with Justin Benson, Founder of Shiloh
EP 03822 minJustin Benson's company has analyzed 3 million real estate and mortgage sales calls, not to grade tone or coach scripts but to find out, statistically, what actually separates the deals that close from the ones that don't. In this episode of the Partner & Profit Podcast, Grant Wise sits down with Justin Benson, founder of Shiloh, a conversational AI platform built for real estate and mortgage teams, to break down the data-backed tips his company has uncovered for closing more deals. Justin shares which habits actually move the needle, which ones don't hold up under real data and where his team drew an ethical line on what the AI could tell them about a person. Justin also shares his own unlikely path here: a biochem major who dropped out of med school, built and sold a tech company, ran a real estate team, got signed to a record label off a song written for his dying father and eventually landed on building AI for the real estate industry he now calls home. Here's what we got into: • Justin's winding path: biochem major, dropped out of med school, a real estate team, and a signed record deal off a song written for his father - 01:02 • Why setting a defined next step on the first or second call is the strongest predictor of long-term deal success, and the 74% drop-off Gong found when teams skip it - 04:42 • The restaurant cancellation study - how one word change to a confirmation script cut no-shows dramatically overnight - 05:48 • The 3x increase in closing rates Shiloh found across 7,000 users when a clear next step gets set early - 07:18 • Why asking 9 or more discovery questions on a call outweighs even asking for the appointment - 07:50 • The moral line Justin's team drew when they realized how much they could infer about a person's fears and psychology after just 10 calls - 11:08 • Whether routing leads by personality fit could outperform how most teams distribute leads today - 13:22 • The two unglamorous values Justin says have quietly built every company he's ever run - 16:51 Whether you're leading a real estate team, scaling a brokerage or just trying to close more deals with fewer wasted conversations, this episode hands you real data you can put to use immediately. Connect with Justin Benson: Find him on Instagram at @JustinBenson or learn more about Shiloh at shiloh.ai. Don't forget to subscribe, leave a review and share this episode if it brought you value!
Host1
The robots take over all the jobs, like what do humans still need?
Host
And you're helping people grow big companies using AI to build those relationships.
Host1
It's scary how much you can actually find out about humans, like what their core fears are.
Host
You have to know how to trigger certain behaviors. You have to know how to communicate in a way that's going to get people to take this specific action.
Host1
Oh, some of those deep dive studies from social media being able to tell crazy stats. Those relationships that get built like that are more valuable than money itself, honestly.
Host
What's up, everybody? Welcome back to the Partner Profit Podcast. Pumped for my conversation today. I've had a number of conversations with people that are experts in the AI space, but I am particularly fascinated. I can imagine what we're going to talk about today. We've got Justin Benson. Justin, man, thanks for spending some time with me.
Host1
Dude, thanks for having me. It's an honor. I feel like I like I made the cut. I finally made it on Grant's podcast. This is awesome. Yeah, I've arrived.
Host
No, man, we're honored that you're here. I really appreciate it. For people that are listening to this and maybe don't know much about you, give us a little bit of the backstory. How'd you get to where you are today?
Host1
Oh, geez. AI resident nerd in the real estate industry now at this point. But uh the short story is biochem major that dropped out of med school, started a tech company, then started a real estate team, then did some I got me and some friends got signed to a record label, and then I started a tech company in the real estate uh world, and now here I am building Shiloh, which is uh conversational AI for uh the real estate and mortgage industries.
Host
So that's fascinating. I I think what is fascinating to me is that you got signed to a record label. I didn't, I I guess I never knew that.
Host1
It's real. You can go to my Instagram. I got to like play a sold-out show to the Red Rocks Amphitheater. That's like top when people ask me like what are the like top three moments of your life? You know how you're supposed to say like the birth of your children and then like getting married like first. I was honest with my wife. I'm like, I don't singing to a sold-out show, the Red Rocks Amphitheater is like really, really high up there as far as like gotta be.
Host
That place is amazing. What kind of what was the band name?
Host1
Uh Renew Music. So it was uh church music stuff. So uh when my dad, my dad passed away like six years ago, and when he was going through his like struggle with cancer, I uh wrote a song and I sang it at this event. And a friend's the uh Cody Carnes signed a Capital music. He texted me after watching the live stream and was like, hey dude, that song's special. You guys should do something with it. I'm like, yeah, tell your overlords of capital to buy it from me. You're the real like performing artist making tons of money, like singing. And he's like, No, you for real, you guys should do something with it. And two months later, we had a signed deal with Tooth and Nail Records for three albums, and we had no previously published music, so yeah, it happened real fast.
Host
That is insane. That's really cool. I'm gonna ask you uh more about that outside of the podcast, but getting back to the show. So I've had this conversation a couple of times with different people, and I find it fascinating. So I'm gonna ask this first is like, how do you think not how do you think you have so much data? You guys have been doing this for a long time. I saw you put out something yesterday where you have like three million calls that you've analyzed.
Host1
Yeah.
Host
How do we build relationships through AI and still have a lot of success? Because I think that there's a lot of people that argue like you don't, this is a relationship business, you don't want to automate yourself out of the business, you don't want to replace yourself with AI, but you guys are going right at it and you're helping people grow big companies using AI to build those relationships. So I'm curious from your perspective, what are you seeing in the data as far as like building relationships using AI to navigate the real estate industry?
Host1
Yeah, you know what's interesting about that is that like obviously we're conversation and intelligence, right? So we'd like analyze calls. We don't just coach and grade them. We create like these, you know, you can role play your call that you just got a three-star and see if you can get a five star on it. It's it's pretty fun to see that, but like the the magical data is on like what the behavioral trends are. And there's some interesting like things that we know, you know, like okay, on phone calls, we should ask lots of discovery questions, right? We should, we should do that because that surfaces objections, and then we can overcome those objections, we become, you know, the subject matter expert in that person's mind, right? And there's things like ask is setting defined next steps and asking for appointments and stuff like that, where we know in sales industries that, like, okay, people have been saying that for for for forever, right? But most of the time it's just like anecdotal, right? It's it's uh people, oh, because I closed more deals like that, right? Well, now, you know, we got 19 years and growing of continuous talk time analyzed with Shiloh data. And now we have like a lot of the science behind it. I'm actually preparing a big case study right now about how setting a defined next step on your first or second call with your very first initial interaction with a new contacts, lead, you know, client, whatever you want to call it, uh, is the like single greatest indicator for downline success. And that's not just from us. Like I'm cross-referencing this. Like Gong did a study on like the B2B SaaS world, and they saw that if next steps, a defined next step, not like let's check in next week, but like, hey, how does Tuesday at four o'clock sound for you? If that didn't happen on the first call, Gong's client saw a 74 uh percent drop off on future closing success, right? So we're starting to be able to gather all this data and understand, oh man, we can deep dive into that. And what we're starting to realize is it's not just about setting the next step. There's like psychology behind this, right? I forget what study it was in that book, uh Influencers. It was a super popular book, where a restaurant owner had a cancellation rate of 30%. And he was trying to figure out how to get that down, and he changed one script in his confirmation for uh reservations, which was instead of saying, Hey, let us know if you need to cancel, he changed it to, will you let us know if you need to cancel? And then he waited for them to say yes. And when they said yes, they committed to an action step, his cancellation rate dropped by 20% literally overnight. It was like a 67% decrease in cancellation. So we're starting to understand that there's like psychology behind setting clear, defined next steps is one, we're like setting precedent for how this relationship interaction happens from like the onset, but two, also really deploying the psychological reality that when somebody says they're going to do something out loud, they are much more likely to actually do it, right? So we have so much of this data at our disposal that we're now like a year and a half in of collecting it, starting to try to make sense of it all, right?
Host
So that is fascinating. I'm I'm actually intrigued, like what other revelations have you come across as you've because like it's I think you're right, like it's one thing to say, hey, you should be doing this, because that's what I did, and this made me really successful. But when you have a central source that's able to analyze as many conversations as you have with as much historical data, you really do get to the science of conversations, persuasion, those types of things. What what other things have you recognized beyond setting a clear next step that are really critical to having conversations and building relationships?
Host1
There's obviously subtleties to geographic regions as well, the kind of the way things work, the way that things work in Canada, slightly different than America, but like the the big trend is has has always kind of held true. That setting clear next step thing, by the way, at least in the real estate industry, it across all of our Shiloh users, like 7,000 users and like 400 some odd accounts, it is on average a 3x, so like a 3x conversion increase in closing rate, not like appointment set rate, but like actual closing rate. Dude, thanks for having me. This is also my next step up front in your interaction with them. But the next strongest correlating thing is actually asking questions on calls. So it sounds egregious, but you want to try to ask nine questions on a call. You want to try to ask nine discovery questions on a call. Keep probing, keep probing, get the whys out, basically get keep asking questions. It obviously builds relational rapport. That one's like obvious, right? There's we want objections to show up. We want to do those things, but the appointment set rate whenever you actually ask nine or more questions increases by like 60 some odd percent. Like between like setting a clear-defined next step, not don't do the, yeah, let me just check in next week or whatever. Like, don't do that. Like, for the love of God, please. I'm like on a tirade right now with all of our Shiloh clients. It's like texted our advisory board and sent them everything, like all the big teams. I'm like, for the love of God, please set a search inside of your Shiloh right now and start gamifying this. But asking discovery questions happens to be the like second strongest correlation to anything, actually, way more than even asking for the appointment, which is we think we we've been trained in sales in the past that like asking for the appointment is the most important thing, but it's actually not true. Asking discovery questions is is uh vastly more important than actually asking for the appointment.
Host
Is there a commonality to the questions? Is there a pattern in the conversation that's like, hey, this question first, this question second, this question third? Or are is there a lot of like just like dynamic conversations taking place where it's kind of all over the board? Are there patterns to the types of questions that you should be asking?
Host1
I'm sure there is. We haven't done it yet. I'm in the throngs right now of like trying to use the data to create more of like a predictive model where like when t equals zero, like the very first call that happens, this thing happened, these questions were asked, and then this outcome happened on the back of it. Okay, the next interaction t equals one, kind of trace those questions and the pattern recognition of those questions all the way through to create a predictive, like, okay, now by call number two, we know exactly what to do on call number six now moving forward, right? That data exists in there for sure. It's no surprise, like people go to a therapist and they think that therapists are like mind reader, like Jedi's or whatever, but it's not true. There's humans fall to patterns, and we don't have that many patterns as humans. So as far as like a pattern recognition of questions to ask and the sequence, it it's gotta be there, is my like my hunch.
Host
So I would agree with you. Uh, I've done a lot of therapy. I'm I'm a big fan of it. I think human psychology is fascinating. That's all marketing and sales and advertising is, is it's human behavior. And I I've had I've heard that same thing from the therapist. It's like, no, human emotions, it's one plus one equals two. Like it's it's just like a math equation. If this is happening, then this is the answer. And um, I find that stuff just so interesting.
Host1
You can go real far down that and start questioning whether or not we actually have like self, like what do you call it? Like what whether or not we're actually control of like willpower. Yeah, will or whatever.
Host
It's um it is truly fascinating. That kind of stuff is amazing. And and as a marketer, right? You're always you have to study this stuff. You have to know how to trigger certain behaviors, you have to know how to communicate in a way that's gonna get people to take this specific action, and you have to have to be able to do the same thing in sales. There's so much human behavior injected into this. It's it is definitely fascinating.
Host1
You know what's interesting about that is we hit this like moral gray area as a company where uh I was telling you before we started here that we're very close to having these like kind of full-blown psychological analysis being able to be done on somebody after just 10 calls. And it's it's scary how much you can actually find out about a human's not like their disc profile, like what their core fears are, what like who they are deep down inside from vocal intonation and things like that. I mean, we know some of those deep dive studies from social media being able to tell crazy stats about who a human is just based on the pictures that they like, basically, right? We will also know that on the consumer side. So we were kind of going after this, like, okay, well, then if I can match up the salesperson side to the consumer side, I can create pretty clear, like, this is the way that you communicate. Here are their fears and weaknesses, basically. Here's exactly how you should communicate to that person. And we're like, should we stop this? Like, this might be bad for like humans, and I don't want to be on that side of things. And we got to this point where we realized like really good salespeople do that automatically. You know, they know who they are. It kind of starts there. Like you have to really know who you are as a human. And then you start to figure out how to pick that up in other people. And as you're having the conversation, you are structuring your language to be attuned to that. So essentially what we're doing is we're teaching people how to do that when they didn't innately come, you know, some people are just kind of like more gifted at that than others. But I guess if yeah, we built some like outbound sales outreach bot that was just like exploiting people's fears. Like, I guess that's that that was the point where we went, yeah, that's probably uh we become the we become the Death Star at that point.
Host
So it's so true, you know. I was had I was having an amazing conversation yesterday with Jason Sheppardak out of the DMB area. And I asked him, you know, it's like, how do you know how to connect the right salespeople with the right customers? Because we were having that discussion. And he was like, it's not about the customer at all. It's it's about having self-awareness, it's it's about knowing oneself. And when you get to know the people in your organization, you kind of get to know like this person's probably gonna be good for this experience, this person's probably gonna be good for this experience. I think it's fascinating when you have the data there stored to kind of start doing predictive work.
Host1
That's a hypothesis. I'm actually, it's on my plate to prove that right now is like, is the old school lead distribution system that we see in real estate and other industries, is it the wrong one? Is it an outdated one, basically? Like distributing leads based on, oh, they serve this price point and they've been around for X amount of years and they live in this neighborhood. Is it actually better when you talk to smaller organizations, like five or so, where you can, like you can talk to a lead and know, like, oh, Sally is gonna be best for this person kind of thing. But when you scale, that becomes impossible. Like, right? You can't know 300 people in a sales organization that well to distribute leads on like a personality match basis. But I've I've wondered for a little while as we started kind of this personality assessment thing here in Shiloh. I wonder if routing and matching leads to personality fits is would yield higher conversion rates than the way that we currently do it, which is like, you know, dat-based, you know.
Host
Yeah, I would be apt to believe that it would, you know, everybody's got to connect. I've here I've heard of other teams that have gotten really good at asking questions related to like disk profiles and stuff like that, to be able to tell people's personality types to try to make those connections. Kyle Whistle, you know, a good friend of all of ours, his team is really good at doing stuff like that. I think it's a fascinating philosophy, and I think it's one that works. I'm excited to see what you guys do with it. I I always like to ask this question. It's like, okay, you're using AI to build these relationships. You have so much data to help start really creating patterns and predictive uh things that you know in transactions and relationships. But at the end of the day, like, how do you turn those relationships into revenue?
Host1
How do you turn it into revenue? I don't know. That's like such a loaded question. Depends on who you ask, you know. Like, I'm what are they, whether they call me like an assumptive closer? I'm no good at staring somebody in the face and waiting for him to talk. I just kind of I don't know. It seems like we're getting along and this makes sense for everybody. So on to the next step, right?
Host
Sounds like my son, sounds like my uh my son. He's he's the best assumptive closer I've ever met in my life. He's yeah, he's very good at it.
Host1
It is to the point when people don't do it. I'm like, I don't understand. Like it seems like this is really good for everybody here, you know.
Host
He will be like, You said that I could have some cheddar bunnies, right? Like, it's like no, I didn't say that. It's like he'll be like, You told me that we could watch the movie, right? Like, he's always like bringing it's like, hey man, take your assumptive clothes somewhere else. Like, no, I did not say that. No, I don't agree with you. He's like reading the energy in the room and be like, it's okay if I do this, right?
Host1
It's like my daughter will get me with things like that, and when she actually does get me, I like actually reward it. Like to have like you when I don't my wife is like, Oh my gosh, stop doing this.
Host
I'm like, no, no, no, no. This is a this is an amazing quality. Parents that are raising like skilled, willful, strong, self-aware, good sales, like those types of children are having a fun time, is what I would guess. I would describe that as. Uh, it's hard, but it's absolutely worth sticking through that.
Host1
I think that the only thing that I can say to that is like speaking from my experience, right? Because like even like the Shiloh data we can give like mechanical, you know, like set a freaking defined next step for the love of God in your first two interactions with the human, you know, we have all the data to do that, but there's also kind of like the spirit and the soul in which people go about doing that, which will not be the same for everybody, right? So for me and every company that I've ever led, our two core values are always like leave people better than you found them and do what you say you're gonna do, you know, like help everybody out, make every if you make enough people's dreams come true, then yours will come true as well. And like just be a reliable, dependable person, and then like life will sort itself out, basically. And what's pretty interesting is that that happens to be a pretty good like marketing revenue engine as well, in a world where like you just don't, you know, when we founded an agency. I found out before going into agency land, like how many just agencies are out there that don't do what they say they're gonna do. And we're like, so literally the bar's pretty low. We just need to like do what we say we're gonna do. My little brother is getting into like the uh electrical world, right? And he was like, dude, like contractors like just literally don't show up when they say they're gonna show up. The bar's so low. Like I just have to do what I say. I'm show up on time and do my job, and I will be a gajillionaire, basically, right? I think that there's some magic to that as far as like turning relationships into that. And like Sharon is like, I really love his stance on things as well. Like, it's not a I'm not helping people for the sake of like calling in favors one day. Like it really does come from a spirit of like, if I can help, I'm gonna help. And uh there's no tally system, right? And what ends up happening is that when you launch something, like when we launched Shiloh, I had a lot of people cheering for us and wanting to be in on it and root for it and move forward. And I don't know, those those relationships that get built like that are more valuable than money itself, honestly.
Host
So without question, I think it's been a central theme in a lot of our a lot of my conversations as I've interviewed, you know, dozens of people now at this point talking about how do you turn your relationships into revenue. And that part about building a relationship in the first place is like just give, just give to people. And I find it really interesting. The people that are just giving and contributing to other people with no expectations of anything in return are typically those that are having the most success compared to those that are thinking, like, well, I'm gonna give to you, but I need something back, like I need this happen soon, like you know, I've got a timeline, I've got expectations. And I think it's really interesting.
Host1
Nobody will also wants to accept a f favor from that person either, because you know, you know they're gonna call at 11 o'clock some night and be like, Yeah, it's time, you owe me one.
Host
I think what I hear you saying though is like, at least from my perspective, is like trust the data. Like if you're saying, hey, you need to set a next step within your first second phone calls because 70x% of the time, you know, it translates to whatever, you know, like a 3x increase in conversions. For me, it's like how do you turn your relationships into revenue? You trust the data, you trust the process, you you do what you know you need to do, you ask a lot of questions, you you are there to serve, there to help, and then you set next steps. And everybody, I think, has a predefined way that they generate revenue, but uh not everybody has a very good process for doing it. And I think that's probably how I've made a lot of money in marketing and advertising, is like I help people get customers. But I I think that the entire thing is fascinating and and relationship development right now are very intriguing things to me. But the data that you guys have is remarkable to be able to say, hey, just one plus one equals two. Like if you just do if you just do these things, you're gonna get these results, and that's how you can take those relationships that are being developed and and convert them into revenue. I think it's I think what you gotta do is really cool.
Host1
Thanks, man. I don't know. I I'm an oversimplifier, so I like think about great, if the robots take over all the jobs, like what do humans still need? Like they still need connection, they still need friendship and relationship and things like that. So like those are the core building block components of you know, it's just like you've been in it, you get into like very affluent environments where like I'm drastically definitely the poor token kid that somehow made it into the room, basically, you know. In those environments, like you can't be the person that like takes, and none of them are that either, actually, you know. So it is like a pretty interesting commonality to seeing it actually turn into, I guess, revenue. But you're right, there are some building blocks to like good best practices, like even me seeing all the next step data changed the way that I wrote some emails today. I was like, oh geez, yeah, I'm I'm even not doing it. Holy crap! But like also the spirit in which you do the activity matters equally as much, in my opinion, right?
Host
So I want to respect your time. I always like to ask this question to wrap us up, man. How can the listeners of the podcast partner with you? What's the number one way we can support you right now?
Host1
If you know any real estate team leaders or uh mortgage brokers, loan officers that would, you know, benefit from this stuff that we're talking about, conversational intelligence and helping scale the quality of the conversations that they're having in their org, you can uh send them to Shiloh.ai probably be the best way, or you can find me on social media at Justin Benson on on Instagram. I I got lucky, I got my real handle. So but I would love to connect and I don't know, if I'm also very collaborative human in nature, and we're always expanding ideas into industries where we can bring this into as well. So if anybody listening has an idea, they're like, oh my gosh, something like this would be super useful in this industry that I'm attached to. I'm always all ears on things like that as well.
Host
So awesome. Well, I appreciate you, man. Appreciate you being here today. This has been awesome. We'll make sure that we link up all the ways people can connect with you in our show notes. And if you're listening to this, I highly encourage you to do it. Justin, thanks for being with me today.
Host1
Dude, thanks for having me. This is awesome.
Host
Of course, awesome. And thank you guys for continuing to listen to the Partner Profit Podcast. This is another fascinating conversation. I'll see you on the next one. Peace.