team. Just mention you're interested in working with Katie and we'll lay that out for you pretty clearly. So pretty straightforward.

Seth: Katie, anything you want to add?

Katie: I mean, you know what? Right now I am in such an exciting place to be able to spend more of my time dedicated to supporting other business owners within the land space, because of where my team is at today. So if you are interested in learning more, whether you're starting or growing your business — in regards to your people, your process, the systems that you use, and getting additional support in sales — working with myself, as well as with Land Closers Academy, I would be honored at this point to continue to help other people be successful in this space.

Seth: Awesome. We'll have links to everything we talked about in the show notes for this episode, retipster.com/277. Katie, Ajay, thanks again to both of you for being here. And all the listeners out there, we will talk to you next time.

Katie: Thank you.