Official Caddying Story: Rod Trump
Rod Trump is the founder and chairman of High Point Golf Club but worked as a caddy at Caves Valley early in his career. Rod successfully started, built, and sold two companies in distinctly different industries - both to publicly traded companies, all prior to age 40. In each instance, he identified an opportunity and leveraged innovative technology to disrupt the marketplace. His first company, Integrated Group Benefits, combined employee benefits and payroll into a streamlined, single source platform, creating significant administrative and financial efficiencies. The second venture, Converge, was a well-timed entrant into the enterprise social software space. Enterprise-level companies and colleges and universities utilized the technology to connect, communicate and collaborate.
Now Rod has embarked on what he calls, “his life’s work.” Long passionate about the great game of golf, he has partnered with renowned golf architect Tom Doak, whose resume includes having designed seven of the Top 100 ranked golf courses in the world, bringing back to life Tom’s first design, High Pointe, as a national golf club in the Traverse City, Michigan area. The revival of High Pointe has captured national attention and demand among golfers near and far has been tremendous. The reclamation project has been covered by The Golf Channel, Golf Magazine, Golfweek, Forbes, Links Magazine, The Golfers Journal, Golfwrx.com, Detroit Business Magazine, and many other outlets.
Rod is active in charitable endeavors throughout his community and the great game of golf. He is a founding donor for the West Palm Golf Park; involved in the formation of The Scotty Foundation, Pine Tree Golf Club’s Charitable Foundation; and plans for High Pointe to partner with the Western Golf Association’s Evans Scholar program. He has also established the High Pointe Golf Club FORE Foundation to support veterans and children in his communities. “FORE,” spelled like the well-known golf term, stands for Friends of Rod & Eileen, in honor of his deceased parents.
The following transcript is AI-generated and has undergone only minor edits. Please refer to the video recording for direct quotes.
Kai Sato: We are live Caddyshack to Corner Office. I'm your host Kai Sato and have the great pleasure of talking to my new friend Rod Trump today. Rod, how are you?
Rod Trump: Kai, I'm doing great. Thanks for having me on. How are you?
Kai Sato: Couldn't be better. This is the first Official Caddying Story of 2024. We've got a great one. You don't often get to talk to anybody who has been building a golf course and creating his own ecosystem doing with Doak and caddied no less. So right off the bat with would love to hear a little bit about what's going on with High Pointe Golf Club.
Rod Trump: not kind of you to say that. I'm really flattered to be on you've had a ton of awesome guests on this side of the podcast. So to go in that group is great and I love the game. I late started playing in college and then started caddy and just after college interestingly enough, but I've loved the game ever since it's just a part of my soul. And decided a few years ago after a shuffle in life that whatever I did next from a business perspective really wanted to be super passionate about and I embrace that years earlier, but it was time to fully enacted and I decided I wanted to be in the golf business and pursued acquiring a couple properties. Those deals didn't come to fruition for a multitude of reasons and then someone
Rod Trump: To me about High Pointe Golf Club, and I'd fall in love with Northern Michigan earlier that year spent the summer largely there and was just blown away by Northern Michigan Summers. There is something to be said for Pure Michigan. I found out what it was all about. And I discovered it was High Pointe was the first golf course Tom Doak had ever done. It had fallen hard times and didn't survive the financial downturn but it was something he was passionate about and as I learned a little more about it a lot of folks that were really passionate about golf architecture or the game in general it held a special place in their heart and I was able to reach out to Tom and start working on the land and the Domino's began to fall and here we are just a little over two years later from when I first kind of heard that whisper about it and our goal is to make High Pointe the next greatest Golf Club in America, if not one of the greatest in the world
Rod Trump: And now we're off to a great start. We built the golf course this past summer and Tom lives in Traverse City, which is about 15 minutes from where high points located. So it's for a number of reasons a personal project for him and I couldn't be more excited to be a part of it and just really feel blessed with a lot of the success that we've had so far.
Kai Sato: The buzz has been incredible. It's been so fun to talk to you a little bit about it. Look forward to learn a lot more and explore and further. If you wouldn't mind just indulge a little bit about your career and how you kind of came up and some of the businesses that you started.
Rod Trump: Thanks, I like to say that I worked my way through high school and paid my way through college and I also always found that the harder I work the luckier I got and I'm embody that and try to embrace it even to this day but I started out in sales a friend of my dad's who had been very successful. It's spent a little time with he took me to lunch a couple times and he kind of said early on there were three ways where you could really create Financial Independence and it was through being a professional doctor and attorney an It was being an entrepreneur and kind of when I graduated from college. I was too poor to be an entrepreneur. So I took option three I got into sales and did fairly well in sales and then just saw some opportunities so created a couple businesses in Tech that we were able to start and take full Cycles out of public.
Rod Trump: Companies are relatively young age, and I'm just really id A problem develop the solution and just right time without question. The hard work was a big part about it, but always also surrounded myself with folks a lot smarter than I was or I am and it's something that we're doing in High Pointe as well between Tom and gentleman Dan Lucas who runs the job is our directive Agronomy, same approach but the world's been kind to me and I'm blessed with a lot of good friends and people are helpful, but without a doubt, I started out working hard and saw some opportunities and was fortunate enough to take advantage of that.
Kai Sato: I know you got some great friends our mutual friend Todd Mohr thankfully put us in touch Good luck to your Huskies today, but he's a special one and you only attract great friends by being one, so I'm not surprised at all their run.
Rod Trump: Right agree. I'm happy to be your friend now Kai.
Kai Sato: Yeah, It's been great. I mean unfortunately for our listeners you and I could go for hours and hours, but we'll keep it relatively concise and condensed. But before we talk about Golf and even caddying you were pretty serious baseball player, and I think that that is a bit of a segue you might talk a little bit about that career.
Rod Trump: I mean, I grew up eat sleep dreaming baseball Maybe by what have was cut a little short with an arm injury before, kids were specialized and rehabbed and got Tommy John at 16 17 18 or 19. But I love the I loved everything about it when I was growing up and had a Facebook car collection and I could tell you probably every player on every major league team their uniform number the current batting average. He was gonna get called up from the miners that week who went on the 21 Day disabled list back when they called it the DL and so I was a pitcher I was always a much better picture than a hitter and I was kind of a late bloom or so it's a little undersized but growing up as an only child. I didn't have a ton of siblings to play with and I was kind of the younger kid in the neighborhood where I grew up so I wound up a lot of times.
Rod Trump: To throw in a ball, off a wall and it started out, maybe my parents backyard banging a ball off their backyard until back of the house. I should say until once or twice. I got a little while and took a window out that was maybe just highing outside of the strikes and set brushing a hit her back. I was taking out some glass but I thought that's how I worked on pitching and I was fairly proficient and Knows what might have come I still have a fondness for the game. Don't follow as much as I used to but I think that same kind of passion being a decent baseball player and I could hit a 90 mile in our fast ball or a curveball started at my chin and maybe flick it over the shortstop's head. But the first time I ever went to the driving range with friends here, this ball was
Rod Trump: heat up sitting still and I'm on embarrassed to say swung and mist and I'm hitting a Big Slice. I'm trying to hit it, over to the left. I'm hitting a big hook. I was instantly hooked by The Challenge and then everything else. That's so great about this game. it really drew me in but baseball kind of led me there and not necessarily being able to baseball play it a good enough level anymore. I wanted to do something and golf became it and it's just, filled every day since
Kai Sato: There's a lot of pictures as we know that are rather accomplished golfers Clearly Verlander still playing he hits a great no surprises there. Let's have it.
Rod Trump: I play with JV he can fly out. Bomb I mean, he's a big human being even bigger than he looks on TV. But yeah, they're pitching transcends well to golf but not like hockey does and we got a bunch of hockey guys stand in pine tree. So it's always good to be around those guys and they create some speed.
Kai Sato: No, no question. We're cumulating quite a collection at our club at Bel Air and jv's there as well. So you don't try to maintain any club head speed competitions against those kids.
Rod Trump: a place
Kai Sato: They've done it for 11. So where did cadding come in?
Rod Trump: there
Kai Sato: Where did you first start to caddy and as you get started?
Rod Trump: so I guess it kind of after college I'd gotten bitten by the golf ball pretty strongly and I had some friends that played on the golf team in college. I was just kind of starting out at that point. So I was a really bad 10 handicapped probably I thought I was a 10 about the before and I was probably a 16 masquerading as a 10 that in this day and age we call a vanity handicap and was the last guy you want as your partner and that's all match but these guys they carry The Caves Valley and they told me it was, pretty good pay and it was the idea of being outside kind of being around the games spending time with them. And guess what?
Rod Trump: On weekends when there wasn't a tournament once the members were going you could play at three o'clock or after and I mean, back then this is the early 90s. I mean, I thought Keys Valley was Augusta National. I mean, it's still a story place in Dennis satishers, one of the most decorated guys in golf it is his marks are all over that place my buddy burning age ours been a directive instruction there for one going back, but back in the early 90s, I mean caves was who it was sacred land and as a young guy, in my late teens, I mean it was just whoa, so the idea of playing that
Rod Trump: I was part of the draw but it paid pretty good too. And it was a good workout. He got to be outside and he certainly got to interact with some extremely successful people and learn how to interact with them and maybe listen to some of their stories and maybe pick up a stock tip here there were a lot of things about it.
Kai Sato: What was it just getting started? What was that yard like? how did you learn to actually become a caddy?
Rod Trump: I mean, obviously playing some I kind of knew a little bit. I know enough to be dangerous. And I can't caves still to this day has one I think the best caddy programs in the country and Dennis would and his team would always refer to us as the red shirts because at that point you can't even a red t-shirt. It's come a long way since then we can't even read t-shirts and you had the towel kind of between money or belt loops and by the time you've done 12 or 13 Loops like the size of your khakis were worn out and you were looking to buy another pair you were just wearing those but I remember I think it was one of my first Loops might not have been my first Loop, but I was out with the veteran caddy who will just believe him nameless at this point, but after the round he asked me a question with a bunch of the other caddies around
Rod Trump: I didn't really get it at the time, but it's probably eight or nine of a standing around and he says Hey Rod, how heavy the flag stick is? And who's kind of somewhat of a studious kid. I'm like, I don't know. He's like no, of course, you don't because you never picked one out today. and so it was a little bit of baptism by fire there. So I think just kind of as a new caddy going out with one of the a or honor caddies and
Rod Trump: they would give you some direction or obviously in this particular instance. I was clearly told what I didn't do well or at all. So you kind of figured it out though. I think my parents raised me to be polite and to be courteous and to kind of observe. So I think some of that things that it's important in a cat it kind of know when to talk and know when not to talk those things were innate so it was more about the intricacies of I stand here? I grab the flag? Should I ask him? Wait a second that guy if you lose his ball in the woods he's cutting your tip in half and he's gonna curse at you for the next three years old different things you learned on the job. You didn't know and they did it but there were some things that I think, I had walking in the door. because
Kai Sato: Along those lines. Were there any glaring mistakes anything particularly noteworthy or especially embarrassing along the way because we all seem to make plenty of them out there.
Rod Trump: I think I can't really think glaringly embarrassing. I can remember there was a particular relatively famous guy former major league baseball player and obviously, when you're cadding you stand facing your player, with the bag there and he might ask for a three wood.
Rod Trump: And if you pulled it out or if you let him pull it out and you didn't take the head cover off as it's coming out you could be standing obviously on his right facing because he's about to hit the shot. But if he had to take the head cover off the head cover got cost left on the other side of him. So now you got to sit your bags down Shuffle over pick it up wrong grab, if he took a bit crap, so I won't forget that one. I think that really something that here it is. It's just 30 couple years later and I still remember it and it's kind of a lesson and you know how you treat people and how memorable that might be. So, I think it's always important to be respectful people. He could easily said right out of the gate. Hey, make sure you take the head cover off, but he kind of wanted to teach you a lesson in his way or just show you who he was boss. but still remember that one all these years later.
Kai Sato: What were the bags when you were looping were they of these big burden bags people talk about with extra shoes in them. Were you doing two at a time? What was that lamp?
Rod Trump: And I'd say all over the board. I mean we would switch some bags out it was a corporate Club. So there were events and there was a lot of business entertainment. So I remember once standing where caddy would normally stand.
Rod Trump: A guy hit a three wood so far off the toe it hit my foot 89 degrees to his right? I mean you can't hit a three wheel off the housel, If you do it's not going directly, right if you're right handed player, but somehow it was so far. the toe was off the toenail and fortunately I think one of the bags I had that day might have been a burden bag or instead of hitting me in the foot. It might hit me somewhere much more important to me, but you got some big bags, but there were no out terrific bags or anything like that. If you got something that was really bad, you typically swapped it out.
Kai Sato: Can you elaborate a little bit you said the membership is Corporate who are some of these people. What was that membership like did any of them ultimately contribute to your career in a meaningful way?
Rod Trump: It was who of the Mid-Atlantic business Community as well? As guys like the former professional baseball player that I talked about. So when cave started it had to be your second Club if you were a local member and obviously you're National member. I mean, it's almost a given that it's your second club and when Kate started everybody wore pants all year round. That was Mr. Disharoon, who was the founder that was his Rule and
Rod Trump: Your pants and I'm telling you there are days in the summer in Baltimore 98% humidity. I mean, you could bake bread down there, at the turn. I mean you were looking for the Gold Bond anything that you could get it was brutal, but you wore pants and the players were pants and then that changed. for the members in their guests at some point Memorial Day to Labor Day, they could wear shorts and I believe I've gone back I've Had The Good Fortune of going back many many times as a guest and playing in some time. It's there, which is really cool. It was the first time
Rod Trump: the first time that you did that it was in a sense of accomplishment. It's like wow I used to be here and I used to carry bags for these guys and now I'm one of them and I had a good fortune of playing Seminole with the dear friend last Thursday. We played in 40 mile an hour when I mean it was Seminoles, it was out of 10 day meaning. It doesn't play much harder there. And I wound up the caddy and the caddy was counting for me. We have a mutual friend who actually Connecticut's with me. We went to high school together. he's a catty this day caddies at Seminole. He did the loop between Seminole and amazing guy. He was an amazing golfer and we were growing up. And so whenever I'm there inevitably his name will come up his name search.
Rod Trump: And in a surge is a great friend and he's had a great experience great life in golf and he's amazing Storyteller and it got sometimes I'll grab them I'll grab a rake and grab a bunker and depending who the caddy is no, I'll get that for him strong. I mean that I spend time on that side of the bag you go help my host. Let's keep this moving. I got this don't worry about me and I've seen some of the most successful guys that I know a dear friend who I know is I believe it on your podcast. He's part of that 13 billionaires collection. I played with him in number of times and
Rod Trump: he's the first guy to win a caddies get split to throw his bag on the shoulder or to grab a break and I know he catted obviously because he was on your podcast but it's just about we're kind of all in it together and we're all just sharing this game and it's just my opinion the best way to play so having that experience of being on that side of the bag and now most of the time being on this side of the bag it's special but since those days Academy caves I had a long time girlfriend who was a USGA level player not caddy for her and a couple ladies us mid-ams and my buddy whose name I mentioned early burning age or a caddy for him a couple times in US Open qualifier. So I still spend some time on that side of the bag and two years ago. We took a team from Pine Tree to play any inaugural of St. George's Hill outside of London and we were in a playoff for the gross. So the A and B player go out and play A&P play. I think we're playing Port rush into playoff like Port Russia.
Rod Trump: Guys a shot better ball like 63 in the final round so they caught our gross team. So that team I'm not embarrassed to say, I'm the D player. So I go out and I'm catty and for our B player and another guy's catting For a player to see players County 48 player and somebody's watching this happen and they say to my body's back. I'm carry anything. Is that the captain of your club cadding for you? And he's like, yeah, we're a team and yeah, that's probably the last time I had one song on my shoulder carrying into playoffs, but I mean, it was great. it was fantastic.
Kai Sato: I always have a back my mind. Maybe try to caddy when I in retirement get some exercise travel around see some courses. You haven't seen maybe help sponsor and back a player or something like that and Shepherd him or her along in their career. I mean sadly this is one of the few things I was ever decent at so it's something I don't necessarily rush to come out of retirement and that regard but I'm happy to hear that you're still getting on the bag and looping and obviously it translates to so many things that we do in life and in business. Were there any kind of big lessons that you pulled out of your caddying experience? It sounded like it was always a really formative time and you're in your life and making this transition to a different sport figuring out a lot of the career stuff, but then anything that stands out something that you took away from certain people or certain instance.
Rod Trump: But I think first of all was the rules Academy right show up up keep up. I think you can add on to that listen and pay attention and I think that in some ways all those five bullets would help everybody a little bit in business. I mean certainly you don't want to shut up forever, but you learn a lot more by listening to others you do listening to yourself most of the time. So, I think just those rules can apply in a lot of ways and I remember I have a good fortune of caddying in the 1995 us mid-amp, which was a caves was a caves in woodholm.
Rod Trump: I caddied Academy for a gentleman from Albuquerque, New Mexico, which is a mile high city. We found that out the hard way, but he stood up on the First hea caves the players practice round and he's asking me art. what do I hit here? And I said, what do you hit I said you want to hit something 245 right on that line right over the corner of the bunker 2:45 covers. It'll give you a great angle in degrees said that's my two line. and he proceeds to get up On the team it is too hard.
Rod Trump: It's at about 185, doesn't even get to the bunker and quickly. We were realizing okay, we're not at a mile high city anymore. We're playing at sea level in Baltimore and heavy humidity. So he did not make it through but because there's two sites you caddied for one guy. The next is the other John. I'm like, I was just a complete Class Act His Name Was Harold Payne. He was from Hurricane West Virginia, and he was what a gentleman a really good player. I believe we're coming out of stretch. He missed it by shot and we're standing there looking at the board together and there was a gentleman in his group that got through dark most from Westerville, Ohio and dark. I think it played at George attack. He had a bunch of stories about taking down or playing against Davis Love in college really good player, and I'm dark it been in the herald Pain Group.
Rod Trump: And he went to our Pro and he said hey, I've had someone so Cathy for the past couple days. There's this guy Rod out there that He was cat. He's got in get through. I'd really like to use them and I kind of wasn't like and I was not an honor caddy. I was still a relatively new caddy. That was my first year out there and he just liked my temperament and kind of liked my Approach and you could see I was a hard worker and that's something that here all almost 30 years later. I can remember that story. It was just about kind of doing the right thing right like Hardware pay attention. So those things ring true today, whether it's for me and what I'm doing with high point or anything else and if it's somebody is
Rod Trump: Catty and thinking about Hey, how can I make a difference if you're carry for somebody chances are they've done or they're doing something in life where they're successful and if you make a good impression on them, you never know. What doors may open up. So just in anything no matter what job, if you take on the challenge if you accept the responsibility, do it and do it well
Kai Sato: Perfect example you anticipated too. I wanted to see if there was anything specific Rod that you'd share with a lot of the bed and…
Rod Trump: Good.
Kai Sato: Scholars and the women at Scholars, but you were so lucky to work with organizations like that and help highlight some of their alums but part of my job in this is that I get to come across people like you and have a beer after around or just get to know people in the golf community and playing tournaments and whether you're an Evan scholar or metskal or anything like that, these stores are just so perfect. And so you hit the nail on the head of what you would say to some of these kids but it's just always be vigilant always put forth your best effort and you never know. what may come out of that here are much further down the road. And so I think that that's honestly something that we hear a lot of inquiries about because people might be transitioning in their 20s and trying to kind of figure out what that next step is and may not even realize that they have this incredible Network already entrenched as a young something person oftentimes.
Kai Sato: And you can go do anything much like you and sales and go into entrepreneurship and there are people if you do it right who believe in you and vouch for you and want to support you and succeed. And so that's where caddying can be so unique.
Rod Trump: you completely agree that the folks that you meet when your caddy and obviously you don't say at the end of the day. Can I send you a resume or mind if I look you up on LinkedIn, but People want to help people.
Rod Trump: Most people are inherently good. and everybody's been through stuff and people want to remember who helped them and they want to pay forward. And so I think that somebody's Loop and they're on that bag and the person that they're caring for. There's maybe not everybody's that way but the majority of people. They're looking for ways to help and ways to make Society better, especially with this great game of golf, that the people that you meet and the relationships you develop on all aspects of scream. It's just some of the greatest people in the world what so without doubt, most people that are playing this game. They move to a different beat
Rod Trump: and just the whole what's unique about golf are we police ourselves? We call penalties on ourselves. So that says a lot about our character and as a result, it says a lot about I think who we are as human beings and that there is a willingness to help and that we want to do things the right way for the right reasons.
Kai Sato: What case in point you're willingness to help me out with this you had to twist your arm quite a bit, but it's a story that not even taught new and so I was so Keen to want to make sure that we got that down and people know not only what you're doing now, but where it all started so I really appreciate it before I let you move on with your day. Have you come across any other stories other people that you think we should talk to that would be inspirational like yours.
Rod Trump: There's a couple people that I can remember, being on the back with I can think a couple people that I'm close to now. So I've already mentioned it to them and some as you probably know sometimes certain folks want to fly the blow the radar I want to stay out of the Limelight, but hopefully when I can share this with a couple friends of mine that I think would be good at telling their story that it would be inspirational that would help others that maybe they'll change their mind. Maybe they all won't but maybe a couple of them will not sure if a couple of these guys do you want them on and their stories will make positive impacts on others?
Kai Sato: I will look forward to that. Thank you if I can Pander to them or anybody else always I get to see what's written in I get to see and I need to share even more of that. But you just never know which little kernel or little C can germinate into something so big for someone in his or her life. And so that's why I kind of got off my ass to start this thing going and…
Rod Trump: Okay.
Kai Sato: fortunately a community is kind of kept emerging and we'll keep growing but it's exactly that just trying to make sure that you use those stories to maximum benefit to others.
Rod Trump: But I question I command you for what you're doing. I'm really honored to be a part of it. And I can help you by all means. I'm happy to and I just say keep up the great work.
Kai Sato: Rod Trump. Thank you so much sharing your official chatting story with caddyshacked corner office. Have a great day.
Rod Trump: Thank you You too.
Rod Trump: man Hey, brother, I hope that was good. It was awesome on my end. That was incredible. I loved it was great. It was great. Thank you for the opportunity.
*This interview has been edited and condensed
