Interview with Kyle Gustie and Brinson Strickland of 262 Five

Continuing our series of looking at people who work within the music industry, we caught up with Kyle Gustie and Brinson Strickland of 262 Five.

Here at Loud Hailer, we’re interested in all aspects of the music industry. As well as chatting with various musicians, we have also caught up with acclaimed music photographer Paul Natkin and music publicists Selena Fragrassi and Fiona Bloom. This time we are covering another aspect of the business with Kyle Gustie and Brinson Strickland, owners of 262 Five, Ltd

262 Five is a full-service event and production company that deals with all aspects of customized live experiences. As well as co-owning 262 Five, Brinson is also the President of The Collective which is an artist management business. 

We chatted about how 262 Five began, what is involved in their day-to-day work, how they came to work together, and some of their war stories from over the years.


Kyle Gustie and Brinson Strickland’s career paths had slightly different origins. During his college days at DePauw University, Greencastle, Indiana, Kyle was the Social Chairman at his fraternity which gave him a lot of early experience with organizing events and booking acts.

Kyle: “I think I still hold the record for the greatest absentee day at DePauw. We booked a band called Dr Bop and the Headliners from Chicago, who wore these spray-painted tuxedoes. They had a bartender on stage and all these dancers. They played all this old fifties stuff. I convinced them to come down and play our fraternity but we couldn’t afford a Friday or a Saturday night, so it was a Thursday night during Old Gold Week which was the Homecoming week. So we convince the Dean that it was just for our own people and meanwhile we were loading in kegs and stuff. DePauw was only like 2,400 students, not even as big as some High Schools around here but the next day there was like twelve kids in class!!”

After college, however, Kyle initially took a path into the Corporate world before being pulled back towards music.

Kyle: “So yeah, in college I hired bands and loved that part of music. My friends have always loved music but after graduating I just did the normal thing and got a job for GE Capital, and every day was like going to a final exam I didn’t study for. So one day, I was driving around and I was listening to a DJ on The Loop in Chicago called Kevin Matthews. This was back when The Loop was a real powerhouse. I started thinking, “I want to go back to college and do a party and everything.” I had one of the first car phones and I called the radio station and they put me on the air. I said to Kevin, “You should come down to my fraternity” and he said, “Sure. You’ve got to hire this band Dick Holliday and the Bamboo Gang.

So I said sure and I went and met these guys that were playing at Biddy Mulligans on Sheridan Road and I hired them for the show at my old fraternity. We became friends and they mentioned they needed a manager. And I was like, well I don’t know what the f*ck that means, I guess I’ll just drive the van and I’ll book shows and I effectively became the de-facto manager. So I helped them get sponsorship and booked them a show at the Chestnut Cabaret outside Philadelphia which was a venue near my brother’s house mainly because I knew we’d have a place to sleep afterward! We then got to know this band called The Daves and they were in the process of getting a deal with Miller Brewing Company. They used to do this thing called the Miller Genuine Draft Band Network and we got on to the Band Network thanks to the Daves,and toured for four years and did amazing gigs. We opened for Alice Cooper at Universal Studios for a Halloween party!”

When the band broke up Kyle was asked by GMR Marketing (one of the US’s largest marketing companies, who managed the MGD Network) whether he wanted to work for them. He spent the next ten years working with GMR on all their Corporate Sponsored tours and events including tours with Jimmy Page & Robert Plant, Clint Black, Garbage, Miller Lite Super Bowl concerts/events, and Tim McGraw, to name just a few. 

Brinson’s first step into a music-based career was actually as a musician.

Brinson: “I kind of accidentally came up as a musician. You know, my dad played a little bit and my brother played, still plays actually. We would play together and then I played in different bands in college to help pay my way through College. But being a musician was never the plan because I was an accounting major! So after getting out of college, I get an offer from a band who have stuff going on in the South West. And I think, I’ll do that for a year and it’ll be fun and I join up and it was intensive. We were doing 300 nights a year and it was one of those things – one year becomes two, two years becomes three and then it’s five. And you wake up and you’re like, “f*ck – I’m a musician, that wasn’t part of the plan!!”

So I keep playing with them, end up opening for another act in Las Vegas who had a deal with Capitol Records in Nashville. They were losing their guitar player and drummer, so they hired me and our drummer Dave McAfee who actually now plays with Toby Keith. So my thought was “we’re in it this far, let’s see where it takes us.” So we’re in Nashville and I’m not there six weeks and we lose our deal! We were managed by Glen Campbell Management. Glen has a management company, a publishing company, he was the greatest. Also managed by Glen Campbell Management was this kid called Bryan White. And he used to come out with us to sell merch at our shows. He was terrible at it, he’d sleep through shows – we’d get back on the bus at the end of a show and he’d be asleep in a bunk having not sold anything! But when we lost our deal, this guy Bryan got his deal so we became his band and it was one of the greatest things that happened to us because Bryan blew up in the nineties. He won top new male vocalist at the ACM’s – he was like the hottest thing and suddenly we were playing arenas.

But I quickly realized that when you’re a sideman, you effectively work 75-minutes a day, and I can’t do that. I realized that, like the joke is, I’m not a good human being, I’m a good human doing!! I did help with some recording. Me, Bryan, and the other guitarist shared this crappy house together and we had this great ADAT recording rig. I’d just met my wife, who was a record rep out on the West Coast and I came back to the house one night pissed off because I wasn’t going to see her for a while. I get back and Bryan and Derek and a couple of the guys had written this great song and they were going to cut it in our kitchen. And there’s this complicated vocal part, so I jumped in to help engineer the song, and ultimately that song became a number one and I got an engineering credit to my name!

Anyway, I realized that being a sideman wasn’t cutting it and at the time our tour manager was leaving and I thought “Well, I could do that,” so I became tour manager and guitar player. And that’s the time that Kyle and I originally met on the road, around ’97. Kyle was with the Vince Gill tour and we were rehearsing in Lake Charles Louisiana because there was this little 8500 seat arena and we cut a deal for the Bryan White and Vince Gill tour that we could rehearse there for a week if we would do opening night. We were assigned an office together and, first of all, Kyle is there and he’s like the more of everything guy……. He has this huge road case called Pizzatainment. You open the lid and this flat-screen TV rises up out of it and there are like two Lava Diablo lava lamps and a pizza oven.”

Kyle: “Wait, there’s kind of an evolution to this!! The year before I was working with a tour for Kraft Foods, and they had the DiGiorno Pizza brand so they sent us all these little pizza ovens like you’d see at a little bar. I spoke to the company who made our normal road cases and asked whether they could make a case that would fit the ovens. I then also thought it would be great to get a TV fitted and, yes, it had lava lamps, a stereo system and the whole top was a cutting board. We’d be on tour and the Kraft people would come and drop off like a hundred pizzas and the guys at the venue would ask, “What are you going to do with that?” and, I’d be like, “Just watch!!!” And we’d be at the Pizzatainment case rocking out to Led Zeppelin and eating pizza, wondering why we were twenty pounds heavier at the end of a tour….”

Brinson: “But the reason we started working together (outside of Pizzatainment) was that we’d overhear each other on the phone. I’d hear Kyle on the phone saying something like, “So you need a G3 jet with Bacharach crystal and albino Alpaca by tomorrow??? Alright………” And we both realized – you’re that guy too – we have to make money off this!”

As Kyle and Brinson became a little disillusioned in their respective roles it became clear to them that they should be working together and as a result 262 Five came into being.   

Kyle: “It wasn’t like we met and, boom, the next day we started a business. I was still at GMR and Brinson was still on the road.   It was an evolution.”

LH: Oh, so you continued playing guitar for a while?
Brinson: “I kept playing guitar through around 2001.  But the moment I knew I didn’t want to really be playing was, I think, New Year’s Eve, ’98. We were at the Target Center Minneapolis on a tour with Bryan and LeAnn Rimes and the promoter was a scumbag…. I’ll not name names. And I knew that there would be unmanifested seats in the arena, I just knew it. So where’s the best view of the seats? From the stage! And we were in the middle of our show in front of 17,000 people and I found myself counting seats getting ready for settlement. There was 20 seconds or so when I was just zoned out and, thankfully, we’d done our show like seven billion times so you have muscle memory. But there’s a moment when you snap out of it and you realize that’s not right. You know, I love music and I love playing guitar but I don’t love it as much, or in the same way, as these other guys. We would get on a bus after a show and the guys would get guitars out and I’d be thinking – what are you doing that for? We play like the same 14 songs every night!? And it brought home that these guys had a passion for music that I maybe didn’t have.”
Kyle: “You put it much more eloquently than me. I always remember there was a Far Side cartoon and there’s a trainer with three bears and he’s whipping one of the bears. The two others are stood waiting to be whipped and one has its muzzle in its paws and is saying to the other “you know these come right off?”  I’m not saying I hated what I was doing, we both had great times doing what we did, but it felt like we were a little like the bears, standing there waiting to be whipped! We just realized that we can do this and we can do it better than the people we’re doing it for. We can serve our clients better, serve our artists better and we were just like, hey, we’re ready to go. We started doing bits and pieces in 2001 but in 2003 we fully jumped in.”

LH: So, our understanding is that 262 Five is a full-service event production and entertainment company. Do you typically provide an end-to-end service for your clients, arranging events from start to finish?
Kyle: “We can do as much or as little as the client needs. A good example is the thing we did for Sparkle Paper Towels where they were doing a hometown concert award, folksy event with Lee Ann Womack and they wanted us to come in and we just effectively acted as part of their agency. We did that with AARP as like a virtual agency. We were on the Mall at DC and it was effectively like organizing a concert. We coordinated satellite uplinks with a sister event that was going on in New York the same day.”

262 Five were also the business that Netflix chose to work with when it wanted to stage the 70th-anniversary reimagining of The Wizard of Oz in Central Park. The artists involved in the event included Jennifer Hudson, Julianne Hough, and Questlove & The Roots were the house band. The event was Post 9/11 and it was during UN week so it was necessary to coordinate with the Secret Service and the NY Police. 

Kyle: “For that one, we did everything from ground transportation, artists acquisition, venue acquisition,
production, client logistics, artist rehearsals, security, and artist hotels. We have relationships with a couple of people in the NYPD who we worked with but we also had to coordinate with the Secret Service people to arrange for transport of talent to the show in Central Park as it was UN week in New York City and dozens of diplomatic motorcades and everything was crazy on the streets. We really are able to do just about anything our clients need. From a production side of things, it’s a very small world and our reputation is very good. We use good people that we trust, who we want to work with and they want to work with us. I’m not saying that we’re the greatest or anything but you’ve talked with us tonight, we like to have fun, we like taking care of people and we do a great job. You’re not allowed many f*ck ups in this business, maybe one or two, if it’s out of your control due to the weather or something, so you have to work hard to build a good reputation.”
Brinson: “Doing The Wizard of Oz show was great but there were a lot of challenges in the post 9/11 world. That is the fun part to us. We had The Roots as our house band and they were re-imagining the soundtrack so we were in the studio with Questlove and Jennifer Hudson and all these different artists which is fantastic. And the client goes this is amazing but…… we want to land a hot air balloon in Central Park. And we just go “ok” and then you have to figure it out. This business is relationship-based and we talk to people who know about what we need to do to make this happen fast and then we get it done.”
Kyle: “For that one, our head of security who does stuff with us nationwide had to take a propane gas course for the City to approve. He had to get certified in dispensing propane gas. And he worked really hard and went off and studied and we landed a balloon in Central Park!”
Brinson: “We also had to get The Roots from filming the Tonight Show that afternoon over to Central Park in time for the start of the show because there was a strict curfew at 11pm. You know you have people at a show who hear the sound and see the lights and think wow – and that’s not even the hard part!!  It’s all these other things that are the challenge but that’s also the fun part to us and that’s what the client pays for. There are all kinds of production companies who can do the lights and sound but we pride ourselves on the hard stuff. You know – the client’s writing a check and that’s coming out of someone’s pocket and we never discount the importance of that.”

LH: So how do you identify musicians to work with for particular events. Do you have typical go-to people who are easy to work with?
Brinson: “Well, we have 262 Five and we have The Collective which is our artist management side. So we’ve done it long enough now, our relationships are on two levels. We have relationships with the agencies and the agents and with the artists themselves. And actually, we have MGC which is a sports and branding agency. As Kyle says, we’re players coaches so we take care of our corporate client but it’s very important to us that we also take care of the artist. We want them to have the most fun and have a great time.”
Kyle: “Not to the detriment of the client, of course, but we want to make it a great experience for everyone. Brinson can tell you a story about when we had to handle a difficult artist to make sure they delivered on what was promised to our client.”
Brinson: “We arrange for Mr X (a very famous musician who shall remain anonymous for the purpose of the article) to perform and do a meet and greet for one of our clients and the meet and greet actually included a very sick kid. You know, this guy’s a recovering alcoholic/addict/everything and he was having a bad day and we respect that but, honestly, that’s not our problem!  His tour manager is a lovely guy and we try to make everything as painless as possible for the artist. Where do you want to do the meet and greet, when do you want to do it – all that stuff. So his tour manager says he’ll do it right after the show, he’ll walk off stage and do it in the backstage area.

So anyway, he’s having a bad day, he plays four songs before even acknowledging the audience and then calls them by the name of a competitor! He then walks off stage after the show, right past the meet and greet and onto the bus. So his tour manager comes over to me and says, “He’s not doing the meet and greet” and I say “Well, then we have a problem” and he says “Because you have the check and you’re not going to give it to me are you?” and I say, “No, I’m not!” So anyway he heads back to the bus and it starts to pull away, then the brake lights go on and it reverses. We’re still sitting in the same place and the tour manager comes back and says, “He would like to do the meet and greet!”
Kyle: “Ultimately, our goal is just to make everything as easy as possible for both the client and also the artist. And that is why we get business, it’s why Brinson is also so heavily involved in the artist management and why I’ve been asked to be a tour manager for a few of the artists who we’ve worked with.”

There were, quite honestly, too many fantastic stories recounted during our discussion to include in full here but some of Kyle and Brinson’s other highlights included:

  • Working with Netflix to stage a screening of Field of Dreams and a live show with Kevin Costner and his band at the location where the movie was filmed. The movie was a really important one to Kyle and getting to work at that location and eat in the town nearby with the locals was a really special experience for him (though the local Sheriff threatened to shoot him if he cried on the field during the movie!). The stage was set up on centerfield alongside a huge inflatable Netflix envelope and the event was a huge success. Netflix subsequently decided to make it an ongoing thing. They would bring the lead actor of an iconic movie back to the filming location, and that actor would perform with their band. It was called Live On Location and over a two year period, 262 Five worked on Live on Location events with the Bacon Brothers, Dennis Quaid, and Bruce Willis, to name just a few. 
  • Flock of Seagulls requesting one cheese pizza and a pint of vodka on their rider and Brinson feeling so bad for them that he increased it to five cheese pizzas and a liter of premium vodka along with a liter of whiskey and other spirits (again acting as player-coaches for the musicians they work with!).
  • Booking Judith Hill for an event, helping her out of a bind on the night of the performance by getting her the insurance she needed to perform at the event and ultimately picking her up as a management client.
  • The time Vintage Trouble’s management asked for their help getting them from their performance on the Letterman show which finished at 6pm, to the venue two hours away at that time of day in New Jersey where they were opening for The Who…… by 7pm. Using their contacts in New York, Kyle and Brinson worked with members of Doc McGhee’s team (Vintage Trouble’s management company) to “make it work.” After working their magic, the band left Letterman’s show and were on their way at full speed, with a police escort and, at times, the wrong way down one-way streets. They made it to the venue in an incredible 20 minutes with time to spare! 

It has to be said that this was probably the most enjoyable interview we’ve done at Loud Hailer so far. Our discussion ran to well over three hours and involved the consumption of more alcohol than any professional interview should!! Hopefully, what clearly shines through above is just how much Kyle and Brinson seem to genuinely love what they do and how important it is to them to properly look after their clients and the musicians they book. It’s an attitude that’s clearly borne from a genuine love of music and an understanding (gained through experience) of what is involved in putting on a great show.  

So,  if you ever find yourself in the position where (for example) you want to parachute a couple of live lions and a gorilla into Chicago for a Jungle Book musical but are being told it’s not possible, just remember there’s a couple of guys at 262 Five who might be able to help. Not only that, but they’ll probably enjoy themselves doing it!   

262 FIVE LTD.
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About Phil Walton 32 Articles
Phil grew up in the UK and loved listening to and playing music from a young age. He moved from the UK to Chicago in 2011, falling in love with the city and its music scene. He enjoys nothing better than spending time with musicians, whether it be watching them perform, talking to them for the website or reading their autobiographies.

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