Vegas Timeshare Tour

I’ve had a number of occasions to research the topics of vacation and travel in the last few years as the industry tries to recover and re-orient itself in a post-pandemic era.

What I’ve learned is this: Americans aren’t just tight on money, they’re tight on time.

We heard this over and over again: people just don’t have the time they wish they did to spend on a vacation, let alone have the money.

And this is precisely why I jumped at the opportunity to experience firsthand the Great American sales pitch where money and time converge: the timeshare.

And not just any timeshare pitch in any American city, but in the city of no shame: Las Vegas.

And not just a timeshare pitch hosted by any American brand, but one hosted by hotel chains bearing familial names synonymous with the most gauche, nouveau riche American examples of wealth, fame and ridiculousness: Trump International and Hilton.

——

Saturday morning, 10am. “Absolutely no alcohol allowed’. It was reiterated to me multiple times. This is to be a sober affair, although one gets the impression that this has less to do with promoting an air of serious business and more to do with avoiding potential problems brought about by drunken impulse buys.

It all starts with a glossy, yet generic Preview Center, which is essentially a rebranded hotel lobby, complete with inspiring words such as “Discover the world, Rediscover yourself.” The energy feels like I’m somewhere between a cultish empowerment workshop and an MLM onboarding seminar. I’m given a login card attached to a color-coded lanyard that I can wear around my neck and be distinguished from the other guests. I don’t have a name tag, but the lanyard lady reassures me that I can be identified by the staff as Yellow.  I have to insert my card into a self-serve kiosk so I can input all my vacation styles, travel preferences, and, of course, my hopes and dreams. There are unlimited free fountain drinks, coffee, granola bars, string cheese, and beef sticks, perhaps to nurse one’s pre-noon Vegas hungover.

It’s in this room that my timeshare spirit guide, Rocco, found me, Yellow. Rocco, wearing an black blazer with a black mock-turtleneck and sporting a black puffy hairdo that has a whisper of a boomer combover, is a young guy artificially aged by his ensemble. I have a feeling that he has been taught that age equals serious salesman. In our introductory small talk I reveal that I’m from Chicago and he enthusiastically whips out his Cubs insignia wallet and declares that he, too, is from Chicago. His level of excitement at our shared origins seemed like he felt he had opened his sales pitch with divine serendipity. I cringed inside, a bit embarrassed that there wasn’t a divine intervention of any kind that was ever going to help him make this sale.

I’m sufficiently amped up on mid-morning beef stick nitrates and caffeine, and so Rocco decides that I’m ready to be led to the group presentation, reassuring me that I’d see him again in about 20 minutes. The presentation room is full of re-purposed office furniture and flat screen TVs, attended by about 20 other older couples. I’m the youngest in the room, and definitely the only single person.

A friendly woman evangelist begins the presentation, a 20-minute powerpoint on the Power of Points in a points-based vacation economy. We’re not talking money here, we’re talking points. And the beauty of points, I am told, is that they are not subject to inflation and they roll-over each year*, leaving me to conclude that an investment of my money into points is simply a smart, low-risk investment. I’m wondering why I don’t have a financial advisor, and why they haven’t told me about this kind of opportunity.

Along with birthdays and anniversaries, she checks to see if there were any men and women of the armed forces in the audience. There aren’t any, but she extends a salute of gratitude to them. This is truly an American show. No birthdays or anniversaries either, so we’re off to a great start. 

From here, the pitch moves from something less economically rational to something darkly magical. It has some of the classic markings of a cult recruitment, including lofty praise and near deification of the founder of the whole operation: Conrad, great grandfather to Paris Hilton. I learned that he “filled the Earth with the light and warmth of hospitality.”

Our dear presenter now takes us all around the world, showcasing Hilton properties and offerings, fondly weaving her family’s stories and photos at these places, and teasing us with our potential futures with a Hilton timeshare.  

We see her glowing girls growing up through visits in the Disney parks and in the Rocky mountains, at graduations, and at the birth of her first grand baby, building a beautiful narrative of how she successfully raised her kids as a single mother.

And then, a photo of a man, previously unseen in the string of images. She shares that she had met her love, we’ll call him ‘Dave’, and that he would become her husband. We see pictures of our guide and Dave, getting married on a nondescript, but stunningly beautiful tropical beach somewhere.

For the rest of the presentation, in between the nods to the many properties and unbeatable ‘inflation-proof’ nature of the points, we also hear about the incredible, invaluable memories she made visiting these properties with Dave and her grown children.

Inexplicably, we hear all about Dubai over and over again in the tour. Of course, our guide and ‘Dave’ went to Dubai and you, dear audience, could also go to Dubai if you’ve never been to Dubai because Dubai is the new hotspot in case you didn’t know: Dubai**. 

With a backdrop of smiling faces of her charming family, we learn about the legacy potential of owning a timeshare. This seems a particularly apt selling point to the many silver hairs in the room: these timeshares can be willed to one’s children and grandchildren***. 

Now we get asked, one by one, where we would go if we only had one more trip to take. A foreboding hypothetical, but we’re a captive audience so we oblige. She only liked half of our answers, probably because no one said Dubai.

She brings up the conversation that we most likely had with our wives on our way to the session: promise me, dear husband, you will sign nothing, buy nothing. Now the presentation was self-aware and I knew I’d better get my guard up. 

Oh, and not to be forgotten, we are reminded of how great it would be to come back to Vegas, in exactly one year’s time, when the city will be hosting its first Super Bowl. Better get that timeshare now and plan for that all-American pilgrimage. If her projected Super Bowl weekend room prices were to be believed, this timeshare was really starting to sell itself.

And, then, like a gut punch none of us asked for, we learn of Dave’s stage 4 cancer diagnosis.

Our host tells us what it was like to learn that her husband only had 6 months to live and their decision to honor his life and their love in the only meaningful way possible: literally sharing the last days of his time with their Hilton timeshare. I’m not trying to be cheeky about someone’s last days. What I’m saying is that the sales pitch is that intense.

My literacy is in observing people and reading a room. It’s kinda my job. And from what I could read, this pitch, so suddenly and acutely dark, is working.  

She closes the presentation by describing what it was like to be alone again; she is fortified by the memories she shared with Dave through Hilton. “I share this, not to make you sad,” she said, “but in the hopes that you make the most out of every day. Thank you for coming today. And I hope you enjoy the rest of your tour.”

And with that, the lights are back on and the room filled with aggressively loud Ol’ Blue Eyes singing “Come Fly with me, let’s fly, let’s fly away.”

I’m a bit shaken and confused by the rollercoaster of emotion, but I’m ready to learn more. Luckily I’m greeted again at the door by my man Rocco, and he whisks me away to what I can only describe as our own private sales pod.

This appears to be the point in the process where Rocco’s job is to personalize the sales pitch. Perhaps bolstered by the information I input at the kiosk in the beginning, he seeks to learn more about me, my family, our current travel style, as well as our aspirations for the future. He asks where I would like to travel next. I say Ireland. “Ummmm, we don’t have property in Ireland, but let’s look at Scotland”. He asks about our next planned trip. I tell him I’m about to take my boys camping near Rhinelander, Wisconsin. He pivots our discussion to Dubai.

The whole thing vacillated between messages of carpe diem, YOLO, and “the future depends on what we do in the present”. He shares all the many things Hilton points could buy and how that would delight my kids now and forever. Not to mention the ways that “owning” a timeshare is about leaving something for my boys’ future, a legacy and debt-free asset “just like land.”

The money side of this whole experience is totally surreal. Everything money is mediated through the concept of points, whose value is thus far unconnected to the dollar. Rocco works hard to obscure current costs by continually referencing unknowable future expenses, like inflation and inheritance taxes. Rocco asks me if the ‘buy-in’ tier of 23,000 points annually is right for me to create memories with my sons and leave as a legacy asset when I’m gone. I have no fucking idea, Rocco, but it’s weirdly hard to say no, it’s definitely not not right.

It is not until the very, bitter end of Rocco’s and my time together that I am told what the “buy-in” would cost me.

The answer is $139,990 American Dollars.

Rocco is asking me to put down a deposit, on this unsuspecting sunny Saturday in Las Vegas, before I had even had a lunch buffet, of $27,998.

And then pay nearly $3,500 each month for the next 5 years.

And then pay HOA fees each year.

I’m sorry, Rocco, but thank you for the meat sticks. Perhaps we will run into each other again in Chicago.

——

The pitch is rather incredible: the timeshare is buying points, which are like land, but not land, and like money, but not money, and like a home, but not a home. And so what does the timeshare tell us about time and money for Americans today?

Thinking back to poor Dave, it dawned on me.

The real pitch is this: the only way to salvage the little time we have to vacation in America****, let alone make the most of the short time we have on this earth, we need to spend what money we do have on making memories, leaving a legacy, and visiting Hilton Dubai.

-Brian Flannery

• (*for a fee)
• (**Dubai has indoor skiing where they fabricate islands and you can ski in the desert.)
• (***with HOA fees in perpetuity)
• (****roughly ten non-consecutive paid vacation days each year if you’re lucky)