In short
The Intrinsic Value Podcast - Episode Summary: REI186: The Power of Zigging While Others Zag w/ The Duke of Dirt
Overview In this episode of *The Intrinsic Value Podcast*, host Patrick Donley interviews The Duke of Dirt, a former sports agent turned real estate investor. The discussion explores the Duke's upbringing, education, and insights into real estate investing, emphasizing the importance of unconventional thinking and personal responsibility in achieving success.
Key Takeaways
- Early Life Lessons
- Background: The Duke grew up as the son of a Super Bowl-winning football coach, which taught him resilience and adaptability.
- Influence of Coaches:
- Nick Saban and Chip Kelly: Learned about systematized success (Saban) and the importance of human performance (Kelly).
- Key Insight: Observing successful figures shaped his approach to real estate; understanding what works and what doesn't.
- Transitioning to Real Estate
- Path to Real Estate: After a stint as a sports agent, he pursued an MBA while re-engaging with real estate.
- Education:
- Expressed mixed feelings about the value of higher education versus practical experience.
- Emphasized the importance of real-world application and learning from mentors.
- The Perils of Conventional Wisdom
- Dangers of Following the Crowd: The Duke warns against blindly adhering to conventional advice, which often leads to dissatisfaction.
- Personal Reflection:
- Resisted the urge to follow traditional corporate paths, emphasizing the importance of pursuing one's passions.
- Current Real Estate Strategy
- Investment Focus: Targeting multifamily, Class B properties in tier-one cities, with a specific strategy of acquiring under-managed assets.
- Long-term Relationships: Building connections with property owners to facilitate potential acquisitions.
- Twitter and Content Creation
- Twitter Threads: A significant part of his strategy for content creation; curates insights from industry leaders through podcasts and books.
- Value of Writing: Advocates for writing as a means to clarify thoughts and communicate effectively.
- Advice for Aspiring Investors
- Effort and Talent: Success requires hard work more than innate talent. Hungry individuals often outperform sharper counterparts.
- Networking: Building genuine relationships in the industry can lead to opportunities that cold outreach cannot.
Recommended Resources
- Books:
- *The Obstacle is the Way* by Ryan Holiday
- *Am I Being Too Subtle* by Sam Zell
- *What It Takes* by Stephen Schwarzman
- *Endurance* by Alfred Lansing
- Blogs:
- Mose Kagan's blog for real estate insights.
Conclusion The Duke of Dirt exemplifies the value of unconventional thinking and the importance of self-directed learning in the pursuit of success. His transition from sports to real estate highlights the significance of adaptability, networking, and maintaining an open mind to opportunities.
For further insights and connections, listeners are encouraged to follow The Duke of Dirt on Twitter (@TheDukeofDirt) and subscribe to his newsletter for additional content related to real estate investing.
Additional Links
- [Become a premium member](https://theinvestorspodcastnetwork.supportingcast.fm)
- [Join the TIP Mastermind Community](https://theinvestorspodcast.com/intrinsic-value-community)
*Disclaimer: All information provided in this episode is for entertainment purposes only and should not be considered financial advice.*
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Transcript
Automatic transcript. May contain errors.0:00You're listening to TIP. There's one that every single one of these people has. It is they have a tremendous belief in themselves to accomplish what many thought they could not accomplish. It starts with you. If you don't believe truly about what you can do, I mean, I'm not going to say it's not going to happen, but these people don't exhibit that quality. But when you look at Steven Ross, who he was working for a company, he was fired from his job because he went out with his boss one night and I don't know, punched him. He went out the next day and said, I can do this better than you. And guess what?
0:35He did. So he, obviously he had some help. He had his uncle, but these people really, truly believe in themselves.
0:45Hey, everybody. In this week's episode, I got to sit down with sports agent turned real estate investor, the Duke of Dirt. You'll learn what the Duke learned growing up with a Super Bowl winning football father, how he took control of his own learning and his thoughts on getting an MBA, the dangers of following conventional wisdom, and what his current plan is as he moves away from the W2 world into real estate entrepreneurship. The Duke is looking to acquire multifamily assets in the suburbs of a tier one city. And on Twitter, he is known for writing threads on lessons learned from the foremost leaders in the real estate industry and has put countless hours of research into his threads.
1:20The Duke and I covered a ton of territory in this episode. I really enjoyed learning what it was like growing up with a father that coached with Nick Saban from Alabama and who later won a Super Bowl trophy, what the Duke's top takeaways from his outstanding Twitter threads have been, and what his strategy is as he navigates the world of real estate entrepreneurship. And so, without further delay, let's get into this week's episode with the Duke of Dirt.
1:47You are listening to Real Estate 101 by the Investors Podcast Network, where your hosts, Robert Leonard and Patrick Donnelly, interview successful investors from various real estate investing niches to help educate you on your real estate investing journey.
2:10Hey, everybody. Welcome to the Real Estate 101 show. I'm your host today, Patrick Donnelly. And with me today is a guest that I met on real estate Twitter, the Duke of Dirt. Duke, welcome to the show. Hey, Patrick. Thanks for having me. This is very exciting. Just, you know, it seems like a few years ago, I was on the couch listening to podcasts like this as much as I could, trying to learn as much as I could. And now I'm here talking with you, hopefully providing some value to your listeners. So it's humbling and I'm excited to be here. I'm happy to have you. I've gained a ton from your real estate Twitter threads, and we're going to get into that later.
2:46But I kind of wanted to get into early on, you had a very unique and interesting childhood because of your dad's profession. I wanted to start there and ask you a little about what your early years were like. Also, if you could just go into some of the lessons you learned about just being around the people you're around due to your father's job. My dad is a football coach. And with that means you move very often. The first question when I go to a new school and people ask me, oh, how many times have you moved? And I say, oh, seven, eight times. They say, oh, are you in the military? Is your family in the military?
3:21No. You got to guess again. Athletics, football coach. might seem glamorous from the outside looking in. And not to say it's not. There are a lot of benefits from it, but it is a tough life. It's a very public profession. People sit on their couches on the weekends and analyze your dad, how he does his job. And they have very strong opinions. And as a kid, when I used to come to school on Monday and maybe the team didn't do so great. Oh, I'd hear about that. Your dad stinks. He should be fired. You need to leave. You're the reason the team stinks. Stuff that kids say that makes no sense. But growing up in this was a really good learning lesson, how to kind of take negative feedback, take it and just say, okay, that's that.
4:11We're done with that. And I think also growing up, being able to walk into a room filled with people I didn't know. And that's a very uncomfortable position to be in. And when you do it over and over again, you become more comfortable with it. And as a young professional, it's quite advantageous to be able to feel comfortable to walk into a room knowing nobody and strike up a conversation and be able to relate to most people. I mean, I lived in a lot of different states in different cultures and people are different. And just understanding that early as a young kid, how to relate to people, I think it's been helpful.
4:55Were there any particular coaches or players that made an impact on you? Yes, certainly. The first person that whenever we moved as a family, it was obviously due to my dad's job and I am my dad's biggest fan. I'm an advocate for his career. And thankfully, and really not so thankfully because my dad is, I think, a tremendous football coach. And there was a reason we were going to better place and better place. But we went to the University of Alabama and I was kind of at an age where I was really observing the football team, what was going on, how the operation was run and why this football team was so much better than every other one that my dad had coached on.
5:39and Nick Saban has a system. And people sometimes wonder, how could he do this? How could he be so good? Well, it's because he started his career as an assistant coach and he was extremely observant of every little thing that led to the success of those teams that he was on. He took all of those tidbits and added them to what he would then produce as his own system. And it's dynamic now, don't get me wrong. I mean, football or sports are changing. They change every year. And obviously he changes it, but there is a rhyme and a reason to every practice, every meet, every day. And me seeing how this happened taught me that at the beginning of my career, my real estate career, I need to be highly observant and understand what makes specific operators succeed and what makes other operators not succeed.
6:37And I want to avoid the latter and take as much of the former as I can. And that's what I've done early on in my career. So that's something I've learned from Nick Saban's. You better have a system. And if you don't have a system and anything you go into, you are setting yourself up for issues. And then somebody else that I was also able to have a front row seat in how they ran a program is Chip Kelly. And more so on the human performance side, he is a leading figure in sports, how people treat their bodies and how they get the most out of them. And this was also, I was kind of, I just got into college and, you know, my priorities were not in human performance.
7:21They were with college things, parties, other stuff. Well, I quickly understood the importance of sleep, hydration, and nutrition and how that can impact somebody's performance. And I've taken that into my life. I'm always very cognizant of how much water am I drinking? How much sleep am I getting? And what am I putting into my body? And being so aware of this, if I don't do the right thing, I can just look back at my day and say, oh, that just, you know, there's the reason I didn't do so good today. I'm not familiar with Chip Kelly. Tell me more about him. He kind of people probably started to know about him at the University of Oregon.
8:03He ran a fast paced, cutting edge offense and was very successful at Oregon program that has capital resources with Nike and Phil Knight, but had not traditionally been a national championship contender. And Chip Kelly kind of came in there and made them a perennial contender. And then he kind of parlayed his career into the NFL. He had two stops in the NFL and now he's at UCLA. Okay. But he's really into human performance and how to maximize. Oh, yes. Okay. Yes. When he came into the NFL, he brought all of this stuff and this was brand new. And this is something I also learned from just this scenario is this was the first time this type of program had been brought into the NFL.
8:49This was brand new and with leagues and systems and organizations that are used to a one way of doing things, when you bring in a new thing, it's often not well received and it wasn't totally well received. But looking back, now the whole league's doing the same stuff he was doing 10 years ago and very well received. So it's interesting how that happens. I'm going to have to check him out. I'm getting into all of this more. I've been listening to a lot of podcasts with Dr. Andrew Huberman is his name and Dr. Peter Atiyah. I don't know if you're familiar with those guys, but they've both been on Tim Ferriss and just really great podcasts about health and human performance and longevity.
9:31Just fascinating stuff. I'm going to have to do a deep dive into Chip Kelly, though, and find out more about him. I mean, I don't know how much you'll find directly from him, but he had these people that you just mentioned. And these type of people were surrounding him 10, 15 years ago. And you probably don't know about them now, but this was the sort of person that was involved with the program. We had talked earlier, we've got a mutual friend that kind of is an assistant for Nick Saban at Alabama. Are you familiar with Ryan Holiday? I am, yes. Did Nick Saban bring Ryan Holiday in for some coaching?
10:05I believe he does. I can't say that I've ever been in the room when he's spoke, but yes, he does. Ryan Holiday's got a great book called The Obstacle is the Way, and it just seems like totally in line with Nick Saban's philosophy of practice and constant and never-ending improvement. And it's just really good stuff and really cool that you got to hang around those guys. I mean, it's both the players and the coaches just kind of having that influence and that discipline, I guess, has had to have had some carryover for your own, both academically and then later in your career, it's had to have some carryover in effect.
10:41I hope so. I mean, when you're surrounded by highly, I don't know if successful is the right word, but high performers, people who are at the absolute peak of their profession, there are qualities that these people exhibit that it's the rule, like you are what you surround the top five people. This is the same type of situation. So hopefully that happens with me. I wanted to jump into a little bit about your journey before real estate. Talk to us a little bit about what you were doing. Your early career is interesting to me. And I kind of want to hear some stories about what you first did right out of college.
11:17I was in undergrad and I just backtracked to my junior year. And where'd you go to college? I went to Alabama. Okay. And so I'm in business school, I'm getting a marketing degree. and usually you're supposed to spend your junior year doing an internship with a business that you then parlay into a job. Well, I didn't do that. I studied abroad in Spain and had the best summer of my entire life. I absolutely loved it. I made memories that will stay with me for my whole entire life. And I came back and I'm going to school and I'm a little bit stubborn. And I told myself, I am not going to sit at a fixed desk under fluorescent lights with no windows at a desk.
12:06It's just not for me. I'm not doing it. And everybody's asking me, all right, well, that's fine, but you have to do something. And I kind of took inventory of where my life was, what's going on. And I said, I want to go back to Spain and I want to become more fluent in Spanish. And I just want to experience that because I'm never going to have the opportunity to do this again. And so I got a job teaching English in Sevilla, Spain, and it was 20, 30 hours of my week. The rest was up to me to do whatever I wanted. And I spent a lot of that time thinking about where I wanted my career to go because, you know, it may sound that I didn't care about work.
12:42I'm a very ambitious person, but I also feel like I'm aware of kind of the bigger picture. And I took the opportunity to go to Spain. Look, I spent the whole year like seriously considering all the options that I have. And I missed a little part here. So I graduated senior year and I went back home. And that summer, while I was waiting to go to Spain, I did an internship with a real estate development company. Very startup, very entrepreneurial. And I really liked it, but it didn't bite me then. It didn't say, this is it. So I went to Spain. What kind of projects were they doing? I was there. Mixed use, multifamily over ground floor retail in urban core transit oriented city.
13:26And it was cool. It was cool. And I was thrown into the fire. I mean, I'll get to this in a second, kind of how that job happened. But anyways, I come back from Spain and I determined that I know all these people in the sports industry. I've grown up with them. I have a competitive advantage in this industry. it makes sense for me to go into it. And I think I like it. So I got a job at a sports agency representing football coaches, which, huh, duh, like that makes sense. I grew up with these people and, you know, I came right in and it was going well. I mean, I did my internship and then I got a real job in Manhattan, pretty much in another situation where they said, all right, we do players.
14:12You're going to come in and do coaches 23, 24. And they're just, all right, you're taking the range. And that was really cool, but it was scary. And I would say a year into that, I said, I don't know if this is for me. And there was a lot of travel and I started seeing kind of what the industry was like and the business model. Was your dad encouraging of that or what were his thoughts on you being a sports agent for coaches? He lets me do kind of, he's a tremendous dad. He's supportive. And if I needed help, he's always there to help. And he was supportive of this. And it made sense. On paper, it makes tremendous sense.
14:57But another thing that I kind of started realizing pretty quickly, and this was a young person making decisions. I look back on this now and say, this was probably not the best thought out decision. But whenever I would do business, everybody said, oh, you're your dad's son. I was never who I am. I was always my dad's son. And that irritated me a bit. Looking back, you put your head down and you work hard, you become your own person. Yeah, early on, that's all your identity is like, ah, you're, you know, so-and-so's son. Yeah, and that's fine. I mean, I was proud of it, but I didn't want that to be forever.
15:31And it wouldn't have been. You put your head down and you work hard and you make things happen. And that doesn't happen anymore. You look around the world. I just, you know, I was young and dumb. It wasn't even the dumbest thing. It just, that's what happened. So what was your next step after that? Did you go get your MBA? Yeah, we'll talk about this later on, but it's okay. I'm at another dead end here. I just did Spain, didn't know what I was doing. Now I went into this industry and now I'm flaming out. Okay, what is going on with my life? This is not how I drew this off. And growing up with the people around me, there was a lot of, well, you should go to law school.
16:10You should do your MBA, business school. This is what you do. This is the way. This is how you succeed. You just go get more education. And I bit the cheese. I said, okay, I'm going to do it. So you take the GMAT. I got my score. I got into the school I wanted to get into. And there I went. Did that, specialized in real estate and finance. And while I was there, circling back, I started working for the real estate developer that I had interned with before I left for Spain. And it kind of came full circle. This company was a little more mature, but there was a huge hole in the financial analysis of firm.
16:56And the guy who ran it said, okay, you need to do it. If you want the job, this is what you can do for us. Fantastic. Going to school, I'm getting the formal education. and now I can put it to work. But what a lot of people think about the MBA is it's education and then there's real world. They are two different things. And when I was asked to do the job, this was all new stuff. I was thrown into the deep end again and there was no help. Nobody really knew how to do it. And so there I went, searching for knowledge, podcasts, Twitter, anything online that could teach me how to model deals in Excel.
17:33And it was awesome. I mean, I was, again, into another entrepreneurial venture where I'm leading conversations with equity and debt. And three months ago, I'm sitting here to me, I'm saying, three months ago, I didn't even know what this was. And now I'm here faking it till I make it and telling these people this stuff. And it was tremendous. It was great. But I did that. So say more about that. What exactly were you doing? You were doing Excel modeling on some of these projects and deals that you guys were looking at? putting the concept onto paper and pretty much making a business plan. And a lot of that was in Excel, modeling out the cash flows.
18:13How is this going to work? What's the timing? How much is it going to cost? How you would model a development and then taking that information and going out to the capital sources, going out to the city, going out to the necessary third parties and trying to get a project off the ground. And this is while you were getting your MBA? Yes. Wow. Great experience. Yeah. Tremendous. But if you can read between lines, it was kind of the wild west. I was just shooting from the hip and I, along with kind of some people who gave me good advice surrounding me, said, you may benefit from some more institutional experience.
18:53And from the outside looking in, oh, institutional. That sounds great. Everybody wants to get into that. And now I have this shiny new MBA. I could probably do it. And so I said, all right, this is what I'm going to do. So I went and got a job in an institutional shop doing asset management. That was my entry into kind of institution. And again, great experience, learned, I don't want to say the right way to do things, but the more formal, the way people have I've done them for years, tried and true methods. Now there are different ways. I'm sorry, what was your role there? Were you doing asset management for multifamily apartments and things like that?
19:39So yes, it was an LP. So it was a limited partner in across all, pretty much all asset classes across all geographies. It was just constrained by the deal size. So they were writing checks between two and like 30 million bucks. So it was like sub, I don't want to say sub-institutional, but it's not like mainstream equity checks, hundreds of millions of dollars. It was in that sub-range. And working with a myriad of different operating partners and circling back to the first thing I said about learning how to create a system, here I am, a front row seat with 20 or 30 different operators and different asset classes, understanding what makes them successful.
20:22Why are they better than others? And for me, in asset management, I'm aggregating data from all of these operators. I'm putting it on paper and then I'm reporting back to the company. And it's very easy to compare all of these operators to each other because mainly doing the same job. And so you start seeing, okay, what these people do is better than how these people do it or just little things like that. It was very good. Very good experience. Let's take a quick break and hear from today's sponsors. Even Einstein had blind spots. That's why modern science is built on the idea of peer review. Investing may be more art than science, but that doesn't make peer feedback any less valuable.
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23:41And for a limited time, you can use code stocks15 for a 15 % discount at checkout. All right, back to the show. I want to kind of get into that. You talked about listening to podcasts and books and things like that as you were getting more into commercial and institutional real estate. Talk about some of those, whether it's people, books, podcasts, some of the things that made the biggest impact on you early on in your career. Twitter was one of the first resources that was eye-opening and a real source of, I felt, pride and true knowledge. There's a lot of other sources that are a bit suspect.
24:21I'm not going to go into names, but I was a little bit thinking, I don't know if this is actually how it happens. You get on Twitter and the proof is in the pudding. These people are doing real deals, solid deals and just reading as much as I possibly could of them. Moses Kagan has a blog, which I devoured. I know he doesn't like to talk about it too much, but it is top-notch content. It is tremendous. I recommend everybody who's getting into real estate, read it from back to front. It is great knowledge. And then just general books. I mean, you've got the whole group of these big guys. You've got Sam Zell.
24:59You've got Francis Greenberger. You've got Steve Schwarzman, guys like that. I mean, that's just great stuff you can consume. And then podcasts. I mean, there's a handful. You've got this podcast, which is great hearing from actual people. Something I used to like to do is I find people who I really respected, like Sam Zell. Listen to every podcast Sam Zell is on and you start hearing themes and general kind of ways of investing. That's another way. That's kind of how I did it. I wanted to hear your thoughts on, you are a huge fan of Twitter. You've learned so much from Twitter. I think a lot of us in the community have.
25:36It's incredibly, I don't know, just giving, how giving people are on there is kind of has blown my mind in some ways. I haven't been on it as long as you, but it's amazing what you can learn on there. Looking back on things, I wanted to hear how you would view advanced education. Is that something you would do again or advise somebody young to go get an MBA in order to have a career in real estate? Or do you think there's just so much information out there that you can kind of create your own MBA in a sense and learn what you need to do or learn what you need to learn outside of a traditional educational model?
Read the full transcript
26:12This is a tough question. And I don't think there's a right or wrong answer. There are tremendous benefits of having an MBA. I'm not going to lie. And a lot of it is perception. When people see MBA from school that they know or respect, they just immediately put a label on you that, oh, suddenly this person knows what they're doing. It's the same thing with working experience. Well, that doesn't always mean you are better or more knowledgeable about doing something. And real work experience trumps everything. And like you said, mixing the real work experience with the content that is widely available across internet is a recipe for success.
26:58But you have to put in the work. You can't just hope for it to fall in your lap. You have to go out and do it. With the MBA, I mean, it kind of, you have to put in the work, obviously, to get into the school. And there's, you have capital investment potentially. But I'll be honest, it's been tremendously helpful. And if I were to redo it, I don't know. I'm certainly proud of it. And it's been tremendously helpful. Now, look back and say, all right, if I know now everything and I use those two years that I demand to get real world experience, would I be in the same place? I don't know. That's a political question that I'm not sure I can answer.
27:36But I think you can succeed in both ways today. That's my best answer. Both things work. Yeah, it's a tough answer. I interviewed Kevin Clark, who got his MBA in real estate finance at NYU. And at the end of the interview, I asked him what his best investment had been. And without a hesitation, he said his education. Because he was in commercial real estate brokerage, he was able to go in and work with the seller and really look at the financials and really understand them. And just having that MBA gave him credibility that a guy that didn't have it just didn't have. But then there's the opportunity cost of what you're spending on an education.
28:21Yeah, I've had different answers to this. So it's just kind of interesting to hear people's thoughts. Look, Kevin Clark may have had a different, better experience than I did, but I think I'd probably be better off going in and looking at financials of a piece of an asset in real estate or a company, doing it, doing the actual work with somebody who is an expert as my mentor, as my boss or something, I think I would be better off doing that than going and doing, sitting in a classroom and learning out of a book. But that's just me. I learn in a unique way. That makes sense. I wanted to get into the topic of advice following.
29:01We kind of touched on this a little bit. I wanted to get your thoughts on just the dangers of following conventional wisdom. I mean, you were in an environment where a lot of people were telling you to whatever, go get your law degree, go get your MBA, go whatever, get kind of a more conventional path versus what I find a lot of successful real estate investors are contrarians. They go out and do their own thing. They do not follow conventional wisdom. Talk to us a little bit about that, going out on your own and doing what you think you should do versus doing what you want to do. That's a tough path and a tough struggle, I think, for a lot of younger people.
29:36Talk to us about just how you think you can navigate it. Any advice you have for navigating that journey, I guess you would say. Yeah, that is an interesting concept with following conventional wisdom and going down the path that people tell you to do versus doing what you truly desire to do. And I want to caveat this by saying, I personally am in a situation that has enabled me to be a little more bold with taking action of going out on my own. And I am grateful for that. And not everybody can do that. But when you look at your life in the bigger picture, at least here's what I did. I go to work and I say, this person who is a few steps higher up than I am in the hierarchy.
30:26Does this job intrigue me? Is this a job I would be happy doing in 10, 15, 20 years? And the path to get there, am I going to be building something on the way that I can look back on and be happy I spent 20 years doing it? And for me, the answer was clearly not. I was certain that I did not want to be the people who I was looking up to and I was starving to go build something for myself. Growing up, I was taking advice primarily from people who have followed the corporate structure. They all tell you, education, corporation, just follow the leader. And even I just had this thought, even with your dad's situation, there's still a hierarchy of working your way up the football coaching hierarchy, you know, like, and that's a, not that it's a well-trodden path, but it's somewhat laid out.
31:23Yeah. You fought, you work hard and you go up the thing and great. And many people succeed and live great lives and I am happy for them, but I'm not one of those people. And I think there's a lot of other people that probably align with me. And some days I would wake up and look in the mirror and say, what's wrong with me? Why can't I just be like that? Well, I haven't figured that answer out yet, but I can tell you, I'm not going to force myself into being a corporate warrior. It just was never going to work for me. And it was very clear early on that I didn't want to, I don't want to say waste, but I didn't want to live 20, 30 years of my life just to retire and do nothing and look back and say, oh, what did I do?
32:06I want to do something that I'm proud of, that I'm passionate about. And that means I needed to go out on my own. Again, one little caveat. It is extremely important for me that I felt that I had the requisite training and experience to be able to execute on a strategy and succeed. and I'm at the point now where I feel that, but that wasn't true. And I put my head down for a couple of years unhappily. It was always that carrot at the end of the road saying, all right, we're working towards something and then we're going to go. Was that your thought process rather as you were at this institutional real estate firm that you were just trying to learn as much as you could, build your skillset?
32:52Was that how you thought about it? Yeah. If I'm being frank, yeah. I mean, it's not something an employer wants to hear and it's a little bit shallow, but yeah, I was a paid fill-in for a couple of years in my mind. I was there to do my job effectively. I certainly wanted to do my job well, be thought of highly and do great. But I was certainly there to learn as much as I possibly could, make the connections with the necessary people and build a foundation to jumpstart my real estate investing outfit. This is kind of a common theme I've heard with several of the interviews that I've done of people that have followed a traditional path.
33:34I interviewed a guy, Raleigh Williams, who got a law degree at Chicago, University of Chicago, got like a top law job right out of college, but he was, you know, absolutely hated it. Came from a family of lawyers. And that I think can just be, and I had a similar experience in my own life, kind of following traditional advice. And then you hit this point where it's just like, crap, this hasn't worked out for me. I have what I'm supposed to want and I'm still unhappy or I'm still like, this just isn't doing it. I think that can be a hard realization for people. And it's like, all right, what's next then?
34:07If this path hasn't done the trick, how do I segue into doing whatever the next chapter is? And I think that can be a really tricky road to navigate. And you're kind of in the middle of that right now. Talk to us a little more about that, like how it's been for you, the transition. You've recently gone out on your own. So can you talk to us just about leaving more of an institutional job and going out and doing your own thing? Yeah, I'm happy to. It's been that carrot at the end of the road for years. And I can tell you, I was certainly scared to wake up those days and weeks after thinking, oh my gosh, I've made a tremendous mistake.
34:44I'm very happy to say I wake up every morning jumping out of bed so happy and invigorated and passionate about what I can do today to move the ball forward just a little bit. I'm as excited and really invigorated as I've been in my professional career ever right now. I were to look back and if I were to do something different or I don't think I would, I just advice I would give to people trying to do the same thing is you've got to work really hard side of your job to set the framework so that when you do make the move, you're not just, okay, what do I do now? Have things set up, make those relationships, communicate to people in the realm of the industry you're going into about what you're going to do.
35:34For me, that was brokers, lawyers, accountants, people like that. I mean, I've been working on this for a couple of years now. And now it's like, okay, call each one of these people. Here's exactly what I'm doing. Here's the criteria I'm looking for. And do you know anybody that is doing anything in the realm of that? I'd love to meet. Cool. So tell us what you've been up to, like since you've left your company, what are you been focusing on? Talk to us about the niche in real estate that you've focused on. I'm looking to acquire multifamily, Class B in particular, I mean, I'm not, I'd look at some class C plus, let's call it class B, anywhere between five to a hundred units on the main line.
36:20Let's call it a tier one city. And the thesis is you can take a lot of these assets, which are owned by a large portion of them are owned by the baby boomer cohort, and they are sub-institutional in nature. They are often self-managed or managed for occupancy's sake. Their interiors are not renovated or they're outdated, I should say. And oftentimes the rents are under market. Now, this is the perfect storm. You don't find these assets and they don't trade hands often. But this cohort of people is growing older. And when people grow older, oftentimes assets trade hands. So I am looking to acquire those assets.
37:02And how I'm actually doing that is trying to establish relationships with as many people as I can, oftentimes those owners. And I'm playing a long game here. I fully expect to sit back and maybe I won't acquire something for a year. But over time, over the next 10 years, these properties will trade hands and I hope to be the one to acquire them. Can you talk to us? I've got several questions here. Are you bringing in outside partners for capital? Are you bringing in any kind of partners with a different skill set? Talk to us about that. On the capital front, I am raising capital from a couple sources.
37:37I mean, there's going to be a large family and friends portion of it. And then from an institutional LP side, I mean, that's still in the works. I don't know on that front where that's going to be. In terms of operational partners, no, not yet. I'm open to it, but you're looking at it. I'm the show. So have you made your first investment then? Have you purchased anything yet? I've got some promising. I don't have anything tied up yet, but I hope to report back soon that I do. Okay, great. We'll have you back on the show and kind of get an update. But how are you looking for deals? Is it primarily through brokers that you're reaching out to or what's the best way you're finding to find these deals that are baby boomers that are tired of managing their properties?
38:23Yes, there's the brokerage, which the brokerage community provides tremendous value. In my particular instance, what I found with broker deals is the asking price is wildly off from the price that I'm willing to pay. and I am going to stick by the fundamentals that I've set out. And I'm looking for specific metrics. And if they don't hit, I'm not gonna throw in rent growth that I hope to happen. I'm just not gonna do it. That's what I've seen with broker deals. I've had more success with talking to people and getting warm introductions to owners. That's where I've had the most success. And having conversations with these people who are oftentimes, I wouldn't say, there's no fire sales going on that I'm dealing with, but there's reasons these people are selling, whether it's repositioning capital or they have a bigger deal and like this deal is just too small, it's not worth their time and they need to get it off their hands and put the money back into this bigger deal.
39:28That's where I've had more success. So yeah, direct to seller. And I'm not oftentimes cold calling. I know everybody loves the cold call, not hating on the cold call. but a warm introduction. Now that, now you're playing with fire. It's really good. Yeah. I am glad you mentioned that. I did an interview with AJ Osborne who does self-storages and he had an interesting strategy where he would just ask, let's say in his case, it was a self-storage mom and pop owner out for a coffee or just take him to lunch, just saying he'd like to just learn a little bit about the business. He would never say he wanted to buy their property.
40:05But what he would say is like, develop a relationship with them, develop rapport, some trust that's involved, and then just ask if he knows of anybody that is interested in selling. And a lot of times, maybe they wouldn't be at that point, but they'd still keep him in mind. And he was able to generate a lot of deals that closed because using that method, which I thought was... And I like your idea too, just a warm... What did you call it? The warm... Warm intro. Warm intro. Yeah. Yeah. I mean, you're not coming out of left field and saying, hi, I'm calling about one main street. I was like, are you going to sell?
40:39I'm going to sell for 10 million. Okay. Well, it's worth 1 million. No deal. No, a warm intro. Hey, I have a friend that's looking to buy X in this area. I think your property fits. Would you like to meet them? And I'm not the way I'm at. Usually a friend's making the intro and then I'll take it from there. I found success. I mean, you obviously have to be connected or have a solid network, which is something I'm always working on. And I'm not coming in hot. Hey, let's make a transaction. You're making friends here. This is all, we're playing a really long game. I'm not looking for a quick buck.
41:11I'm not looking to screw people over. I'm trying to make connections and make deals sometime down the road. Yeah, your reputation doesn't go away, right? So it's something you want to maintain and develop. We mentioned, I mentioned early on, like you and I became friends through real estate Twitter. I just wanted to hear how you just first got involved in the community. why you chose to remain anonymous, kind of the pros and cons of that, and then just the benefits that it's provided you so far, just being involved in real estate Twitter. I am an advocate of real estate Twitter, as you probably can understand.
41:45I was one weekend trying to learn as much as I possibly could on - How long ago was that? Just how, like a couple of years ago or - 2018 or 2019, but I didn't start with my actual The Duke of Dirt account until the summer of 2021. And this is when I kept telling people, there's real value here. There's a lot of smart people that are sharing tremendous information and I want to be involved. But for me, issue was always my job. You work in a antiquated, let's call it what it is. Real estate is mostly an antiquated industry with a lot of rigid rules. And most of the times when you work at places that are a little more institutional, that have reporting standards and stuff, social media, you can have social media, but once you start talking about real estate and opinions and stuff like that, it gets dicey.
42:40For me, being a young person, it was a complete no. I couldn't do it. And I kept telling myself, you're making excuses. You're just not getting involved. You're making excuses. Well, I said, we're not making any more excuses. We're going to make an account anonymous, and I'm not going to tweet anything that I wouldn't say myself with my name. But there's that layer of, I don't want to call it safety, but there's just like a layer where if you search my real name on Google, it's not going to come up, which that was my solution. And it's been, I mean, the connections I've made on real estate, Twitter, people that I have somewhat quick access to is remarkable, really.
43:22I mean, I've had conversations with people that if I would have sent them a message on LinkedIn with my real profile, no thought, no way I would have gotten conversation. Well, I sent it from Twitter. Oh, sure. When do you want to meet? I mean, not always, but I've gotten responses where it's sure, whenever, what's good. And that's powerful. That's really powerful. Yeah. I've experienced the same thing with Twitter. I'll invite different people that I follow to be on the podcast. And everybody, I don't think I've had anyone say no. So it's just like that power of the relationships that you can build has just kind of blown my mind.
43:59And it's just been wonderful. I've really loved it. Let's take a quick break and hear from today's sponsors. Hey, it's Sean O'Malley, just popping in with a quick message. If you like this podcast, well, I've got great news for you. We've got a handful of other shows for you to explore. from learning about Bitcoin to embracing a richer, wiser, happier lifestyle. Just go into your podcast app and type in We Study Billionaires to find our collection of shows. We Study Billionaires is our flagship podcast, and we've made a name for ourselves over the years by interviewing the best investors in the world, including Ray Dalio, Howard Marks, Joel Greenblatt, and many, many more.
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47:21That's theinvestorspodcast.com slash tip-finance. All right, back to the show. I wanted to talk a little bit more about the Twitter threads. That's kind of what you're known for is the threads that you do. And we talked a little bit before the podcast started about just what goes into them. So I wanted to talk to you just about the amount of work that goes into it. How do you go about doing it? The research that's involved. Go into a little bit about your process for writing the threads that you do. Okay. You ready? I'm ready. Get your notepad ready. I got it right here. I sit down and I figure out somebody who I would like to learn more about.
48:00And when it started, they were the obvious big names, Sam Zell, Steve Schwarzman, guys like this. And I go on to Spotify or wherever, and I type their name and I queue up as many podcasts as they have done. Okay. For my week, this is when I used to commute a lot and I'm listening on 175 times speed. And whenever a little tidbit of information where I think is valuable comes up, I'll look at the timestamp and I'll write it down on a notepad or in my notes. If I'm driving, I'll try to scribble it. And at the end of the week, I'll sit down with my timestamps and I'll put it on paper. And that's really it.
48:45I mean, doing that takes a lot of time and it's not always podcast. Sometimes I'm going on YouTube and I'm queuing up a list there. Sometimes it's a book. Sometimes there are news articles. But the point is, I'm really trying to understand these people and then taking stuff they've said and using the same first tweet. That's the most important part because if you don't have the first tweet that really says, whoa, I want to read that. If it's not, you could say I'm giving away 10 bars of gold in the fourth tweet and nobody's going to say, oh, I'd like that. No, you just won't get it. Pretty much what I've found something that works.
49:27And if you look at my tweets, it's mainly the same thing. You say the person's name, you say they're worth an ungodly amount of money. And you tell the audience that they have so much experience. And then you tell them, well, they have all this money. They have all the experience. They must know something. Well, I've gone out and I've curated 10 golden lessons from them. And here they are. And usually they're pretty darn good. I think, I mean, I like to say something. They are. They're very good. So anybody that doesn't follow you, follow the Duke of Dirt for sure. I think the one that caught my attention was the one on Sam Zell.
50:01And I love Am I Being Too Subtle? The book was, I just think he's a character and enjoyed reading that. But do you have any favorites that you've done of the threads that you've done? What are some of your favorites and some of the lessons that kind of stand out? Yes. I would say the first one that I ever did and how this all started was kind of have a rule for myself now that I am producing content on Twitter. It's hard. It's not easy. I've come up with ideas. Whenever I consume content, I have to produce at least one piece of content. And so it's the weekend and I'm just on YouTube listening to John Gray of Blackstone who headed their real estate.
50:39And now he's the president of the whole thing. And he's dropping, I like to say, bars of gold. Just tremendous pieces of knowledge. And I'm writing all these notes and I finished listening to two or three YouTube videos. And I said, what? This is like 15 tweets. I might as well put this into a thread and then cherry pick parts of the thread for the rest of the month. And that's what I'm going to do. I said, oh my gosh, I have so much content now. This is amazing. Well, I did that for the first time and obviously it went great. So I said, okay, I'm onto something. But he, to answer your question, he is, one, he's very wealthy, but he's relatable and he doesn't speak in, I may have said some big words to make me sound smart.
51:22He doesn't do that. He's obviously very intelligent person, but he is so eloquent with how he presents an idea and explains it and talks through an investment thesis. I think that's, for me, that's a sign of just, I like that. In very simple terms, like just the way he explains things. Yeah. Yeah. I mean, if you look at some of his lessons, they're gold. One of my favorites that I've taken or that I tell people he tells people when they take their first job two things. You want to look for a culture of meritocracy, somewhere you can go, work hard, be great, and be rewarded for it, and a culture of teaching, somewhere where people are happy and enjoy teaching younger people because this is how you're going to grow and become successful.
52:10He always tells people that. I've always taken that one. I mean, a few other lessons, And there's a lot. Yeah, there's a ton of them. Definitely. Like you said, read some of these. They're really great. Sternlich, Barry Sternlich, too, is not opposed to an interview. He really likes it. And I think that's one of my better threads just because he's spoken so much. He's CEO of Starwood. Is that right? Yes. Yes. Yeah. He's on Squawk Box a lot, correct? Yeah. You've got it. Yeah. He says, find the freight trains in your life and get on them, not in front of them. That's not actually his direct quote.
52:43I remember he said that he was told that by a professor in college, I believe. But I think that's pretty basic, but it's very true. Look in the world today, and I'm sure you could see a handful of things that maybe wouldn't be something you want to get into. I could think in real estate, I mean, I'm going to listen to this in 10 years and say, oh, what an idiot. But you look at office sector, you say, that's an interesting sector. I don't know what's going to happen there. and I could be totally wrong and it could boom. But that's one where I don't know I would get in front of the tree. Now, I could be totally wrong.
53:20And that's just an example there. Another Barry Sternlicht is hope is not a business strategy. And I like to think that, you know, you see people acquiring assets and today I do the numbers. I really look at the rents. And I say, how in the hell are these people getting to that number? And the only thing that I can come up with is their assumptions are entirely based on hope. And that is not something I am interested in investing on. That's kind of one I fall back on. And then just two quick ones. Steve Shortsman founded, created Blackstone. He likes to tell people, write or call the people you admire.
54:02You never know what can happen. And Steve Schwartzman's famous for writing presidents or big time people. And this is before he was who he is. And he said often he would get invites to go to houses and interesting things happen. And I think that's kind of relatable to Twitter a little bit where you don't know what's going to happen. And somehow you can get a thread and all of a sudden you have Sam Zell in your DMs. That's not what's going to happen here, but it's just cool. that one. And then Sam Zell just says, when people show you who they are, believe them. I think that's my favorite. His. His main takeaway that I took from his book was like, always buy below replacement cost.
54:39Yep. And don't buy with negative leverage. Correct. Right. Any other qualities that kind of stick out for you of all of these investors that you've focused on for your threads that have made them successful? What are some of the commonalities that you've seen? There's one that every single one of these people has. It is they have a tremendous belief in themselves to accomplish what many thought they could not accomplish. It starts with you. And if you don't believe truly about what you can do, I mean, I'm not going to say it's not going to happen, but these people don't exhibit that quality. When you look at Steven Ross, who he was working for a company, he was fired from his job because he went out with his boss one night and I don't know, punched him.
55:25That's the story. And he went out the next day and said, I can do this better than you. And guess what? He did. So he, obviously he had some help. He had his uncle, but these people really truly believe in themselves. Yeah. They're also independent thinkers, contrarians, it seems like to some degree. anything else that comes to mind of some of these guys? I would say yes. The contrarian thinkers, Ira Lubert says that often. He's another thread that I've really enjoyed writing about. He doesn't talk publicly very often, but I wish he would. He has tremendous mind. Okay. I wanted to kind of segue into your newsletter.
56:06I think you may have mentioned that a little bit. Talk to us about that. What the content is you're producing? Is it kind of the threads that the newsletter is, or is it totally unrelated? No, it is. I read a newsletter that I've, you know, selfishly, I like to tell people, when you write, when you put things on paper, you really grasp them that much better. And for me, it's been that. I try to take the reader from zero to one, and it doesn't have to be this broad, crazy topic. It's how do you do something better in your real estate operation or if you're part of the real estate community? And so that's kind of the general thing.
56:45And does that involve doing lessons from famous investors? Yes. Does it include how to make sure that you're going out to market with the right rent on your apartment unit? Yep. Does it include my tech stack? Every part of my real estate operation that I'm using? Yes. All things that I pretty much try to look back at myself four or five years ago and say, would this have been valuable? I look at my Google search history. If I can go back, I don't think I'd go back then, but there's just any of these types of things. That's what I try to provide. Yeah. And how often does it come out? Try to do weekly, but it just hasn't always been that way.
57:26Yeah. I shared with you earlier that we do a daily newsletter called We Study Markets, and it's hard to come up with and produce a bunch of content on a weekly or daily basis. Yeah. And you want it to be good. You want it to really provide tremendous value. And some days I don't read it and think that's tremendously valuable. And maybe I should just take my own lesson, just hit send. And somebody probably could take value from it. I listened to an interesting podcast yesterday with a guy named Kevin Kelly, who was the founder of Wired magazine and fascinating guy, kind of a futurist technology kind of guy.
58:01But he was talking about just how everybody should write. And for himself, he doesn't really know what he thinks until he starts writing. And I think the practice of writing is something that anyone at whatever level could get benefit from for sure. I wholeheartedly agree. I think writing is a tremendous resource to anybody to conceptualize your thoughts and better understand a concept. let's jump into a fire round here real quick we're uh we're kind of at the hour mark and i wanted to i know that you're a big reader researcher that kind of thing so what have you read recently that you think i should read endurance shackleton's incredible voyage this is a book about a group of english explorers that went to the arctic and experienced let's call it a tough voyage and if you're looking for perspective, if you want to feel a little more resilient in your life, this is the book for you.
59:02I'll check it out. This is totally unrelated and this might get edited out, but I met a guy in Asheville, North Carolina who did, you've heard of the Iditarod, right? The dog sled race, which is a thousand mile race. Well, a week before the Iditarod, there's a week before, a week after there's a human powered Iditarod race. So it's a thousand miles by yourself. And I met this guy in Nashville. He was working at a running store and his boss came up. He's like, has this guy told you who he is? Like, Oh, no, we're just kind of talking. And he ended up winning this race. Like he won the Iditarod foot race and he wrote a book about it.
59:40He's like a motivational speaker now and went through a bunch of personal hardships in his own life and got into running and just a really interesting story. And I love those. I'll definitely check out Endurance and give it a good read. I've heard it mentioned a couple times, so it's time to probably read it. It is the best book to gain a little bit of perspective and be just a more resilient person because you read what these people went through and you say, holy smokes, I might not have it that bad. Good perspective. Next one, where have you traveled to? You've done a bunch of traveling. I know that.
1:00:15Where have you traveled to that I should travel to? San Sebastian, Spain. It's where I studied abroad that junior year. It is, if you enjoy great food, if you enjoy water sports, maybe surfing and you like good wine, this is the best place in the world. I'm not biased, but... Is it in the Rioja region of Spain? It's in the País Vasco, which is Rioja. Yes. Okay. I will check that out. I've been to Spain, like Madrid and the airport, but that's about it. I've not kind of gone out and ventured around. You got to go off. And then my special edition here, Rio de Janeiro. Great city. Beautiful, beautiful city.
1:00:54Definitely on my list. Best purchase under$250. I think this was one of your questions. It was, and I'll do you one better. How about under$100? It is a Josephine number two universal wine glass. I really enjoy wine and drinking out of this wine glass, you know it's going to sound odd to many people who just drink to drink but it is really an experience every time i have a glass of wine and it is delicate it's fragile but it is it is an experience so josephine number two wine glass yes i heard that right okay yep i'll check it out i'll check it out my parents are both big wine drinkers i'll i'll have to get a great gift yeah if you're looking for a gift for somebody that likes wine or something two of these oh primo Well, last one here.
1:01:41What's your best real estate book that you would recommend? I would say Steve Schwarzman, What It Takes. I really found tremendous inspiration from reading how he started Blackstone. And he was in an enviable position at his firm. He had the world. He could have sat back and extremely successful. He said, I want more. And he did. And he built something more. Very cool. that's one I haven't read either but I've read your thread on it which was great often I got a lot of reading to do endurance and then what it takes so Duke thanks a lot this has been a lot of fun I've enjoyed talking with you getting to know you a little bit better do you have any kind of words of wisdom or like a takeaway one big takeaway you'd want for our listeners who've been listening today yeah I think two things and Patrick this was quite enjoyable I'm appreciative of the invite and I hope I've provided a little bit of value.
1:02:35Two things here. In life, effort requires no talent. You don't need to be smart to show up every day and make something. In fact, in real estate, the hungriest people often outperform the sharpest. So that's one. And then two on that is hungry dogs run faster. I mean, if you truly want it, go make it happen. No excuses, just do it. Love it. So Duke, a lot of fun here. Definitely have enjoyed it. Definitely you've provided some value. I encourage our listeners to check out your threads. Ton of knowledge there to pick up. What's the best way aside from Twitter or on Twitter? What's your handle on Twitter and what's a good way for maybe another way for people to reach out to you?
1:03:19Yeah, at the Duke of Dirt on Twitter. That's really the best place. Direct messages are open. I enjoy hearing from people. I love going back and forth. And then there's the newsletter on the profile of Twitter. That's probably the easiest way to get to it. Thank you so much for your time. This has been a lot of fun. Thanks, Patrick. Okay, folks, that's all I had for today's episode. I hope you enjoyed the show and I'll see you back here real soon. Thank you for listening to TIP. Make sure to subscribe to We Study Billionaires by the Investors Podcast Network. Every Wednesday, we teach you about Bitcoin and every Saturday, we study billionaires and the financial markets.
1:03:59To access our show notes, transcripts or courses, go to theinvestorspodcast.com. This show is for entertainment purposes only. Before making any decision, consult a professional. This show is copyrighted by the Investors Podcast Network. Written permission must be granted before syndication or rebroadcasting.
From the publisher
Patrick Donley sits down with sports agent turned real estate investor, The Duke of Dirt. You’ll learn what the Duke learned growing up with a Super Bowl-winning football father, how he took control of his own learning, his thoughts on getting an MBA, the dangers of following conventional wisdom, and what his current plan is as he moves away from the W-2 world into real estate entrepreneurship.
IN THIS EPISODE, YOU’LL LEARN:
00:00 - Intro
03:35 - What The Duke learned growing up as the son of a highly successful football coach.
04:54 - What he learned from Nick Saban and Chip Kelly.
14:30 - What it was like working as a sports agent representing football coaches.
15:36 - How he transitioned to real estate while getting his MBA.
15:36 - His thoughts on higher education.
20:38 - How he took control of his own learning and the sources he turned to.
29:46 - The dangers of following conventional wisdom.
30:03 - How to navigate going out on your own.
32:01 - His current real estate strategy he’s implementing.
41:58 - His experience with Twitter and writing high-quality threads.
51:42 - The commonalities of successful real estate investors.
52:39 - How anyone can benefit from writing regularly.
And much, much more!
*Disclaimer: Slight timestamp discrepancies may occur due to podcast platform differences.
BOOKS AND RESOURCES
Join the exclusive TIP Mastermind Community to engage in meaningful stock investing discussions with Kyle and the other community members.
The Obstacle is the Way by Ryan Holiday.
Mose Kagan’s blog.
Am I Being Too Subtle by Sam Zell.
What it Takes by Stephen Schwarzman.
Risk Game by Francis Greenburger.
Endurance by Alfred Lansing.
Related Episode: Listen to REI180: The Intersection of Education and Real Estate w/ Kevin Clark, or watch the video.
Related Episode: Listen to REI182: Escaping His 9 to 5 w/ Raleigh Williams, or watch the video.
Related Episode: Listen to REI179: Resilience and Triumph w/ AJ Osbourne, or watch the video.
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SPONSORS
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