ROADSIDE ATTRACTIONS: Tech Bros, Tequila, and Looking for the Life of the Party

I’ve played shows on sheep farms, in backyards, rodeo grounds, living rooms, gas stations, empty bars, on open flatbed trailers, and in small caves. I’ve also played shows in beautiful churches, fancy music halls, big festivals, in slightly nicer living rooms, on top of mountains, and, one time, a castle. The longer I’ve been a “professional musician” the more the line between a good gig and a bad gig is blurry. Nothing will ever be perfect, so it’s best to just enjoy what you can in any given situation. Being able to enjoy yourself comes in handy a lot when working in such an unpredictable profession.

I was hired by a Bay Area-based band that I’m not sure would want to be named in this story. They wrote a lot of original songs influenced by folk, bluegrass, and gypsy jazz music. Their sound used to be more traditional, but they had started to add drums and more electric instruments to their songs. It seemed like they would hire me to play mandolin when they had a gig that required them to sound more like a bluegrass band. I really enjoyed their music and was excited whenever I had a chance to play with them.

I had done some shows and even a tour with them, but the most memorable gig was this one-off party. They had recently funded an album using Kickstarter and offered a private concert as one of the perks. In this case, the person who donated wanted us to play for his housewarming party.

This sounded pretty innocuous. I’ve played many random house parties in my day. But, as I would soon find out, this wasn’t a normal house or party. At least not by my standards. The owner had made a large amount of money creating a social media platform, selling it shortly before it began to fail, buying it back at a lower price, fixing it up, and selling it once more before its ultimate demise.

We drove north of the city through the hills of Sonoma, past vineyard after vineyard, until we finally crested the hill that revealed the valley the home was built in. This “house” was an enormous mansion situated on a large, manmade lake. If I knew more about architecture I’d be able to describe the style better than just saying “fancy,” but I thought it looked a lot like if Jay Gatsby built a Southern plantation-style mansion and then moved it to Northern California for some reason.

We were set to play in a nearby meadow that was also where the chill-out teepees and one of the half-dozen open bars were situated. We played really early, around 4:30, if I recall. This was before anybody really showed up, so we played to essentially no one for an hour and then we were just free to be at this party.

The Great Gatsby vibes continued as we found out that the attendees were mostly rich try-hards from the tech industry (Gatsby definitely would have been a tech bro if the story took place in 2019). Not even a hot tub and free mixed drinks could make someone’s pitch about their tech start-up less grating. The theme was, loosely, the Wild West, so many of the guests wore cowboy hats and vests while they walked around ordering free food and Old-Fashioneds (there was an open whiskey bar) from the Western-themed food court options: Chinese or Mexican. (Racist? Historically accurate? Delicious? All of the above?)

There was a weirdly sexual theme to the party as well. The food court also had a cartoonish “peep show” in the form of a wooden wall with some small holes drilled into it. Behind it sat two women, just sitting and chatting with each other, naked all night. The host had also hired a traveling circus to perform. The ring leader had built a nifty portable stage out of an old-model truck (again, I don’t know the names of things that aren’t mandolins). The troupe was made up of comedians, magicians, musicians, and a group of women dancers who did belly dancing, silk dancing, and burlesque.

As the night went on, I began to question my feelings about the situation. I was conflicted by how much I wanted to enjoy this display of extravagance far beyond what I was accustomed to, but I couldn’t help but feel like an outsider. As per usual, I was probably 10 to 20 years younger than most of the people there. It was like being invisible. I could still enjoy the liquor and the hot tub and the paddleboarding but they were solitary activities. Music, which seemed to be more of a decoration here than anything, was my only tie to this event, and because I wasn’t even a full-time member of this band, that connection was tenuous at best. Music was also my only way to really connect with people and since we were not a prominent part of the party, I felt the panging insecurity of wondering if I would have been more welcomed if I just wasn’t so shy.

Around 2 a.m., all of the bartenders were let off duty, leaving behind all of the prepaid liquor. Shortly after their departure, clothing became much more optional than before. At this point, we had decided to just stay up all night and someone would drive me to the airport in the morning. As the sun rose, we loaded up as many handles of tequila as we could fit into the mic bag and hit the road. I promptly passed out, leaving the driver alone to fend off sleep. Based on his account of how hard that was, I’m glad I was asleep for it.

I stood on the airport departures curb saying my goodbyes as I wrapped a handle of tequila and two bottles of whiskey in my dirty clothes and hoped they wouldn’t break in my checked luggage. My bottles survived the trip but the band later found out that storing mics and tequila together is a bad idea.

Perhaps I stole the liquor as an extra payment to myself for what I thought I didn’t get out of this gig. That might not have been fair of me because, after all, I was paid well and the show was done as thanks for a donation. Validation isn’t part of my contract. But as someone who is insecure and has trouble talking to people, music is my way in. I found that I was disappointed with my inability to connect with anyone there. I had been able to keep myself entertained but not satisfied.