The CEO’s Caddie

April 25, 2019

“A tradition unlike any other…the Masters.”

If, like me, you are still in awe of Tiger slipping on another green jacket. And if, like me, you are obsessed with growth stage investing. Then this piece was written for you.

When Tiger won the Masters he didn’t scream “I’m back! Baby” a la Shooter McGavin. Instead, he grabbed his caddie, Joe LaCava, and excitedly shouted “WE DID IT! WE DID IT!” Now, I have only played golf at a high enough level to warrant a caddie in my dreams, but that moment stood out to me. It stood out because golf, a notoriously individualistic sport, had team connotations that had never before been that clear. At Mercato, we play the growth game, not as players, but as caddies to our player-CEOs.

1. Should you hire a caddie?

Our first job as caddies is to help the CEO know whether their goals align with that of a caddie partner.

At their most basic level, investors invest money and caddies carry the bag. Hiring an investor caddie means you don’t have to shoulder the financial burden alone. When the player wins so does the caddie. Typically, a caddie earns a percentage of the players winnings for that week. There is economic alignment between the CEO-player and the caddie-investor.

Players and CEOs don’t need a caddie to play the game well, but they are required to play on tour at the highest level. When a player takes on a caddie, she is signaling to the world that they are willing to play a different way. As an ex-PGA professional told me, “when you hire a caddie, that caddie and his people expect your best. They trust you.” And like golf, you only know the caddie-investor if the player-CEO is a winner (or an epic loser).

2. What kind of caddie do you want?

The next step in the process is helping the player-CEO know that there are four broad types of caddies and caddie investors. There are no wrong choices, but like any good player, the CEO should know her game well enough to choose the type(s) that suit her.

  1. Buddies — Friends and Family
  2. Bag carriers — Passive Investors
  3. Phone-a-friend— Engaged Investors
  4. Partners —Lead Investor Board Members

Buddies — Friends and Family
Buddies are there for the player. They are there for the player and not the tournament or the competition. In fact, if the player-CEO needed someone to show up and caddie at the local putt-putt, this caddie would be willing to do that too.

Bag Carriers — Passive Investors
The player-CEO here needs someone to carry the bag. That’s it. She can’t play the growth game without a caddie, so she needs the caddie to carry the bag and otherwise be invisible. The caddies are willing to do it because that CEO is a real player and can make it worth his while.

Phone-a-Friend—Engaged Investors
The player needs someone to carry the bag and let her do her thing. Except when she needs help reading the wind, the yardage, or the green. The player needs a bag carrier and a lifeline—a Phone-A-Friend. The player needs the caddie to provide that one thing so she can get back to mastering the game of growth.

Partners—Lead Investor Board Members
The player-CEO needs a partner to carry the bag from the first hole to the last hole and provide advice, support, and collaboration before, during, and after. There is a relationship of trust and understanding. The player knows when she’s got a read and 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.

When Tiger won the Masters he was asked about his caddie after the win. This is a transcript of that conversation.

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 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 sync on 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 an all-time 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. Like golf, a true CEO-investor partnership is a competitive advantage when playing at the highest levels of the growth game.

3. What makes a great caddie?

The third step is being the type of partner the best player-CEOs want on their bags. When I asked former professional golfers what makes a great caddie, they responded with some variation of “partner with a top player.” As growth investors, we don’t hit the shots. Even if we have the perfect strategy for a certain course, it is carried out by our player-CEOs. First and foremost, a great caddie investor must first find a way to stand with a great player-CEO on the first tee. The secret is 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 is reactive. One golfer shared that one of his caddies “helped calm me down, just by being calm himself.”

Honesty — Player-CEOs are the boss. They are used to people deferring to them. Great caddies, will tell them what they need to hear, not what they want to hear. If the caddie investor has done his/her job right, the player-CEO will accept honest feedback.

Trust — The player-CEO will only listen if she trusts the caddie implicitly. Does she know that the caddie is giving her the best feedback and information possible? Does she know that the caddie is helping give her the best opportunity for greatness? Ultimately, does the player believe the investor has done the work to help her win?

4. How can a caddie help you win?

At this point, we hope player-CEOs have decided they want to play differently with caddies, they have decided to form a true partnership with those caddies, and that those caddies possess the attributes necessary to be great. Now, here are 10 ways that a caddie can help a player-CEO win.

  1. Knowing your role — A caddie can’t hit shots for the player and he shouldn’t take credit when the player hits a great one.“Caddies don’t make the shots — although a lot of them like to take credit for the good ones.” — Arnold PalmerThe caddie’s job is to help where he can and avoid unnecessarily changing the shot. A longtime LPGA 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.”
  2. Vision of what’s possible —Sometimes a good caddie can open the player’s eyes to what is possible. A PGA Professional had to make the cut in order to qualify for playing privileges on tour. He needed to make up a few strokes on the back 9. He was on a par 5 and he was going to lay up when 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 he gave me a chance to win.”A good caddie will help the player see what’s possible, approach it with confidence, and provide a better chance to win.
  3. The growth mindset — A good caddie will exude positive confidence in the player’s game, help her stay in the moment, take one shot at a time, and grind out a good score even when she’s not playing her 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 PalmerProfessional caddies know that getting their players 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.
  4. Long-term Perspective — Success in golf and entrepreneurship isn’t linear. “The road to success is always under construction.” — Arnold PalmerThat road to success isn’t without potholes, construction cones, or detours. Players and caddies will make mistakes. But what they do with those mistakes determines the eventual outcome. On his way to victory at the Masters, Tiger Woods made 9 bogeys. Helping the player-CEO take a step back and see the world with a long-term lens will help her play with confidence and make the most of each new opportunity.
  5. Knowing the Course — A great caddie doesn’t need to be a good player himself. 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 who 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 showing the player-CEO the best routes to take on every hole to give her the best chance to win. And then he lets her hit the shots.When it comes to the growth game, few people have seen the course played as successfully as Mercato has. There are certain similarities in entrepreneurship from company to company and year to year: expanding headcount, setting up sales, building a marketing, establishing processes. The themes must be tailored to the company, but the shots are the same. A caddie who knows the course can help you navigate it well.
  6. Equipped to Succeed — Investors 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, he will make sure the bag has everything needed: scorecards, grips, towels, rain suit, extra food and water, and most important, 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.
  7. 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 players 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 players establish go-to-market strategies that maximize conversion. “Drive for show and putt for dough” is common golf adage. A great caddie can help 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 players understand their customers, make observations, and help them adjust.
  8. 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 players 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.”
  9. Game Plan — A great caddie investor will make sure they understand the game plan 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.
  10. Analyzing Performance — After a round, good caddies analyze performance with their players. Together, they will measure against plan. Good caddies help the players keep KPIs 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 next round and ultimately about winning the tournament.


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 1) know their role, 2) provide a vision for what’s possible, 3) establish a growth mindset, 4) have a long-term perspective, 5) know the course, 6) equip players to succeed, 7) provide on course help, 8) read the elements, 9) adhere to the game plan, and 10) analyze performance. Partnering with a next level caddie can help you win in the game of growth.


Mitch Rencher is a Senior Associate Investor at Mercato Partners and not a scratch golfer

You can reach him at

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