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From six figures and a house to a futon and food stamps

My first experience at an open mic was at twenty years old in New York City. I let my aunt come with me. My first bit was something about going through the five stages of grief when you stub your toe. I was embarrassed to give my full name of Dennison Sleeper fearing it would be too noticeable so I just went with ‘Dennison’. When the host pulled my name from the bucket I said something like ‘first name only, just like Seal’ to which she very reasonably responded annoyed ‘that’s what you wrote.’

I spent a summer in NYC on my aunts couch in her studio apartment that she kindly bought an AC unit for. I had won a school award for an opinion section of mine in the school newspaper called ‘Between the Sheets’ (I didn’t name it) which was focused on sexual health and education. Mostly I used it as an excuse to write things I thought were funny. A professor that was far more eloquent than I took offense and lampooned me in a letter she sent to the editor, intimating that I had a small dick. I guess she was my first heckler.

My aunt had some connections at the Post and Times and I went to find out more about the wild world of journalism. When I toured the NYT building, this must have been in 2012, the journalist took me to an empty floor of cubicles. He was a caricature. Older, gravely voice, lined face, tough talk. Probably had a bottle of Jameson in the top drawer of his legal-pad strewn desk. He took me to that empty floor of cubicles and said with a wide gesture:

“You see this? That’s the future of journalism.”

I ended up dropping the degree.

My other goal was to try out standup comedy. I had spent months watching specials, reading books, analyzing comics, and taking notes. I had also spent the first two years of college failing classes, living in a dilapidated (I cannot stress that word enough) fraternity house that was on probation, and abusing copious amounts of drugs and alcohol.

So it’s no surprise that my goal didn’t adjust too heavily when I was in NYC.

I attended improv and standup classes and was supposed to attend a few open mics a week. But I was nervous. I was always nervous about things I might be good at. What I was really good at was self-sabotage. So I spent most of my free time that summer working out, finding places that would let me drink, and playing League of Legends on my laptop.

I performed on a bringer at the end of that summer. For those unfamiliar, bringer shows are a predatory right of passage for new comics that promise to ‘bring a real audience’ which is actually composed of friends and family of every comic that suckered them into paying for a $25 ticket and two drink minimum. The reward on the lowest end is cash or stage time. On the highest, being passed at a club. The booker determines who wins.

Nowadays bringers usually provide a high-quality tape with the background behind you so you can show the world on social media that you’re an honest-to-god comedian with a unique take on why dating is so weird and whether or not the audience met on the apps.

Eleven years ago there was no taping. There was no club booker, either. Just some guy named Aaron who is now doing NFT’s and Web3 projects on LinkedIn (no joke.)

Eleven years ago, this club off West 9th on West 53rd, a few blocks from where I stayed, was called the World Comedy Club.

Eleven years later, when I did a second bringer there, it was called Broadway Comedy Club.

With barely a handful of open mics under my belt I sat in the green room which was, and still is, an area next to the bar, in a hallway past the bathrooms, where frustrated waitstaff corral comics into a square of chairs as they sprint back and forward to fulfill the stream of two drink minimums.

I lied to the bartender and said I was 21 and they didn’t check which was great because I was nervous as hell and needed all the rum and diet coke I could get which was my drink at the time. Sailor Jerry and diet coke. The previous Halloween I went as Sailor Jerry for our fraternity party and drank an entire fifth of the namesake. That’s about all I remember about that story. That’s about all I remember of most stories in college. A few months later one of my best friends from high school would visit me to get a drink. She would order a whiskey on the rocks after I ordered my mix. She shot that straight. I never ordered a rum and coke again.

My five minute set was mostly divided into two jokes. One was about porn having a share button, the other was about me looking like a lesbian. That one killed. I placed in the top three based on an audience decibel meter that registered laughter. The person who came in first brought a couple dozen people to the show. I brought my aunt and four of her extremely kind and very sober friends, who frustrated the bar staff with double orders of soda. I like to think they sat far from the decibel meter.

I called my parents to update them after the show, elated. The guy who ran it, Mr. NFT nowadays, told me he would get me five minutes a week if I stuck around. At that point in my life, it may have been the most excited I had ever felt.

I had to seriously consider if I would go back to college. Certainly nobody was pushing me to stay on the path to standup comedy. And I didn’t see a future in sleeping on my ends couch in her apartment living room, the couch that had armrests that opened up to sleep on because it was too small for it to fold open into a bed.

I thought I would go back to Ohio and finish college. I would keep doing standup around Columbus. Then, after graduating, I would go back to NYC, and I would make this my career. A writer and a comedian.

I thought I was old for 20. I had gone to treatment centers for fourteen months of my life as a teenager. I had near-death experiences from drugs. I had flirted with suicide. I had been to impossibly dark depths for a suburban kid. I thought this would make me a successful comedian.

When people dwell on the past they say things like;

“I could have been a _____ if only I _____”

“I should have married _____ except I was ____”

And I like to respond that no, you couldn’t. You never could have. You couldn’t have done that because you weren’t that person at that time. The version that you were took the actions you did and that’s that. You only think you could be a lawyer now because you had to go through the pain of not achieving it. You never could have asked Mary to the dance because you weren’t courageous at that time. It took years of regret and growth to get there.

So when I think about the fact that I abandoned comedy for a decade, abandoned writing, abandoned my dreams, shelved them all for any other possible road, harmed myself with abusive choices, substances, people, everything I could- I don’t say;

“I could have been a comedian. I should have started then. I should have stuck with it.”

I say:

“I’m a comedian now”

Because that’s all one can do. Make a choice now and stick with it. As the saying goes;

“What’s the best time to plant a tree?”

Ten years later and I had lost just about everything other than my amazing friends and family. They are the reason I’ve been able to press on for so long in spite of myself. And I think about them every day.

I was living at home temporarily figuring out my next move. I had just left the only relationship I took seriously and took this way too seriously because I thought it would be a fix. A rock to anchor myself too. I moved in as we were long distance. It didn’t last three months. The entire situation was miserable.

I was making a comfortable six figures at a high stress tech startup and focused on that. This was the only job I had taken seriously. The previous ones you can sort of read about here. A weird underground cannabis business that became sort of a cult and sort of a scam. Then some strange tech company that was also sort of fake and then the owner went missing until he was found dead. I had tried to be the entrepreneur. Tried to be the grad student. Tried to be the picket fence painting, dog walking, 9-5 family man. And I had failed at absolutely everything.

When this last job let me go the CEO said something akin to:

“You know we kept you around because we liked you, right?”

Of course I did. I had a job because I was good with people. I was funny. I made people laugh and feel at ease.

What I was bad at was everything else.

I didn’t pay attention to the contracts I was sending or the quotes I was providing. I lost us money on deals. I forgot to send follow ups. I didn’t wrap my head around industry trends. I didn’t go the extra mile. I just didn’t really care.

I never did.

I ask friends who are in a tough spot the ten million dollar question (formerly one million but adjusted for inflation):

If you had ten million dollars tomorrow, what would you do?

Get the obvious out of the way. Pay debts, buy mom and dad something, fix this etc. Ok so you still have like nine million left. Now what?

What job do you do, if any? Where do you go? Who do you see? What do you do? Who do you become?

My answer? I just wanted a deep breath.

I had been white-knuckling life for years. I had been in pain for years. I just wanted some space. I wanted to rent a cabin in the woods for a few weeks with no internet and write. Write about what? I don’t know. Just write.

Before losing that job I had said, if I ever got fired, I wasn’t doing anything like it again. I was out of the corporate world. I didn’t care. I would find something else.

With some money saved up I traveled. I spent time with friends in different states. That same friend who shot whiskey in front of me years ago, who switched me overnight into a whiskey drinker, went with me to Zion national park. I went to a music festival. Camping. I ate mushrooms and stared at a tent ceiling and decided that I was going to do it finally. I couldn’t let it eat at me any more. I was going back to NYC to do standup. 

It feels odd to say I took ten years off because standup never left my mind. Part of me never got on that plane ride back to Ohio with me. I picked right back up with it the moment I returned. In fact, one of the first jokes I wrote, the first that landed, stole heavily from the ones I had written ten years prior.

I bought a one-way ticket to New York with the plan of staying for a week, more if things went well. I was shit at staying committed to a task. So my thought was that, I would do at least one open mic a day for seven days. If I couldn’t, then there was no reason to stay. And if I could but I really sucked, then there was no reason to think of standup ever again. 

This latter event is kind of what I hoped for. That I would be so terrible I could write it off in my head as an option. Go back to Ohio, get a rental in Columbus near my friends. Find a lower stress job. Write in my spare time. Meet a girl. Go gently into that good night. 

I landed at 8pm and got to a mic by 9pm. I went to two that night. Then I got drunk. I went to eight mics that week, and drank at most.

It turned out I didn’t suck, but I also wasn’t good. So I stuck around. I scheduled that bringer again. Same place, same time, ten years later. I would end up doing good there, but not great. So I was given spots. Nine in total over the next six months. 

A month turned into three and then into eight. 

A lot happens during this but, damn, if this blog isn’t already an overly long boring piece of shit.

How it relates to the tour:

I wasn’t sure I wanted to be in NYC forever doing comedy. I turned 31 during this time. I had great friends in many places and none of them were NYC. I had (and still have) no job and my savings were drying up rapidly. There were more comics than had ever been and I was battling with performers many years younger than me with many thousands of social media followers more which was something I didn’t anticipate being so important. I didn’t do skits, or TikToks, hell I barely had any social media presence at all. Unless I really impressed someone I would be in New York scraping by for years, hoping to get noticed, hoping to make enough to make this a career before 35.

I considered what advantages I had over others in the scene. I wasn’t as funny, naturally talented, young, etc.

What I had was a miserable shitload of life experience that made me adaptable. I loved to travel, I loved meeting people and was good at making them comfortable. I had no attachments to NYC and nothing to lose. 

So I came up with the idea for the NoSleepTour; living in the back of a car, traveling the country, meeting people, filming and interviewing, and doing spots along the way. Part podcast, part documentary, part comedy tour, all an excuse to not return to a real life.

It was a blast but a shitshow and ended up with far less footage than I hoped and far more debt. A story for another day.

It also provided the greatest moment of my entire life, and will forever be so- meeting Liza. Also, a story for another day.

Liza had only been in the US for about a year and all of it was spent in Los Angeles, and she was burnt out. I was burnt out by New York. The first few times we hung out, during our absolutely endless hours of conversation, she talked about wanting to travel the country and see what was out there. I desperately wanted to get back on the road. Our chemistry was undeniable. I had never met someone with such a fierce combination of intelligence, humor, insight, and inquisitiveness. With her unique take on a foreign country and eye for photography, and my…jokes about substance abuse, InsertTownHere was born. 

At the time of writing this we are near Charlotte, North Carolina, and spent all of August in San Luis Obispo. Most of September was spent in my hometown near Cleveland, Ohio, shopping for cars, stressing over our travel plans, and waiting on a lackluster MRI for my knee (patellar tendinitis). 

At the time of writing this, we are still stressed.

Money is an issue. Time is an issue. Stability is an issue. All the things you sacrifice when you dedicate yourselves to a passion project like this.

And nothing is guaranteed.

For all I know in six months, this article will have ten views. Our YouTube page will be dormant. I will once again be sending out contracts after Zoom calls with clients albeit with far more scrutiny this time.

And maybe in six months we will want to say;

“We should’ve done it this way and gone to _____ and interviewed _____ and-”

And it wouldn’t have mattered. Because in the moment we are doing what we love, with the people we want to, when we want to, where we want to. We are producing art we care about with real stories and real people and real heart. 

Anyways we’re real fucking broke that’s the point of the story didn’t you enjoy how heartfelt it got jeez find those social media links follow and Venmo us or Liza has to post feet pics but they’re just gonna be mine anyways as a social experiment.

Love,

Dennison