Official Caddying Story: Matt Desch

Matt Desch is CEO of Iridium (NASDAQ: IRDM), a satellite company based in Washington, DC. Iridium is the world’s largest satellite system, providing communications to ships, airplanes, and other industries across 100% of the planet that are outside cellular coverage. Once the largest bankruptcy in the world, Matt joined the company in 2006 and took it from a small company to a multi-billion dollar global company, launching a new $3B satellite system in the process. Matt has spent over 40 years in telecommunications, starting at AT&T Bell Labs, and was an early pioneer in the cellular phone wireless industry. He has a BS in Computer Science from The Ohio State University and an MBA from the University of Chicago. He is a Board of Trustee for the Aircraft Owners & Pilots Association (AOPA) and also sits on the board of Unisys (NYSE: UIS).

At which golf course did you first caddie, and how old were you when you started?

I caddied at Dayton Country Club starting the summer after I “graduated” from 8th grade and caddied solidly for the next four years, as well as the following college summers to make money.

Why were you compelled to become a caddie?

I was the second of six children in a blue collar family without tremendous resources. Our parents encouraged us to work from an early age, and my older brother had discovered caddying several years before. Given his success, we were all encouraged to follow. Once he earned a full Evans Scholarship from the effort, it wasn’t really a choice, as it would have been impossible for our parents to have paid for all of our college educations. I won an Evans Scholarship to Ohio State after four years of caddying, and two additional brothers followed along later also winning Evans Scholarships. Caddying was very good to the Desch family.

While we had a very “Noonan family (Caddyshack) experience,” it was really a great way to spend the summer. Fifty to eighty kids would show up on a typical day for a loop. Being around golf, becoming very good at a skill that adults seemed to appreciate, and being outdoors all summer were all very attractive to me growing up. It was also the best way to make money for other things, like learning to fly, which I also did during high school.

Take us through your first day on the job, who was your first loop?

After caddie training, I was assigned a single bag on a weekday afternoon. I wish I could remember the member. He was a doctor, but I forget his name. I do remember the bag, however, one of those really huge Burton bags, lime green and white.  It must have weighed 100 pounds. By about the 7th or 8th hole, I was exhausted, shoulder hurting, lagging behind my player and had to be replaced which was devastating to me at the time. I felt humiliated but didn’t ever even consider that I wouldn’t show up the next day to try again. Over time, carrying two of those bags and running ahead many holes to ensure tee shots couldn’t be lost (forecaddying) became routine and almost a guilty pleasure. 

What was the biggest mistake that you made during your caddying career?

While caddying is a physical endeavor, the greatest skills you learn are psychological ones – what subtle things to say to encourage your player, how to think ahead to support two golfers you’re caddying for as well as two other golfers in a cart (all at the same time), and how to get along in the incredibly complex “Lord of the Flies” social dynamic that was part of an active and bustling caddy shack, which was filled with scores of teenage boys from all over the city and multiple schools and varying socioeconomic backgrounds. Play the wrong card and win too much money from an older kid in the three card “caddie poker” games that were played waiting for a loop and you could be subject to a “fountain job,” where the older caddies forced you to sit on the step fountain near the caddie shack to soak your pants and underwear, making for a very uncomfortable rest of the day. I got plenty of those, and am ashamed to say I might have given a few as I got older, but all provided valuable social skills at a formative age. That’s a long-winded way of saying I don’t remember a huge mistake but remember plenty of little mistakes that have turned into the stories I still tell that shaped me during my youth.

What did you most enjoy about caddying?

I think that it was the first activity that I had where I could develop a level of expertise that was appreciated and rewarded. Over a few years, I became extremely good at caddying to the point that the head pro and others would ask for me to be their caddie, as they knew it would help their game. I developed “status” with the other caddies, and the pride that developed from doing a great job and getting a big tip was very satisfying and fulfilling. Plus, I’m sure girls loved my “caddie tan.”

Tell us about some of the people for whom you caddied, did any of them contribute to your career in a meaningful way?

I have a lot of great memories of the members I caddied for, particularly the ones that showed interest in me and my future. A few stand out though; one member was a pilot and had an airplane, and I was in love with aviation. He would take caddies for a ride some Saturday afternoons, I finagled my way into his foursome many times to ensure I was that kid. He became a mentor, and I think I washed his airplane about 30 times over a few years but got many airplane rides as a result. I got my license during high school and have been flying ever since, for over 45 years. I still make sure to encourage kids, like I was, giving them an airplane ride every time I get the chance.

Another critical loop for me came following my senior year of high school, after winning an Evans Scholarship to Ohio State and was about a month away from attending college. I had drawn a good loop, someone I respected. He asked me on the 13th hole where I was going to college and what I planned to study. At the time, my aspiration, not knowing any better, was to say “patent attorney.” I didn’t know what a patent attorney did, but it sounded like a great combination of science and law, and something that would pay well. I remember my golfer replying something to the effect of “than you’re an idiot,” though probably a bit more direct than that. I was shocked! I thought this adult I respected would be terribly impressed with me, but he had the opposite reaction. I stammered a reply, Then, what do you think I should study?” He replied without hesitation “computers!” He ran a tool and die shop, so I doubt he had a lot of experience with them. And in 1976, remember, computers weren’t that big a thing yet. Several weeks later, I signed up for Computer Science as a major, and that took me into the technology career I have today. I will forever appreciate that golfer and the advice that set me down my path. I don’t think that I would have been a great patent attorney.

What was the biggest lesson that you learned from caddying that helped you succeed as you progressed in life?

So many lessons come from caddying but one of the most important is listening and observing. Being a leader requires vision, the ability to communicate and inspire, but if you aren’t perceptive to the environment around you, you’ll miss critical information needed for success. Sometimes the most important thing is to watch and listen, and only speak when the time is right and you have something to say. That’s what a good caddie does; he or she watches and observes carefully before starting to provide advice. Getting along with 60 other kids all summer in close proximity between jobs was also invaluable experience. It toughened me up and helped me relate to anyone at any level around the world.

Did you ever caddie for someone famous?

Dayton Country Club in the years I caddied was host to an event every summer called the “Bogey Busters” that attracted celebrities from all over the nation to play for two days, raising money for charity. It was a fantastic opportunity for DCC caddies to meet and caddie for TV, sports, and political stars. My brothers or I caddied for the likes of George Bush Sr., Tip O’Neill (Speaker of the House), McLean Stevenson (of MASH fame), Glen Campbell, Ara Parseghian (Notre Dame coach), Paul Brown (coach of Browns and Bengals), and so many others. I was a Cincinnati Reds fan, and this was the era of the “Big Red Machine,” so pulling Johnny Bench as your loop was a big deal for a 15-year old! Being in a foursome with Bob Hope, Foster Brooks (the comedian), Bobbie Goldsboro (the singer), and Robert MacNamara (Secretary of Defense) was commonplace. While exciting, it also showed us that these people were approachable, human, and for the most part, lousy tippers. It was the highlight of the summer, and we all got free tickets to the gala, which was a big deal for a kid from Dayton, Ohio.

If you could nominate one former caddie who went on to enjoy success, whose Official Caddying Story would you like to hear?

I don’t know who has been a caddie, but you hope to hear that your heroes and others you respect did so. I’d love to find out that Neil DeGrasse Tyson caddied, or Elon Musk, or Larry Ellison caddied. Did Gen Chuck Yeager caddie? I’m pretty sure Bill Gates was too scrawny and nerdy to caddie.

But either way, I highly recommend that you talk to my brother, Joe. He’s certainly the most unique of the Desch boys. While we weren’t entirely sure if Joe was completely right or normal growing up, he’s become a really fine, fine person. Just kidding, that’s merely a big brother talking. Joe is larger than life, literally the biggest of us. He’s also the best golfer of all of us. He’s given a lot back to caddies and to the Evans Scholars. He is the lead director in the state of Ohio for the Western Golf Association and was instrumental in getting new houses built at both Miami of Ohio (his alma mater) and also Ohio State. Joe is very involved with the selection of new Evans Scholars. He’ll have some great stories for you and also represents an entirely different approach to caddying than I did. He never stopped flapping his gums!