Scenes from an Insurance Conference

Matthew Smith
6 min readOct 9, 2022

Sitting on a stool in Robert's Western World, a honky tonk in downtown Nashville. One wall is lined with shelves of well-worn boots, making it look like a vintage western wear store. Behind the bar, to the other side, a short-order chef slings diner-style greasy burgers and crinkle fries off a well-seasoned flat-top griddle.

Chris Casello's three-piece rockabilly band slides between the Jimi Hendrix Experience and Johnny Cash. He starts playing Yakety Sax with an over-the-top grip on the fret I've never seen done before. This is what I'd hoped for after leaving the Jason Aldean impersonator across the street.

The guy at the high top next to me is digging it too. He says he recently moved to Salt Lake for the skiing (and his girlfriend second). He pulls out his phone and scrolls to a picture of the couple at a house party in Billings. Over their shoulder, John Mayer is playing guitar and belting out a ballad. My new friend says Dave Chappelle did the next set after Mayer but told the audience,

No recording! I'm getting f'ed up tonight.

I spot a man about my height in his late twenties standing by himself on the street. I recognize him from the conference. Earlier that day, he interrupted a conversation with a prospect to testify to the benefits of our software. I go over, say thanks, and we start talking. I can immediately tell he's on the Path.

I've made enough money to be comfortable. They never tell you growing up as a young black kid how much money there is in insurance. At first, I wanted to keep that secret to myself. Now, I know I need to create little versions of myself and help others succeed for me to take things to the next level.

We spend the next thirty minutes in esoteric discussion on living from the seat of consciousness, staying present while still planning, and remaining open to life's surprises. We part ways so we can both wander where the night leads.

My Uber back to the hotel has a package of hermetically sealed cheese curds sitting on the back seat when I crawl inside. I hand them back to the driver.

These yours?

Yeah, gottem from my last ride.

You often take tips in dairy products?

Don't look a gift cow in the udder.

He's got long dreadlocks and a head full of philosophical questions. He's eyeing the cheese curds with happy and hungry eyes while driving 45 mph on the freeway. I put two-and-two together.

What do you think of religion, man? Something tells me you're a guy who thinks about these things.

He glances back through the rearview to see if his read is correct.

I tell him the story of the blindfolded man led up to an elephant who misidentifies the different parts he feels: a palm tree (leg), a bowl (stomach) and a broom (tail).

Anyone can touch the elephant, but most people take other people's word for it. That's religion.

I'm short on cheddar, so I tip him in dollars.

The next day, my co-worker spots a vendor wearing an animal print suit in the exhibit hall.

What's the story behind the cheetah suit?

I sell companies fast…like a cheetah!

Oh, ok.

Well, that's my line, and I'm sticking to it.

An agent walks by wearing a styrofoam poop emoji hat. 💩 He's worn it at every conference for the last five years. A while back, I asked him about it.

What's the story with your hat?

I specialize in flood insurance. A couple of years back, I wore it at a conference. Got some laughs, so I brought it back. Everybody knows me as the poop emoji guy, so I have to stick with it. Helps me sell more insurance.

Humans are an interesting species. We would rather be remembered for anything than feel alone, unseen or forgotten. Sometimes it's hard to let go of old identities for something better, even if it means being known as a literal shithead.

Another man stops and introduces himself. Says he has five kids.

Five kids, huh? Impressive.

Yeah, I'm not Mormon or Catholic or nothing like that. My wife's just smoking hot. Let me show you something. It's a video of my son coming home from his first day of school.

*pulls out his phone*

"Hey, buddy! How was your day?"

"Fine, I guess. Just thought there would be more hotties."

"That's my boy!"

*Dad beams.*

A Will Ferrel impersonator stops to take a selfie doing his best Ricky Bobby in full NASCAR getup.

Shake…and…Bake!

*fist bump* *wink*

Last year, he was Buddy the Elf. The year before that, Ron Burgundy.

We pack up and take another Uber to dinner. This time it's a local farm-to-table joint. The driver is a former used car dealer. Says there's no money in used cars anymore. So, he sold all his commercial property, retired and moved back to TN from California for family and better quality of life.

A boat slip in Nashville costs $400. That same slip would run you $4,000/mo in California. I ask if he misses the natural beauty of California. He says he can boat all the way from the Tennessee River to the Gulf of Mexico via the Mississippi. That’s good enough for him.

Now, he earns $150k a year Ubering. It helps to keep him out of the bars. Says Nashville is the new, country Vegas. By his last count, there are two million Nashvillites (Nashvillians?). When he was a kid, there were no major skyscrapers. Churches and honky tonks were about as tall as buildings got. Now, forty-two highrises are going in downtown. The California exodus pushed all the $100,000 single-family homes upwards of $700–800,000.

A red-eye flight the next morning finds me walking out of the Grand Ole Opry convention center at 4:00 am. We spot a client from Georgia rolling in after a long night on Broadway. She's been scuttling around the conference on an electric scooter all week, but there's no way she can pull that off now. Insurance folk party like no other. Dierks Bentley told the crowd at the Opry he'd never seen those hallowed grounds look like a honky tonk until the insurance conference rolled into town.

I listen to a doctor on Instagram. He says drinking helps to down-regulate a highly evolved part of our brain, making it easier to temporarily access our primal brain. People in high-stress, high-pressure jobs–like insurance–use alcohol to escape. He says when you learn natural stress relief methods or remove the stressors altogether, alcohol loses its potency and benefits.

I drank a lot more when I was an agent or attended to real estate conventions. These days, my favorite state of mind is clear and well-rested (but I still tried the old-fashioned last night).

Wheels up. The sun's rays glint off the airplane wing. Fog hangs over the Cumberland River. It's no wonder so many storytellers call this place home.

A flight attendant breaks the silence over the intercom. Beverage service ceases. There's a medical emergency. They ask if there is a doctor onboard. A woman tried flying while still drunk, dehydrated and hungover. Lucky for her, a nurse lends a hand, and an ambulance meets her on the tarmac.

Sitting in the Des Moines Airport waiting for a ride, I jot down memories of my strange week in Nashville. I look up and hear Pauly Shore ask for directions.

Maybe it's not Tennessee. Maybe, it's just the times.

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Matthew Smith

Religion major turned real estate investor, tech company founder and food truck operator. Part-time adventurer, writer, full-time dad & loving husband.