Think Like a Caddie Play Like a Pro
Book 14 of 52 in the Mitch’s Notes Project
Why This Book?
Because I was totally inspired by the Masters. I’m still in awe of Tiger slipping on another green jacket. I got into golf when he won the ’97 Masters and have loved the game since. This book was inspired by one moment in particular this past weekend. When Tiger won, he embraced his caddie Joe LaCava and shouted “WE DID IT! WE DID IT!” See the video below.
I have never played golf at a level that warranted a caddie. The team aspect of the game stood out in my mind. I realized that as an investor, my role is that of a caddie. I read this book to develop that heuristic.
What is in it for you?
Whether you are a CEO, or an investor, this book teaches you how to think like a caddie and improve your performance. If you are considering taking on an investor, have an investor, or would like to learn how an investor thinks, there is something here for you.
Where Should You Start?
Start with a love for golf. Without it, this sports simile will get a bit tedious. I started by talking to someone that really knows what a caddie relationship is like. So, I got an expert’s opinion.
Former PGA Champion and World Golf Hall of Fame Inductee, Lanny Wadkins was kind enough to grant me an interview. Lanny won 21 times on the PGA Tour and was the Rookie and Player of the year in ’72 and ’85, respectively. He won the 1977 PGA Championship at Pebble Beach and finished 3rd at the Masters on three separate occasions in the early 90’s. He knows a thing or two about the player caddie relationship. His insights informed my thoughts throughout.
I boiled the book, the articles, and the interview down into four distinct parts.
- Should you hire a caddie?
- What kind of caddie do you want?
- What makes a great caddie?
- How can a caddie help you win?
Should you hire a caddie?
In order to make that decision you should know the implications of hiring one.
First, at their most basic level, investors give you money. And at their most basic level, caddies carry your bag. Hiring an investor caddie means you don’t have to carry your own bag. In theory, it is easier to play golf faster and at a higher level if you shoulder less of that financial burden. So, the money, bag carrying duties, are table stakes.
Second, caddies are mandatory to play professionally. You don’t need a caddie to play the game well, but you need them if you are going to play a certain way. You may just enjoy playing the game with a cart you can control, buddies, beers, and a no expectations. If you take capital, you are signaling to the world that you are willing to play a different way. As Lanny explained to me, “when you hire a caddie, that caddie and his people expect your best. They trust you.” Hiring a caddie means you are able to play professionally, but it also means you are agreeing to play the game at a professional level.
Third, the player / caddie relationship is economically similar to the CEO / investor relationship. Like golf, you only know the caddie investor if the player CEO is a winner (or an epic loser). The economics are aligned the same way as well. Typically a caddie earns a percentage of the players winnings for that week. So, the more the CEO player wins the more the caddie investor wins. Hiring a caddie means that you should be economically aligned — if you choose one that fits your game.
What kind of caddie do you want?
There are four types of caddies and caddie investors. There is no wrong choice, but like any good player, you should know your game well enough to choose the type(s) that suit you.
- Buddies — Friends and Family
- Bag carriers — Passive Investors
- Googlers — Engaged Investors
- Partners —Lead Investor Board Members
Buddies — Friends and Family
Buddies are there for you. They are there for you and not the tournament or the competition. In fact, if this wasn’t the Masters and you needed someone to show up and caddie at your local putt-putt, they would be willing to do that too.
Bag Carriers — Passive Investors
You need someone to carry the bag. That’s it. You can’t play in the Masters without a caddie, so you tell them to carry the bag and otherwise be invisible. They are willing to do it because you, a real player, can make it worth their while.
Googlers —Engaged Investors
You need someone to carry the bag and let you do your thing. But every once in a while the wind changes, you need a new yardage, or a read of the green. You google your caddie to provide that one thing and let you get back to winning the tournament.
Partners —Lead Investor Board Members
You need a partner to carry the bag, double-check strategy, and everything you ask for in between. There is a relationship of trust and understanding. They know you got this and you know when to ask for help. This is a video that highlights one of the best partnerships in the game today: Jordan Spieth and Michael Greller.
We highlighted Tiger’s relationship with his caddie earlier, but he was asked specifically about it after he won while sitting in the Butler Cabin.
Jim Nance: Joe LaCava…what a great teammate he’s been for you as you have risen back to the top of the game.
Tiger Woods: one of the most loyal human beings you will ever meet and if anyone deserves a major championship its Joey. We’ve been through the fires together. Unfortunately, we just haven’t got one as a team but now he’s been a part of two coats around here 92 and today. It’s pretty special, you know, for the two of us to go out there and be lockstep all week. He had a wonderful feel for club club selection out there and you know people don’t know how much the wind swirls around this place but a lot of that is we have to be in sink on what what club to hit and obviously the trajectory so our communication was really solid this week.
On the 16th hole in the final round Tiger sealed the win with a beautiful 8-iron to a few feet.
Per Ian O’Connor at ESPN, the conversation before that shot went like this:
“Do you like a cut 7-[iron] or a good 8?” he asked.
“It’s nothing but a good 8,” LaCava shot back. “You know that. What, are you trying to be nice to me?”
Tiger and Joe LaCava are partners. They have lost together. And they have won together. Spieth and Michael Greller are partners. If you are going to win at the highest levels, a true partnership with your caddie can be a game changer.
What makes a great caddie?
When I asked Lanny that question, he answered, “partner with a top player.” It doesn’t matter if the caddie investor know the course better than anyone else. It doesn’t matter if the investor can perfectly describe the pitch shot yardage, the false front, the severe up-slope, and the spinner lie. If the player CEO lacks the skill to execute the shot, or worse, doesn’t listen to the advice, their shot will roll back to their feet. A great caddie investor must first find a way to stand with a great player CEO on the first tee. It is about relationship development — demeanor, honesty, and trust.
Demeanor — Knowing how someone operates under certain circumstances will help both caddie and player. Entrepreneurship is never linear and the emotional ups and downs will be more extreme if the caddie’s demeanor permits. Lanny shared that one of his caddies “helped calm me down, just by being calm himself.”
Honesty — Player CEO’s are the boss. They are used to people deferring to them. A great caddie, will tell them what they need to hear, not what they want to hear. If the caddie investor has done her job right, the player CEO will understand that the advice comes from a good place.
Trust — The player CEO will only listen if they trust the caddie implicitly. Do they know that the caddie is giving them the best feedback and information possible? Do they know that the caddie is helping give them the best opportunity for greatness? Ultimately, does the player believe the investor has done the work to help them win?
How can a caddie help you win?
Knowing their role — A caddie can’t hit your shots for you and they shouldn’t take credit when you do.
“Caddies don’t make the shots — although a lot of them like to take credit for the good ones.” — Arnold Palmer
The caddies job is to help where they can and avoid unnecessarily changing the shot. Mike Patterson, Karie Webb’s longtime caddie, put it this way, “Even if there’s a little bit of doubt in my mind, I have to make her believe it’s absolutely right. She can’t go into a shot thinking, ‘This maybe isn’t right.’ I’d rather a player put a good swing on it and be slightly wrong than put a bad swing on when it could be right.”
Vision of what’s possible — Sometimes a good caddie can open your eyes to what is possible.
In one event Lanny had to make the cut in order to qualify for playing privileges on tour. He was going to lay up and his caddie chimed in.
“ You’ve got the strength to go for the green, and if you don’t hit the green, and you go over the green you have a much easier chip coming back.” He had confidence in me. He knew me as a person. He changed my mind and I went for it. I knocked it on the green and gave me a chance to succeed.
A good caddie will help the player see an stretch opportunity, approach it with confidence, and provide a better chance to win.
The growth mindset — A good caddie will exude positive confidence in the player’s game, help them stay in the moment, take one shot at a time, and grind out a good score even when they’re not playing their best.
“Like any golfer, I made a few shots and missed a few as well but, having that base of information and the confidence that a good caddie instills, making the good shots was much easier. “ — Arnold Palmer
Professional caddies know that getting their player in the right mindset is the most important thing they do. Golf, like entrepreneurship is about one thing: making the most of the next shot.
Long-term Perspective — Success in golf and entrepreneurship isn’t linear.
“The road to success is always under construction.” — Arnold Palmer
That road to success isn’t without potholes, construction cones, or detours. You will make mistakes. But what you do with those mistakes determines the eventual outcome. On his way to victory at the Masters, Tiger Woods made 9 bogeys and won. Helping the player CEO take a step back and see the world with a long-term lens will help them play with confidence and make the most of their opportunities.
Knowing the Course — A great caddie doesn’t need to be a good player themselves. It helps, but it isn’t a requirement.
What is required is someone that knows the course. Good caddies have done the forethought, the preparation, and the course mapping to help the player CEO establish a strategy. Someone that has mapped the course and knows what is expected. A good caddie will have a custom yardage book suited to the player CEO’s game. In the end, a caddie needs a book of strategy that shows the player CEO the best routes to take on every hole to give them the best chance to win. And then they let them hit the shots.
One of the things I love about the Masters is that it is played on the same golf course every year. There are certain things in entrepreneurship that, like the course, are the same from company to company and year to year. Expanding headcount, setting up sales, building a marketing engine, establishing processes. The themes must be tailored to the company, but the shots are the same. A caddie that knows the course can help you navigate it well.
Equipped to Succeed — Investors give you money and in that sense they carry the bag. What differentiates caddies is their ability to equip that bag for success. If the caddie really knows the course, the player’s game, and the strategy, they will make sure the bag has everything they need. Scorecards, grips, towels, rain suit, extra food and water, and most importantly the right clubs for the course. The best caddie investors make sure that the player CEO has the right clubs for the right shot. Recruiting and making sure those clubs are in the bag is the job for a great caddie.
On Course Help — If you have decided to partner with a type of caddie that offers on course help, that help can take several forms.
Here is a great example from Jordan Spieth and his caddie Michael Greller on hole 13 of the Masters.
A tee shot is used to position the ball in the fairway. A caddie investor can collaborate with you on the correct strategic positioning. An approach shot puts the ball on the green as close to hole as possible with the best possible chance of converting the putt. A caddie investor can help you establish go-to-market strategies that maximize conversion. You “drive for show and putt for dough.” A caddie can help you establish a sales motion to convert more approaches to sales. Because 40% of the golf shots in a round come from around the green, a caddie can help read the greens. A good putter studies the green, observes the putts and makes adjustments. Putting is a constant exercise in observation and adjustment. A good investor caddie can help you understand your customers, make observations, and help you adjust.
Reading the elements — a good caddie reads wind, weather, lie, stance, and circumstances. A good caddie investor can help the player CEO read market trends, address unexpected circumstances, course correct from bad strategy and execution, and understand competitive circumstances that require a change in strategy. Good caddies understand that you should never make a bad situation worse. Getting frustrated with the elements “will not put the ball in the hole in the fewest number of strokes.”
Game Plan — A great caddie investor will make sure she understands the game plan for that round. It can change from round to round, but he knows what it is for that round. In one of his interviews this past week, Joe LaCava described a conversation he had with Tiger on Saturday night when Tiger decided he wouldn’t hit a driver again on number 5 (which he bogeyed the three days prior.) On Sunday, Tiger pulled a driver again and LaCava reminded him of his plan to hit a 3 wood. With his help, Tiger pulled the 3 wood and striped it down the middle. Great caddies know the player’s plan and provides a steady influence to help the player stay the course.
Analyzing Performance — After a round, a good caddie will analyze performance with their player. After each round, a good caddie investor will help the player CEO measure against plan. Good caddies help the players keep stats that are specific to their game, round, and strategy.
Steve Williams, caddie to Tiger, Adam Scott, Greg Norman, and others said this about analyzing performance:
“After a round you should summarize how the day went, where you did particularly well, or where you had trouble with this hole, whether we can work it out on the practice tee afterwards. You might tell the player what you saw earlier that he was doing wrong, how he was swinging it. Or you may just say, ‘we had a bit of trouble on this hole’ or ‘we struggled on this hole, perhaps we should play it this way tomorrow.”
These sessions and KPI’s aren’t a comment on ability, but a tool for improvement. They are about improving the teams chances of improving the next round and ultimately about winning the tournament.
Summary
Partnering with a caddie investor can be a strategic unlock for CEOs looking to play at the highest levels. If you create a partnership with an honest caddie you like and trust your results will be better. Next level caddies know their role, provide a vision for what’s possible, have a long-term perspective, know the course, equip players to succeed, provide on course help, adhere to the game plan, and analyze performance. Partnering with a next level caddie can help you win.
