Official Caddying Story: David Dorros
In this episode of Caddyshack to Corner Office, Kai sits down with David Dorros, Vice Chairman at Eastdil Secured, to discuss how his early days as a young caddie shaped the foundation for a career in real estate investment banking. Dave reflects on growing up outside Washington, D.C., riding his bike to Burning Tree Club for early morning loops, and learning discipline, preparation, and resilience in the caddie yard. Along the way, he shares stories about the culture of the caddie shack, lessons learned from members and fellow caddies, and how those early experiences helped him develop confidence, relationships, and a strong work ethic. The conversation explores how the lessons from carrying a golf bag - service, anticipation, and accountability - translate directly into leadership and success in business.
Prior to Eastdil Secured, David spent seven years as Vice Chairman of Cushman & Wakefield’s Capital Markets Group, overseeing its loan sales business. Prior to his time at Cushman & Wakefield, he founded and led CBRE’s National Loan & Portfolio Sales Group. Mr. Dorros also served as an advisor to the Federal Deposit Insurance Corporation during the global financial crisis, where he led over 110 assignments on its behalf.
The following transcript is AI-generated and has undergone only minor edits. Please refer to the video recording for direct quotes.
Kai Sato (00:01.932)
Welcome to Caddyshack to Corner Office where we recognize the most accomplished people who once caddied and grow the game by assisting those following their path. I'm your host, Sato. Today I'm lucky to be joined by my friend Dave Doros. Thanks for taking some time,
David Dorros (00:17.15)
Thank you. It's a pleasure to be here and I'm excited to share my experiences and really how caddying shaped me as a person and those lessons I learned at a really young age and how they've, I'd say they've really transformed my life and probably many others. And I think the positive attributes that, you know, that you get from caddying that so many people forget or don't even know about. So, I'm happy to share that with you and really look forward to the conversation today.
Kai Sato (00:47.362)
fantastic. Before we dive in on just some of the catting stuff, you mind telling us Dave a little bit about what you do? I know you're at East Hill with some dear friends of mine, but tell us how you've gotten to this corner office, what you do every day and what your career has been like.
David Dorros (01:00.916)
I am involved in real estate. Okay. And real estate, you know, is a big profession. Many avenues, can go to. I'm with a company called East Steel Secured. We are the largest real estate focused investment bank in the world. Okay. And we serve, you know, institutions really in their decision making and facilitating transactions at the highest level, the most sophisticated transactions.
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people are really advising on our technical expertise and experience to really guide them through to have the best outcome for themselves and their organizations. And so my career didn't always start out working at East Hill Secured. we are the, and I like to say that everybody knows Goldman Sachs, but we're the Goldman Sachs of the real estate business. And for example, Goldman Sachs hires us if that's any kind of accolade. So,
You I started my career, you know, I caddied, you know, and I'd always been working really my entire life.
to undergraduate. started a construction company, moderately successful. Interest rates went to over 20 percent and that was the end of that. I have an engineering undergraduate degree from the great University of Maryland and an MBA from Indiana University and I got into really development.
David Dorros (02:35.321)
after I received my MBA from a company that's no longer existing, but they were the largest multifamily developer in the country. And, you know, my role for them was to help them raise money. And really we were syndicating properties, you know, around the country that were all multifamily. That led me to, you know, we had one of our seven recessions I've been involved in. So don't feel bad if we go through another one.
learned something from them and come out the other end better. And you know from that I went into brokerage.
And I worked at multiple brokerage firms and led CBRE's group, led Cushman and Wakefield's group, and kind of fast forwarding. But now with East Hill Secured, and I've completed really some of the largest transactions that have completed to date around the country. And I've worked on some global transactions as well. So I think I'll stop there. And maybe you can ask some questions, and we'll see how it all started.
Kai Sato (03:35.274)
Yeah, you've got it. The one thing, as you know, I have some dear friends at East Hill, including a guy like Jay Borzey, who's the salt of the earth and one of the best. I would venture to say that it's almost a disservice to call East Hill the Goldman of investment banking because you guys are head and shoulders by far and away better than everybody else. know, having started my career at a place like Mace Ridge, a large public read, you just not only
saw that in the proof of work. also those guys were having a lot more fun than we were. Their office was right down the street. And so it's a fantastic culture. It's a fantastic group of people.
David Dorros (04:10.088)
Yeah, don't don't don't confuse having fun with hard work. OK, it's I'm telling you, it's that's why catting is such a good foundation. You got to work hard. mean.
Kai Sato (04:22.102)
No question, no question table stakes. All right, so caddying. Where did you first caddy? How older when you started?
David Dorros (04:28.724)
So my first cattying experience was I grew up outside of Washington DC in the suburbs.
Okay, my first caddying experience was a place called Bethesda Country Club. And I had my first loop and the guy proceeded at the end of the loop. This is after like hours waiting for you know to get a loop and I was 13 years old. Okay, I rode my bike there. All right. You know, the bags at the time were these huge leather bags. Okay, they were bigger than I was. And I remember the caddy master hands me this little bag. It looked like
he kept the bowling ball in it, okay? Never seen it, all right? And I knew how to play golf, okay? We weren't in any country clubs. I grew up playing public courses, which I was thrilled with because I didn't know any better, okay? And...
this bag, I opened it up and it was a little bit torn and dirty and it was full of golf balls. So said, huh, maybe I get to keep these. The guy says, hey, come on over here, sends me out and you, and you know, you go out to the field and it's target practice. You know, you're shagging golf balls. They hit them as hard as they can at you and you better pick up every one of them because these guys, you know, they, they count them all. So I was like, all right, round one, they're shooting golf balls at me. How bad can this be? Okay.
Next I get to the bag and the bag is bigger than me this great big leather bag. Oh My god was huge. Okay, and the guy I know the guy's looking at me. I'm looking at him like I Don't know if I can make it. Okay, so I made the loop. Okay, I got back The guy goes what a terrific job. He did I had no idea what what I had done or what I was doing There's no instruction. He gives me two dollars two dollars. Okay, and he goes I want you to have these golf balls and I'm looking at him like
Kai Sato (05:52.802)
Big old Burton bag, probably.
David Dorros (06:19.158)
I'll take $4. I don't really need the golf balls, okay? And so he gives me these golf balls and the $2 and I went on my way and I said, you know, this was a really good experience. There's gotta be other clubs out there that, you know, have a different type membership or where I can caddy. So I went to, I had a friend and you know, we went over to a place called Burning Tree. It's a private country club outside Washington, DC. To this day, it's still men only.
And back then it was really men only. Women couldn't even drive down the driveway. really, you know, very prestigious group of people that belong there. And at the time, it was predominantly politicians and some business people. Okay. And there weren't a lot of business people. There were more politicians, generals, people like that. And so, you know, I really, I learned so much there and they paid more. Okay.
and you got to play golf on Mondays, okay, despite we had school, okay, you got to play golf all day Monday if you wanted, okay, they're closed Monday. I think to this day they still have that rule. So it was, that in itself, and I loved golf, was like you'd never get the experience of playing a course like that. I played and I think I learned a lot of lessons. lot
I learned, know, look, life isn't fair every day. You get there at seven o'clock, okay? And you learn about if you're not on time, you know, you're not going out, okay? And you sit there and all these other people for whatever reasons get to go out first, okay? You you gotta earn your way up, you know, as you do with everything, into, you know, better people, you know, better rounds, okay? And maybe get to be a four caddy and then
they go on a cart where you're really lucky, okay, and you don't have to carry two bags. By the end, you can't even walk, they're so heavy. So, the lessons that you learn, I think, and the ability to be around people and to hear the conversations that they had, these were pillars in the community, okay? My first loop was with a senator, okay? I'm 13 years old, I didn't know what a senator was, okay?
David Dorros (08:43.732)
remember like he hits and at the time the course of a really heavily treed you know they were you had the fairway then you had the trees and it was woods okay he's hit it square in the woods and he's like son did you see where that ball went and looked at me like you better tell me yes okay so lo and behold you know we found his ball right away I was like
This is how you know, caddying works. Okay. And, but I think what you really learn is, and what's really important is that you learn you learn how to be a good listener. Okay, first and foremost, you know, they don't want you telling them, you know, you know, you keep your left arm straight, how's your posture, you know, change your grip a little bit, you know, it's, you're a good listener. Okay. And as you I think, as you get older, and you know, if that's your profession, you know, then you
can really advance it to the next level, where you can really articulate your skill set to what they're really trying to accomplish and really help them. But for these rounds at that age and at that time, it was really, you become a good listener. And why is that so important is you're sitting there raking the sand traps, okay? And you're listening to these people that you would never have the opportunity to be around, okay? They are, some of them are CEOs of companies.
You know, some of them, all of them were very successful. They wouldn't have been there if, you know, if if they weren't that successful. And I think so you listen and you learn quickly. OK, what to say, what not to say, more importantly, and when to say it. Those are all skills that in business. OK, critical. You master those skills. You're probably going to have a pretty good career. OK, and you. Yeah. And you combine
Kai Sato (10:33.943)
Well said. Well said.
David Dorros (10:36.598)
that with hard work. Okay, and let me tell you, it is hard work. And you combine that with hard work. And I think it's a recipe to really, you know, kind of set yourself up. And I had so many experiences, I can I can tell a few stories, guy, you can prompt me and tell me where you want to go here.
Kai Sato (10:54.702)
I'm going to make yeah, we're going to unpack this even a little bit further. What was the caddy yard like at burning tree? You to get there early. You know here here you're a public course player and then you get this idea to start caddying and then you I think very adeptly look for the best opportunity after this $2 round. But you show up there at 7 in the morning. What were the other caddies like? Was there more training? You're going out with senators and then.
I want to know what your friends thought of this or maybe what your family thought of this because all of sudden you're transported into really a completely different world.
David Dorros (11:32.84)
Yeah. So, you know, here's the experience. You had professional caddies. OK, you had the caddy quote caddy shack. OK, we've all seen the movie, but the caddy shack was a cinder block building. OK, you had to get there at seven o'clock. OK, there was no like being late, you know, anything else. And you had to be ready to go. OK, if you're fortunate enough and you learn these things as you as you go. But again, these are lessons you take with you in your life. Like you better be prepared.
prepared. Because you could go from seven until five or six without any food. Okay. You'd hope that they'd feed you. Okay. And you'd hope that you'd get a loop. Okay. So, you know, you get in there at seven o'clock and you're looking around and you're the youngest guy and they had, you know, an experienced crew that, you know, knew the caddy master knew who to get. You know, the members would request them. They knew their way around and they're older. Okay. So it started
out you start playing cards okay there's nothing else to do nobody really comes on until maybe nine you get a few early birds but so you sit there and there's absolutely nothing to do so you better be a good card player because you're just gonna lose the five dollars you're gonna make okay and then probably then some okay so not a lot of fun all right if you didn't know how to play cards and they played other games like you know dice and you know just all kinds of you know inner city games essentially that I've really I grew up in the
suburbs like I didn't even know what these were. Okay. And so then you sit there and you you had to bring your own food basically. Okay. So, you know, you each, you each are, you know, mangled up peanut butter and jelly sandwich that, you know, don't know if I could eat one today, but you know, that was the best thing you ever had. Okay. And then you hope you got called. Okay. If it rained, you're out. Okay. You know, and if it wasn't crowded that
day you're probably out and you know so what'd you learn you learn that you know life's not always fair okay those guys that you know had been there a long time you know they got precedence over you and you know they may not even done a good that good a job but you know they were going out first and then you learn like all right who's controlling the shots here it's the caddy master okay so how do you have watching these guys like you know they're giving handshakes to the caddy master I'm like huh
David Dorros (13:59.634)
What's that all about? Okay. I learned at a real young age. Okay. You know, not a bad thing to give appropriate handshakes, you know, to the right people and, know, and, have them on your team. Okay. So.
Kai Sato (14:11.992)
Some of those yards, sometimes the caddy master just got a little sticky fingers before anything happened.
David Dorros (14:17.084)
Yeah, yeah. Unbelievable. look, it's it's all life lessons that you know that and they were innocent lessons back then. You know, so I think that, you know, we can keep talking about it. And I think you'll see, you know, for people watching this video potentially like, what do I get out of it if I'm a caddy? You know, what's really in it for me? There's a lot more in it into it for you, which you may not realize other than the money.
And, you know, I didn't realize that.
Kai Sato (14:46.318)
Sure, fire away on some of those things because like you said, the EQ component, the soft skills, just how to interact with people, being a good listener. But what are some of those things that when you maybe got your first job or things that you still use in your daily life now that were forged as a looper?
David Dorros (15:07.09)
Yeah, I think that, you know, like I said, you know, your listening skills. OK, really, really, when I say everybody says that, OK, but what is your listening skills? Your listening skills are what's that person really saying or doing? OK, so, you know, and you learn that quickly, OK, because you're just not going to get, you know, paid well, you know, absent that. OK, and I'm not saying pander to the person or, know, that kind of conversation, but it's really
It's like what's this person all about? Okay, what is the situation? Okay, are they out there with the guest is trying to have a great time not really caring about their score or You know is score everything is winning everything Okay, is are they scraping every putt that's you know, five feet away where they shouldn't be Okay, just to win the whole and that's so important for him, you know You're not gonna be the person that says hey, yeah, you're not taking that putt. Okay, you know that
that's how you know, articulating that into how I play today is like, that's how you win. It's like, no, no, no, no, you got to put that three footer. But you know, I think you learn what's important to people. Okay. And it could be as simple as you know, when you get to the turn, he or she who's back there, hopefully serving you a little food after the members have gotten theirs, you know, you learn real quick that if you're nice to that person, you get an extra, you know, candy bar or
these are small little things but if you if you really look at it and say these are big things okay because that's how life works and you yeah you you learn and I think also what was another big thing is like just being around men at the time older men okay because I was really you young
Kai Sato (16:45.879)
No question.
David Dorros (16:58.676)
And, you know, I never would have had that opportunity. OK, because you're around your peer group and you you ask what did some of your friends say when, know, you talk about, know, who you played with today and what your family say. you know, I don't think they and I couldn't probably articulate it clearly enough to them how great it was. OK, like the conversations you're listening to, they just I felt that
they wouldn't understand it. But you as a young man listening to this, it was like you're going to school. Listen to these guys are already successful. What do they say? What do they do? And you learn. So now when I go out and I get a caddy, and we'll get to that in a little bit, but when I get a caddy...
you know, it's not about me. Okay, I'd love it to be about me. Okay, but it's not about me. It's like, I want my guests to have the greatest experience. Okay, so like they're like, you know, the every caddy starts doting over you right away. Okay, it's like, no, you don't need to do that. All right, I'm good here. Okay. It just go, I want the guests to have a great experience. Okay, give them your knowledge and share that knowledge with them. Okay, and don't tell them I said that. Okay, but share that knowledge with
them, okay, so that they have and walk away thinking like this is my greatest day, you know, and then you've kind of paid it forward. Those are all the little things you learn that are I think life lessons. And I think the biggest one is is hard work. You are not getting anywhere without hard work. And anybody who tells you that, you know, is, you know,
It's ill gotten because you know, caddying is hard work. Okay. Maybe if you're lucky to be a forecaddy, okay, it might be a little bit different. And you get you can quote get your steps in. in reality, it's, you know, it's hard work. And you know, you have to be humble. Okay. And you know, you've got to, you know, take a lot. A lot of the people that you caddy for, you don't get to pick and choose. Okay. That's one thing about caddying. You don't
David Dorros (19:15.918)
pick who you want to. You hope that they pick you once you earn that, but you don't get to, so you all walks of life. All walks of life. So you
Kai Sato (19:24.778)
Absolutely. Well, you you mentioned some stuff that I think is important for anyone here, but especially our mutual and dear friend, Skip Bronson, who listens to every single episode of these. But he was a looper himself. And, you know, when I showed up to Bel Air in college and was caddying, you didn't get Skip's loop, right? You had that was Tommy's loop. And back to that was four putters, two cards, four putters. Tommy's no longer with us, but he.
Do you think he was a little protective of that thing and maybe not very nice to new caddies? Right. That's just how it went. And so you were dealing with grown ass men and you had to pay your dues and get there even a little earlier than seven. And sometimes you didn't get out. But, you know, it's it's the way you and I met was through our dear buddy Skip, who you obviously was looper himself and loves this game maybe more than anyone you'll ever find. But it's all encapsulated in that right for each of us. It's figuring out how to do the job.
how to do it well, most importantly, adapting to the people. And then also just not taking yourself too seriously out there and making sure that when you have guests out there like he had you at Bel Air, that it's the best day they can possibly have. so I think whether it's New York on the bag or my dear friend Geraldo or anybody like that, those guys, understand that. And they're going to make sure that when you're at Bel Air or you're congressional or anywhere, they're having a great time. But there's so much nuance to that.
Jimmy Dunne, who's obviously a legend in the golf community, he says that he can spot a former caddy within a couple of steps on the first tee. How people interact with people, do they go introduce themselves? If you've been a looper, I think you have a lot more empathy for what they're up against that day, and especially if it's 116 % humidity and all that type of stuff.
David Dorros (21:12.488)
You know, so true and skip who, you know, many of you have heard his, his podcast, I guess. But, you know, I really didn't know him and I had the pleasure and the honor really of being paired with him through my friend. And I'm telling you.
He articulated what it's like to be go from being a caddy, okay, to really the the top of his industry. Okay, he listened, you know, he told great stories. Okay. He listened to your stories. mean, he made you feel good. You know, I told my friend after my loop with you and it it it Bel Air and look Bel Air is a special place. But you know, we have caddies that can
I like to think that's a special place and I came home from I took the red eye back from Los Angeles to Washington DC and Got up the next day. I said, you know what? I'm gonna go play congressional because I want to see if it's as good as Bel Air and the experience with the caddies is as good and I'll tell you that my experience with with you was It was unsurpassed. Okay, because you know, you're a true professional if you look you've learned all these things But I'm gonna give you another example why it's so important
We played the next day and you just saw on TV What's the course they had the Genesis Riviera we played Riviera and look nothing against Riviera. It's an unbelievable place, but the caddy wasn't you Okay And you know, I don't know just didn't have you know, the greatest day wasn't hitting it that well and
Kai Sato (22:35.512)
of year.
David Dorros (22:52.72)
You know, it it it just was a different experience. OK. And, you know, regardless of how great something is, whether it be, you know, a golf course or whether it be, you know, your job or, you know, your relationship with your family or your friends or whatever, all these little skills add up. And I think make you, you know, really a much better person. And I'll say when I started my career, when, you know, I was looking for people to hire.
Okay, two things I look for, well many things, but two important things. If they said they were a caddy, okay, they probably would get hired. Okay, they probably would get hired. They're pre-screened. Regardless of all the other stuff on their resume or you know and everything else, they would get hired because I knew they knew what to do. Okay, there wasn't a lot of downtime explaining things and you know why are we doing this and all the other stuff. Caddy or an eagle scout, those two you know.
Kai Sato (23:51.95)
Mm.
David Dorros (23:52.534)
went to the top of the pile. In fact, my partner for 15 years was a caddy and I'll tell this story. He goes, you I'm interviewing and he was employed at the time and he really wasn't in our business. And, you know, he had a good skill set and he said, I was a caddy. And I said, you're hired. Okay. And I said, I want you to start. You know, can you start on Monday? This was like a Thursday. He goes, I mean, I got to give two weeks.
I said, do you know how to work hard? I know you do. OK, so this guy worked two jobs, OK, for two weeks. OK, and he was a caddy and that was the start of it. He and I would only hire caddies. Now, unfortunately, we've run out of great caddies to hire because, you know, I think there's probably a lot of opportunities for people to pursue out there without really realizing how great the skill set this is. you know, I'm not sure whether it's, Kai, whether it's like
I don't want to talk about being a caddy because it's not glamorous and I didn't have an internship at wherever, but I'm telling you that people know how to talk about what they did and the skills that they learned. Those are the life skills. That is what you need. mean, good and bad, had some bad ones too, but I mean.
Kai Sato (25:13.74)
Yeah. I didn't put it on my resume when I was in college for a little while, which was a mistake. And it would inevitably come up in conversation. It's really all people wanted to talk about. I was super fortunate because I was a caddie in college. I had a plethora of job opportunities and was super lucky and had a lot of guys that helped me navigate those opportunities. But there were two things. Being the captain of the lacrosse team in college and being a caddie were two things that people wanted to talk about, right? Because you can have all this other stuff and
It's fairly comparable. And then to your point, I'd work two internships every summer. And so in addition to looping, I would start in May and then not finish until almost September, because I wanted to get as much experience as an intern. Obviously, you're not tasked with running the ship, but just some proximity to different industries, try to figure out what the hell I was going to do with my life. no, I think anybody who's ex-CATI, it's a skill set. It's super unique.
Former military, former athletes, you you just, you've generally had to go through that hard work piece. It tends to be pretty well ingrained. And also a good buddy of mine, Josh Isner was on last season. He runs, you know, $50 billion publicly traded company is now a 40 year old. And he's just a super impressive guy, he was the manager of the Harvard basketball team. In addition to being a golfer when he was there and just got his ass kicked, right? But got to learn leadership from someone like Tommy Amaker and he recommends to everyone just
get outside of the classroom, work as much as you can, and work thankless shitty service jobs, right? Like whether it's anything where you have, you're the lowest on the totem pole, you just have to deal with it. And if you can get through that stuff, it really just kind of forges who you are. And I think you touched on something that's so important, Dave, why I love caddying and we love caddying. You you get to play golf, you're learning so many lessons, it's nice outdoor job, but the people that you're around.
David Dorros (26:46.302)
to it.
Kai Sato (27:08.878)
for four to six hours, you don't get that doing anything else, right? You can, you might be a valet and park their car, or maybe you wait on their table, but the reality is you are an integral part of that experience, and like you touched on, you can make it a lot better or worse. And so there's real responsibility that comes with it.
David Dorros (27:27.892)
Yeah, I'd say and we didn't rehearse this you and I before we got on the phone, but you couldn't have said it any better. And I think you're you're a shining example of the skill set that you learned. didn't know you're Captain Lacrosse team because that may that that may be ahead of caddying, but because the amount of discipline involved there. I think that, you know, look, my friends now, you know, we're all golfers for the most part. And, you know, once
Kai Sato (27:42.082)
Ha ha ha ha ha ha.
Kai Sato (27:49.56)
Yeah.
David Dorros (27:57.856)
later in life, you'll learn that, you know, anybody who, you know, who's worth their salt, that you want to be around, okay, and they've been successful, they're all pretty generous, okay, especially if they started out with humble beginnings like most of us did, especially if they were a caddy, and they want to share that with other people, both the experiences and their wealth, which is phenomenal. And that's what you find in golf. Okay, so not only do you get all the skills that you just talked about, Kai,
Okay, you get the pleasure of really like, okay, now let's go play the game. Okay, let's really appreciate it. And you know, the people that you're around, they're just they're generally pretty phenomenal people. And if you're not, you're not gonna be around them. But you know, you can go play, you know, once you get to certain level, you can probably go play just about anywhere you want in the world. Okay. And golf has a common theme. Okay. And as a caddy, you learn the game. Okay, that's another thing, you know,
Kai Sato (28:41.89)
Yep. Yep.
David Dorros (28:57.686)
you really learn the game, like how it works, how to read the greens. Okay. And it's like, I get out there and it's like, I get these caddies and like, I mean, you know, I asked him the first couple of holes where I hit it and you know, it's completely wrong, but you know, you don't say anything. You just, you know, let them read and, know, and say, I think you can go really help them a lot better, you know? So, you know, it's, you learn about the game and you take those skills and transfer them, you know, to your own game and your friends games, but.
And if we're fortunate enough to be able to play, it opens up world of opportunities on top of all the skill sets you have.
Kai Sato (29:40.246)
Yeah, I mean, look, these are cathedrals of golf. To me, these courses are walkable works of art, and we're so lucky to be there and have proximity to them. You said I'm super lucky I got to play RIV yesterday because we wanted to see the tournament conditions as much as possible with my mentor, Patrick Whitesell. just I've got a very cool wife and she's supportive. She's like anything with Patrick, you get to go. And so, you know, just the two of us just wanting to I got to.
David Dorros (29:46.12)
they are.
Kai Sato (30:06.99)
play in a pro am there and I get to play that course a fair amount. It's actually my favorite golf course. It's certainly not Bel Air in terms of culture, but for just a golf course, it's I think it's an incredible place. But to see it right, mean to see the ball not stopping when you've got a downhill putt and you know the rough is still out and you're you're taking a seven would just trying to advance a ball for something that's a 180 yards or all that stuff. But you know, we're super blessed to have these things.
David Dorros (30:20.329)
Yeah.
Kai Sato (30:36.855)
And you certainly gain, I think, a deeper appreciation when you've been packing bags at places like this, too.
David Dorros (30:43.762)
The physical let's not let's not just for one second, but the physical beauty of these courses. Again, you learn later in life how extraordinary they are. I mean, they're they're meticulous, meticulously kept. You know, they're thoughtful. It's you know, it's really, you know, you try to keep track of your own lawn and keep take care of it. It's like you learn like, my God, how do these guys do this? So, you know, again, it's a lot of hard work. But go ahead. I'm sorry.
Kai Sato (31:10.83)
Oh no, no problem. Back into your looping days and your at Burning Tree, is, I mean, for my vote, one of the greatest places there possibly is. The course is incredible. Gil Hans redo, the fact that there's no menu, you can get some fabulous food just at a snap of the finger. And the members are just so cool. And I also like a nice golf logo and they've got a very cool one. How long did you caddy though? You started there when you were around 13?
David Dorros (31:15.731)
Yeah.
Kai Sato (31:37.509)
how long did this persist you want to go into maryland you continue to carry it all in your marilind's we will
David Dorros (31:41.82)
No, no, you know what, that lasted probably, you know, five years. Okay. I'd say till 18, you know, kind of off and on, know, for, look, it's only warm here, you know, X months a year.
Kai Sato (31:59.352)
Two weeks.
David Dorros (32:00.486)
Yeah, it's snowing right now, unfortunately, but go figure in March. it's it's not, you know, we have golf weather, you know, maybe three or four months a year, really for, you know, the country clubs, okay, for the people that are taking caddies. So it's not an infinite amount of time. But so I did that for about five years.
I did not caddy when I was in college. I took that skill set and I had other jobs as I went to school. And again, but I think the discipline of it all and the hard work just paid such dividends. So it was a good run.
Kai Sato (32:41.89)
You mentioned the first loop being with a senator. Who were some of the others? I know the membership can be a little bit clandestine at times. Is there any anyone who stands out and maybe you were just in awe of maybe one of your favorite loops when you were there?
David Dorros (32:56.372)
I think that...
know growing up in Washington DC, you know, nobody will ever say it's a government town. OK, but I played I played. don't remember who it was with, but I played with this guy and obviously very successful. OK, very successful like I don't think I've ever gotten a tip like that. OK, and I was like, what does this guy do? OK, and you know, wasn't dressed, you know, extravagantly or anything else, but he was quote, you know, a government
Contractor okay, and I was like what is that? Okay, you know because you don't think that the government has contracts I'm just telling you when you're 14 15 years old. That's not what you're thinking about and It turns out this guy was one of the largest government contractors, know in the whole United States Okay, big big defense contractor fast forward, you know, where did that go kind of mentoring guy? It's when I was in one of the
firms I worked with, we became the largest government contractor, okay, in the real estate business, okay, that nobody else was doing, okay. And, you know, they didn't even, people didn't even understand that the government, you know, used and owned a lot of real estate. And, you know, I'd learned that little lesson from this guy, like, huh, that, you know, there must be good opportunity here, or this guy wouldn't be so generous. So, I mean, I think, you know, a little lesson like that was very interesting. worked
They had a lot at the time they had a lot of generals.
David Dorros (34:34.042)
admirals, okay.
people like that to this day. You know, I play a congressional. play with a friend of mine. He's an admiral. Awesome person. Okay. I met him on the tee at, you know, congressional. We've been, you know, friends ever since. And, you know, it's just that, that kind of person that you learn how you can relate to them. You know how they're going to play the game of golf. Okay. You know, if you move your ball out of a divot, they're probably going to report you. Okay. That's cheating. Okay. So, you know, you, you learn,
integrity how critical that is okay and you you get up on the green and it's you know it's a three-foot putt you could probably make it it'd be a lot easier if they gave it to you okay he's like you gotta putt this okay and your scores go up unfortunately so you know I think some generals you know some military people that candidly I wouldn't have been exposed to okay I didn't have any my father was in in the army but again that was
ages ago so really didn't have any military people in the family so I got exposed to all that okay got exposed to like you know really some Titans in in the industry if you will okay and you know that back then was car dealers okay and it was you know people like that okay contractors
home builders, you know, and now it's, you know, more refined, have more much more corporate, you know, at Burning Tree and, you know, really, it's the titans of the industry from around really the world, if you will, you know, a lot of them have memberships there. So I mean, those are the kind of people at the time that, you know, I was I had really got to be around, I never would have had that experience. Okay, never would have had that experience and it matures you. It matures you.
Kai Sato (36:28.888)
Sure. Why did you get your MBA?
David Dorros (36:34.012)
You know, I was, I had an engineering degree. Okay. Probably should have stuck in engineering, but I had an engineering degree and you know, I really didn't have much direct business experience. Okay. I had started some smaller businesses and I said, you know what? I'll go get an MBA and they were popular at the time. And I said, I'll go get an MBA and you know, and see what that's all about. And also I wanted to see what the peer group.
you know, was doing. And at the time you could literally go from a good school. You could go get your MBA. You know, Indiana is top 10 business school and it always has been. You go get your MBA, you're going to get a good job. Okay. And, you know, you can see where the world takes you. So I think that's why, you know, it was attractive to me. And, you know, I really want to see who the peer group were. Who are these people getting MBAs and getting all these great jobs?
What did they have that I didn't have? And you know, it's a two year program, you know, that goes quick.
Kai Sato (37:40.3)
Was golf part of your MBA experience? Was it part of your undergrad? Were you always playing? When did you join your first country club? All that stuff.
David Dorros (37:49.844)
So I joined my first country club to answer the question. Yes. Playing, you know, all throughout all those years. OK. All all public courses. And I knew a few people that, you know, belonged to country clubs. if they took you, it was a thrill. OK. It was like there wasn't the proliferation of clubs that there are now. OK. They've really become popular. And look, we're seeing some go away, but there's still a lot of great ones out there. And the good ones are even getting better.
So the first country club that I joined was a place called TPC outside of Washington, just being built. And I really didn't have enough money to join as an individual, so I joined as a corporation with some other people and did that for like 10 years, great course. They had a lot of pro...
Events there and at the time for many years. It was the venue for anything that came through Washington DC Through you know the PGA, you know to play the the course the tournaments there, you know fast forward all my bucket list was to playing a pro-am and You know, I've played in several now, but one of them was there So I got to play the course with a pro, you know and see how you know They hit it versus how I hit it hit it terribly that day, but that's
beside the point. But so yes, I played golf, you know, continuously. And then the second place I joined was a place called Kings Creek. It's in a place called Rehoboth Beach, Delaware.
And that that town and that club is really mature. I joined it as you know, it's brand new. It's one of the initial members. I think it's just had maybe its 30th anniversary. Gravel parking lot, you know, lots of beer. It was great. Okay. No tea times. It was awesome. No caddies. Okay. And that was in Hobart Beach, Delaware. I had a beach house down there. And then I went from there. And then I joined congressional, which I'm a member
David Dorros (39:58.1)
now, still a member at the other place as well, but joined Congressional finally. I should have joined it many years ago. And it's been a really extraordinary experience. And it's for all the reasons that we've talked about, but they have a have a caddy program. And you you take caddies and, you know, they they it's much more advanced now. You know, they grade the caddies.
you can request them via email, none of that existed. The caddy master administrates everything, you get the, I'd say the level of caddies ranges from beginning caddies to very advanced senior people who do it professionally.
And again, I think I said it before, when I get a caddy, you know, it's really I want them to for my guests, okay, if I have a guest, I want them to focus on the guest. Okay, not obviously, but focus on the guests and make sure that guest or guests plural, you know, have a great time. And you know, the caddy can make it or break it. And you walk away, even if you played poorly, okay, you walk away and can say, God, what experience I had, that was
unbelievable okay even though you play terrible okay I remember I was playing with this guy and he was a client and you know terrible golfer I mean the divots were like longer than him they looked like the top of my head you know he's done
And so I kept saying, oh, great shot. You advance it 25 yards, finally he turned and he goes, Dave, you don't have to say that. You don't have to tell the caddy to say that. I know I suck. I'm having a great time. We're good here. I over to the driving range, got him a bucket of balls, and just brought him out. We were good.
Kai Sato (41:50.518)
If you're not good, just be fast. Yeah, when I when I was caddying in college, you know, my main loop on the weekends was getting Randy Brand, who's a Mayswitch executive, I later went to work for that company. And then May Siegel became kind of a quintessential mentor in my life until he passed away. That's actually him hanging behind me. And, you know, seeing Randy do deals was always really fascinating seeing a lot of people do deals. And so you know, there's the
David Dorros (41:52.211)
Yeah.
Kai Sato (42:17.006)
gambling, drinking golf, then there's the, you know, some of that, but mixed with a lot of, lot of transaction. And it was the time we were doing a lot of the forever 21 deals. And so at Larry Meyer out there, who was really good guy, wouldn't say the strongest golfer, but a really, really good guy. And so, you know, obviously my job was to make sure that he was having a good time and he was well taken care of. And I really kind of took it like a sport. I prided myself on if you were, you know, an occasional golfer, but had some decent athleticism, a lot of it was just course management.
right? Green reading and course management. So hey, you don't need to hit this hero shot. Lay up, right? Take the big number out of play. And then green reading, right? Like if you're not used to it, you can especially place like Bel Air, you could put it off the green. I have. And so you know, the things like that would really factor. loved I don't know if you got to be around some of these, but the big cash games were super fun. But you know, seeing, you know, maybe some Asian billionaire in town.
who runs one of the largest conglomerates in the world, squaring off against someone that you really looked up to. And I, one time, had the real conflict that I was catting against someone that I really looked up to. But I still have to do my job, right? And try to bludgeon them to death and win the match. so just understanding what there's a job to do, get it done. And you do that objectively, and you do it to the best of your abilities. But there was one, you mentioned Monday golf.
I quit playing lacrosse my senior year and I just played as much golf as I possibly could because it's hard to golf in LA and to have have proximity to a place like Bel Air was really really special. But there was a guy named Merle Hopkins. He taught the basic accounting class at USC and I ditched his class very deliberately one time to go caddy for Randy and a guy named Jeff Brodman who helped build Costco right one of the founders of Costco and I was just like look you know I'll figure out the accounting stuff later.
But the opportunity to meet with someone like Jeff and understand site selection for Costco at the time, a store that I'm still a Black Card member of and love almost as much as someone like Charlie Munger did who was on the board, that really just opened my eyes. And I think that's kind of back to, Germaine, what we've been talking about. It's just the assimilation and the proximity that you gain and doing a pretty cool job. And hopefully you make a little more than $2 at it.
David Dorros (44:09.81)
page.
David Dorros (44:36.092)
Yeah, and not only that, you spend four to probably realistically five hours, you know, of unencumbered time with someone. I'm telling you, you get to know them and they get to know you. It's a true test of, you know, what is this person really made of and who are they? You know, after five hours, you know what you have. OK, and it's like you said, you know, you may not be doing deals on the golf course. Everybody thinks that, you know, people
don't play golf think, you're out there five hours doing deals out there. You're really forming relationships. It's all about relationships. You're forming those relationships and everything else is much easier once you have that relationship. To the extent that you're just kind of parachuting in without that or you don't have that skill set to form that relationship, it's really hard. I guarantee you, Kai, you wouldn't have had the opportunity, okay, forget your accounting class to be around the founder of Costco.
go. Forever 21, like how do I pick a site out? You know, what am I really looking for? You know, screw those demographics. This is what I'm looking for. Okay. In three sentences. Okay. And you know, there are really experiences like that, that I think last, you know, a lifetime. And it can't be replicated. And or I think are extremely difficult to be replicated. So I think it's, you know, I hope that anybody, you know, listening,
and feel free to reach out to me and Kyle, I just volunteered you or myself to share some of this, because I think it's invaluable what you're gonna learn, invaluable.
Kai Sato (46:15.566)
That's why we exist. Very well said. We'll bring it to a close with that. You mentioned something that not a lot of people do. I've heard a lot of people saying, before I hire someone, I want to bring them on the golf course. And I want to see them putt those three footers. I want to spend those five hours with them. Even if they don't golf, I just want to see how they interact with maybe the valet, the caddy, the people in the girl room, just how that goes. But you guys deliberately hired former caddies, including your business partner.
David Dorros (46:20.148)
Okay.
Kai Sato (46:44.342)
Are there any other stories that you've come across, people that you thought were really cool and maybe you shared the fact that you guys looped that we should explore on this show and shed further light on?
David Dorros (46:57.64)
Yeah, I think my old partner, good Irish Catholic, John Howley from Boston, you get the accent. I think he would be a good one. I'd have to think about that. You can say it in your next show. I should have been more prepared, I guess, and come up with who I think would be a...
you know, somebody really great. Maybe Ed Lasier, another guy. did some caddying. went on to become CEO of a company called Billabong, and with most people I've heard of. But he's figuring out how to pick retail locations. Let me see my notes here, what I had here.
Kai Sato (47:43.118)
Don't worry, don't worry. No, that's that's perfect. It's it's it's just like day when you and I met right? I mean, it's something that skip and I always share but for the most part people have found that it was a really really unique job and it kind of transports them back to a time where they're really coming up and trying to figure out what this thing is all about this whole life thing this whole career thing and then I think most important like you said you're around adults especially men who are usually rather accomplished and you're learning a ton.
Or a lot of women have shared, I got to caddy for other women. And they were badasses. And they inspired me. And long before Lean In, they were that version for them. so yeah, think it's just you can learn so much by working. You can learn so much by being around people who aren't your parents. And you have to build a bond and a relationship with them. And so I really appreciate you taking the time and sharing your story. And not surprisingly, it's
helped forge an extremely successful career.
David Dorros (48:45.32)
Yeah, one thing I would say that it just it just spurned. You know, you said that, you know, as you progress, OK, you belong somewhere, you can take someone out on the course. That's a different level. OK, you know, you want to see how they interact with people. You know, you could put them through the paces when you're starting out. You know, your resume is pretty blank. OK. And, you know, most people that are in the hiring.
not most, but a lot of them
have an interest or play golf or whatever, but it's something that when you're just starting out that, you you're not even thinking about it how important it is. Okay. But it's, it's really, you know, you'd wish they'd take you out on the golf course, but in reality, you know, you can talk about it talk about your skillset, et cetera. So I think it's sequential as you build that up, you know, and as you advance your career, yes, you go out and play, okay. And you see how you interact and treat people. But in reality, if you don't have a whole lot to say,
and you start out, it's a lot better than a lot of other jobs. You're really not getting a lot of skill set, just kind of resume stuff.
Kai Sato (49:55.086)
Yeah, yeah. The one thing that I did see, and I think it's important enough to even dovetail on there, so many people golf now. And it's cool, right? The fact that Tiger was a person who inspired me to play golf. No one in my family played. And I was a baseball player. And I was 12 years old. And Tiger burst out on the scene. And I just said, I want to do that. And very similarly, didn't own a college for the first time. I went to play nine holes and was using my grandmother's hand me a down, hand me down, turquoise Wilson's.
and look totally ridiculous and couldn't have loved it anymore. But I think you generally have to love the game. And so we are seeing this amazing resurgence of the game. And, you know, especially my generation, I'm not playing pickup basketball anymore, but I've long been a golfer. But the point is, when I was at Mace Ridge, I worked with some people who they knew that I came in through caddying and they knew that that I'd already forged a relationship with a lot of the senior executives.
And so, you know, I didn't stop to think about that at all. It wasn't like, you know, I got my foot in the door and I already know the C-suite and all this stuff. But for them, it was I think blatantly, it was very intimidating. So they said, we're going to start getting golf lessons and we're going to get into the game. But you got to be authentic about it, right? You have to actually love going and playing and being a part of it because it is a big commitment. And guess what? It's deliberately hard. It's a hard game for almost anybody to play. You can be good at it and suck in any given.
And so I think for people that are listening, that's where you get such a leg up, especially if you're looping, you learn the game. You learn how to read greens. You learn what club selection is like. You learn what course management is. Or you don't last. And so I think people have to genuinely love it. I think many people do. And we're seeing a really unique chapter in the sport of golf. for anybody who's listening and thinking about that, just like anything, you've got to love it.
David Dorros (51:48.412)
Yeah, and I think I'll leave you on this is like, it really probably one of the more important points is, you know, these people now, and people you get in these companies are like, how could you possibly know that person? Okay. And how could they genuinely be so, you know, I don't want to say affectionate, but like, like, I like this person, okay. And they're sitting there grinding and out, okay, trying to get the relationship with that person that they're never going to get like you have by spending all that time with them. Okay. It's really, I think it's, it's
really something that's critically important. So hopefully, know, some of the listeners probably are experiencing that, you know, and raise themselves up and see where they go. Well, I appreciate you taking time today, so thank you.
Kai Sato (52:29.335)
Well said.
Thank you so much, a lot of fun and I look forward to teeing with you soon.
David Dorros (52:36.936)
and you have an open invitation to play congressional anytime you want.
Kai Sato (52:40.376)
I've never been and I will absolutely take you up on that. I appreciate it,
David Dorros (52:42.644)
And there's two courses, so we'll test your skills.
Kai Sato (52:46.398)
Well, as you know, our fun Malo is based in Chevy Chase and my business partner lives in Potomac. And so I'll absolutely take you up on that and look forward to the experience. I appreciate it.
David Dorros (52:58.344)
Yeah, and Kai, I'll have to put you through a test and see how you treat everybody. Okay. All right. Thank you. Yep. Thank you.
Kai Sato (53:02.815)
I'm open to it. Alright buddy, lot of fun. Take care.
