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Top 10 - Lessons I Learned From Donald Trump


Love him or hate him, Donald Trump is certainly a very intriguing celebrity. During my final couple years of college, I was blessed with the opportunity to work at one of his facilities - Trump National in Bedminster, New Jersey. While I was a lowly caddie at the course, I have always valued the fact that I had the chance to be a part of such a prestigious facility.

During my time at Trump National Bedminster, I was able to get up close and personal with Mr. Trump himself. Through these experiences I gained some insight into why I believe he has become so successful within the golf industry. Please notice the wording, I believe. I realize that some of the “lessons” I learned may actually not have been ones which he intended for me to learn. It is very possible that some insights I gained are not actually business practices that he seeks to follow. I don’t pretend to have the man all figured out, but nevertheless, my time with him allowed me to develop the perspectives described below.

As mentioned, there are a wide variety of opinions that people hold about Mr. Trump. It is not the purpose of this article to promote any one perspective. What I will say is that I was fortunate enough to work for the man, and in the process had some up-close and personal experiences with him which allowed me to gain insight into why I believe he has been so successful within the golf industry. I believe that the man has wisdom to share, for he shared some with me whether he realized it or not. I thank him for the lessons and for the fun memories I gained working for him at a world-class facility.

10 . Surround Yourself with Good People - Mr. Trump made sure that Trump National Bedminster was stacked with well-respected individuals who would take his course to the next level within the golf industry. Three individuals who come to mind are Mr. Mickie Gallagher III, Mr. Jim Herman and Mrs. Jackie DeCarma. Mickie Gallagher still serves as the Director of Golf and has for years been a very well respected member of the golf community. Jim Herman served as one of the golf professionals during my time at the club. A very kind man, Jim can now be found enjoying some tremendous success out on the PGA Tour. Jackie DeCarma is the golf shop merchandiser. I remember her as one who treated everyone with dignity and class, ensuring that those who came through the golf shop had everything they needed and enjoyed a very pleasant experience in the process. Mr. Trump understands the importance of surrounding himself with valuable team members such as these three individuals. This wisdom has allowed him and his team to be awarded as host to the 2017 U.S. Women’s Open as well as the 2022 PGA Championship.

9. Have Confidence - The first time I ever caddied in Mr. Trump’s group, I was impressed to discover that he is actually quite a good golfer. He had a great round, hitting some very solid shots. Following yet another great shot, this one from the 18th fairway, the group started up to their golf balls leaving me and Mr. Trump standing alone together in the fairway. “It’s been going pretty well today,” he said to me. I was very quick to agree, for he had enjoyed a great round of golf, and he just happened to be the owner of my place of employment. “Not bad for an amateur,” he continued. I agreed again. He then further qualified the statement by saying, “Not bad for an amateur, real-estate genius”. I didn’t laugh at this point, for I wasn’t in a position whereby I thought it would be appropriate to do so - even though I did find it funny. As I think back, he must have meant for me to find humour in his statement, but regardless of his intentions, it did reveal the confidence that he has in his professional abilities. It is this same confidence I believe he has relied upon to fuel his successful efforts within the golf industry.

8. Constantly be on the Lookout for New Talent - On his show “The Apprentice”, the entire premise was to discover talent that could fill a position of employment within the Trump organization. This next story is on a much smaller scale, but I believe it reveals Mr. Trump’s desire to give his employees a chance to shine and prove their worth. I was caddying in Mr. Trump’s group for a couple of his guests. We were on the 16th green and Mr. Trump’s caddy was busy raking a greenside bunker. Mr. Trump was standing over his putt when I heard him say something. “Left edge?” he quietly asked me. I was being given a shot to prove myself. As I knelt down behind the ball to make my read, his caddy came running over from completing his work in the bunker and himself told his boss that he agreed with the initial assessment. Mr. Trump then stepped up over the ball, hit the putt at the left edge, and rolled it right into the centre of the cup. As our group left the green, I walked off a little dejected, but also thankful. I was dejected because I felt like I his caddy had robbed me of a great opportunity to prove myself. I was thankful because I had seen the putt breaking the opposite way.

7. Respect a Job Well Done - There I was caddying in the annual member guest tournament. The event required members to compete with their guests in nine hole matches against other two man teams. Our team had drawn Mr. Trump and his guest, and I wanted to win. We were on the eighth hole when Mr. Trump hit a shot down by a creek, and it looked as if he may be in trouble. As we couldn’t quite see the shot, his caddy began going up ahead of everyone else to see where it had ended up. I quickly decided that I too would go up to see, for this was a very critical shot in the match. I ran and caught up to my counterpart, and we both discovered that the ball was in play, and in good shape. It was then that Mr. Trump pulled up in his cart with a smirk on his face. He looked at his caddy and said, “You’re friend there ran up ahead to make sure that everything was being played fair”. I quickly realized that Mr. Trump had interpreted my actions as me making sure that nobody was cheating. Now, this could have got me in some hot water. There was a very real possibility that I had just offended the man who had made popular the phrase, “You’re fired!” Thankfully, I was wrong - I had not offended him. Mr. Trump had respected my effort. Following our match, which we did in fact win, he walked passed me, pointed just like he would in a board room before telling someone that they were officially canned, and said, “Good job”.

6. Always be Looking for Ways to Improve - I remember hearing a story in the caddy yard about Vijay Singh coming to play the golf course, and providing feedback on a particular hole saying that he felt it needed to be longer. Little time passed before the hole was lengthened with a brand new tee box. This story was never officially corroborated, but it holds true to norms at Trump National Bedminster. The staff always had Mr. Trump’s approval to find anything that could be improved upon, and to make those improvements a reality. It’s a fundamental principle that I believe has allowed Trump National Bedminster to host the 2009 U.S. Junior (won by Jordan Spieth), and be a future host to the 2017 U.S. Women’s Open and 2022 PGA Championship.

5. Value Opinions - A very good friend of mine, Nate Rayl, was the one who got me the job at Trump National Bedminster. He was very well respected at the club, and would often caddy for Mr. Trump. Nate would tell me stories of how he would at times be asked by Mr. Trump for his opinion on how particular parts of the course looked. Mr. Trump truly wanted to hear what Nate, a mere caddy, thought. I respect the fact that Mr. Trump would care about the opinions of those who worked well below him. It shows respect, and a commitment to improvement by seeking insight from a wide range of perspectives.

4. Believe in Your Product - I cannot recall a time where I ever heard Donald Trump say a negative word about his facility. You would hear him speak of ways that he would like to improve, but he never put his products down. I believe this stems from the fact that he always ensured that things were done correctly the first time, making future improvements that much more effective.

3. Appreciate Your Clients - Mr. Trump has always been known as someone who is not afraid to speak his mind and tell you exactly what he thinks. As a result, many view him as crass. While there is no doubt that he has made comments in the media that are unkind, I noticed something different at his course. He always took the time to speak with the members of his club, and in my eyes I always thought that he desired to treat them with respect and appreciation. I believe this revealed his understanding that anytime you have a client, it is important that you not only appreciate them, but make sure that they feel appreciated. This leads to them coming back, and grows your business on various levels in the process.

2. Never Stop Selling - I’ve been around the golf industry for many years now. To run any successful golf facility, you need to be constantly selling. In doing this, it can be very hard to find the balance between bringing in new clientele while still serving the ones you already have. Mr. Trump and his team at Trump National Bedminster always sought to ensure that the members they had were well taken care of. I believe this to be one of the reasons why new clients would come knocking.

1. Play to Win - Donald Trump is a competitor. We’ve seen it on the political campaign trail, his television shows, as a real estate mogul, and within the golf industry. Mr. Trump has taken his love of the game, and has not only turned it into a profitable venture, but continues to become increasingly influential within American golf. Now with courses overseas, I wouldn’t be surprised to see this influence continue to grow to a more significant extent.

About the Author This article was written by Jonathan Carr (@jonathanwcarr) as part of our weekly 'Top 10' series. As a scratch golfer himself, Jonathan has a keen eye for what it takes to be successful on and off the golf course. His passion for golf is surpassed only by his passion for his faith and his family.

Read some of Jonathan's other articles here.

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