Tour Tales | Jay Santiago talks Post Malone’s tours, private dinners with Drake, and taking the rapper to the next level

Musicians are barely getting a slice of music industry revenue, largely eating off of live performances instead. For ’Tour Tales,’ we dig into the rider requests, delayed shows, diligent preparation, and future of touring by talking with the multitude of people that move behind the scenes. Record executives, photographers, tour managers, artists, and more all break down what goes into touring and why it’s still so vital to the livelihood of your favorite artists. What happens on tour stays on ‘Tour Tales.’

It’s 6:00 a.m. on Oct. 3 and Post Malone’s operations manager Jay Santiago isn’t asleep. He’s in Toronto, charged up and too excited to feel any exhaustion. The 35-year-old Camden, New Jersey native has worked with the recording artist since 2015, and after a private dinner with Drake, he’s appreciative of how far he and Post have come.

“When I first met Post, he wasn’t a great public speaker. He turned that around real quick. He took a couple of coaching classes on speaking,” Santiago told REVOLT TV. “As far as music, he started practicing a bit more and practice makes perfect. All his early shows, in the beginning, were intimate shows. If they weren’t sold out, they were close to sold out.”

In this installment of “Tour Tales,” Santiago explains how much the Dallas Cowboys affect the star’s traveling, things older women have done to try to get on his tour bus, what happened at that private Drake dinner, and much more.

How did you link up with Post Malone?

I was Post’s tour manager for his first two years of touring. After that, I moved into the role of an operations coordinator. I’ve been best friends [of] Post’s head manager for about 10 years now. I met him even before we worked in music. He moved to L.A. in 2014, met Post, and I met Post at the end of 2014 going into 2015 — a little bit after he made ‘White Iverson.’ I believed in him. I listened to ‘White Iverson’ and got goosebumps. A lot of people called me stupid after I made that decision. But, now they’re still calling me to get into shows and trying to work with me.

Fast forward four years later, you’re talking to me at 6:00 a.m. while you’re in Toronto on ‘The Runaway Tour.’ Why are you up?

Tonight was special. Drake reached out to us and we decided to meet up with him. He rented out [Japanese restaurant] Kasa Moto out in Toronto for a private event. We first had a private bowling alley event with Swae Lee. From there, we got more private at Kasa Moto. It was very discreet. The show is later today. We’re here for four days, relaxing, taking it easy. We have two show dates back to back and then another day off.

Since you’re in Toronto all of these days, what’s the possibility of a Post Malone/Drake collaboration?

I’ll tell you what, those two guys are very organic. I can’t even answer that. That would have to be done in-house. The right people would have to talk to each other.

Are these sorts of nights common from all of your years touring with Post?

To be honest, I can’t compare anything to this night right here. This night was a little more special than all of the other ones. As far as us getting together with other artists, we’ve had nights where we’ve hung out with 50 [Cent] and nights where we hung out with Nas, But, they weren’t as big as this night. Usually, when we get with other artists, they’re very private about who they’re around. But, since Post has taken off and we’re reaching A-list celebrity, things are moving a whole lot different now.

As operations manager, what are your day-to-day duties on this tour?

Day to day, I overlook the tour as a whole, whether it is production or talking with the other tour managers for the other artists on the tour. I deal with Tyler Yaweh and Swae Lee’s tour managers directly. I overlook everything dealing with Post. That includes his dressing room, his jam room, making sure he’s in good spirits. I make sure his team is in place and doing what they’re supposed to do. I take care of all A-list celebrities that come to shows, as well as any of his personal guests. I take out all the fires.

When did the tour planning begin? Was it while he was making the album?

The tour is planned way ahead before the album. We don’t run the tours off the album. We don’t have to.

So, you’re already working on a tour before Post tells you that he’s working on new music?

Hell yeah. We have to. There are so many moving parts on tour. Hiring workers to build the stage, getting things shipped out to the city you want to start in, and all of that takes months of working in advance. You have people in the first arena two weeks before the show starts testing to make sure everything runs smooth. It’s a big, big, big process.

You’ve been there since the beginning. How has Post’s show evolved over the last four years?

When I first met Post, he wasn’t a great public speaker. He turned that around real quick. He took a couple of coaching classes on speaking. As far as music, he started practicing a bit more and practice makes perfect. All his early shows, in the beginning, were intimate shows. If they weren’t sold out, they were close to sold out. He always had great crowd participation and feedback. Even if we did ‘White Iverson’ three times in a row, they were still into it. He had a real cult following in the beginning.

At that time we had a DJ. FKi 1st was deejaying for us. He produced the August 26th mixtape and first Stoney album. Now, we’re on a playback rig. So, things are a lot different. The shows are still intimate. There’s still tons of crowd participation.

Wait, did you ever do ‘White Iverson’ three times in a row?

Hell yeah. The first few shows weren’t major. They were in venues of maybe 500 – 1,000 people. Post would come out to ‘White Iverson’ and we closed that bitch twice with ‘White Iverson’ (laughs). There were never any complaints. It worked out.

How has Post’s rider evolved over the years?

His rider? Oh my god. Alright, here we go. In the beginning, his rider was still vodka and orange juice, tons of Bud Light, chicken tenders, and fries. That was the very first rider. As we got bigger, we added mozzarella sticks, chicken parmesan. But, now? It’s a couple of bottles of 1942 [liquor], a couple of bottles of vodka. Lay’s [Wavy] chips with at least an ounce of Helluva Good Dip, gummy bears, mint gum, Snickers, Twix, Backwoods, Raw papers, and Camel cigarettes.

What was that first touring experience like with Post?

His first tour was the Fetty Wap tour [in 2016]. I didn’t have any advice. I didn’t know what I was doing. I went to school for international tourism, but I had no idea about touring in the entertainment industry. I didn’t even know about per diems (laughs). I wasn’t feeding the crew for a couple of days because I didn’t know I had to go grocery shopping for the bus. I was like, ‘These niggas are on their own. They have to figure this out’ (laughs).

But, I learned quick. He travels well now compared to how he used to travel. I remember he used to have water leaking on him from the fucking air conditioner on our first bus (laughs). The driver used to turn and water used to fall on him off the A/C.

Is there a Post song that grew on you as you went along on the tour?

Hell yeah. It was ‘Better Now.’ When it was on tour, it was different live than hearing it on the record. It knocks different live and it’s a whole different tone.

What was Post’s most memorable show before he became this megastar?

At Irving Plaza, 50 Cent came out with the whole G-Unit (on February 10, 2016). About 30 minutes before the show, it was like, ‘Yo, 50 is coming out. We’re going to make this happen. He’s coming here to soundcheck.’ I was like, ‘OK, cool. We’re running with it.’ I let his DJ at the time know. It was crazy.

What are some of the wildest fan reactions you’ve seen at a Post show?

I’ve had older women that were at least 50 years old flash me trying to get on the tour bus. They were claiming, ‘Hey, we did this with the Red Hot Chili Peppers back in the day.’ I just had to say, ‘Times have changed. We don’t move that way’ (laughs). There’s been some crazier stuff than that, that I don’t even want to call out.

I know Post is a big Dallas Cowboys fan. Has he ever adjusted a tour or anything around to be able to watch their games?

He hits me up now, saying, ‘Make sure I can watch the game in my room.’ Or, we’ll stream the game off somebody’s phone. He’ll also be like, ‘Hey, we’re stopping here to go watch the game.’ There have been times where he’s been like, ‘Oh, the Cowboys play Thursday. We’ll stop here and go to the game.’ He’s a big fan. If they lose, it can change his whole mood.

You said earlier that you put out all of the problems that may arise on tour. What’s an example of that?

We had one show in Miami, a while ago, where our bus broke down six hours from the show. We had no equipment. We were done. In a matter of three to four hours, I went out with the DJ and picked up everything. We set everything up. We put everything together. We had no visuals, but we found a way to make it work.

How involved is Post in putting the tour together?

He’s involved in every aspect of it, as far as creativity and the direction it goes. He’s involved with visuals, music cues, song placements and all. He’s involved totally.

Has anyone approached you about booking him for a residency?

That request would go directly to his agent. I’ve heard a few things in the air, but nothing’s been confirmed. Nothing has been brought to the table about that.

With his rise in celebrity, who have been some surprising celebrity fans to appear at his shows?

Mark Wahlberg, Dennis Rodman, Julian Edelman, Danny Amendola. No [Tom Brady], yet. He did comment on a picture, though (laughs). Cam Newton’s been to a show. The Undertaker’s been to his show.

As his star rises, do you already think about taking his show to the next level? If so, what would that look like?

We’ve all thought about what the next level will be. Everything has been surreal up until this point. The way it’s grown has been a surprise by itself. I can guess what the next level will be, but I won’t know until the next few songs are made and see what direction he wants to go. We go off of his lead.