Howard Tager on the Good, Bad, and Ugly of AI [FUBCON Session]
21 Nov 2025 · 21 min
This is a FUBCON podcast interview (Real Estate Team OS) featuring Howard Tager in conversation with Ethan Butte and another host. Tager discusses characteristics of high-performing teams (diverse, non-overlapping skillsets; healthy, constructive disagreement), his entrepreneurial journey founding Ylopo (early years of trial-and-error, resilience through multiple near-failures), product development practices (using a community of real users in alpha/beta, delaying release until product readiness, example product named "Maverick"), and practical views on AI’s role in real estate (AI will automate repetitive tasks, act as a productivity companion, not replace the agent; risks include deepfakes/fraud but benefits far outweigh if embraced). The interview closes with personal reflections on lifelong learning and not retiring.
Chapters
No matter where your business is today or where you want to take it, you'll get there faster and more profitably with an operating system. Welcome to Team os, your guide to starting, growing and optimizing real estate team. Here's your host, Ethan Butte.
Howard. Great to spend time with you again. It's been a long time since I've seen you.
Same here. Thanks for having me.
Yeah. And you've done a lot since I've last seen you. So we're going to get into some of that. We're going to start where I've been starting with everyone, which is a must have characteristic of a high performing team. What comes to mind for you on that?
I think a must have characteristic is to have a village that's diverse, that just has a lot of synergies. So in other words, it's just a village of people with varying strengths. And that's the critical thing you can't have, you know, for a high performing team, you cannot have a people with. With too much overlap. Right. It's really, you've got to curate a team that is, is, you know, each person brings this unique thing and then you create this magic and this synergy. So that's what I really look for, is to create that village of not all the same people. Right. And not. And I don't like group think where someone says something and then everyone just agrees. I like a little bit of the clash in a healthy way to get down to the right path and the right answer.
Yeah, love it. I did watch the Y Lopo Inside Edition episode with you so that it takes a village concept that like really res. Resonated with me when I heard it. And I love the way that you broke it down here and implied in that approach is that you have some level of self awareness. As you said, this isn't your, your first rodeo in building a company. Talk about your own journey into self awareness from a leadership perspective where you knew, for example, starting Y Lopo almost a decade ago, looking forward to 10th birthday party coming up, not just the future. What has that process been like for you? And what did you know? You wanted to surround yourself starting the Y Lopo journey.
Right. So you know, G had come to me, you know, to two of the years in the decade we really kind of, we were kind of zigging before we zagged. So it's, it's almost like the Google story. Like they didn't even know when they started Google that they were going to do pay per click. Right. Like that was something they fell into and it became the world's largest business. Right. So when G came to me, I was actually sort of on this other path and I was going down this other path and I was set on this other path. And then he came to me after, like a whirlwind tour and he said, I've got this idea for Y Lopo and this is what we're going to do. And I just thought about it and I, and it was a really difficult decision. The other path was safe for me. And this path with crazy G, who was the most brilliant person who had ever worked for me, I just thought it was too exciting, it was too much fun. And so we did it right. And, but it was two years of just learning and zigging and before we actually sort of in 2016, kind of went really like down the, down, down the journey here. So, you know, I, I, I think, like, honestly, for the first, like four years, the number one characteristic, which is talked a lot about today because of the light of the macroeconomic, you know, real estate condition, was the number one thing that I had to lean into was resilience. And that, you know, I don't want to lean into it as this cliche term that everyone's talking about here. But, but we literally almost lost this company four times. Four discreet times of bye, bye, you're no more. And so I think it was tapping into that reserve of, yes, sleepless nights, but waking up, although you're not waking up because you're sleepless and saying, yeah, we're not going to give in. We're going to figure it out and, you know, or die trying. So, so not, not a lot of people know that. They just think, oh, why? There was always this success.
Yeah.
But, you know, we had to come back from the grave four times and be super, super flexible and creative to then find the path to kind of where we are now. Yeah.
Yeah. Would you be able to share some version of one of those four stories? When did you see that threat? How did you adapt to it in the moment? And what were some of the positive and negative or, or even more interestingly intended or unintended consequences of the decision you made in the face of that?
Right. So, you know, people are always asking me, like, so what book should I read?
Right.
You know, tell me the books I should read.
Yeah. Where's the magic answer I need?
Right? And so, you know, I always tell them, you know, I could give me a few titles, but I always tell them it's really this book of life and I studied intelligence, the psychology of intelligence. And one of the. One of the strands of intelligence is experiential intelligence. It's just your ability to actually learn from experience and like, really learn from it. Meaning that you change your behaviors over time to the plus. Right. And so, you know, I'm always learning. Like, literally this week I'm learning, which I, which is why I get up in the morning. If you're not learning, like, you've got to do something else. So one of the times we had kind of put all of our eggs in one basket from a revenue standpoint, and we had one major client that literally accounted for like 75% of our revenue.
That's overweight.
Okay. Yeah. But, you know, you're a startup and that's a lot of money and it's paying the bills and you're hiring engineers for it. All of. And I wake up one day, don't see this coming. I wake up one day, basically get a call and it's like, yeah, we bought that company that was providing 75% of your revenue and we're going to turn you off as soon as we can. You've got 90 days. Okay. That was like episode, like number whatever of four times we almost lost the company. And I was just sort of like, you know, I had raised a little bit of money from a bunch of people who had always wanted to fund me, and I'd never taken money before. We took a little bit of money. We've been very capital efficient. And literally, how am I going to get these people their money back? Right? Like, what am I going to do? So, you know, we, we did it. Like, we absolutely did it. We figured it out and ultimately landed in this great place where no one customer represented more than 1% of our revenues. Here you are. You know, I've already sold a couple of companies to public companies. I'm on my third journey. I'm supposed to be the seasoned executive and I broke like a serious cardinal rule of whether it's a dependency on a critical employee or dependency on a critical technology supplier or. Or a dependency on a customer, don't have all your eggs in one basket. Right. So now it's one of my like 12 commandments, right. You know, that I'll. That I'll preach upon. So that is. That ties it together.
Love it. So you've got a couple realtors, accomplished realtors, who are not just alongside. I think anytime you're running a good company with legit customer intimacy, you know, have you really good access to your customers. And they want to give you feedback and insight. But you taken that next step of bringing some of them in in a more formal manner. Talk about how important it is to have a customer, like a true ideal customer inside the organization, committed, truly partnered in a very direct and meaningful way inside the business.
Yeah, that's a really cool question, not a question I've received before. So.
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In my prior company, again, like leaning into this. The book of life is the most important book. Are you paying attention? And so I looked back when we started Whelopo, I look back, back at my tigerly journey, right? And in my tigerly journey, what I saw, like in our, for example, Facebook community, occasionally, you know, you get a hater no matter what company you have. Like, you get someone who doesn't understand they're a hater. And we had this one woman, this woman, Susie hall, who I'll forever be indebted to. And she like the second someone came on, before even we could respond, she was there saying, no, you've got it wrong and here's what you need to do and blah blah, blah. And it's just swatting it down like every single time, right? And then teaching like, and helping them, right? And so she just always gave of herself at our events online and she was teaching, never asked for anything. She passionately believed in it. She loved the product. It had transformed her life. And so then there were a few others that did that. And so, so on this sort of experiential journey when I started Yelopo, I thought, you know, it would be really cool in this company to more formalize that, right? And, and don't just be this group of technologists who think we can figure things out for our real estate clients, but make sure that as. As part of the heart and soul of the company are people who are walking the walk, who have our product, who are using it every day. Coming back and telling us, hey, man, you really need to. You're nibbling on the edges, but you've got to do this. If you do this, that's a game changer, Right? Yeah. Or this is amazing. We've got to really lean into this. So. So people who are, as you said, like in the lab using the product and we've got like a whole fleet of them. Right. And so there' like levels. There's. There's the realtors and residents, senior realtors in residence, like Barry and Gabe, who are amazing. And then we have like, more like WO ambassadors and we have WO coaches and we have WO professors. And so, yeah, so that's been something that we had never done before. We do it here and I think that it is really helped, you know, the journey of the product built a lot of trust with our, with our other clients. And there's just so many times where someone will come to us and they'll say, I'm kind of overwhelmed, I'm swimming. I know I'm not using like 75 of your tech. And then we have people who are using it in the field that they can trust. Not just as people trying to sell them stuff.
Yeah.
But people who've used it to transform their real estate business.
Yeah. Love it. Barry was in this chair the other day and I ran into him before, really fubcon got going. Like the day before it got going. Hug chatted for a minute and I was like, what are you up to? And he's like, I'm, you know, it's just fun not to. To be the dumbest person in the room. Of course he's being playful, but he was in with. With your engineers.
Right, right.
Going deep, like for back and forth, in depth stuff. And, and that access. I just can't imagine how helpful it is to productive. Actually I can because we have a little bit of that going on at Follow Boss as well. But I think that gets lost.
I think it gets lost so many times. And so many times the engineers and the AI folks and stuff, they all get walled off. Right. From the. Just the reality of day to day being in real estate. You know, even that. Although I've never been a real estate agent, I have a whole real estate sort of career. I'm a real estate professional. Outside of this. And I have transacted, you know, hundreds of times in real estate and just having that pragmatic on the street knowledge of what that's all about and what the daily life of a real estate agent is like is really important to bring that human and real estate perspective to the hardcore sort of software development side. Yeah. And so it's just critical getting that input from Gabe and from Barry and from everyone else. And when we go on the product journey, you know, we start in the lab, but then we have this long alpha stage, right. And it's a very, very small community of people who are kicking the tires and testing the product and, and then.
Coming back know what they've signed on for. So they're not expecting anything finished.
Everyone loves to be like, right. In that you're right. It's really the beta stage where it's more, it's going a little bit.
Right.
And then you got people who are not so much in with us every day but, but they're really out there a little bit more removed and then they're really giving us the, that the beta stage is the critical thing because I will not release a product until it's time. And take Maverick for example, right. Which is our newest release. We're having a big release party this weekend. We're excited about it. I mean we are literally probably six months off from when we thought we would be releasing this, this new product and this new company, but we just refused to get it out there and sell it until it's really, really correct and really, really right. It would be, you know, short term gain and long term death.
Yeah, it's good vision and, and again this, this idea of a village, it includes a lot more than the people that are on, you know, the team directly.
Oh, it's the whole, it's the whole community, it's the whole family of clients for sure.
Yeah.
I don't, I don't remember whether it was as we hit record or before, but you know, there's certainly a lot of confusion as well as excitement and concern around AI super high level. Take away some of the overhyped fear dynamic around all of this and then maybe roll into what is going to be. How is this going to be a true helpful companion to the team leader and to the agent.
Right. Well look, with a concept like AI there's the good, there's the bad and there's the ugly. Now the sort of in the middle ground is not going to get any headlines. Right. The ugly is going to get headlines Right. So deep fakes and fraud and all the ways that, you know, evil people will use any technology in an evil way, right? Yeah, but that's really sort of, I always, I always sort of point out to people like, is that the tail or is that the body of the dog? Right? Is that, are you talking about the 2% or the 98%? And for us in the real estate community, what I'm trying to get across is that those real estate professionals who really embrace AI, it's a whole new amazing world. Like they're literally going to excise from their world every boring, repetitive, time consuming, high cost task in their lives, right? Like that's going to be amazing for them. So they're going to save a massive amount of time, which is absolutely their most precious commodity, right? They're going to actually save a, a bunch of money. Okay? They're going to be way more productive and they're going to save up all this time to be able to actually do what they need to do, right? Which is not sort of, you know, updating status fields themselves or sending countless emails, texts, calls and all this stuff where they actually don't have time in the data, truly engage on a personal basis with their prospects and their clients. And so all of this AI, this AI is not here to replace them at all. The real estate professional is that, that final mile in that connection. And, and it's never going to replace that, right? They're always going to be their coach, their counsel, their, you know, their, their, their guidance advisor, their emotional support, you know, the person getting them through a 200 page document, all that kind of stuff. Right? But what AI is going to do is it's going to tee up all of these personal conversations. It's yes. Will it communicate by voice to that prospect? It absolutely will. But it's not to be the final mile. It is literally just to get that person conn client real time so they can then take it from there. So I would say if you're nervous about it, if you're scared of it, if you're not going to embrace it, you are going to become a dinosaur. You're literally not going to be able to compete in this world because you're not embracing technology that's there to help you and those folks that embrace it, that use it, it's a whole new world of productivity that they're going to absolutely love. And that's why we got so much excitement about it, you know, here at the conference and yesterday. So I think most people are getting and I think also, you know, Ethan, what's going to happen over time is we all, you and I, we're going to start normalizing our reaction to AI. So I showed the opening scene from 2001 A Space Odyssey yesterday, which everyone loves. It's one of the most brilliant sort of film sequences.
Yeah, yeah.
And. But. But it's really like the heart and soul of that movie where, you know, folks are communicating with AI and it's very normal. Normal. It's part of their lives right now. It goes a little bit of a rye, which is. Right. You know, makes an interesting movie, but that's what's going to happen. I think we're going to go through this really uncomfortable rough patch. Right. And then it's just going to be as you and I sit here again in the podcast five years from now. Yeah, right. You know, you know, everyone's going to be here. Right. But AI is going to be setting everything up. We'll talk to them. Like, we'll just talk to a. Hey, can you adjust the lighting? And can you do that? Whatever it's going to be. Right. It's just going to be part of our lives. And I think that, you know, the stuff that's truly evil, I think hopefully will get protected from us. And the stuff that's really going to make your life in doing these podcasts all day a lot easier. You'll use it. You'll embrace it.
Yeah, absolutely. It's so easy to emotionally fall prey to always, never, yes, no, on, off. And all the answers are all. That's why we talk about the middle way. There's a middle way, and in this case, it's both. And it's just another leverage point for anyone working or even living. And I think if it was presented as such, as opposed to like, this is going to take your job, you know, if you're doing a job that can be automated, well, it's probably not that valuable a job. So this I appreciated, especially that layer in that passage you shared there of essentially, it's putting people in their best place to do what they do well, which is connect, communicate, manage emotions, manage expectations, provide explanation, provide comfort, and all these other things that an awesome real estate professional does. Howard, this has been an absolute pleasure.
Awesome.
Before I let you go.
Yep.
Fun pair of questions for you. And you only have to answer one.
Okay, thank God.
What is it?
What does it look like for Howard to continue learning, growing and developing? Or what does it look like for you to be relaxing, recharging and resting?
Yeah. So First, I'm going to backtrack for a second because I was excited. You're one of the first people I'm always preaching about. I live in the gray, not the black or the white. Most humans live in the black or the white. And it's not black or white.
It's easy and fun and like, like satisfying to feel like we understand. But once you let go of the need to understand truly and just accept that, you're going to understand as well as you can.
Right, right.
It's way more fun and loose.
I grooved on that. So anyway, so it's really the truth is like always in the middle and there's a bit of black, there's a bit of white, and like we get the truth. But anyway, so really timely question. You know, I think about that from a financial standpoint. I don't need to work. Like, I'm fine. My kids are fine, my grandkids are fine. I don't need to work, work. Right. So it is a question you wrestle with, right. When you see your friends who are like golfing and wake surfing or whatever, they're traveling or whatever they're doing. But whenever I've like, put my foot in the water of that, all right, I'm just really, just gonna kind of, you know, kick back a little bit. Like it's even could just last a week. It, it doesn't make me fundamentally happy. Right. And so like, what are we here for? Right. And it's, it's that constant brainstorming with my, with my partners and it's tackling a problem. It's playing this game of chess that, that we're playing. It's being in this competitive environment that we're in. So really, like that's, you just have to know yourself going back to your first set of questions, know thyself. And I've just come to that in a really happy place. I've come to that saying, sure, it's great to go play a little golf or, or get into pickleball. Like, I'm going to do some of that stuff, but it'll be just like these small parts of really what defines me. And my main part is this is the most fun game that I play in and I take it really seriously, but I have fun with it. And if I'm not doing this and I'm not learning, what am I doing? Right? So I am, you know, it's a dead on question. I've wrestled with it this past summer and I got to the answer pretty quickly. Like I'M never going to retire ever. Like, I am going to be fully engaged and always be learning right till the final days. That's, that's what I'm going to do. That's my DNA.
Awesome. Continued success to you. Thanks for doing this.
Thanks, Ethan. Appreciate you.
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