
In this episode of That Real Estate Tech Guy, Jordan Samuel Fleming sits down with Steve Trang of Objection Proof AI and Real Estate Disruptors to unpack how real sales expertise and cutting-edge AI can transform a real estate investing business. Steve shares his journey from top-tier sales trainer to AI innovator, explaining how tools like call-review bots, role-play bots, and voice agents for speed-to-lead, inbound, and follow-up can dramatically improve sales performance and consistency. They dive into why empathy, real understanding, and skills-based training beat scripts every time, how AI can help you coach your team faster, and why tech should be rolled out intentionally, not all at once. If you want to scale with better sales processes, smarter training, and AI that actually solves real problems, this episode is packed with practical insight.
About Steve Trang

Steve Trang’s mission is to create 100 Millionaires. Why 100 Millionaires? Steve saw that assisting someone become a millionaire by building their business is a key measurable to helping them fulfill their dreams. People change and update their visions over time, but having the means to achieve them remains a necessity. Thus, creating millionaires means helping people live their dreams. To further this mission, Steve started the Real Estate Disruptors podcast in 2018 to inspire wholesalers and real estate agents to double their incomes by adding a second leg to their business – working together on investment properties. The podcast has grown to over 100,000 downloads per month and over 3 million YouTube views, with new guests sharing their success stories and imparting advice every week. As a sales coach, Steve has helped thousands of clients generate millions in sales over the past few years in a variety of industries. His Disruptors Selling System teaches salespeople to ethically work with customers to discover their true needs, then craft a solution that works for the customer. One of Steve’s favorite quotes is from the great Zig Ziglar: “You can have everything in life you want, if you will just help enough other people get what they want.” He heard this quote when he first got into real estate, and it has stuck with him throughout his entire career. In fact, it’s one of the core values Steve lives by. Steve is also a successful businessman. On top of owning single family rentals, he also owns apartments, co-founded a bank, and is a part-owner in several other businesses.
Important Links
Watch & Listen
- Objection Proof AI – Upload a call or transcript for a free AI call analysis.
- Role-Play Bot Demo – Text ROLEPLAY to 33777.
- AI Appointment Setter Demo – Text CASH to 33777.
- smrtPhone – The only phone system built for real estate investors. Claim 5,000 free minutes.
- ThatRealEstateTechGuy.com – Explore all episodes and exclusive tech discounts.
Using AI In Your Sales Process to Become Objection Proof ft. Steve Trang
I can tell you one thing. Technology is the single most important aspect of every business that has successfully scaled. It’s time for That Real Estate Tech Guy. It’s your weekly chance to explore how technology can help your real estate business explode. Each week, you’ll hear from real estate investors who have been there and done that and find out their favorite technology tips.
Listen in as Jordan speaks with tech companies and learns about new technologies and new ideas that will help you scale your business. And now join your host, Jordan Samuel Fleming, CEO of smrtPhone, for this week’s episode.
Hey everybody, and welcome to another episode of That Real Estate Tech Guy. I’m your host, Jordan Samuel Fleming, and what a great episode we have today. My friend Steve Trang from Objection Proof AI. You’ll also know him from Real Estate Disruptors. Steve is, let’s be honest, a bit of a legend in the sales training sphere in real estate investing.
You’ll know his name. You’ll know his face. For good reason. He’s amazing at it. And he has pivoted into the AI space hard and built some amazing tools. Tools that smrtPhone actually – apparently, we’re still the only ones who fully integrate with it. But we immediately integrated with it because of how much we value Steve and how much we believe in his vision.
This is a great episode. It’s got a lot of gems in it, from talking about core sales training, talking about some of the ways that Steve’s tools can reinforce and identify good habits, bad habits, reinforce training, and, of course, pivoting to the conversations around voice agents themselves and what they can do and what Steve is building, what we’re building.
It is a phenomenal opportunity to hear Steve articulate a great vision and really give a behind-the-scenes look at some of the amazing things that he’s done in this space. It’s always a pleasure to speak with Steve. I like him very much, and I’m always honored when he comes in and speaks in one of my things.
So do enjoy this phenomenal episode with Steve Trang, Objection Proof AI. And at the end and in the show notes, there will be how you can get in touch with Steve and how you can try out his amazing tools. And I recommend you do that.
All right. And I’m live with my friend Steve Trang from Objection Proof AI. Steve, absolute pleasure to have you on the podcast. In case someone doesn’t know, give us a little introduction on you and what you’re doing these days. These days, I am basically building an AI that can more or less sell for you. We’ve been doing AI for call reviews, we’ve been doing AI for role playing, we’ve been in AI for appointment setting, for following up with calls, scheduling appointments. So yeah, we’re basically doing everything with AI that, as a business owner, you’re frustrated with your sales team about. We take care of those menacing headaches so that you can do what you do best: build relationships, focus on strategy, focus on the vision.
Getting the company moving forward versus getting into the nitty-gritty and dealing with the salespeople, because that’s where the biggest headaches are. Well, and I think what’s really interesting about this is you are uniquely kind of qualified from this angle, because for years, if people don’t know of you around AI yet, because this is a newer part of you, what they’ll probably recognize your name from is the sales training, being a leader in sales training. And I think that’s really interesting because a lot of times, it’s technology first when people approach these problems as opposed to real-world experience first. And you come at it from a real-world-experience-first point of view. So can you give a little background for those who aren’t familiar around your experience with sales and sales training, and why that kind of crosses over nicely?
Sure. Yeah, I appreciate you asking that. So, I mean, just real quick, right? I started in real estate in 2007 as a realtor. I went the wrong way, but started as a realtor and, you know, eventually started buying houses and this and that. In 2019 is when I started actually training other organizations on how to sell.
So looking back over the last six plus years, about six and a half years now, I’ve literally trained thousands of salespeople. I’ve coached hundreds of business owners, and these days I’m consulting with nine-figure companies on sales. And so, yeah, sales is something I’ve been deeply passionate about. I went all in on it back in 2018, learned everything I could, picked up every book, tried and tested everything.
We know what works. We know what doesn’t work, because we do objection handling every single Wednesday with, again, thousands of salespeople. We know, like, hey, when you say this, this signs the contract. When you say that, in theory they should have turned to a contract but actually it doesn’t work in real life. That’s just the book theory.
We know what works. We know what doesn’t work. And that’s what we put into our AI. Well, let me dive into a few things around that, because there’s the AI element, which is pure technology. But that doesn’t interest me as much as its direction to the problem solved. Right. The technology itself is the technology.
But the problem solve is more important for most business owners. So, you know, sales – I don’t have nearly your experience of training sales, but I have trained a lot of salespeople over the years because I was good at sales and figured some things out. None of your qualifications, but I have noticed over the years that there are certain undeniable skills that you can teach people and that you can train.
Absolutely train. And I prefer the skills versus the script. My view is skill-based teaching will be far superior to teaching scripts because skills allow you to move with the conversation. What do you think some of the key sales skills are – not just objection handling, but some of the other key sales skills that you’ve trained?
What do you think matters most? And what do you think translates easiest to your AI tools? So, Chris Voss did a podcast with Andrew Huberman. Chris Voss wrote the book Never Split the Difference. If you guys haven’t picked up that book, pick up that book. Andrew Huberman, well-known brain guy, has a podcast, and they did a podcast together. And on that podcast, Chris Voss gave the coldest, most sanitized definition of empathy. His definition of empathy is the transmission of information.
And so where I’m going to go with this: I can demonstrate that I heard Jordan and I can articulate back to Jordan everything he told me in his words. If I can communicate that I understand you, that’s empathy. Right? And so if you look at, like, what is the core human need? You learn over the years, the core human need is not necessarily to be right. It’s not necessarily to win. The core human need is to be seen, heard, appreciated, understood.
So if I can demonstrate, “Jordan, I see where you’re coming from. I understand what you’re going through. I can articulate back to you how you got into this mess, what’s keeping you up at night, what you’re hoping the future looks like, and how this problem or this solution solves your problem. I can articulate all those things back to you,” you’re good. Right? And so when we talk about getting that back into AI – well, AI can do all those things. That’s super trainable. That’s super trainable.
If you look at, like, I remember Jamil came on my podcast. Jamil and I, we’ve been friends since 2012, right before he took off, before I took off. He was my wholesale guy. He actually mentored me quite a bit in wholesaling. He was the guy I’d call like, “Hey Jamil, I’m on the way to this property. What can you pay?” And then I just have to knock off 10,000 from that. That was the approach. So he was on my podcast, and he said that the reason why he recommends everyone train with Steve is because Steve is a robot. And if Steve can sell, if a robot can teach you how to sell, you should learn from that person versus the guy that’s charismatic and charming.
He’s got the great smile and this and that, right? Because that stuff, that’s the intangible. I’m not saying you’re necessarily born with it, but there are definitely people that have more of that than others, right? The charm, the gift of gab, and so on. But the skill of connecting, demonstrating empathy, demonstrating connection, trust, being able to build the relationship that a doctor or lawyer or a financial planner will create with a client, that’s what we teach.
Again, we can put all that in AI. I agree actually, and you know, you and I are in a weird situation in some ways because, you know, people may not know that, obviously, first of all, we have two separate technology products, but we collaborate very closely. You’ve got amazing technology. We’re also building technology, but we’re maintaining our collaboration.
Yes, because we both win. But I’ve been really having a blast with some of the agent training. Because your point is so valid. The idea that empathy is about being heard and seen, I think, is a really good point, because I think people think empathy is about an emotional outpouring. That’s what they think it should be, and empathy isn’t that. You’re absolutely right. What most people want is to not feel like they’re on – particularly if you’re talking about phone sales – to not feel like they’re on the phone with someone who’s going, “Yeah, so, and how many bedrooms is that?”
They want you to hear the fact that they’re worried about paying the bills because their husband died. They want you to hear that, and go, “Okay, I understand your situation, and I want to work with you to help.” That’s what matters. The more you can communicate to me, and the more I can demonstrate to you I understand you, the more you’re bought into my solution, because you think, “If he gets me and he’s suggesting this solution, well, it must make sense.”
But if I haven’t taken the time to understand your situation and I give you a solution, it’s like, “Well, that doesn’t work for me. My situation is different.” And that is such a classic shitty salesperson thing, right? To come in with the solution right away. You don’t even know my name yet and you’re telling me you’ve got a solution for me, and you haven’t even figured out where my property is if you’re in real estate.
And that is such a bad salesperson, that kind of used-car-salesman approach, where they just come in pitching product and pitching all of that, as opposed to coming in and going, “All right, first off, how are you and what’s going on?”
Exactly, exactly. Another thing too is, so we’re talking about the feelings and this and that. So many people think sympathy is important, and I will say this based off my experience and all the people we’ve trained: empathy is way more important than sympathy. And I can say that because you’d be really hard-pressed to ever find me crying. I am emotionally broken, right? My wife says I’ve got a stone heart, like nothing makes me cry.
But I’ve always had a lot of success because I understood what you’re going through. I didn’t feel what you’re going through. I understood what you’re going through, and I could articulate back to you what you’re going through. And that’s what demonstrated the trust and the connection. That’s what built that, not me putting my hand on your forearm and crying with you and praying with you. That’s not what builds trust. That’s what builds rapport.
But you don’t buy based off rapport. You buy based off trust and faith that the other person has your back.
I think that’s – I mean, okay, people listening to this and watching this, that’s the masterclass right there on core sales, and a masterclass on understanding what really matters when you sell. Because I think so many people have this erroneous idea that sales is projection, that sales is patter, it’s flash, it’s speaking quick and tricking people almost.
Where I have been successful in sales is because it’s just me and we’re talking and I’m listening. I’m listening to you and finding out what’s making the anxiety. And that’s where – let’s now pivot to AI, let’s do that. You’ve got Objection Proof AI, which is your new venture, which is going great.
And I’m very proud that smrtPhone, what I believe is the first, still the only system that integrates with you. I wasn’t going to go there, but I’ll tell you, eight months later, still the only company that integrates with us. That’s crazy. But in fact, just yesterday, we had a customer that you referred to us reach out to me directly because they wanted to set up. They were using another rival product of ours, which I will not name, and it doesn’t integrate fully.
And so you said, “Hey, just use smrtPhone,” and we’ve got that now, we’ve set them up. Today I had my team get involved. So Objection Proof – I think what’s really exciting is you’ve got a suite of products that can fit so many different needs. It’s not just the one. And so let’s start with the agent-training side, because there are two essential products that you have that work well for agent training.
So let’s start with that before we move on to the AI that can actually make the calls and talk to people. Start with the training. Give us an outline of how those products work.
Sure. So some time ago, we actually had a client ask us, “Steve, what do you look for in a call review?” Because we’ll do call reviews on our coaching calls and, by the way, when we do a call review, if it was an hour-long call, it’ll take me an hour to get to the end. So we never get past – one of the complaints I have from my team is, “Steve, we never get past the eight-minute mark, because it won’t be good in the first eight minutes,” right?
And so we do the call reviews and the client’s like, “Steve, what exactly are you listening for on the call review?” I said, that’s a good point. So Ian and I, we took the time over the course of two hours and we just wrote down every single thing I’m listening for in a call review. After we wrote down all those things, when we rolled out this AI call review bot, basically we just had AI listening for those same exact things.
And so the reason why this is important is that nothing makes me want to run into a brick wall harder than doing call reviews. Call reviews are painful because they know better and they still deviate from the process. And so with call reviews, now we have the bots automatically doing it. What happens is AI does all the dirty work and you come in and fix what they find.
So for example, if you look at a doctor, a heart surgeon, right? When you have a heart surgery, you have one person that checks you in, one person that checks your insurance and your driver’s license, another person that checks your blood pressure and your heart rate and your weight, another person puts in the IV, another does the anesthesiology, another person opens up your chest, and then the heart surgeon comes in.
So if you look at call reviews, what we’re doing now with AI is that AI will do all the other work that’s not the highest dollar-per-hour activity. And you come in and do the heart surgery on the call review, and you don’t have to lose your mind and get high blood pressure listening to the call for 30 minutes or an hour.
And also – we call it like… I 100% agree. And the other exciting bit about this is historically, because call reviews take so much time, because you’ve got to invest the time to listen and critically analyze, otherwise there’s no point, because it takes so much time, what we used to do was select three calls: three good, three bad, etcetera. We’d do our best, and a lot of times that was arbitrary based on the outcome of the call. The call went well because we got something out of it.
But you were never able to really see patterns of behavior with your agents because you were only cherry-picking a certain amount of calls to review, because you had to. Whereas now, and I don’t think we’ve finished the dashboard element for Objection Proof yet in our system – I don’t know, I’m going to think about it – but what I love about it is because with our integration with you, every single call gets pushed over and scored.
You can actually see true performance patterns on a day-to-day, hour-to-hour, call-to-call basis, which identifies the outliers, both good and bad. The good outliers of the people who are crushing their calls so that you can zero in and figure out why, and the bad outliers for people who aren’t. And it’s no longer the guesstimate based on a few calls. That’s what I think is where your call-scoring tool is for the win.
Yeah, there’s that, absolutely. Because as a sales manager or a business owner, you can go there and you can look at trends. The other thing too is we require our salespeople – and we suggest it to all the clients – but we require our salespeople to have all the call reviews go into a group chat that they can all see, and we require our sales guys to actually go in there and digest the call review and give feedback on it.
And what we’ve seen is by having this type of feedback loop, our guys are getting better, faster. They’re getting better faster. And the other thing too is I can see where they’re at based on how they digest it. Meaning when they say, “Oh, this is what happened,” or “This is what they said,” or “Here’s the reason why we ended up in this situation,” by the words they put in there, I can see even more clearly – because I have the call review and I have their response to the call review – I know exactly where they’re stuck and I can fix it even faster.
Now, I’m sorry to interrupt this amazing conversation, but I wanted to make sure you knew that smrtPhone, the only phone system built for real estate investors, connects to the best-in-class real estate investing CRMs. And because it’s my show and I am co-founder and chairman of smrtPhone, I’ve got some great deals for you. Click the link, take advantage of 5,000 minutes free calling with smrtPhone, the only phone system built for real estate investors. Click and call, close more leads. Back to the show.
And what people don’t realize, I think, is the best people want to improve.
Yes, absolutely. The best players – I mean, I remember watching Michael Jordan’s documentary on Netflix, The Last Dance. Fantastic documentary, which I’ve watched at this point maybe ten times. I don’t know why, and I’m not even a basketball guy. I’m not even a basketball guy. But it is – I mean, I’m at the age where my young life was the Chicago Bulls of that era, right? I’m 47. So that is exactly in my teenage sweet spot.
But there’s something about that documentary that keeps me watching it over and over again. And one of the things he says all the time is, “I want to play with the best. I don’t want to play with the worst. I want to be around the best. If I can play with someone who’s better than me, then that’s my new target, because now I’m coming after you.” And he would say, “I’m coming after you,” basically to kill you.
But salespeople – good salespeople – are the same. They don’t want to be B players. They don’t want to be C players. Good salespeople want to always be A players. And this is a tool that will help them maintain or get to A-player status. Or quit, which is great too, which is equally good.
Yes, also great. Weed out the shit. Yes. Yeah. This is the standard. If they don’t like the standard, they can go away and burn someone else’s marketing dollars.
100%. And I’ve talked about this before, but the idea of AI replacing people – well, there are going to be some people who are replaced. It’s usually the shit people. And I don’t mean that as a person, like I don’t mean that as personal, as a human being, of course not. That’s not about who you are.
It just means the top performers are likely going to maintain their status as top performers, and the people who are kind of just getting by or not doing well, they are going to be weeded out. That is the nature of the game, and I don’t think that’s a bad thing. It’s not a bad thing. Well, I worry about what they’re going to do, but it’s not a bad thing because really, all we’re doing now is improving efficiency and effectiveness within every organization.
Right. Which is the goal for every business. We are an organism that has to get better every day, every week, every month, every year. This is helping us get better, faster.
Absolutely. So now you’ve got the call scoring, then you’ve also got the role playing. And role playing is something I think most people – I don’t think a lot of people – I think a lot of people are self-conscious with role playing. So I think this AI element is a great opportunity. Just briefly talk us through that part.
Yeah. So what we did was we created some role-playing bots, because this is what you want to use for two different things. One, for training your salespeople, but two, also we use it as a screening tool. We’re not even going to bring you in for an interview if you don’t do well with our role-play bot.
And so with our role-play bot we have five different ones. You can practice with them, you can train with them, and you can get better. Right. And the other thing too with the role-play bot is that it actually scores it the same way that our regular call review does, so you still get the same test, you still get the same analysis.
But the other thing too is the reason why I think the business owners like our tool is because, as you know, Jordan comes in here and is like, “Hey guys, have you role-played today?” And they say no, then Jordan needs to role-play with the team, and that sucks, right? So now we have this role-play tool.
I can log in, see they haven’t role-played today. “Hey guys, what’s going on? Go hit that, go role-play with the bots.” Or you can set a time for it. You can have the bot call your team. And so the point here is that you can make it a normal routine.
You practice. Dean Rogers, Stratton Brown – these are good friends of mine. One played professional football, one played D1 football, and they both said the same thing: practice was always harder than game day. They practiced harder. Game day was easy. Why don’t we do the same thing in sales? For whatever reason, people hate practice.
Game day’s the fun. Game day is the fun that you get for the shit you eat in practice.
Yes, yes. That’s the party. I do a running program right now with a coach on my treadmill. I just finished a 10K training program, and at the end of it, he was like, “Guys…” because then I had to run the 10K. At the end of it, I remember him saying, “Guys, the 10K is the party. It’s a celebration. You put in the six weeks of work and graft to get here. The 10K, you just get to that and you just smile the whole way and enjoy it, because this is the payoff.”
And I see that – role playing or any sort of training – as the graft you put in for that payoff of making the sale or of improving and doing more and more.
Absolutely. That’s absolutely right. That’s the right mindset. I mean, I know for myself, I’ve always hated running 5Ks and so on. Why? Well, I don’t want to put in the work beforehand. And it gets a lot easier when you put in the work.
So let’s move on to the voice agents, because this is a space that we’re all in now – that you’re in, we’re in, we’re in together. We’re going to continue to collaborate on it. It’s definitely an enormous opportunity. Talk to me a bit about the types of agents that you guys have right now, and where you’re going.
So we have three different agents today and we’re going to have more. But the three we have today: one is for web forms. Someone fills out a web form, we call it instant speed-to-lead. The AI calls them, books an appointment or does a live transfer. We have two different versions of that bot: book an appointment or a live transfer.
We have another one for inbound. So if you’re after hours, weekends, holidays, or if someone calls during the day, after two rings have AI take the call. So you have a high-quality answer. So we have AI here now taking inbound calls and booking appointments. And then the third one we just rolled out last week is a follow-up bot, which is basically you go in your CRM, you tag these 50 people, and then AI will call them.
AI will call them, get them to raise their hand, do a live transfer into your organization, and now you get an appointment again. So you’re able to reactivate your CRM, because literally everyone has six figures easily in their CRM that’s just waiting to be talked to. But we’re all too busy, right? We’re always chasing the hot leads, the new leads. We’re putting out fires in our organization. We’ve got escrows falling out. We’ve got lenders screaming at us. We’ve got sellers screaming at us. Title is wondering where we’re at. All these things are happening.
We all have these in every company. So now we’ve got a follow-up bot. I’ll give you an example. Eric Brewer just signed up with us a couple weeks ago. He has 60,000 people that raised their hands in the last five years. How much money do you think he has in his CRM right now?
So yeah, absolutely. I know Eric, and he’s got a great company. And your point is so valid as a general problem for real estate investors that this solves, which is you’ve got these – I think all investors are at heart slightly shiny-key people. They’re slightly drawn to new leads. Everybody talks about the new leads as opposed to the leads you already have – the gold, as you say – that’s already in the system. And I do think that AI and these sorts of structures play such an obvious role and a more qualified role in many ways on chasing up and never letting these things go.
And I love the idea – your point is also really valid on 100% answer rate, because nothing makes a lead go cold quicker than having to leave a voicemail and wait for a callback. And that’s, I mean, I used to use an agency. And then you listen to the calls in the agency and it’s awful. Right. And it’s like, “What the hell happened here?” Then you see you’ve got a bunch of minimum-wage college kids treating the leads as throwaways. No shit.
And they’re basically ruining – a lot of times if you’re outsourcing this to an outside call center like this, you’re getting zero qualification. They know nothing about your business. They know nothing about the industry. They know nothing about these leads. And they’re kind of running a script, not very well and not very enthusiastically.
Yeah, exactly. So I worked in a call center. One of my first jobs out of high school was a call center. Listen, that’s not the place you want sending your leads.
No. And that alone – I’ve always sort of taught people: never go to voicemail when you can, never get a callback when you can do a live transfer. Any time you have someone on the line, keep them on the line and try and get to the next stage. Don’t – the moment you go, “Yeah, I’ll get my manager to call you back,” you’ve lost the impetus right away.
And that’s where I think I’m so excited about technologies like the voice AI agents that we’re talking about, because it takes some of those pain points and it 24/7 automates it. It’s never going to be a problem again.
Yeah. It doesn’t have to go eat, doesn’t have to sleep, doesn’t have to go to the bathroom. And the best line I heard – I was talking to someone – you don’t ever have to worry about AI getting pregnant.
Oh, well, as I get my HR rep for the company asking me why. Right. But these days, look, there’s maternity and paternity leave in a lot of companies. So it’s a problem.
Absolutely. And you don’t have to worry about someone having a bit of a shit day. They’ve had a crappy time at home. They didn’t sleep well. AI is going to answer that call every single time the exact same way, with no variation of external mood.
No “I’m in a good mood,” no “I’m in a shit mood.” And so oftentimes the variance I see in agent performance – not AI agent, but in-person performance – you may have a really, really top person, but if they’re having a shit day, that performance will drop 50% because they’re just not there mentally.
I mean, how many times have we had this conversation, these two different conversations: “Hey Jordan, when you go out with your buddies this weekend, can you just do me a favor and drink enough water before you go to bed?” We’ve had to have that conversation. Or another conversation: “Hey Jordan, look, I appreciate and understand you’re going through some tough times at home. I need you to check all your personal issues at the door when you walk into the company.”
We’ve had to have that conversation. It’s also impossible. You can say, “Check your emotions at the door,” you can say anything, but we carry everything with us all the time. And AI doesn’t.
Exactly. That’s all there is to it. It is the future.
Now you’re continuing to build agents. One elephant in the room of all this is always going to be around compliance. You and I have talked about this, which is also why I believe both of us have taken the stance that cold calling isn’t where we’re going with our agents, because cold calling is, to me, a compliance nightmare that is already fraught out of the box. Out of the gate it’s frowned upon, and there’s a lot of “no-go,” and it’s going to get worse.
But where do you see some of the other opportunities coming? Do you see it as different capability? How far do you think an agent can go? Because you talk now about agents actually closing deals. To me, the danger…
Well, to me, the danger of that – and I’m fascinated with it – is, you know, with all of our agents, we’ve built in a certain amount of guardrails where they’re not allowed to make offers because, of course, your parameters of offers have to be decided upon very rigorously. How do you see that kind of game going?
Well, so what are the challenges in making an offer? The biggest thing is: can you underwrite it in real time? That’s the biggest thing. So as long as we can underwrite it in real time, it’s not really an issue. And there’s not a great AI underwriting tool today. There’s not one that I’m aware of that exists. However, four months from now I’m convinced it will exist.
So if our goal, our stated goal, is September of 2026, my internal goal is March of 2026, and I’m convinced that someone will be able to figure out underwriting before then. There’s a company, Bestia – I believe you’ve talked to Vac over there – they’re some smart, smart guys and they’re figuring out a bunch of stuff with data and AI and houses and so on. We’ve got Robert Wensley with InvestorLift. He’s also working on the same problem. We’re going to be building AI bots for InvestorLift at some point. I’ve talked to him because they’re all opt-in there, so it’s compliant.
So once you know what the deal can sell for, once you know you can underwrite it, then you’ve got parameters.
Yeah, exactly. And actually, as long as you have that information, then the training of the agent and the parameters you give the agent is relatively black and white. The question is knowing the underwriting, because if you’ve got that quick enough and in real time, that can feed the parameters the agent gets, and the agent will know, “Well, the lowest I can go is here, the highest I can go is here, and my goal is here, and this is a super-extra goal,” or whatever it is. But you can – AI is all about guardrails.
I think people think a lot of times it’s all about the training. Yes, of course the training is critical, but guardrails, to me, are as equally important, if not more, with AI agents. And what you’re saying is, I think, very true. As long as we get the data, we can put the guardrails up.
Yeah. I actually had coffee with Nick Perry a couple of days ago, and what he shared with me is that his AI underwriting is now doing better than his human underwriting as a company.
We really are there.
Yeah. So, I mean, it’s not surprising in some ways because underwriting should be a relatively black-and-white process. I don’t know why you need a human involved with it in many ways.
Well, I know there’s a lot of nuance. For example, in the older parts of Phoenix – older like 40s and earlier – it’s harder. But in my neck of the woods, Chandler, Gilbert, Tempe, pretty much they’re all pretty similar in the neighborhood. If I know what three houses sold for in the neighborhood, I know what the fourth house is going to sell for.
So in newer markets, the bigger markets, it’s going to be easier to underwrite. But there’s always other challenging markets, like I know New Jersey is notorious for each street being different than the other. But even then, that’s just machine learning, and with machine learning you can figure that out too. So yeah, I think underwriting accurately will happen before we can buy a house over the phone. So I’m not worried about that parameter because I think what we’re doing is much harder and a much more difficult problem to solve.
Yeah, I agree with you. I agree with you. And I think you’re solving it. These problems of that kind of human connection and the ability to establish enough trust to be able to move forward. People ask me why do I think this is going to be successful, and I’m like, because I’ve also dealt with call centers and I’ve dealt with – we’ve all dealt with VAs who don’t…
We all know that the game is usually played right now with low-level staff doing initial qualification and then higher-level staff doing closing. That’s basically how most people work. Why do you think that lower-level staff can’t be AI?
Listen, I’ve done so many trainings. I’ve listened to so many calls. Even the best organizations struggle in this department, right? Because like you said, it’s a lower base compensation. These are not – if you look at Predictive Index, “high A,” if you look at DISC, “high D” personality types – they’re more typically in the acquisition roles or the disposition roles. They’re not so much in the lead-manager roles.
So the lead-manager roles, they’re kind of people, but they’re less driven just by the very nature of the people you hire in that role for the compensation you pay them. Lead managers make a third, a fourth, a fifth of what a good acquisition manager makes. That’s the reality of the compensation schedule. So yes, I genuinely believe we can replace them.
Now, the other thing too is, I have people asking me all the time, “When can I replace all of them?” Don’t replace all your lead managers. Keep at least one awesome one.
Yeah, keep your best one.
That’s where this is going. I’ve said this so many times. It’s like, guys, I’m not about trying to replace everybody. I’m trying to replace the dross. I hate to say it, but I don’t need C-level players in my company. I want A-level players. That doesn’t mean all of them are high drivers, because that would be a horrible place to work.
But you can be an A-level expressive. You can be an A-level amiable. You can be A-level across all the personality styles, but you have to be an A-level. And that’s where I’m super excited about the work you’re doing, the work we’re doing, the work that’s going on right now, because if I can focus my company on the A players only, I can squeeze an enormous amount more juice from what I’ve got.
Yeah. Yeah, absolutely. And I still – we were talking the other day – like Elon Musk, right? He can just go hire the best person in the world, and that guy pays for himself many times over. And we’re trying to hire someone that’s like 40,000 a year and try to get him to perform like a $120,000 person, right?
But if we can hire the best, then we can hire more of the best and even more of the best. I’m at an exciting point now in my business where everyone I bring into the organization has to be at this standard, because if you’re not the standard, you’re just going to feel terrible. It’s going to be a terrible experience.
Yeah, right. I’m at a point now where everyone’s an A player. But I wasn’t in this place five years ago, seven years ago, ten years ago. Ten years ago I was like, “Man, I hope Jordan makes calls today.” That’s where I was ten years ago. “I hope Jordan called that lead that came in this morning.” That’s where I was ten years ago.
Right now, I’m like, “Jordan, what the hell happened? That lead came in.” Well, now we have AI, we don’t worry about it anymore. But I used to say, “Jordan, what the hell happened this morning? That lead came in and you didn’t call it. What were you doing?” And you’d feel bad about it, but you’re also not going to take it personally like I’m going to get sad about you. You’d be like, “You’re right, I messed up. Let me fix it right now.”
But ten years ago, that’s not going to happen.
You get smarter.
Those mess-ups don’t happen nearly as much when you’ve got A players. A players still make mistakes – OG or present, we all do. I make mistakes, you make mistakes, everybody does. Those happen. But A players will always fix those mistakes or address them head-on and be like, “Okay, how do I fix this?” And also those mistakes don’t happen nearly as much.
Exactly.
Well, all right. Before I get you to tell us how everybody can get in touch with you, how everybody can experience the magic, I do have three questions I always ask people on the podcast. Rapid-fire questions that should be very easy for you. So, the Real Estate Tech Guy Fast Five.
Number one: What is the biggest mistake you personally have made with real estate investing technology over the years?
Oh, with technology? I don’t know if this is quite first, but I went way too hard on media. So in 2021, with COVID, everyone was in the media, social media and so on. And I’m looking at my friends, Kong and Ryan Pineda and all these other guys, and they’ve all got all these media guys. So I hire a bunch of media guys, and I nearly buried myself. At my peak, we had seven media guys to create all the content, pump all the content.
Now we only have two and probably have even more content because of AI. But we had seven guys in our organization and I nearly killed myself financially. When things slowed down in ’22 with real estate first and then as a vendor second, man, that was a really tough time. But because I did it to myself, I went too hard on social media.
I’ll take that. I’ll take it. You know, there’s no wrong answers, and that’s an interesting story.
Question number two: What’s your best advice on how to integrate technology into a real estate investing business?
I would say move slowly. The greatest mistake I see happen all the time is people think about this as an all-or-nothing – like, “I’m going to have no AI, I’m going to be all AI.” It’s like, no. You just roll it out, take it one step at a time. Roll out – I mean, you don’t have to use our tool. You can roll out Fixer, you can roll out Fathom, whatever it is inside your company. Add something once a month. Every month, add something to improve the efficiency and effectiveness of the business.
Because those efficiencies really do compound. Like I said, I have two guys that are pumping out more content than when I had seven guys working full time. It compounds so long as you are being intentional, you take steps. Don’t wait for it to be perfect. Don’t try to conquer it all at once. Just add one tool, get that rolling, add another tool, get that rolling, add another tool.
That’s great advice. That is very good advice. And it’s something that everybody needs to listen to, particularly the all-or-nothing, this kind of weird, mentally deficient view of it where I’ve got to go no tech over here and then I’ve… Just iteratively bring this stuff in and you will also be able to adjust your business model in step as well, because it’s not just technology. You’ve got to change your processes. You’ve got to change how you function and how you think as a business.
And so if you just go ping-ponging, you end up causing disruption that is almost irrecoverable.
Yeah, you’re going to destroy everyone in your company. There goes morale.
Final question. You’ve got a lot of people listening to this and, you know, we’ve got people who are just starting out in real estate technology and you’ve got a long history. So if someone is starting out as an investor, what three types of technology or products – not brands, it doesn’t have to be brands – but types of products would you recommend they start with if they’re starting out in their real estate journey?
Technology – you’re saying technology?
Yeah.
So I mean, selfishly, I think our stuff – I think the highest bang for the buck is what we’ve got going on. I think what you’ve got going on at smrtPhone, and then pick a CRM that you can commit to using. I will say those three. Let’s see what else there is before we settle on those three. So the things that are important: you get marketing, you get sales, operations. I think we kind of cover it, because our stuff covers sales. CRMs cover operations. You cover operations.
The only thing left is marketing, but marketing doesn’t require nearly as much technology. So I’d say, really, me, you – we love LogMeIn, right? So if you’re looking at that, go with that. If you want to go with something that sucks, you can go with that too.
On that note, let’s end. Steve, it’s always a pleasure, genuinely a pleasure, to meet you. I’ve been blessed. You and I haven’t known each other that long, but I feel very fortunate that Stephanie – in fact, Stephanie Betters from Left Main, shout-out Steph – introduced us. We’ve been able to really develop a great working relationship and a personal one.
How can people find you? How can people get started? I want to make sure that everybody listening to this has a chance to experience the magic.
Oh yeah. So there’s a few different ways. We have ObjectionProof.ai. If you go there, you can upload a call, you can upload a transcript and you’ll get the call analysis. That’s free.
If you want to check out our role-play bot, text the word ROLEPLAY – one word – to the phone number 33777. And then the last one: if you want to listen to what our AI bot sounds like in scheduling appointments, if you text the word CASH to the phone number 33777, you’ll get started on figuring out how to recapture all the leads in your CRM.
Turn that into $100,000, a quarter million, or for some instances, guys who have been in the business for a while, maybe $1 million that’s sitting there in your CRM.
You heard it live directly from the man himself. I will make sure that in all the posts, socials, the recording notes, everywhere you can hear this, I’ll make sure all those links and all of those numbers and instructions are in there.
Steve, as always, I’m grateful for you coming on with me. It’s a pleasure to see you, and thank you so much for coming on That Real Estate Tech Guy.
Thank you for having me. I’m glad we got to talk about some things I don’t normally talk about a lot, so ask me again.
Well, thanks for listening to another amazing episode of That Real Estate Tech Guy. Head over to ThatRealEstateTechGuy.com to check out all episodes and get special discounts on tons of awesome real estate technology platforms.





