This past Valentine’s day weekend, Ahana and I stayed at the Westin Desert Willow Villas thanks to a classic timeshare offer that came in the mail. 5 days and 4 nights for $299, providing we listen to a timeshare pitch. In exchange for listening to the pitch, we’d get a $75 visa giftcard, bringing our nightly rate down to just $56 a night.

All in all, it was a steal, and I’d never been to a timeshare pitch.

The resort was pretty awesome - four different pools, the main one is open 24/7, beautiful golf courses, and a ton of activities and hiking. The weather was pretty amazing, and overall it was a much needed relaxing vacation. We visited the Palm Desert zoo, ate a bunch of good food, and walked around the El Paseo shopping district. We also got a pretty amazing view of Coachella Valley and did some hiking near the San Andreas fault line.

For this blog post, I wanted to focus on the timeshare pitch itself. You can see their website for yourself.

Phase 1: Getting to Know You

When the word timeshare comes to mind, most people imagine a class of 10 to 20 people in a powerpoint presentation of sorts. That’s what I imagined it would be as well. But timeshare pitches have gotten far more sophisticated than that! This pitch had a five phase approach.

As you can imagine, the classroom style doesn’t lend itself to a good conversion rate. Not only is it sleep-inducing, but lumping in a group of unrelated people allows a sort of disinterested herd immunity where there’s no risk of saying no. You’re not going to offend anyone, since it’s a large group. And even worse, if one person loudly declines, it may sway the others.

Instead, this time share pitch begins with a casual, one on one conversation (or in this case, one on two since Ahana was there as well). We chatted for fifteen minutes or so about my various hobbies like motorcycling / dirt biking, how we organized a wedding in India from afar, and how we met.

In many time share pitches, you get the gift card at the end, once you decline. Surprisingly, as soon as we checked in we got the promised $75 giftcard.

In retrospect, it’s a miracle everyone doesn’t run their timeshares like this. Could you imagine anyone making a purchase the equivalent of a car while anxious? By giving the gift card immediately, they let you relax and put you in a “well, let’s see where this goes” frame of mind.

Phase 2: The Villa Lifestyle

After this conversation where the salesperson establishes a rapport, they start moving the conversation to Westin, and vacationing specifically. We walked to a room which hard four large monitors showcasing various beautiful Westin properties. The goal is to awe you with the incredible views and locations, and really sell you on the vacation lifestyle.

The salesperson will ask you where you want to go, and as you give answers, they’ll pick out the Westin resort close to that location. A key component of this pitch is establishing the villa lifestyle. Unlike many of the fancy hotels you’d stay at in other places, the villas have a private balcony, a fully functioning kitchen, and other amenities you’d expect of a townhome.

They then took us on a nice golf cart road trip around the property. Naturally, it was gorgeous, and quite a few levels higher than the typical hotels that Ahana and I book. (We’re both quite frugal.)

We then looked at three different kinds of villa rooms, ranging from the basic one that we stayed in, to the medium sized one, and ultimately the top end one. The top end one had a built in hot tub, a separate room for kids versus parents, and a whole host of amenities. The whole time they really want to sell you on the idea of the villa over the traditional hotel room.

Phase 3: The Pitch

By now it’s been about 50 minutes, and we finally go into his office.

So then they have us list 5-6 locations we’d like to visit going forward, and ask us how often we travel. We then opened up a calculator that had some rough estimates on how much the average American family at our income level spends on vacation, over a ten year period. How many days of travel (non-staycation) per year, what’s the average dollars per night you spend, some adjustment for inflation at 3%. The whole time they’re more than willing to go conservative.

For example, their initial calculator had us spending $200 / night at hotels. I told them we were much closer to $100 / night, and they were more than happy to oblige. We then adjusted inflation down to 2.5%, and days of travel per year from 15 to 10.

One red flag is when, regardless of how you adjust their numbers, they’re more than willing to go along with you. :)

After all this, we arrived a total close to $100k over ten years, spent on vacation. Isn’t that a lot? Well by golly, it sure is! If only we had some way to put all this money to better use, especially as we grew up and had kids - after all, vacations only get more expensive, not less!

That’s where Westin vacation rentals came in. For a small monthly fee of around $200, we’d get 7 peak days at any property, or 14 non-peak days. If we weren’t already going to say no, this is where they lost us. Someday I’ll do a separate blog post on how Ahana and I do our finances, but we have a pretty tight spreadsheet where every expense is inputted and categorized. $200 a month is massive for us, and I could see Ahana’s eyes boggle with disbelief right there.

In addition to this fee, there was a “small” maintenance fee based on how many days we used the resort.

When I asked what the fee was, they were careful to say this wasn’t a pricing discussion, but rather just the vision. We’d move on to discuss pricing and specifics in the next section. I shrugged and said ok, as we kept talking about villas, how awesome they were, and the various Westin properties.

Throughout this whole pitch, they had a slideshow of the various Westin properties throughout the world.

Phase 4: The Numbers

Then they brought in a more experienced sales person for the ‘numbers’ part of our pitch.

He then re-iterated the idea of paying the small monthly fee to get points - about 70k points. 70k points, he said, translates to about 7 peak days, or 14 non-peak days. In addition to this, owners received several benefits.

Owners had access to a special portal where they could find and book excess inventory rooms at unbelievable resorts for insanely low rates. When I mentioned this would be something I was interested in, they sadly smiled and said unfortunately, only owners get access to this portal. Made sense, as otherwise it’d be a huge loss leader.

The second benefit was the actual ownership part of it. Unlike a standard rental, an ownership can be sold, gifted, or passed on to family.

They set us up an ‘entry’ package at the previously mentioned price, $200 a month. They then mentioned how we could use more days if we wanted, but then we’d have to pay market rates for this. I asked again what the maintenance fee would be, and they never clarified.

I then finally said thanks, but I’m not going to purchase a timeshare. I said I’d be glad to consider this overnight, as we were staying at the property for another day and a half. If we changed our mind after taking a look at the numbers once more, we’d be happy to come back here.

Like any good salesperson, they didn’t take no for an answer.

The first counterphase included mostly guilt tripping. They weren’t angry or even sad, they were mostly disappointed in us. Look at how much money we were going to waste over the next ten years. They’d seen this time and again, trust them - we’d be back. Or even worse, in ten years, we’d regret not saying yes. They’d seen tens, no, hundreds of cases exactly like us.

I mostly shrugged, smiled, and said, well, this is kind of like buying a car. I just wouldn’t do it right there. No matter the car. I’ve never been the type to walk into a dealership and walk out with a car (a lie, by the way - I’d done that twice - but it was a bad idea the first time).

Finally, he agreed and asked for feedback. Where did we lose them? How could they improve future pitches? Naturally, this wasn’t an actual genuine call for feedback. Instead, this was still a clever way to pitch us. I’d throw out something, like the fact that this seemed too good to be true, and that made me skeptical. He’d instantly explain how their business was failing, and how this was a last ditch effort to get new customers. I’d then throw out another aspect of the pitch I didn’t like - the maintenance fees - and he’d respond with something like “but what if we could guarantee you low fees?” He never actually clarified what they’d be or how he could guarantee that.

After another twenty minutes, he finally sighed and said we’d be off to an exit interview to make sure that we were treated professionally the entire time. We sighed, thinking it was over at last.

Phase 5: The Exit Interview

We went back to the front desk for our exit survey, ready to give the sales people relatively high ratings. After all, we had definitely been treated professionally.

Surprise! This wasn’t an exit interview at all. Nope, this was a final sales pitch.

He began with something like, just out of curiosity, why did you happen to say no today? I mentioned that, as a couple, we decided to never make big financial decisions without sleeping on it. Just like buying a car, we wanted a couple days to sleep on this. I said if you could guarantee me a price freeze, then I’d be willing to think about it and consider it, but I definitely wasn’t going to say yes the day of.

Here came the counter offer.

Okay, what if we froze the price? And gave you 18 months to reconsider? In fact, we’ll ask you to come back for another 5 days and 4 nights, 18 months from now, but this time at the better villa version. We decided that wasn’t for us. While the stay was enjoyable, we definitely weren’t going to come back to the same area. Palm Desert was fun as far as a relaxing vacation went, but Ahana and I discovered we just werne’t good at relaxing. After two days we got antsy and wanted to do things.

He then quickly pivoted - ok, if that was the case, he could offer us a different location and 50,000 Bonvoy points for just $800. This definitely wasn’t worth it to us, and we calmly declined.

This was then followed up with another round of guilt tripping, and by this point it was almost 2.5 hours in. I think even he realized how tired we were, and that this sale simply wasn’t going to happen. So we ended up walking off, feeling quite relieved it was all over.


Like anyone who’d just passed up an offer that seemed too good to be true, we immediately googled the offer. You can see various reviews of the same offer. And those Bonvoy Points? 0.8 cents each.

Obviously, we were never going to say yes. But after reading all of this we definitely felt great saying no.

I have a pretty standard philosophy of try almost anything once, and staying at this nice a resort for $56 a night was well worth it. Would I do it again? Honestly probably not. I’ve learned that, at least for now while I’m young, I’m more than willing to slum it, and I’ve fortunately married someone who’s willing to as well.