Official Caddying Story: Brian “Sully” Sullivan

Brian Sullivan is the founder of Five Oceans Capital. Previously, Brian was a co-founder and partner at Troy Capital Partners and Troy Capital Group. From 2003-2015. Brian was also the co-founder and Managing Director of ForwardLine Financial (sold to Vistria Partners 2015). In 1997, Brian founded Rolling Oaks Enterprises a bridge lending and venture capital firm with portfolio exits to E*Trade, Adelphia and Hewlett Packard. From 2004-2014, Brian taught as an Adjunct Professor of Entrepreneurial Studies at USC Marshall and currently resides on the Board of Advisors for the Grief Center for Entrepreneurial Studies at USC. He received his BS from Northwestern 1993 and MBA from USC 1997.

The following transcript is AI-generated and has undergone only minor edits. Please refer to the video recording for direct quotes.

Kai Sato (00:02)

Welcome to Caddyshack to Corner Office. I'm your host, Kai Sato. On this show, we recognize the most accomplished people who once caddied and grow the game by assisting those following their path. Today, I'm joined by my dear friend, Brian Sullivan, founder of Five Oceans Capital. And it's really weird calling you Brian. We always refer to him as Sully. So Sully, thanks for being on the show.

Ty Webb (00:22)

This will be the last time.

It's awesome to be here. Thank you for having me during Masters Week. I purposefully wore Augusta Green for Masters Week. So this is a rarefied air to be here at this time.

Kai Sato (00:39)

It looks good on you. And yeah, we're doing a lot of our episodes this season around the majors. And we're going to bring on some big PGA folks around the PGA and US Open and different things like that. But kicking things off with someone like you is rather fun and esteemed, especially because you were a touring comic long before you moved into Five Oceans Capital. But if you wouldn't mind, we usually give a little background on what you're up to now and your career today.

Ty Webb (01:06)

Yeah, we can briefly touch on that. I would say Jack of a lot of trades and truly master of none. If there's any claim to fame for me, it's that along with my partners, we created the very first online business loan. And that was a company called Forward Line Financial. Literally, we watched it happen. 2003, we were in an office building.

We came up this creative idea to lend money to small business online. There were nefarious companies out there doing cash advances, so there were digital ways to lend a business. Then they skirted a lot of laws. We decided we want to do the first legitimate online legal loan to small businesses. And we went downstairs to the retail portion of our office building, grabbed a guy who owned a hair salon and said, do you need a business loan? He said, well, not really, but I could.

you know, use $2,500. And so we said, great. And we literally opened the laptop in front of them and had him apply online. And that was our very first online business loan since then. I think we loaned somewhere before we sold the company over two and a half billion dollars worth of originations and bringing relatively inexpensive, fast,

Kai Sato (02:21)

Okay.

Ty Webb (02:27)

efficient, and small online loans to

Kai Sato (02:27)

Incredible.

Ty Webb (02:30)

Anything you can imagine on Main Street USA. So along with hair salons, was dry cleaners and restaurants. Restaurants were about 25 % of our business. And anything when you drive down Main Street USA, that's who we lent to and we sold in 2015.

By the way, to a private equity fund headed by two very accomplished amateur golfers at a private equity fund called Vistria Partners.

Kai Sato (03:00)

I've known you for quite some time, going on two decades even, and I didn't know the origin story. So shame on me. It's actually very Groupon-esque, right? They were running out of money and they went downstairs and they sold pizzas and kind of proved out their model. It sounds very similar for what you guys are doing. And I know you knew you much later when it had scaled.

Ty Webb (03:15)

Yeah.

I was head of business development for the firm and we, I forged that partnership with Groupon. We were doing a lot of business back and forth with Groupon at a certain time. Yes.

Kai Sato (03:29)

No way.

see Sully I always learn something so thank you for taking the time.

Ty Webb (03:34)

I know there's more

there's more than just a stand-up comedy career which was sort of left.

Kai Sato (03:40)

We'll tell people a little bit about that before we dive in on some of the caddying because quite similarly, I didn't know that you had looped until we were hanging on the Bell Airports one day. And that's why I love hearing some of these stories and try to share them with people.

Ty Webb (03:55)

Yeah, this will probably get cut in post, but I was, I was, I was my first real job graduated out of college. was working in Washington, DC for a political and social policy think tank. And the spin doctoring department was one guy and me. I was the intern. think I started unpaid there and we would basically take distill all of this incredibly heady research and information developed.

by the think tank and distill it down to a few paragraphs and spin it to news outlets like the Washington Post and Newsweek and Nightline and all that fun stuff. And it paid absolutely zero dollars in the first three months. So in a way to kind of get a side hustle, and I always had a curiosity about stand-up comedy, I basically walked into an open mic night at the Improv in Washington, D.C. on Connecticut Avenue. I think it's still there.

Kai Sato (04:45)

you

Ty Webb (04:54)

And did a five minute set. They told us that they would buzz us with the, you know, the, very prominent red light

at five minutes. I only had five minutes worth of material. I went through it. The red light didn't go on. Kept ad-libbing. I guess they were trying to see how well I would do and did the, Hey, where are you from, sir? and got hired right from there. So I was one of the MCs of evenings there. got hired by, Gilbert Gottfried to go on the road with him.

And I had about a one year, one and a half year standup comedy career until I went to business school. I literally went to business school because I made more money in that five months of touring with Gilbert than all of my friends, maybe even combined, who had first year jobs. think first year jobs are paying somewhere in the realm of like 22 to $25,000. And in...

Kai Sato (05:31)

It's awesome.

Ty Webb (05:51)

a three month tour, I think I made 45 grand. were doing two shows a day. I think we did nine colleges. I made 45 grand. And I was like, holy shit, need to, I don't know anything about money. And applied to business school at the time. was, you know, communications major at Northwestern. So I needed to round that out with a little, little financial background and a complete math dyslexic, total math dyslexic, which is ridiculous that I have a career in finance. So.

Kai Sato (06:04)

No.

Ha ha ha ha ha.

and ended up loaning out two and a half billion dollars.

Ty Webb (06:23)

Yes, yes, responsibly.

Kai Sato (06:26)

Well,

let's dive in on some of the caddying stuff. Where did you first caddy and how old were you when you got going?

Ty Webb (06:33)

Yeah, this is a classic story. I had been hired. was 17, not much of a golfer. had, my dad was a huge golfer. I would screw around with him on the driving range and maybe play a couple holes at a time. But I don't think before I cat it, I even played a full 18 holes. the tennis player, was very distracted. I should say focused on tennis at the time.

And so really didn't get into golf golf was always in the back of my mind, but never really, came to fruition. And the summer before I went to college, I got myself a job. I was a counselor at a tennis camp and a pro there. And he says, and the job paid $5,000 for the summer, which was a King's ransom in, I'm embarrassed to say 1989.

And so I thought this is gonna be great. I mean, I could make five grand last like two years and from 1989, 1991, right? So I was very excited about that work the whole summer. And at the end of the summer, I got a check for, I think like $550. So like a 90 % haircut, I'm going what the hell is going on? So I didn't realize that I was really working for a sweatshop because first they offer you the five grand.

Kai Sato (07:47)

You

Ty Webb (07:49)

And then the camp charges you for room and board. Okay. We were sleeping in dorms with, you know, 35 campers. Uh, but they were feeding us three, three, you three squares a day. And then that, and then, and obviously payroll taxes and all that stuff. I got a check at the end of the summer for 550 bucks. So I was like, Oh my God, I had three weeks before school started. Um, a lot of folks had already gone back to school.

Kai Sato (08:08)

you

Ty Webb (08:18)

And I had three weeks to make money because my parents basically told me they were not going to me any money for expense. They give me money for textbooks and that kind of stuff, but not for the kind of fun that I like to have at the time. So I really got into caddying because of the women. And in order to basically be able to spend some money going out and probably paying for a fake ID at the time. So I needed quick cash. We lived in Pasadena. I had three weeks before school started.

Kai Sato (08:32)

Yeah.

Ty Webb (08:47)

And the only thing I could think of was caddys. I've I been to my dad's club before I've seen the fact that they got paid in cash, which was very appealing to me. So I called the club and I said, are you guys hiring any caddies? They said, we're always hiring caddies. We're always looking for people. So when can I start? I think I called on a Friday. They said, be here at 7 a.m. on Saturday. So I mean, meaning tomorrow.

great, this is unbelievable, I'm gonna get my first loop, this is like the easiest thing. There were no other questions by the way, other than my name, that was it. And a critical piece of information is that my name is Brian Sullivan, my stepdad who I consider my dad has a different last name, this is germane to the story. So I go Saturday morning, I show up at seven, I know nothing about caddying, I've never played full 18 holes in my life.

Kai Sato (09:19)

Have you ever done this before? None of that.

Ty Webb (09:42)

My literal only reference of caddying is Caddyshack, the movie. So what do I wear to be a caddy at Annandale Golf Club? I show up full Danny Noonan, jeans and literally a gray t-shirt. Exactly what Danny Noonan is wearing and a ball cap, right? I have no idea that a caddy is actually supposed to dress like a golfer.

I show up there, uh, and I think because I was probably the only white caddy, uh, most of, most of the caddies are Mexican and or of Latin descent. So the guy, the caddy master looks at me and he's like, what are you doing? He's like, you got to wear a college shirt. He's like the jeans and maybe you can get away with that today. He's like, but you change those things immediately. So, uh, I ran into, I'm like, where the fuck am I going get a college shirt? I run, I run back into the locker room. I am at.

Kai Sato (10:36)

Yeah

Ty Webb (10:40)

best on my biggest day, a medium. My dad is an XL. He has a golf shirt in his locker. I put this thing on, I must have looked 10 years old in this thing. I tuck it down practically to my knees in these jeans that I'm wearing. And it's about 75, 80 degrees already at eight o'clock in the morning in Pasadena. So, okay, this is gonna be an interesting day.

I learned a lot about golf bags that day. So I show up, I get the eight o'clock tea time, bunch of guys rattling off the bets. And they give me this nice Southern gentleman who was a brand new member of the club, very low handicap. And says, you know, here's your bag today. And actually I carry two bags. His, I'll never forget, it was a Pinghofer. They had just come out. That was the lightest bag at the time. And my other bag was a Jones.

Kai Sato (11:34)

Those were good, yeah.

Ty Webb (11:38)

leather bag. Now, mind you, none of them had the leg stands at the time. And a leather bag adds about 15 pounds to the bag. So I'm double looping. By the way, I have no idea how to do this. The best part about my catting that day is that I was at least in great shape. So I was hustling back and forth, quite literally sweating my ass off. what was interesting about that round, and I had no idea where to stand,

And I confided this in the new member who was too handicapped. He was from Atlanta, Georgia, had recently moved to California and just happened to work up the nerve walking down the first hole to say, what brought you to California from Georgia? His accent was pretty thick. And he said, well, I own FBOs. I didn't know what the fuck an FBO was at the time.

And so, and he said, we just acquired a bunch of FBOs at Valais airport and I'm here to see that investment through. And just kind of coily I said, you know, there was no way look on you. There were no cell phones. There was no PD. There's no way to look up what it is. So I asked him what FBO is and he said, those are private airports. And the reason that that was interesting to me is I grew up.

in the outskirts of Chicago. And anyone who I knew that was successful at the time was in the service business. So they were lawyers, they were accountants, or they were rank and file executives at all of the, you know, the fortune 500 companies that were in Chicago. So a lot of worker bees in Chicago that I was exposed to, I was not exposed to a lot of CEOs and or creative types. And I didn't know there was such thing as owning private

airports. And so not only did I get less than catting that day, and I stood everywhere in the wrong place. I'm wearing jeans. It's now it gets to like 8590 degrees by 11am. All the dew is now evaporating off the grass. I'm wearing Levi 501s, which are not wicking. I'm carrying a Jones bag that's probably about 60 pounds. The Hofer bag is probably about 25.

I kept having to switch shoulders. I'm giving guys the wrong clubs. I'm putting clubs in the wrong bags. They've got about 60 different bets going. And thankfully, I didn't have to keep, they didn't entrust me with the card because that would have been an absolute disaster being the numbers dyslexic that I am. And so the biggest part of that, other than losing about 15 pounds in sweat, was that it kind of opened my eyes to the fact that, wow, there's a lot of different businesses out there other than

being in a service industry and or being an account executive and kind of middle to high level management, which is kind of all I was really exposed to in suburban Illinois. I we had companies like Kraft and Boeing and Procter and Gamble and Motorola. That's where the only people that I knew. And that had very little appeal to me. We had just moved to California. California was the land of opportunity and

beautiful women and a lot of fun stuff that we did not necessarily have great unbelievable weather stuff that you just didn't have 45 miles outside of Chicago. And so that really opened up my eyes to like, okay, there's something out there other than but I guess the term is now entrepreneurship that you can do. And so that was my first day I got paid.

Kai Sato (14:57)

Good weather. Yeah.

Ty Webb (15:22)

I think it was the minimum was 50 bucks per bag at the time. And on top of that, I got a $25 tip. So I got 125 in cash and I was done by 1130 AM. And that day I went and then I rehydrated and then went and hit and worked out for tennis. But then I kind of did the math and realized that if I could do this twice a day, I could make anywhere from, you know, a couple hundred bucks. Uh,

and all cash. And so I did that basically for the three weeks. more I went on the morning games, the more gambling I learned, the more I saw that it was okay to have a cocktail at eight o'clock in the morning. Some of these guys, which I was like, my God, this is just incredible. I was used to shotgunning a beer at 9 p.m., but certainly shotgunning a beer at 9 a.m. seemed like, my God, this just isn't done.

and here are guys, you know, trading cash and, and I was, I think I was the only white caddy that I saw for three weeks there. And there's a reason for that. So I did that for the three weeks, had an unbelievable time. Caddy master was great. He did not skim for me. He did skim from the other caddies. And so, I came back for Christmas break after that, and I called to get a loop.

And he said, Mr. Sullivan, you cannot caddy here anymore. I'm going, my God, what did I do? And they realized that I was the son of a member and children members are not allowed to caddy and or work at the club, which is really unfortunate. So I had to drive further to other clubs that were in the area that were a little rougher around the edges and the

The minimum per bag was very much lower and the tips were a lot lower. I won't say the clubs, you can, if you just drew a line around, around Annandale and the clubs that were around there that I got to caddy for, was a little rougher around the edges.

Kai Sato (17:24)

Before we...

I want to hear a little bit more about that, but can you elaborate on the dynamic with the other caddies? You show up only white guy in the yard. They don't know that you're a member's kid, but clearly you're going to stick out and you don't know what you're doing theoretically. And so what was that experience like? Were guys good to you? Did you kind of have to earn your dues?

Ty Webb (17:45)

Yeah, still

Yeah.

It was, it was not

great in the first week because it like, was clear that I was getting bags immediately because I was white. Like that was, that was clear. So there was, and I definitely got tipped more and I was terrible. I mean, I'm a D I became a decent reader of greens, but that first, those first four days when I got a solid probably.

forceful for a day seven eight loops in me I learned the greens a lot better and other caddies that I was with helped me but they didn't talk to me after I did end up having a few beers afterwards in the caddy shack with them I did learn my first real gambling game that I learned other than you know playing like war or blackjack was I learned to roll dice

with the caddies there. And I would love to tell you that I was a good dice player, but I started losing money real quick. Those guys play fast and furious. And so I learned real quick to get in and get out of those games. So but it was it was. I learned a lot more about how racism is the word, but certainly some prejudice that I mean, I was if I showed up at 730 hours in a bag at 745. And.

Kai Sato (19:11)

Wow.

Ty Webb (19:14)

you know, this is 1989, right? So, you know, I think that the prejudice and racism is probably pretty alive and well, I have no idea why. Now, there were certainly, there were senior caddies who were incredible readers of The Greens, and they would be paired with me. And so we together, we can kind of piece it together. And so once they learned that I was doing two bags a day, four days a week, and I was basically doing it so that I could go out and drink beer with my friends.

They were like, okay, all right, know, skin, skin tone doesn't really matter. We're all kind of doing the same thing. So it, you know, there was definitely some, uh, some relationships to build there and it was not, it was not the IC. It was not the warmest of receptions to begin with. Um, but, uh, I mean, there's two caddies that are still there. just played in and dealt for the first time a couple of years, two weeks ago in a little member guest situation. And two of the caddies that I had caddy with there are still there.

30 plus years later, almost four years later. Yeah.

Kai Sato (20:16)

It's incredible. It's incredible.

mean, you know this, but I learned more from New York Mike at Bel Air Country Club than as much from him as anybody that I've ever known about.

Working hard, doing things the right way, integrity, and you get some of these guys that have been there for four or five decades. I always, mean, Mike's got more pull at Bel Air than a lot of the members, but these guys are truly iconic. They're such big parts of these clubs and their cultures.

Ty Webb (20:33)

Yeah.

And so, and they knew, obviously they knew who the big gamblers were and they knew who the big tippers were. And so that's where things started to warm up a little bit is because I would split my tip with whoever I was with, even though the guy was a much better cat, like a far better catty than I would. And he would always kind of give like a little, no matter who it was, would give a little hint, like, you know, like meeting stand over here on this side of the green instead of standing directly in the guy's line.

which I did a hundred times probably, and where to carry the bags and where to drop them. Again, those bags had no legs. So we were huffing those things everywhere. A lot of members didn't want their bags laying in the grass. So you had to keep them on your shoulder the entire time. You can imagine Pasadena in August, not the most forgiving of climates. So we were out there in a hundred degree days.

I think a lot of times, members would want to see how tough we were. But that was, that was the hard part is that the, was at that time, maybe eight to 10 big tipping, high rolling gamblers at the time. And I always got on those bags. Not because I volunteered. It was just, they just said, Hey, we're going to take Sully and by the way, I also went by Sully then. So no one knew, no one knew my first name for sure. They probably guessed my last name was Sullivan.

but they didn't know my first name. So there was a great deal of anonymity that worked there too.

Kai Sato (22:14)

You were playing, you're working in some big cash games. I think we all know what that's like. It's a fun part of golf, but you're learning the ropes and making some mistakes. Was there anything that stood out to you? Did you ever have a blunder that actually impacted play or a bet? Because you can, you can certainly screw up and lose a guy, a hole, maybe even a match in a fair amount of cash.

Ty Webb (22:35)

The worst problem that I saw this, I saw this in the kind of prep questions and it's really embarrassing. So as a kid, I had terrible hay fever, terrible. And so if you can imagine the grass in California, especially in August, they water it all morning long before the sun comes up. So everything's incredibly wet because they know it's going to evaporate all day. What also happens is that everything spores.

at the same time and including the trees and everything. like it's a hay fever nightmare on a golf course between eight and 12 in the morning. And so I was constantly sneezing until finally, and I would hold it as best I could. I I almost blew my sinuses out a thousand times trying not to sneeze while someone's hitting or someone's putting. A guy.

A golfer, Pat, and I can't remember his last name, literally reaches into his golf bag and he pulls out a handkerchief. He goes, this is a handkerchief. Use it. Is what he says to me. And so I kept the damn thing. I kept it in my pocket. I probably looked like Bruce Springsteen with it dangling out of the back of my, of my pants all the way through it. And maybe they thought it was like an affected look.

But I ended up using it because I was literally blowing my sinuses out trying not to sneeze while gals were putting. And I definitely got some glares, especially if I was on a bag and sneezed or coughed while our opponents were putting. And that probably happened more often than not. Maybe that was subliminal or not, but it happened. And it was brutal. It was so brutal.

My sport was tennis. There's no grass around a tennis court unless you're at Wimbledon. And so I had no issues around a tennis court. But I mean, on a golf course, especially when everything is budding after that morning, watering is just brutal for anyone that has allergies. And so that was a constant battle until I got the handkerchief, which was just disgusting. And I don't think at 17 I learned

any kind of hygiene that you had to wash it or that they saw that handkerchief has probably survived a nuclear winter.

Kai Sato (25:00)

It stands up right at this point in time.

Ty Webb (25:01)

So gross.

It's so gross.

Kai Sato (25:04)

Can you elaborate a little bit on some of the people who are at Annandale? Who are these guys playing in these cash games? The guy who owned FBOs and what was the culture like? What was the camaraderie like? I'm happy to hear guys were cocktailing at 8 a.m. which you and I both appreciate. But what was the vibe?

Ty Webb (25:22)

Yeah.

So I would, well, was, there were two different vibes. So there was the, there were the 8 a.m. gambling games. And then if I did a second loop, it was typically like more of a family thing, like a lot of father, son stuff. So I saw a lot of father, son golf, which I probably, that's probably what spurred me to actually get more into the game is in the afternoons, I would take a father and son loop out there, which was the gambling game aside. So that was, mean, there were only.

Like I said, maybe eight to 10 of these guys at Andale. So it was two groups. That's it. So it wasn't a huge selection of guys that were playing for the big money back then. mean, it was the first time I, outside of the movies, ever saw a WAD 100s that big in 1989. I I saw those in Goodfellas or De Niro movies, right? You never saw those in real life. And guys reeling those off. That was incredible to me.

to see that I never, I I grew up obviously in very kind of repressed demure area of rural Illinois. And that just didn't happen. You know, that was for mobsters and pinky ring guys. playing with those guys and seeing that like that, I saw the fun side of golf. And then I saw the paternal side of golf in the afternoon games, especially on the weekends, where it father sons or father daughters or mother sons every once in a while.

And that was really cool. And that was obviously a lot more conversational and still and learn a lot more about business. there were Nestle was based in Glendale. So there were Nestle executives at Andale. And so I got to learn about the food and confections business from some guys there who was really cool. Joe Weller was the CEO of Nestle at the time and it was for him.

probably once a week for the, at least once a week for those three to four weeks that I was at Andale. And he saw me playing and he's like, is it caddy day? I had to explain that Fabio remembers. There was a lot of sheepishness after that. Cause the guys that I caddy for, you know, see me out there playing as I started getting into it. But that's what really got me into it. So I started playing once I quit tennis, my, after my sophomore year in college, I turned right around and started playing golf.

and I knew so many different wagering games that, you my two buddies that I got into it, you know, we're playing maybe 1 % of the denominations that the guys I learned from were playing, but we played everything from, Las Vegas to pound to, I mean, sorry, hammer. We pay obviously massas, polis, Sandys, Rommel's. mean, I had all the terminology.

I would explain to them what a Rommel was. If your ball went through the trap and then you could still make par, you could get a Rommel. Because Rommel was the desert fox. He was the battalion chief for the Scotsies, which I don't think anyone would play Rommel these days. But that was politically acceptable at the time. And so my friends finally caught on and figured out that I was choosing gambling games that would suit my game because I was hitting a lot of worm burners that went through traps.

We had polis, we had all kinds of So, you know, we learned the art of gambling very early on, even it was 50 cents or a dollar. But we started playing all the time. I went to Northwestern for undergrad and we had, there's, does a few things well. They do sports well. They do sports, fans well. I don't know if we do sports winning well, but they do municipal golf courses. They do an unbelievable job for it.

for a state that has maybe a three or four month season, unbelievably access to golf and why the Evans Scholars are probably based there in Chicago. and with a student ID, you could play any of these courses, 18 holes for like 15 bucks. And so we would just, and they were close by, so we would go and play two and three times a week and that's how we got good. That's how we learned gambling and became degenerates.

Kai Sato (29:24)

The Mecca of Caddying, yeah, no question.

Ty Webb (29:42)

The most expensive thing were the beers.

Kai Sato (29:45)

What was that learning curve like for you? Because you were playing collegiate tennis at a high level and was it just applying a forehand or a backhand for you? Or what was that that curve?

Ty Webb (29:55)

There was a lot of forehand in my game. could not hit a fade. Fade would be a lucky thing to say. I could not hit any kind of slice at all. I was a strictly right to left player because it was like a, it was like, it literally was like hitting a forehand, right? So I still to this day, if I have a swing flaw, I'm definitely aiming too far right of my target because I'm afraid that that right hand is going to come through. So that's, and I play a lot of pickleball these days. So that's, that's always a constant.

concern. So, Troy, yeah.

Kai Sato (30:26)

We always find that with tennis players,

they know how to cover the ball. So they'll tend to work it, work a draw. then baseball players tend to be the exact opposite. They almost always slice the ball or cut it because that sequencing their hips and usually there's a little bit of trail there. So it's just interesting how a lot of these things kind of overlap. And I started playing tennis a lot more during COVID and my golf swing helped me a lot because it's just you're applying a forehand, right? Like your golf swing is basically a forehand, depending on how you're going to conceptualize it.

Ty Webb (30:30)

Yes.

Yeah.

That's absolutely right.

Yeah.

Exactly. But if I found myself on the right side of a hole and I had to hit any kind of fade, it was just a disaster. mean, I think I was the epitome of the double cross.

Kai Sato (31:08)

Will you touch on some of these other clubs? Because I think that's a really fascinating caveat. You rush in, need to make some cash, get to go to Annandale. And for a lot of people who will listen to this that know us and at various clubs in Los Angeles, Jim Ellis is your dad. Jim Ellis has been a dear friend and a huge mentor in my life since USC. And he himself was a caddy. So he knew the game and played it at a high level in college as well.

Ty Webb (31:29)

Yeah, I see.

This will probably be the first time he'll learn that I actually kind of skirted the rules and caddied for as long as I did there. Um, but you should definitely have him on the show. Uh, yeah. So I, know, if you, know, if you drew a circumference around, uh, around Andy, I figure out the clothes, but you know, a little grittier, a little lower membership fees. Um, and yeah. And again, I hate to say it, but it was because I was pretty much the only white guy.

Kai Sato (31:40)

Hahaha!

Was it easy to tap in?

Ty Webb (32:05)

there. And, you know, I guess that that was the white privilege of the day before we even had that term. And so, you know, I just show up and especially showing up on Saturdays and Sundays. A lot of the guys who were during the week caddies spent their money drinking and being the caddies did. And so a lot of guys missed those 8 a.m. games. And I love to do the early the early rounds, get there at 738 o'clock, be done by 1130 12.

and then have the rest of the day. you know, at Annandale I'd make a little 125, a really big day would be 150 carrying two bags. At these other clubs, I'd walk away with like 75 bucks. So it was definitely a diminishing return. The quality of the courses were worse, easier to find balls because they didn't have all the features.

Kai Sato (32:36)

you

Ty Webb (33:02)

that a better course would have where you would be more challenging. it was on the caddying side, it was easier to find balls. It was just harder to get money. There weren't a lot of real aspirational characters there who I caddied for that I'd like, oh, I want to be like you. There just wasn't that, right? I was like, OK, this is definitely a transactional relationship, and we're going to move on.

Kai Sato (33:02)

Yeah.

But therein lies,

I think, part of the curve, in learning. I was a beneficiary of the fact that I was a caddy in college. And certain people liked that aspect. I tend to be kind of an intense person. I took it very seriously. I'm competitive. I wanted my guys to win. And so certain guys, they knew that I probably wouldn't be there forever. And so I did it for five years. And I benefited, I would imagine, that people wanted to kind of support a kid who was supporting himself in college. And so you kind of just play the hand that you're dealt.

Ty Webb (33:31)

Yeah.

Yeah.

Kai Sato (33:55)

I think you learn about the disparity in these clubs though and whether or not they can have caddy programs. And I think one thing that's super important, Sully, that you bring up, because kids or parents will write in, and a big part of why we do this at Caddy Check Corner Office is to help raise awareness of what caddying is. I didn't know what a caddy was. I only learned about it because my cousin's caddied. Right, exactly. And also, people realize it's hard. It's hard to break in, even if you have the right introduction.

Ty Webb (33:59)

Totally.

Yeah, I never had a caddy. I never had a caddy. My whole life I've been a caddy.

Kai Sato (34:24)

and these, these are very competitive jobs, especially here in Southern California. These are year round loops. This is a full time job and you've got, you've got to pay your dues and you've got to earn the respect of the people that you work with. And then there, there is this disparity naturally in golf of different clubs and their levels of exclusivity. And I love the symbiosis of being a caddy and getting to offer information and advice. I've Evan scholars, they refer to it as a four hour internship.

Ty Webb (34:31)

Yeah.

Yeah.

Kai Sato (34:52)

And so, you know, whether you're learning about business ownership or what equity is or these different things, it's important to keep in mind that it is work and you are you are even in this day and age, you're you're hustling, you're carrying clubs. Sometimes people are difficult to deal with. And that's a lot of the learning curve to.

Ty Webb (35:01)

Yeah.

Yeah. See you bring up a really good point there. And that is that whenever I would caddy. And I didn't know the numbers, especially at these other clubs. They would, because I was young and I was white, they would ask me what I was doing. Right. And then they see here that I'm in college and I'm a tennis player and I'm just earning a little extra, you know, money for side hustle. That would kind of up my tip. I didn't see anyone ask caddies that were of Latin descent, you know,

Oh, what are you doing? You know, why are you caddy? Are you looking to get up? So that always stuck with me. And so I find that every single time that I'm caddy, that I now have a caddy, I ask them all about that. Right. If they want to be, if they're a professional caddy for life, they're a professional caddy for life. That's great. But if they're, you know, if they're caddying just so they can, well, you were in LA, right? So there are people who are caddying to write a script.

Or they're carrying, go to grad school or something like that's why the Evan scholars is different, right? The Evan scholars, as as you learn, have a caddys and Evan scholar, uh, as a player, you're automatically interested in why they did it. Cause you know, they're going to school, but I didn't see of all those times I caddied, uh, you know, in California, we, know, largely the caddy base, especially Southern California is Latin and predominantly Mexican items in 1989, 1990, 1991, never saw a member ask a caddy.

You know, so what's, what do you do? Like, what do you do outside of golf? And that stuck with me. That really stuck with me and that, and because if nothing else, the best thing about golf, especially when you're playing really terribly is to have a good caddy relationship. Right. So you can laugh, and have a good time while you're in the midst of a bad round. And, it was, it was that, like I said, that just always stuck with me.

to always treat caddies like family and get to know them because everyone's got a story. Everyone's got stories. As you're learning, I'm sure you've learned this podcast.

Kai Sato (37:10)

No question.

No question, and that's why we do it. But also you bring up a crucial point and want to hear more about what it was like for you as you became a member of certain clubs and we're on the other side of the bag. But a guy that you know well, Geraldo at Bel Air is still one of my dear, dear friends. We used to loop together every weekend and he we would trade on and off every other hole. We'd go from English to Spanish so that I could try to learn Spanish and he could try to learn English. I don't think either of us has ever gotten there with either.

but, he's just, you know, one of the great human beings that I know. And he's got this incredible story of growing up in El Salvador and fighting in a civil war and being shot multiple times with an AK and he's, came to the, U S and it was a taxi driver, which is insane to me. Cause I can't imagine this dude behind the wheel. he doesn't even drive anymore and he's, he's just one of my, favorite people. We've now known each other for over two decades.

Ty Webb (37:50)

Yeah. Yeah. Yeah.

Kai Sato (38:11)

But just the opportunity to get to know what's going on with people, that trajectory of wherever they are in life. it is such a crucial role and such an invaluable part of the experience of playing golf, especially at some of the preeminent clubs in the world.

Ty Webb (38:28)

Yeah. So it's really, so it's absolutely you bring this up. I have so many caddy friends because it's a shared experience, right? Like if you've ever waited tables and you meet someone else's waited tables, you have a shared experience or you've bartended before, right? No matter if you're the CEO or, you know, your rank and file executive. Like if you've bartended, if you've had certain jobs, there's a kinship there, right? Because you get, sometimes you get treated great. Sometimes you get treated like shit.

And that's part of the, you know, that's part of the Pledship. I joined the first, I was, I became a member in Annandale first, but then was never realized. never in pasadena. So ultimately, joined Los Angeles country club. And I only bring this up because, at the time we had, the guy that ran the caddy program, name is Eduardo. Fantastic guy. sent it. He started as a caddy at LA became.

caddy master at LA sent his three dot two or three daughters to Harvard Westlake, which is a preeminent high school here in Los Angeles on scholarship through friends at Los Angeles country club. His only vice was that he had a little bit of problem gambling on the ponies. And so every once in a while, so he'd be he would skim from the caddies. He needs, know, if you were going to get a bag that was going to pay more money.

He would take that 10 % big and that would kind of cover his gambling habit at the time. I don't fault the guy for it, but he got caught. Someone in the cottage reported him for doing it and he lost his job. he's, look, everyone has a vice. Everyone deserves a second chance. And he somehow got an interview at Annandale and knew that I was a former member there.

And he reached out and said, there any way that you can vouch for me at Annandale? And as a massive second chance guy, myself, I was like, absolutely. So I was one of, there's a bunch of crossover Pasadena folks at LA country club who all kind of vouch for him and said, look, you know, this guy's a tremendous guy, tremendous family. You know, he should have been reprimanded, but not fired from LA country club. But I guess you have to do what you have to do.

if, you know, if a guy is skimming, so anyways, he went on to be the caddie master at Annandale. I just saw him two weeks ago at Annandale. He's still there. So that's 23 years later. daughters all grown up, all went to college, all doing great. so, you know, you either lean into those relationships or you're obtuse about them. Right. And.

Kai Sato (40:56)

you

Yep.

Ty Webb (41:21)

There are arguments for both. Sometimes you just don't want to be bothered, but I think you're more enriched in life by leaning in, especially in a day if you're playing shitty or whatever. I find that if I learn more about my caddy, it takes less thought off of the ball that I just snap again, you know, into the woods. So I tend to lean into it and find a camaraderie there and an understanding because I've, you know, having done it.

Kai Sato (41:41)

you

Yeah, and I think part of why I was motivated to tell more of these stories, too, is I think golf gets a bad rap. It's certainly elitist and there can be barriers entry and it's expensive, but it's also the most philanthropic sport by a mile. And not just what the tour does, but what a lot of local clubs do. And these great organizations like Evan Scholars or First T or, you know, I'm on the board of Friends of Golf, which is here in Los Angeles. But even just the things that you mentioned there.

Ty Webb (42:01)

Yeah.

Kai Sato (42:17)

helping people find jobs, their kids. I would imagine that some members helped with Harvard Westlake. And we're talking about life-changing events, right? These alter the trajectory of your life. I was fortunate to go to a boarding school on scholarship. It changes your life. And so these communities, I'm sure they have a lot of affluent people, and they are exclusive, but they do take care of their own. And something that we don't even elaborate on, but Bel Air recently

Ty Webb (42:23)

Yeah.

Kai Sato (42:46)

raised a large fund to help with staff's kids. And so that they can further their educations. And I think that a lot of clubs do that. We're probably even behind. But I also know that various members step up. I mean, there's my dear friend Steve Rader. He paid for new teeth for his caddy when he needed it. And so there's just a lot of great things that happen at these clubs.

And sure, you can say, well, these are rich people. They should do that. But at least they are. And and I think people, misunderstand how crucial the caddy is at a lot of these places and just the staffs in general. And you don't have a Bel Air or a Los Angeles Country Club or an Annandale without the great people that work there.

Ty Webb (43:33)

Yeah, I think that, mean, kind of like everything, anything in life, if you show a little bit of grit and a little bit of hustle, people are going to help you. Right. And any, anyone who wants to further their career outside of caddying with something and they show a little bit of application and gumption, I I've never seen a member look at a caddy and just say like, no, I'm not going to help you. Right. That I've never seen. I've seen guys be a little bit, you know, obtuse, but not really dismissive.

If a guy says, you know what, look, I really got to start making money for my family or I just got married. Like it's just, I've never seen anyone get turned down in that realm because at the base of it all, know, everyone appreciates someone who wants to work hard and better themselves or better their situation, right?

Kai Sato (44:24)

Yep. And on the other side of it, I've seen some of my friends who caddy get really jaded and they're, that guy should be paying me 500 bucks a bag or things like that. It's like, well, look, man, not, everyone can do that. Right. And, also you mentioned it cause we are in LA, I was in the business and film program at USC. And so other loopers were bringing me their headshots or their scripts or things like that, trying to see if that I would put it in front of my professors or things like that. And so

It can be abused. It can go too far. And I think like anything, there has to be proper tact and etiquette. in the long run, the right things tend to happen.

Ty Webb (45:00)

Yeah, you know, I don't mind a bit of a squeaky wheel because like it's right. It's like, you know, look, the worst thing someone could say is no. I like so I don't mind a little bit that. And, know, so we've all experienced that one way shape or another. If you're asking for five hundred dollars a bag of caddy, you've had some great fortune in your life. That's great. If that happens, I'm going back to it.

Kai Sato (45:02)

Are there, sorry, go ahead.

And look, there, there are some guys that are amazing.

Are there are there any other really big lessons you've touched on a few of them? But as you have been able to reflect on this and learning about different things, but what jumps out of you? What are some things you're like? Wow, you know what I kind of that germinated when I was caddy. I started to realize that when I was looping.

Ty Webb (45:35)

yeah.

Certainly, I would say, and I'd be shocked if you didn't have other people say this, is I mean, you learn people's character during the game, right? And I had a front row seat without ever playing the game as a caddy. And in some of those money games, I saw cheating. I saw balls being rolled, kicked, dropped, edged so and.

There are a things that happen, right? So you see that character and as caddy, you know as well as I do, you can't say anything, right? You just go, okay, this guy's a dirt bag and here we go and let's get paid and get out of here. And so you see people's character in that way and twice I've witnessed guys get caught cheating and confronted. And when these guys are playing for hundreds of dollars in the late 80s and early 90s, that's...

That's a good stack of change. And I literally saw a guy said, if you're going to cheat your best friends, what the hell else are you going to do in life? And that was almost a direct quote, but directionally correct. And they kicked him out of the game at the 14th hole. So this game is fucking over. You get the fuck out of here. They paid the other caddy. Wasn't my guy. And so that was probably the most important.

thing to me is just learning that and you know, people forget we have a news cycle that's 24 seven these days and people forget tragedies and wrongdoings all the time. You never forget the guy you caught cheating. Never forget. I know guys that I've caught cheating. I've never forgotten those stories. And that's an important thing I think to remember is learning, especially cattings, you learn someone's character and

My sister has a great saying, if someone shows you who they are, believe them. and that's nothing exposes those things like golf. And so, and that was, that was, so having never played the game and seeing that, that was probably now, if I think reflected by it, I had a note here that that was the cheating thing was the most eye opening. I'm going, oh, fuck, like, okay.

Kai Sato (47:48)

100 % right. 100 % right. It's a great one.

Ty Webb (48:05)

Definitely not doing that and that guy never played in the Saturday or Sunday game ever again. He was like completely stunned Yeah, completely ostracized and I'm not sure He ever lived it down

Kai Sato (48:11)

Completely ostracized. Yeah.

Well, probably not just at

the club. Like you said, this this is your reputation is your character and it's on the line every single time. And I would imagine that translates into that business that whatever he does and people know that. And so it has come up and it is so crucial because golf, unlike probably any other sport, mirrors life, right? You have good things happen. You have bad things happen.

And you get rewarded for bad shots sometimes and vice versa. And to your point, you learn so much about people. Where else do you have this four or five hour session where you are competing? There usually are stakes in addition to just bragging rights. There's teamwork involved. And you see whether or not people have grit and their resilience, because things are going to happen out there. And then especially whether or not people have that integrity. And you bring up a really key point. I don't think anyone's ever done it.

Ty Webb (48:48)

Yeah.

Yeah.

Kai Sato (49:10)

that stays with you forever. It's not just that club, it's not just that instance. Maybe you can come back from it, maybe you can mea culpa, but the reality is people know. And I think people also know who the Sandbaggers are.

Ty Webb (49:12)

Yes.

Yeah,

that stays with you. you get a business deal goes bad or, you know, somebody gets divorced. Those things, someone will get forgotten and forgive it. Golf cheating is not. I will also add, we were talking about members taking care of caddies is that at Andale, there was an abundance of both attorneys and judges because Pasadena is only 15 minutes from the LA courthouse and great.

caddies and great people got in trouble. They a lot of some DUIs or some domestic disturbances or what have you. They got the best legal care and shepherding through the legal process because they members helped them out. If they were off the street and had the same misdemeanors happened, they would be treated. They would have a much different experience. And that was awesome to see.

Because that DUI became, that was probably the most prevalent thing that happened because these guys are driving, having come up years at Annandale, afterwards playing dice, driving back places that are much further away, some even San Bernardino, which is 40 miles away. So the likelihood of getting a DUI was high and these guys got helped out free of charge from a lot of these attorneys that were there. And so that was cool to see this kind of, you we're to take care of our own and

not let these guys get affected by it, which is cool.

Kai Sato (50:51)

Well, I am a little curious. You did this for three, four weeks, trying to make as much cash as you could. Did you get close to that? Did you get close to that five thousand?

Ty Webb (50:57)

There, then I, oh yeah, oh,

no, I didn't close to 5,000, but I at least made, in like the three weeks, I think I made two grand. And in 1989, that went a long way. That was beer money that lasted pretty much the entire year. And so, but I came back and that's when I candid at other clubs in the area. I made a little bit of money there. Like, even if you're making 50 bucks, you know, with.

The tax structure, still like 85 bucks, almost 100 bucks. So, you know, all over the table, obviously, sorry, IRS. was 18. I was 18, I needed the money. And so I think the statute of limitations has outran my caddying career. But yeah, so like, I would just do that. I even cadded a few times in Chicago at places, because we had Evan scholars at Northwestern. And I would just, hey, you know,

Does anyone need any help? And there'd be a tournament there and whether I can't at Medina for because they've got a big membership there and they had a member guest, which was like it was like 300 people in two courses. So they're taking guys from everywhere and we weren't expected to do anything but carry the backs. We'd have to read greens. We have nothing. That was really easy money. So I do that a couple of times and other clubs in the area that we can do that.

Kai Sato (51:59)

Where'd you go? Where were some of the clubs?

Ty Webb (52:24)

I remember Medina, did.

North Shore Country Club. That was also easy money. Also didn't have to read the green. There's a lot less expectation on performance for some reason in Chicago. Chicago is used to having caddies that are just there to carry the bags and find balls. No reading greens, no giving distances. So that was super easy. And if these places all had tournaments, know, just could, the Evan scholars caddies would just say, hey, we got a tournament. You want to come do this?

Kai Sato (52:55)

Well,

it's pretty unique actually that you caddied in Southern California, which is a pro jock yard year round loopers. It's how people feed their families. And then you were also looping in Chicago, which is Mecca for the Evans Scholars, which is a short season, young kids. What was that disparity and kind of juxtaposition of those two worlds?

Ty Webb (53:08)

Yeah.

It was so chaos because like we were all, was, would only do tournaments. And so, you know, you've got, you know, it it was a caddy crew of 30 caddies. Now you've got 60 to 90 caddies all going into different, different directions. So I, other than my Northwestern guys that I knew, I didn't know anyone. And like, we were there to get in and get out. And like, if I met guys, was because we got, you know, we didn't get to park on the grounds. We'd have to go somewhere and park and then be shuttled in.

You were shuttled in, did your job, got your money and got out. So there wasn't a whole lot of, no, there was no shooting dice. was, I mean, there were a lot of really smart kids on not just Evan Scholars scholarships. They had scholarship money and grant money from whatever their academic pursuits were. I just remember them being, especially even the Northwestern guys, like very driven. I don't know if we had female Evan Scholars then.

Kai Sato (53:48)

No, no, no shooting days.

Ty Webb (54:13)

I think they had just started, but none that I knew, but they had just started right there kind of late eighties, early nineties, some female Evans Scholars.

Kai Sato (54:20)

We've had some people

who did not win the Evans Scholarship and it really lit a fire. And so some of those people get hyper motivated because they missed out on that opportunity and they've doubled down and went even harder. that's, I mean, guess it's in some way, Spielberg didn't get into USC, right? And so he stayed even more focused and ultimately is a big benefactor, a big part of the film school.

Ty Webb (54:26)

I could see that.

I could see that. I could see that.

Yeah. But like,

like, also those guys, the other guys were they had they had a golf IQ. I had almost no golf IQ. hadn't really started playing yet. So I was very much behind the eight ball like

Kai Sato (54:59)

Well,

the other thing too is there's no perfect way to do it. There are a lot of opinions as to where you should stand, right? Some people don't want you behind them. Some people don't want you in front of them. Where is a good spot where you're not in harm's way or in line of sight for forecating? A lot of opinions on that stuff, right?

We know more than a few people have never missed a read in their life. So that's a whole nother bag of tricks. So there's stuff like that that it's so subjective. And I think that's part of the service business is figuring out who you've got that day, what the dynamics are. And you are there to kind of be this Sherpa and this guide and hopefully making sure that sure they win. But most importantly, they have a great day.

Ty Webb (55:20)

Right.

Yeah, I mean, the hardest thing for me and caddying was disguising the fact that we had a caddy bet, right, on our guys. And because like, you don't want to like hang your head in sorrow when your guy pumps one out of bounds on 17 or 18. And you don't want to like give a little fist pump or fist pump, you know, when your guy makes a putt or the other team misses one. that was, you know, keeping your cool in that, you know, those were $5 bets, $10 bets. But still they meant something.

to the caddies and to me and the competitive spirit to keep ourselves interested in the game. And so we would get unfocused sometimes and be chatting about the game. can't believe you missed the button. Guys waving to us with a T like, hey, where's my fucking ball? So there was definitely a little of that. It was easy to get distracted out there for sure.

Kai Sato (56:20)

Ha ha ha ha ha ha.

Well,

you bring up how critical that is. And before I let you run to it like Steve Malbon, when he was he was one of our earliest guests and before it was a podcast. But he is the only guy who openly admitted to cheating as a caddy because he's like, look, I was playing in the biggest cash games in Atlanta. And if I didn't cheat, I didn't win. And if I didn't win, we didn't get paid. And so all the caddies, was an it was an interesting it wasn't just him. They all did. Right. So, hey, like, I'm going to I'll give you you get to kick that ball from behind a tree because no one can see.

And then up there, you you need to kind of move it out of a spot or things like that. He's like, he said overall it evened out, but that was just their culture, which I'd never heard of.

Ty Webb (57:03)

Yeah, I've definitely in some of those games, you know, identified a ball a few times for sure. that may have been a little thick rough. I'm definitely, I definitely go to that. Yeah.

Kai Sato (57:12)

Are you kidding? We have a legendary

story about our dear friend K wash who you know of he goes in and somehow comes out with like a 20 year old Callaway warbird and was claiming that it was his ball the entire time. So love you K wash. That's why we call him warbird and it's before I let you hot. Is there is there anybody who you've come across that

Ty Webb (57:25)

Yeah.

Yeah, that's Lassenger.

Kai Sato (57:39)

You know, you think they might have a good story to share with us, similar to yours of kind of what this journey, what this arc, what this learning experience is like.

Ty Webb (57:48)

Well, certainly my dad, who's a great one. Let me think about that. I'm sure that there are. I'm sure there are.

Kai Sato (57:55)

Yeah, it's

it's why that's why I was so happy to get yours down just because people always come out of the woodwork and I like I didn't know this about you and I don't think a lot of our buddies even know this about you and it I think it also makes sense. Jimmy Dunn has this thing right he grew up looping and has gone on to have this huge illustrious career but he feels that he can identify people who caddied.

just as soon as you get out there with them on the golf course, right? Just how attentive they are, do they go introduce themselves, are they asking the question what's going on with people, or are they treating a caddy like, you know, a servant?

Ty Webb (58:28)

That's interesting. I probably subconsciously always have been able to do that too, but now it's going to be in the forefront of my consciousness now. Because it's, it is true. is. It's just like, it's just the same thing. Like, you know, it's people who waited tables, which I also did in college. Like I definitely tip 20 % or more every single time, whether the service is bad or good, because it's like, holy shit, I remember doing that. And it's gross. Yeah. I definitely put my stuff. I definitely put my thumb in a few people's mashed potatoes before.

Kai Sato (58:58)

dear. Thank God. is not a podcast talking about what waiters have done to our food because I don't I don't I mean they made an entire movie about that.

Ty Webb (59:04)

This is your

spinoff. Your spinoff is now from the kitchen to the corner office for anyone who's waited tables.

Kai Sato (59:13)

I'll never eat out again.

Sully, thank you so much for your time. I enjoy hearing you tell stories, tell jokes, for people who don't get to receive text messages from Sully. He's very witty on text as well. But thank you, enjoy Master's Week, and this has just been a real treat.

Ty Webb (59:34)

God, this is awesome. Thanks for having me. Thanks for having me during Master's week.

Kai Sato (59:36)

All right, buddy. Have have a great day.

*This interview has been edited and condensed

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