A couple of years back, in 2001, I celebrated my 20th year of making music for a living. That milestone also happened to coincide with a masters sale I was apart of, so I earmarked a small percentage of that payout as ‘fun money’.
Selling masters was a big deal during a time when there was surplus money circulating and people were trying to diversify their investments. Masters are the actual recordings of songs (as opposed to the melody and lyrics known as publishing), and they held immense sentimental value to me. Deciding to sell them was emotionally challenging—I mean, I remember what the sky looked like when the drums were laid down for ‘Red Meets Blue’, and the journey to finding the perfect mandolin hook for ‘Carolina’. These weren’t just recordings; they were stories of my life.
SOOO, anticipating having a chunk of $$$ to spend on myself to commemorate both of these milestones, I went through a long process of trying to determine what I’d like to use that money for. Being a firstborn (and only son) I tend to be more responsible than I need to be, so I couldn’t allow myself to spend the money on a depreciating asset. I mean, how could I devalue my career and these recordings by blowing the money on something that would ultimately not be worth anything?
That severely limited the scope of what I was looking at to basically one of 2 things: a Porsche or a nice watch. The Porsche soon got tabled and I was singularly focused on figuring out WHICH watch to buy.
A bit of background on my relationship with watches: While I wouldn't call myself a 'watch guy', I've worn one religiously since I received my first when I turned 7—a 34mm SWATCH Rotor GS400. Since then I’d had one experience owning a legitimate timepiece back in 2008, when I acquired an IWC Portuguese. I’d learned about IWC through my friend Leah who had a very special IWC and let me wear it on a few occasions. So when an opportunity arose to trade an IWC for a private show, I jumped at it. What appealed to me about the IWC was its weightiness, the visible movement through the case back, and the lack of stigma I assumed accompanies owning a brand like Rolex.
I owned that watch for a couple years before it was stolen from me as a result of negligence on my part, and I decided I was not to be trusted with anything so valuable that was also so SMALL.
So, needless too say I was skittish about owning a nice watch again, but also trusted that I’d learned my lesson, which is simply: don’t take off your nice watch. Like, EVER.
So here’s what I did: I began my research for which watch I might want to commemorate this milestone. I learned there are traditionally three brands known for holding or increasing in value over time: Patek Philippe, Audemars Peuguet (neither of which I could afford) and Rolex. I learned that for the price, Rolexes craftsmanship is second to none, they have a rich brand heritage and because their availability is limited, if purchased correctly, they can make a great investment. I got over the fear of being judged for wearing one (honestly, the only people that ever comment on my watch are other Rolex people- NO ONE ELSE CARES! 😂)
I started looking at sites like Bob’s Watches and Chrono 24, which are both excellent (and reputable) vendors, but didn’t initially realize that these sites were selling SECOND HAND watches, with secondary market prices, NOT retail. Retail prices of the watches I was looking at were remarkably LESS, but there was one caveat: buying a Rolex at retail was going to take some work. You could not, in the year 2021, walk into a Rolex store a buy a Rolex. Heck, you could barely even find one in a display case!
There are a lot of jewelry stores that sell Rolex, but the majority of them are NOT authorized dealers.
Because I wanted to maximize the value of my money, I set my sights on buying from an AD. I knew that this would be a journey, because there were a LOT of people wanting to buy Rolexes in 2021. I learned who the Authorized Rolex Dealer in Nashville was and went in and sat down with a gentleman and explained what I was hoping to buy. I confessed that I knew nothing of how this process goes, but that I was willing to wait as long as I needed to.
He explained that he would take down which watch I was in the market for, but also that if that was the last time he saw me, chances are- I would not be buying a watch from him. So, I just started dropping by. Saying hi. Talking shop- getting to know the guy, letting him get to know me. We played a round of golf, I invited him to some bourbon tastings. We basically dated, y’all.
Eventually, he let me know that the watch I was wanting (a gold/green dial ‘John Mayer’ Daytona) he would not be able to sell me- was there anything I would want instead?
“I guess I could see myself in a black dial Daytona” I said.
I got a call from him less than a month later on the morning we were leaving for our 1 year anniversary trip.
“Could you come into the shop as soon as possible?”
I knew what this meant.
I rushed over to the jeweler, was ushered into a private room, and sure enough, he presented me with a black dial Rolex Daytona. I happily laid down my credit card.
By the way- I can’t express to you what this felt like, but the closest thing I can possibly compare it to is possibly maybe what it’s like to be proposed to. I know, I know- SO LAME, but Rolex doesn’t make many of these and I knew the hoops he had to jump through in order to get the green light to sell one to ME. I felt CHOSEN.
Oh, and the value of that watch tripled when I walked out the door. TRIPLED. Thats not the case with every Rolex (and that value is more like double now), but needless to say I’d made a sound investment. And one I would be excited to pass down to Walker someday.
*Annie would want to make sure it was known that not only did I buy THIS watch, but I bought TWO others- All on the speculation that the master sale was going through. She would also want you to know that the master sale DID NOT, in fact go through, and that I STILL had purchased THREE ROLEXES. This is something we can laugh about now, but make no mistake, that took about 3 years. 😂 Marriage is fun!
**If you’re curious about learning more about watches- Hodinkee.com is a great resource. Here’s a fun video of John Mayer talking about some of his favorite watches from his collection.
You bought THREE? I just thought you had the OP I saw at your house. Sounds like me with golf clubs. That Daytona is a beaut!