What is the strategy for getting that first Rolex? I have a few ADs around me. Should I take a shotgun approach (including multiple regions I frequent), put my name in/build relationships with all, or just stick with one AD?

Go into an AD, sit down and chat with their sales representatives and just be clear - I’m here looking to buy this particular model, treat it like a civilised conversation between two parties but ignore their attempts to dissuade you, or offer you an alternative entry point.

If you’re looking for a specific model like a Pepsi on a Jubilee, you’re gonna struggle as everyone else is in the same queue. But if you’re happy to accept a Batgirl or a preowned model, then make it known as they can probably source one much easier.

Don’t buy into the nonsense that “You must have a purchase history to buy Rolex”. That’s nonsense just to sell you leftover inventory they just can’t shift.

If you’re a credible customer, who knows what you want and can actually pay if they pull one out of the safe right then and there, then act like one. Go in, prepare to fail in negotiating a good price, but have the conversation.

If they continue to give you any BS, just politely say “Thank you, I’m not interested in taking up any more of your time or my own, so I’ll leave it here.” shake their hand and walk out like an adult.

I see all this nonsense about building relationships, people popping in weekly and offering to buy the staff a coffee or being convinced into buying a watch they had no interest in, it’s a waste of their time and money.

Go grey, I built a relationship with my AD 5 years ago and have $150K in spend. Funnelled all spend from friends and family through them across so many watch brands. Yet, still no Daytona or Day Date money green. Called my AD a couple of months ago to follow up and got the polite ‘piss off’ response with the 5-year wait on the Daytona. Confronted the AD then and there and reminded them of my spend with them and that a ‘relationship’ is 2-way street. Anyway, call ended and I made it clear that they won’t be getting any more of my business until they hold their end of the relationship. I will be going grey henceforth. Done with AD games.

My advice, if you want a Rolex that can be bought at MSRP or even slightly higher, you will be better off in the long run building a relationship with a grey dealer. They can also help you trade in your watches down the road.

Since like 2020 there’s no strategy. Like some of the others have said they will play games and expect you to spend, spend, spend and maybe one day you’ll get what you want. I’ve spent close to 80k and I’m still waiting for a watch I’ve asked for in 2021🤦‍♂️, even stopping by every few months. At this point I’m just done with them and plan on getting my first Patek later this year.

I have bought multiple Rolex , Patek watches from Chrono24. I am happy with the quality.

I think it really depends on the AD. I went to my local one, had a few conversations and met the owner of the store. The third time I went in. We got along well and he told me it’s not like there’s some hard and fast list. The sales people get some say but he makes the decisions.

He made a note that I wasn’t a jerk (ha fooled another one) and that I’m local and said it’s a matter of being top of mind when something was available so to come in every so often so I stayed on their radar.

About 3-4 weeks later, he asked my sales associate if she wanted to surprise someone and she called me with the rarer of the two I wanted (dj41 smooth in mint so not crazy rare but still). All in all, maybe 3-4 months and maybe 3 visits.

What I appreciated was they told me what it would be like and were very up front about it. No ask to buy other stuff (although I had spent about $2k there over the past year or two). They also told me how it works with the rare ones. Daytonas are still a years long wait no matter who you are. They just don’t get a lot of them.

A different place I checked out a year before was much more mercenary. They told me buying jewelry would speed things up right off the jump.

Depends on what that first Rolex is.

I'm open to gray market, but the one I want is about 25% cheaper if buying MSRP, the wait might be years though. I haven't seen rep trying to pressure me or dissuade, just tell me which ones they could get in a few months vs which could take a year or better (like the blue on steel skydweller on jubilee, which is my preferred choice)

Seems your question is how to get an in-demand watch with no purchase history. The answer is grey. The AD ain’t gonna sell 1 to you. They only get so many and the overwhelming majority are going to their whales and VIPs (including grey suppliers…)