Podcast

Episode #191 – From CEO Of Keller Williams to Proptech Investor with Chris Heller Part 1

You will always cap your growth if you don’t surround yourself with a good team. But building a team of talented people that get along with each other is difficult, especially for real estate investors.

So what’s the secret for building a team that skyrockets your growth to levels you can’t even dream about today?

Today’s guest, Chris Heller, has the answers. Chris got his real estate license at 20 years old and quickly became the #1 associate in America at Keller Williams. He went on to become the CEO of Keller Williams — while managing his own real estate group. And today, he sits on the board for several real estate startups and acts as the Chief Real Estate Officer at OJO Labs.

In this episode, Chris reveals his secrets for growing a high-performance team in any venture you try.

Listen now.

Show highlights include: 

  • How to get business advice from billionaire mentors (without paying hundreds of thousands of dollars) ([5:58])
  • The “Timeshare” secret for closing more residential real estate deals (without feeling like a sleazy salesperson) ([13:00])
  • Why trying to fail is the quickest way to unlock life-changing success ([17:42])
  • 4 simple ways to identify great leaders within your company (even if they don’t have a leadership role) ([21:26])
  • The former CEO of Keller Williams’ two-step system for building and growing a high-performing team ([22:35])

If you’d like Chris’s book, Dominant Thoughts, you can grab a copy at https://dominantthoughts.com/. Or, if you want to connect with Chris and see what he’s up to, check out his website at https://chrisheller.co/.

To get the latest updates directly from Dan and discuss business with other real estate investors, join the REI marketing nerds Facebook group here: https://adwordsnerds.com/group

Need help with your online marketing? Jump on a FREE strategy session with our team. We’ll dive deep into your market and help you build a custom strategy for finding motivated seller leads online. Schedule for free here: https://adwordsnerds.com/strategy

Read Full Transcript

You're listening to the REI Marketing Nerds podcast, the leading resource for real estate investors who want to dominate their market online. Dan Barrett is the founder of AdWords Nerds, a high tech digital agency focusing exclusively on helping real estate investors like you get more leads and deals online. Outsmart your competition and live a freer, more awesome life. And now your host, Dan Barrett.

(00:41): All right, Hello and welcome everybody to this week's episode of the REI Marketing Nerds podcast. As always, this is Daniel Barrett here from AdWords nerds.com. And look, you know, if you need more leads or deals online for your real estate investing business, where do you go? You go over to AdWords nerds.com, you grab a strategy session with our team for free. We will help you put together a strategy for online marketing for your market. Okay, this week I have such a fun interview. I'm talking with Chris Heller. Now, if you don't know Chris, if he's not a household name to you, particularly if you're in the investing side of this industry, I need you to stay tuned because Chris is one of the most deeply thoughtful and really insightful people I've ever had on the podcast. If you are not convinced, let me read you some of this man's bio because I'm telling you, you are gonna wanna listen to what he has to say.

(01:37): All right. So Chris earned his real estate license when he was 20 years old and built one of the most successful real estate teams in the US from Rookie of the year in 1989, to becoming the top producing agent in San Diego County and the number one Keller Williams associate in all of North America. Heller has earned the respect of colleagues and clients for the results that he delivers, but that is not all. Chris was named president of Keller Williams Worldwide in 2010, launching the company's first regions outside of North America, leading to record productivity and profitability. In 2015, Heller was named CEO at Keller Williams leading the transformation into the tech company that it is today. Chris then moved on to become CEO of Mellow Home and help them double their growth, drove significant change with the experiential and product landscape for the home ownership industry.

(02:27): And today, Chris is Chief Real Estate Officer at Ojo Labs. They are a fascinating real estate tech company, which recently purchased Movoto, the world's fifth largest real estate website. Look, people, this is somebody who has had their hands in some of the most prominent and influential real estate companies of the last few decades. I'm telling you, this is someone you wanna listen to when it comes to leadership, when it comes to the future of prop tech, when it comes to what the real estate landscape's gonna look like in five years, and frankly, what it looks like to make wise decisions over time. So, without any further ado, let's get into my conversation with Chris Heller. All right, what's up? This is Daniel Ba and I'm here with Chris Heller. Chris, how are you my friend? Thank you so much for coming on the show.

(03:15): Hey Dan, I'm great and thanks for having me on. Excited to talk to You. Yes, I am super excited to talk to you. We talked a little bit before this call and I'd had like so many things I wanna talk about. However, I wanna start maybe in a slightly weird place, which is, I wanna start with your book. So you have a book out, it's called Dominant Thoughts. And anybody who's listening to this, you can go check it out@dominantthoughts.com. But I am fascinated by people who choose to go the route of writing books. And you have had this incredible career. We're gonna go back over it in a little bit, but I am curious why a book, like why decide to go into this whole process, which is a very difficult one, right? Like writing a book is hard. So like, what made you wanna pursue That? You know, maybe a better question, why am I working on the second one, which I'm starting right now, . Um, but Yeah, so clearly glutton for punishment, but beyond that, uh, yeah, what made you wanna do either?

(04:17): So there's a couple reasons. Number one, I thought about it for a long time and thought it would be cool someday about a year, a little over a year ago, I was on a podcast with, with a couple other guests, and one of the, one of the other guests had written several books. And near the end the podcast, the host said, Hey Chris, when are you gonna write a book? And I said, I don't know. I've thought about it, but I'd really have to have Greg here show me how to do it. Um, cuz he's the, he's the pro. Just sort of jokingly, two days later, he called me and said, Okay, I've had this idea. I already have the title in the url. If you have the content, I'll show you how to do it and, and we'll be co-authored. But you, you do all the work, I have all the contacts and I have all the knowledge and, and I said, deal. So that's how it came about. Yeah, probably the real reason why I did is I have four kids between the ages of 22 and 30, almost 32. And I wanted to have an effective way to, to transfer some of the things I've learned to them because that telling them things isn't an effective way. Yeah. They don't want to hear that , um, you know, in a book, maybe one of their friends will read it and say, Wow, this was really good. And they'll cause them to read it or they'll just get around reading it some days. So that was the, that was the, the other motivation.

(05:33): Yeah. I, it does strike me that, and I have this fantasy, right, of like, I, you know, this may be a weird fantasy to have, but in the fantasy, like, I'm long dead essentially, right? And the kids like open up like, you know, like a giant treasure chest in the attic, they've dusted off and they're like, Wow, there's like all these cool things that I wrote in there, right? And this, it's this, this idea of passing things on is so powerful. So I love that. That's like your motivation. Tell, tell people, give people the, the kind of elevator pitch for dominant thoughts. Right. What's it about and why should they check

(06:03): It? No, it's a book on mindset and leadership. It's a, I wrote it in the form of a parable. It's a short read. It's 118 pages. It's about a mentor and a mentee, uh, that meet. And then each chapter as the story progresses, uh, highlights another lesson that I've learned and in my lessons have just come from, you know, like you said, a long career, getting to work and have opportunities, have mentors, a lot of people haven't had. Um, you know, I've, I've worked directly for running the companies of two self, self-made billionaires, Um, and, and how that other great mentors in my life. And so it's just taking a lot of those lessons that have helped me be successful and the achieve things that are maybe out of the ordinary for someone that had the background I've had. Um, and, and those are the things that I think people will, will like about and get out of the book.

(06:55): Yeah. So well, let's dive into that because I think part of what's gonna make people wanna check out this book, and again, if you're listening to this, you absolutely should check it out. It's at dominant thoughts.com, go check it out. But it, but it's like, for, for people who don't know you or maybe don't know your background, sort of what's your, uh, what's your, what was your trajectory into real estate? Right? Which is a lot of stuff. So we, we could cover it at a high level, but it's like, tell people a little bit about what got you into the re into real estate, what your journey has been, because it's been very impressive in touching a lot of different parts of the industry that I think people think is, are really interesting. Yeah. So I'll give the sort of the Reader's Digest version. Yeah, yeah. Give the quick one and then, cuz I'm gonna keep making you go back and dive in, so we'll, We'll get there. Yeah, I'm happy to do that. So I, I was a, uh, sophomore in college and I got my real estate license for a summer job of selling timeshares. You had to have a license in California. Wow.

(07:54): Were you just like, in classic time share? Sorry, I'm already interrupted. We talking like classic like closed room, like sit down, do the seminar, timeshare sales, like that,
That, Yeah. Hardcore 90 minute presentations. Um, and, and, and that summer job turned into like three years of doing that. And I was making really good money, actually, uh, bought my first town home when I was, uh, 20 years old. And, uh, during that time I met a real estate broker. And for three years from the time I met him, he kept recruiting me, saying, Hey, you should get into residential real estate. You'll be great. You know, come work for me, You'll love it. And for three years he'd write me notes, he'd call me every time I saw him, he'd bring it up and, and, uh, and then the reality is one day he caught me at, at a week moment and I was in between, uh, ventures and, and I was seeing him about something else. And, and during that meeting, he was successful and gave me to say, Okay, I'll give it a try.

(08:53): And so that's how I got into real estate. That first year. I was working the year in San Diego. Every year my business went up. I even at that time, as we were heading into a down market within several years, I was one of the top 10 agents in the country for the national, uh, um, company that I was with. Um, in 2004, I switched companies. So after 16 years with that same company and being one of the top 10 agents in the country, I switched to another company, which was Keller Williams. And within a few years opened up some franchises, um, a few more years became the number one Keller Williams agent in the world. Uh, and then in 2010 they asked me if I'd be interested in taking an executive role with them in helping them expand Keller Williams globally around the world.

(09:38): And I did, I knew nothing about it. I knew , I didn't know how to, it was completely new, completely uncharted waters for me and them. Uh, but, um, the good news is I figured it out, became very successful. Uh, within five years. They then asked me to become the CEO of the company, which I did. And, uh, I finally left Keller Williams about five years ago and in 2017 and then, um, uh, I've had a real estate team all, all along and still have a real estate team in San Diego. And after I left Keller Williams, I came, uh, uh, got introduced to the founder of Loan Depot, which is the second largest non-bank lender in the world. And after meeting with him 10 different times, I, uh, joined him and became the CEO of his sister company called Mellow Home. And, and did that, um, during that time I was advising several startup companies and invested in several startup companies. And one of 'em, this one, uh, o Joe Labs I was, became a board member of. And then in 2019, they asked me to join 'em full time. The company was really growing, they could really use me and uh, I thought it'd be a fun adventure. And so that's still where I'm at. And what we're doing is building an exciting company. Yeah,

(10:52): I mean that, that whole journey is so amazing and there's so many different pieces I want to dive into. I actually wanna start all the way back at the beginning cuz like, one of the things I love about this story is the broker who spends three years following up with you being like, Hey, you should come and work with me. Right? Like, I love the dedication. Right? And like, clearly they saw something in you. So I'm curious, what do you think they saw in you that made them wanna put in that amount of effort and time to get you over to their team? Right? Like, what was it that sort of drove them? Because obviously it's like the timeshare thing is like such a particular, it's such a particular thing, right? It's so unique in a lot of ways. What made them go after you?

(11:40): Yeah, you know, Dan, that's a great question. And back then, you know, I would say there probably wasn't much like, you know, I was so young and raw and knew, I think if anything, he probably saw that I was, um, I was very, I was very quiet and very introverted, but I was very driven and he probably got a sense of that, that I, I had this drive, this, this desire to, to achieve. And, and you know, during that process of those three years, um, I, I saw a lot and learned a lot. Like I underst you know, I really got the meaning of, of someone being persistent, of someone being consistent in their efforts and what it really meant, to do that at a high level. And so that is, um, I think, but back to your question, I think, I think you just saw that, that I had this sort of, this, this quiet, you know, pretty high drive to achieve.

(12:32): I'm curious too, uh, and I promise I will move on from timeshare soon, but I'm like fascinated by timeshare sales and actually, uh, was on the podcast of a very good friend of mine, Matt, Kimberly, who also came up through timeshare sales. So it's like his first introduction to sales. He ended up going into sales coaching and consulting. He was very successful. Right. So I'm curious, like, do you look back on that time and feel like you took away, um, you know, you mentioned persistence, but like what were the lessons that you feel like you took away from that? Cause I think a lot of people look at times your sales and say like, Oh, it's over the top super hard sale, uh, you know, trap 'em in the room or whatever. Is there anything from that time period you feel like you still apply today?

(13:13): Absolutely. You know, if I had any fear of rejection, it completely obliterated that. So I had no, no fears of, of rejection after doing that for several years. Um, also the, um, the other thing I took away that really helped me while in residential real estate was being able to make a, a, a concise and effective presentation. You know, so was as I got a residential real estate, if you were thinking about selling your home, you'd probably interview several agents. If I was one of those agents, I had a presentation that wasn't special, but it was effective and it followed a pattern and it the same type of thing when I did, uh, as I was selling time share timeshares. So it was a, you know, a combination of, of questions that would lead us down a path to, to where we wanted to get to. So being able to really learn how to present. Cuz I was presenting three or four times a day, 90 minute presentations, and I was pretty much doing it seven days a week because they would let me and going to school at night. Um, and so I got, uh, yeah, I got pretty proficient at doing that.

(14:18): Yeah, I mean it strikes me, right? It's like you just getting reps in, which is so valuable, right? Especially in a young age. So, Alright, so let's kind of fast forward. Let's talk a little bit about Keller Williams. Obviously it's, it's, you know, a giant in the industry. It's a company that everybody knows, and you were at the top of that company. Um, but I am very curious about this period where you got into, um, you know, you sort of come up to the executive level for the first time, right? And you're not, you just, like you said, like it was a new thing for you. You, you didn't, weren't really sure what it was gonna be like, but you ended up figuring it out. So you've been in a bunch of situations, I think, in your career where you sort of go into new territory. It's obviously related to what you do, but it's some kind of new application. So thinking back to that time, how did you deal with being in a new part of the business, you know, new responsibilities that you didn't have experience with. Was that nerve-wracking? Was it exciting? And, and kind of how do you navigate that? Cause I think a lot of people would hold themselves back from the making that jump because they feel like, well, I don't have the experience, I wouldn't know what to do. Yeah.

(15:28): Well, I certainly didn't have the experience. I certainly didn't know what to do. Yeah, sure. There it was probably nerve-wracking, but, uh, it occurred to me as a big opportunity. And that's super big challenge. And I like those two things, right? I like big opportunities, I like big challenges in fact that in my mind it teetered on the edge of being impossible. Like, how am I going to do this? You know, no one at the company knows anything about, they're not saying, Chris, we believe you can do this and we're hiring you, you to do this, and you need to go figure it out. And so that seemed like, you know, like the biggest mountain decline at the time. And, and I like that. And I liked that challenge. So I, I, I went at it very aggressively and, and, and jumped into it. Now all of it was new, you know, being, having spent 26 years running my own real estate team, um, as the boss and now being in, in a company where you're an executive and you have all these different people and different organizations, I had to learn a whole new set of skills. The good news is I learned pretty quickly and I learned by observing a lot. So in, I, when I'm in this situation, I can, I can quickly assess, you know, what I need to do and, and who I need to work with to help accomplish things I wanna accomplish. But it was a new process, a new set of skills for sure. When

(16:49): You are making that assessment, right? So you say like you, you primarily look, maybe not primarily, but you were learning a lot by observation, you're modeling people, right? You're, how do you assess who to look at and who to learn from, Right? Because in any situation, you have people that are successful essentially by accident, right? Just statistically that's gonna be the case, you know, maybe not by accident, but it's not necessarily what they did that got them to where they are, right? And then you also have people who are very much there as purely a product of stuff that they did. So how, you know, and you could, you could talk about Keller Wells or you could bring it to the future and say, Hey, if I'm in a new situation, here's how I do that. You know, kind of generically, if you don't want to talk about specifics there. Yeah. How do you decide who to, how to, how to model or who to look at.

(17:35): But way, I, I always look, I'm always looking for people who are doing more than me or better at things than I am, you know, to see what I can learn from them. And then I also operate, always operate on this, this, um, sort of this this guise or philosophy of, of failing fast. You know? Like I, I know I'm gonna make mistakes. I'm not afraid to make mistakes. I don't like it and it's not my goal, but I also know if I'm making mistakes, that I'm trying hard and going fast. As long as I'm, I'm failing forward in my mistakes, I'm learning from them, then I know I'm gonna grow and learn very fast. And so there was, the CEO of the company at the time was a great leader and, and has, you know, since become a great friend. And, um, and so he was a great role model for me and, and a great, you know, and a way, a great mentor for me to be able to, okay, see how, what he's done and how he's done it, and to be able to model some of the things after, after that, as I mentioned earlier, I've had a lot of great mentors in my life.

(18:33): So with all of them, you know, there's been takeaways, you know, things that you learn that you, you take on and you do. And then things you learn from 'em that you don't want to do or that, that, that aren't good things to do. That those are, you know, when you jump into a new situation like that, it's, um, you know, I've, I've also I think dis intuitively knew, uh, you know, don't act like I know it. I don't know. And don't be afraid to ask questions and, you know, watch, listen and learn and then, and then start to, to move forward and, and then move faster and faster. So I'm curious, you, you know, you like you mentioned you were a CEO of Keller Williams, you're sort of at the, the, you know, the very top of such a large organization. I am curious what you think that they do particularly well, or if you wanted to take that question somewhere else when you were looking at other companies, how, what do you look for in order to say like, this is a company that's gonna be successful that's that's gonna be able to, to sort of achieve their goals? Does that make sense? Like what, what do you think is either the sort of like, not quite the secret sauce, but something that Keller Williams either does really well or something that you look for in a similar company where you're like, they've got

(19:44): It? Yeah. So, you know, at the time, and, and you know, I've been gone five years, I can't really speak to, uh, you know, I, there's what I observed from an outsider now, but at the time they did some things that they did better than anyone else in the industry, you know, So at the time, training and education, they were hands down the best training education company in the industry. And so they had a unique and unique value proposition that we could build off of. When I look at other companies, you know, those are some of the things I look for. Now when I look at companies, the first thing I look at is the people, you know, the leadership, you know, are they, are they good people? Are they great leaders? You know, are they aligned? Is it a company full of, you know, political maneuvers or is a company that's that really a, a tight team that's, that's on a mission to achieve something? Because I think people are the most important thing. You know, what the company has its assets, it's, it's where it's going, what it's doing, um, is secondary to, you know, the team that, that, that ultimately has to make it all happen.

(20:51): So I love that. I mean, I'm, it makes the follow up question that I would have then I guess is how do you spot a good leader, right? Because if you're essentially saying, Okay, well, you know, you invest in the company, but you really are investing in people cuz the company is just people, right? And you are really looking for someone who's a good leader. You could have a leader that's charismatic per se, but maybe isn't the best decision maker or maybe is a great decision maker, but doesn't have that sort of natural charisma that kind of, you know, flows across the conference table or whatever. So if you're looking at, you know, for example, some of the startups that you've invested in, how have you kind of trained yourself to spot people that are great leaders or, or great at putting together teams that work together well?

(21:35): Yeah, so I think part of it is they gotta be great human beings, right? Um, the best leaders that I've seen and met are the ones that people follow them because of who they are, not because of their position or their title, uh, or that they want to get somewhere they've fallen because they're, they're great people and great humans. Um, another way to judge how effective someone is as a leader is to look at how effective the people are that they're leading. You know, are they building leaders? Are they, are they leading leaders? Are the people below than thriving and growing and progressing? Um, that's, or are they keeping them down or are people leaving them? You know, so those are the things that, that you look at that give you signs of, of whether someone's a, a great leader or not. Um, I think an another thing is, are they someone that you, you are already and willing, you know, to go, to, go to battle with every day? You know, do you like them? Do you respect them? Do you trust them? Those things have to be present. And if they're not, um, then it's probably gonna be a temporary situation.

(22:39): Yeah. Just because you won't last essentially like Allow, then it won't be, you know, it won't ultimately be fulfilling or, or you'll find out that, you know, things were a lot shinier on the outside than they were on the inside once we get on the inside. I wanna get to OJ Labs in, in a moment, but I do wanna ask about building and running a team, because you have built and run teams at basically every different possible level of size of business right down from your, you know, your, for your, your real estate team all the way up to being CEO of, you know, a gigantic real estate company. Now you're coming in as, as an investor and a mentor and a board member, um, working with teams of various sizes. How do you think through the process of building a team, right? Because this is something, you know, I always say like, the podcast is just a secret way for me to ask questions to people smarter than me. Like one of my big challenges has been putting together a team that gels both in terms of just personality. Everybody gets along and has a really high standard performance, right? And I've sort of built both of those, but not at the same time, right? And so I'm getting better, but I'm always curious how people who have done that consistently think through that problem. There's

(23:59): A couple things that I always look at. One is to hire talented people. So, and the most talented, I can find people that are better than me at the things that I need them to do. And I'm not afraid to have super talented people and people smarter than me and better than me. And that, in fact, I know that I need that to be able to get to where I want to go or to help the company get to where it want, where we want it to go. I also look for types, specific types of people, um, people that can speak. Um, no, but you know, people that like to be on a team, people that thrive in a team environment, there's some people that are, that are better on their own and, and they're a, you know, a solo superstar and, and great and good for them. Um, I'm lean for people that are great teammates, are great humans. I have high integrity that are going to be that, that are trustworthy, that are loyal, right? All the pieces that you'd want when you put a team together and, and when you have a team of people like that, then you can really accomplish things. You know, then you, you got everyone rowing in the same direction and march into the same beat and whatever other cliche we want to use to achieve things that are going to be extraordinary.

(25:13): Are there like markers for that? Like, do you look for like they played varsity sports or something, right? Like how, how do you sort of figure That out? You know, that's a, that's one that I used to always ask people, you know, did you play sports growing up? And it, and it wasn't a bias towards someone if they did or didn't. I just wanted to understand, you know, have they experienced being on a team before? Had they experienced winning as a team and losing as a team, or did they play individual sports? And not that that would be deciding factor, but it would help me understand who I was sitting in front of. I would also want to know about their, their past, you know, we've talked a little bit about, you know, my trajectory, but I, I'd wanna see what their trajectory was and I'd wanna understand more about it, you know, and what were the challenges they faced and how did they respond to those challenges? You know, were they, were they a victim about it?

(26:03): Did they blame the situation or the person or the situation or, you know, were they self-aware enough to say, Hey, here's what I didn't know at the time, or what I wasn't very good at, or what I had to get better at and here's what I did to, to do that. You know, did they, you know, every time they fell down, did they, you know, look at someone else to play the blame or look at themselves and say, Okay, here's what I did and here's how I got better and here's, here's how that helped me moving forward. So there's, there's all those signs that people will share with you if you ask the right Questions. Yeah, I mean, it strikes me that, that balance of team spirit or like sort of team commitment and also the willingness to take personal, personal responsibility, right? If you could put those things together in a talented person, that's a really powerful package. I really like that way of thinking about it. Hey guys, hope you enjoyed part one of this episode. It's just too good to limit to one show. Join us next week to hear the rest.

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