What Happens in Vegas: 11 Sales Tips I Learned After Getting Drunk And Buying A Timeshare

I’m out in Singapore all week this week so didn’t have time to write a new blog post so I’m going to repost an all-time favorite.

I’m out in Singapore all week this week so didn’t have time to write a new blog post so I’m going to repost an all-time favorite. Enjoy!

Ok. This is one of my more embarrassing stories, but I always try to learn something from my mistakes. I apologize in advance for the length of this post, but hopefully you will find it entertaining and can walk away with a few tips on how to be on the winning side of a negotiation.

It starts with me in the car on my way to the airport when I got a call from a major hotel chain with which I have a certain member status. I took the call. It was some woman trying to sell me a timeshare and offering me three nights/four days in Vegas in exchange for two hours of time listening to their pitch. Since I had no interest in timeshares based on what I had seen others go through, I told her I wasn’t interested and went to get off the phone. She hit me with: “You don’t like Vegas?” I paused and thought to myself: “Are you kidding me? I don’t like Vegas. I LOVE Vegas.” My wife and I not only go once a year to get our gambling fix and shirk our adult responsibilities, but I just happened to be sitting on a soon-to-expire $1,000 ticket from the Red Sox winning the World Series the year before.

Sales tip 1: You should have a few “go to” questions you can ask people when cold calling to get their attention and to earn a few extra minutes of their time.

She got me to pause and think for a minute. That’s all she needed. I engaged in the conversation. Every objection I had for her she had a response. It was obvious she had been trained well by her company and was ready for whatever I had for her.

Sales tip 2: Know all your objections and have at least two responses for each of them.

She did such a good job that I started throwing out random objections just to see how she would handle them. She nailed every one: price, time, not interested, send me info, etc. After going back and forth I finally got her down to $100 for three nights/four days in a suite with VIP tickets to four shows, dinner vouchers, and some other crap I can’t remember anymore. I still didn’t want the package, but I was so impressed with her sales skills that I decided to sign up simply so she could get credit. In my mind, if I didn’t use the tickets I didn’t really care: it was only $100.

Sales tip 3: How you engage with people throughout the sales process makes a difference and can help differentiate you regardless of your product or solution.

So there I was with a package for three nights/four days and $1,000 burning a hole in my pocket. I told my wife the story and then didn’t think much of it…until she brought it up a few months later. She was itching to go to Vegas and the package was going to expire soon. Against my better judgment I agreed to go. We booked Thursday night to Sunday at the Hilton with the timeshare pitch at 10 am on Friday morning. The plan was to get up Friday morning, get drunk, be completely obnoxious and have fun with the crappy timeshare pitch and then party the rest of the weekend on their dime. She was going to be the good cop, I was going to be the bad cop. We agreed that no matter the circumstance, no matter how attractive the offer was, that we would not buy the timeshare.

We got up Friday morning, went down to the pool and proceeded to enjoy a few cocktails as planned. By 10 am we were feeling pretty good and were ready to go have some fun. When we showed up they escorted us to a computer where we had to register and answer a bunch of questions about what we liked, where we liked to travel, etc. Then a nice older gentleman with an English accent came to greet us. My wife immediately liked him and started joking around with him. If he was some slick sales guy, I would have been able to disassociate and treat him as such. But this guy was super nice and he seemed harmless. It was hard for me to be the “bad cop” right out of the gate.

Sales tip 4: If you can effectively profile the person and company you are meeting with beforehand you can figure out what approach should work best when trying to develop rapport and connect with them.

We sat down in a nice room with a bunch of big screen TVs. The head pitch lady came out and started with: “So which one of you is the good cop and which one is the bad cop?” Doh! She called out the objection before there even was one.

Sales tip 5: If you know the objection is coming then try to get ahead of it and address it before the client can use it against you.

She then went on to set the stage and asked everyone to have an open mind. From there, a sales guy brought us back to his desk. He started by asking us what kind of trips we liked to take, where we’ve been on past vacations, what our most recent trip was, how often do we take vacations, where do we like to stay?

Sales tip 6 & 7: When qualifying, try to ask open-ended “pleasure” questions that get prospects talking instead of diving right into their “pain.” Also, if you want real intel, don’t ask hypothetical questions: ask people to give you specific examples.

After getting a good picture of what we liked and how often we went on vacation he brought out the ROI calculator and asked us to put in our own numbers that we were previously talking about.

Sales tip 8: find a way to get people engaged in your presentation. If you can get them to do something and enter in their own information they are far more engaged and believe the info way more than if you did it for them.

Taking “conservative” estimates, he mapped out that depending on what package we went with (pre-selling the close) we would make our money back and be net-positive within eight years. I’ve seen and used ROI calculators in the past and think they’re mostly crap but because of the way he walked us through this one — along with the constant flow of drinks they were feeding us — it started to make sense. He then piled on by showing us some of the locations and hotels we had been to in the past and displayed how much less expensive our trips would have been if we had used the timeshare instead of paying out of pocket.

Then came the closer. The manager came out from the back room with the “special offers just for us” and started walking us through the options. Our sales guy had actually recommended one of the lower packages but when then the manager came out she started talking about how it wasn’t going to get us what we wanted based on what she already knew about us. She “knew us” and knew we wouldn’t be happy with the lower package, playing into our VIP mentality when we travel.

Sales tip 9: When you know your audience you can play to their psyche and sometimes get them to upsell themselves.

Throughout this entire process my wife kept looking at me as if to say: “What the hell is going on here? I thought you were supposed to be the bad cop and get us out of here.” I train on negotiations and am pretty good when it comes to selling. I never professed to be a great negotiator when it comes to buying, though. There is a difference. I’m good at one and I’m terrible at the other.

As they worked towards the close it was like watching a train wreck without being able to look away, except we were the train. In our inebriated state we closed by telling them if they upgraded us to a bigger suite and gave us a bottle of Dom to celebrate we would sign. They tentatively agreed to both and there it was: we bought a f-ing time share.

Sales tip 10: Don’t get drunk before you go into a negotiation.

As we walked out and started to sober up there was more than a little buyer’s remorse setting in. We went to our room and packed up our clothes to get ready for the move to the new suite. When we got to our new room we noticed it was the exact same room we had before, just renovated. Same size and everything. We actually liked the décor of our previous room better than the new one. This was the first thing that we experienced right after the sale. It didn’t support our decision and make us feel better about it; it actually added to the buyer’s remorse that we were feeling.

Then we had to go back to meet with our sales rep to finalize the paperwork. When we showed up, he had a bottle in a bag waiting for us as we sat down, presumably the bottle of Dom we asked for. We then went through all the paperwork and signed off on everything, still thinking the entire time: “What the hell are we doing?” Once everything was signed our guy congratulated us and presented us with a bottle of… Moet… Wait, what? Moet? We asked for Dom and you bring us Moet? I’m not a Champagne snob but when someone asks for Dom and you bring them Moet that’s like going to a fancy steak house and getting served a Big Mac. He shouldn’t have given us anything. Needless to say, we weren’t impressed. Another thing that didn’t make us feel better about our purchase, only worse.

Sales tip 11: The sale isn’t over when they sign the contract.

We proceeded to try and forget about the whole experience and enjoy the rest of the time we had in Vegas. We decided to use the VIP tickets to one of the shows and eat at one of the restaurants we got the free passes to as part of the timeshare package. Come to find out the only shows we could go to and the only restaurants that accepted the vouchers were in the Planet Hollywood attached to the Hilton. Needless to say, none of the shows were interesting to us (Zombie Burlesque, seriously?) and all the restaurants sucked. This was strike three and four for them post-sale.

We ended up having a great time in Vegas as we usually do and finally got home Sunday night. On Monday we sat down to talk about whether or not we really wanted this timeshare thing and decided we didn’t. We sifted through the mountains of paperwork to see if there was a way out and found out there was a five-day cancellation policy. We could get out of the whole thing by writing a cancellation letter and delivering it to their corporate office by midnight on Day 5. We were psyched. The only problem was Day 5 was Tuesday and we didn’t finalize our decision until Monday night. There were no same-day delivery options that would have gotten the letter there on time. So…

I woke up Tuesday morning, cleared my schedule, went to the airport, bought a ticket to Florida, flew down, rented a car, drove to the Hilton corporate headquarters, handed in my letter, took a selfie and a copy for proof, got back in my rental, drove back to the airport, got back on the plane and came home. Yup, that happened.

As ridiculous as that sounds, it saved me and my wife quite a bit of cash. I considered it my penance for being an idiot.

I definitely learned a few things throughout this experience that will benefit me moving forward, not the least of which is to never plan on getting drunk before going into negotiations with trained professionals. I hope you took a few things away from this experience too. Good luck and happy selling!