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Illustrations by Mike Force

Why I Fired Myself from the Company I Founded

This isn’t the typical CEO eulogy.

Michael Gaston
Mar 20, 2020 · 13 min read

How do you explain to someone that you no longer want to be the CEO of the company you founded? How do you even admit it to yourself? For the last couple of months I’ve been doing a lot of practicing:

Eating lunch with my board, I blurted out, “I don’t want to be CEO.” They nodded their heads gravely as they chewed their shawarma.

“I’m dying.” I told my co-founders over dinner. They paused for a punchline. “And next week I’m no longer going to be the CEO at Cut.” They looked concerned. “I’m not actually dying. I just wanted to soften the blow.” We had just come off our best month at the end of our best year.

“You’re not dying?”


“Well I’m glad you’re not dying.”

I nodded my head. Well, we’re all dying. I thought. But now’s not the time to be pedantic.

Most recently, I explained what was happening in an impromptu all hands meeting while Bryan Adams’s Heaven played over our SONOS. Afterwards, we had tacos from Barrio Luchador.

I was driving into work the other day when whatever algorithm-arranging playlist on 94.1 The Sound did the math and spit out Uncle Kracker’s cover of Drift Away. I’ve been a zombie for weeks. Or at least that’s my excuse. Because I can’t say I’ve ever purposefully listened to Uncle Kracker. Or know anyone who has. Or would desire to. But pop songs have a gift for tickling the truth out of a cliche, and as it played I started to sing along. To Uncle Kracker. This is how I mourn. In a 2013 Mazda singing off-key to soft adult contemporary music. I wish I had been ugly crying and belting it out. It would make a better story.

I started with a couple of friends in October 2014. We quickly developed an imagination within our industry for making repeatable, viral video formats. In our first month we were flooded with offers of investment and purchase. Our inaugural video, Grandmas Smoking Weed for the First Time, found us on TMZ and an interview in the Wall Street Journal. Our series 100 Years of Beauty inspired hundreds of imitators. Celebrities from Zooey Deschanel to Kendrick Lamar shared our work. Even though we thought of ourselves as tiny in the heart of tall grasses, our work left a big impression on our contemporaries. Within months, our aesthetic and concepts became the best practices for a rash of huge or rapidly growing media companies.

Today, we find ourselves in the enviable position of profound growth while many of the companies that were courting us are gone. Most of that is just luck. But I like to think some of it’s because of our values, the discipline to our plan, the incredible team we’ve cultivated, and our resistance to what we see as fleeting industry trends. Still, entrepreneurs are unreliable narrators. So here are some facts about Cut: all of our views are organic; we’ve only had to raise once; a significant portion of revenue comes directly from our audience; we’ve been profitable for the last two years; and if we had achieved 100% YOY growth from our first year to now, we would’ve made $1M less than what we actually made last year. So then here I am. The Founder and CEO of a growing, profitable media company.

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My son called me into his room the other night. He told me he couldn’t sleep. His mind was racing. “What’s wrong?” I asked.

“I can’t stop thinking about how in 500 million years, the sun will turn into a red giant and burn everything on Earth.” He’s six. My instinct was to tell him it was more like 4 billion years, and we’d all be dead way before then anyway. I started to, but my wife gave me a look. We tried to comfort him. He appeared unconvinced. The next night he brought it up again. This time, I told him, “That’s a long time from now. We’ll all be dead way before then.”

“Really?” he asked.

“Really.” I said.

His body untensed. He smiled. I had brought him some comfort. Now, as he climbs up to his bunk bed, he gleefully announces, “In 4 billion years, the sun will turn into a red giant and burn the earth! But it’s okay, because we’ll be dead way before then!” It’s a weird mantra. Then again, people teach children a prayer about dying before they wake, so who am I to poo poo his rituals?

My son is a lot like me. As a child I was scared of everything. Giant world-altering threats (the heat death of the universe) and mundane social situations (a surprise birthday party in middle school). But no one knew that. To my family and the rest of the world I was an extrovert. Bold, even risk-seeking. No one knew I had made a rule for myself―to ignore my instincts. I had decided to do whatever scared me. Even now, it doesn’t matter what it is, I have to do it. Sometimes the rule works out in my favor like when I dropped out of school and apprenticed with a poet in Ireland. Sometimes it doesn’t. Like a couple of years later, when I claimed bankruptcy after trying to make a for-profit poetry press.

As time passed, I stopped being so afraid. To some degree, I shaped myself into the person I was perceived to be. Occasionally though, when faced with something that scares me, my instinct is to confront it. It’s like an autoimmune response. My wife told me that it sounds like when I was a child I diagnosed myself with an anxiety disorder and prescribed immersion therapy. I like the way that sounds. It makes me seem more perceptive than I am.

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A couple years ago, I was flipping through a book. I was attempting to re-read Luis Francia’s The Eye of the Fish. When it suddenly popped into my head to ask myself how I’d feel if I was no longer with the company. The question was a sort of sneaky dare to myself. The kind of intrusive thought that invites you to jump when staring over a ledge. So I did. I peered over and was struck with vertigo. I was afraid to leave. I panicked. My stomach twisted into a knot and the instinct took over.

I put my book down and shook my head like I was trying to knock away a pest that was buzzing in my ear. And for the first time in years, I really tried to undo what I had trained into muscle memory. I thought of my family and friends. I thought of my investors and employees. I thought of what I would do and who I would be. Why was I afraid to leave? Because my identity had become tied to the company. It was like I had breathed life into a golem of myself and it looked like me and talked like me. It had status, and interacted with people out in the world who thought it was me. And sometimes (more and more over time), I mistook it for me. It was suffocating.

Fifteen years ago, I accepted a position at Boeing doing contract negotiation and supply chain management. I remember my first day and feeling like I had walked into a thick gray fog. Everything was the color of cigarette smoke. This is probably just a trick of memory. But if I close my eyes now and try to really picture it, everything is shades of gray, the cubicles, the endless stretches of concrete, even the workers — mostly older white men dressed in button-down short sleeve shirts, practiced in the art of casual misogyny. Boeing had done so many layoffs over the years that there was a major generation gap between people poised to retire and a new workforce just out of college. I was not a “culture fit” and that friction manifested into a chronic depression.

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A couple of years into my suicidal ideation, I made a music video for a friend’s band. I had never made a video before. To my friend’s surprise and mine, his label bought it and it ended up on MTV. That was all I needed. I opened up Boeing’s intranet and pressed a big red button in the upper left hand corner. Below the button it said: self-terminate. Seconds later I received a call from HR.

“Hello, is this Michael Gaston?”


“Hello Michael, this is Boeing Human Resources. We’ve just logged a request from your Total Access profile.”


“Did you mean to press the red button?”

“Uh huh.”

“It’s the big red button that says self-terminate.”


“Are you sure you want to terminate your employment?”

“I do.”


“That’s why I pressed the button.”

“You know once we start the process, it’s very hard to reverse it.”

“It’s reversible?”

“It’s very hard.”

“Why have a button, if it’s reversible?”

“Do you want to reverse it?”

“Not at this time.”



“What does that mean?”

“What does anything mean?”

“…Please return your badge, phone, credit card, laptop, and other confidential or proprietary information before the end of the week.”

The response from my friends and family was mostly positive. I was young and betting on myself. It wasn’t the safe thing to do. I no longer had a steady paycheck or health insurance. But it followed a familiar narrative arc: the creative that escapes the corporate world to take the grand risk. It’s a cliche, but it makes sense. What I’m doing now. This does not make sense to people. It barely makes sense to me. I’m the CEO of a company I founded. A creative company. Known for work I developed, conceived, or collaborated on.

A few months into starting Cut, I flew out to New York to take meetings with people and companies in the digital media space. I remember meeting up with Jonah Peretti at the Buzzfeed office. I caught him at a bad time. He was distracted by something that was pulling at his attention. Half the time I couldn’t tell if he was talking to me or to himself. He offered, unprompted:

“You don’t want to be a CEO. You want to make things. Being a CEO sucks. You’re constantly having to focus on things you don’t want to do.” He held up some envelopes.

“Like being sued. This is nonsense.” Not long after that I was sued over some nonsense. So, say what you will about Buzzfeed, Jonah Peretti is prescient.

Early days into Cut, my father-in-law told me that in his experience as a corporate lawyer, the difference between success and failure for a startup is the leadership’s ability to grow beyond themselves. I believe this. You can’t be a coder and CEO. Or in my case, a creative and a CEO. They are different jobs. The CEO has to shape the vision of the company, embody its values, model the behaviors. As the organization grows, your role becomes very strategic. You lead through influence. So much of what your job becomes is external facing or operational. And sometimes, it even requires a mediator to avoid litigation. Cut has been a thousand different companies over the years. And in order to survive that, I’ve had to become a thousand different versions of myself. I’m grateful for the lessons that I’ve learned. But I’m a different person today than I was when I started this company. Nearly six years and two thousand words later, I suppose that’s the point.

Last night, I was slacking back and forth about whatever this is (imagine hands gesturing at the computer screen) with Chan, Cut’s Director of Content. I hadn’t seen him in a few days. He’s been home recovering from surgery. I’ve missed his insight. After reading my draft, he asked me:

“Who is this reader that you want to reach? Is it an early career person? Somebody seduced by the myth of the great entrepreneur? Kindred anti-authoritarians? Because I think it becomes a different parable for all of them.”

“I don’t know, man. I just wrote this for me. This is old school live-journaling. A return to web 1.0.” He laughed his ass off in the internet fashion as we all do so effortlessly. Then he typed,

“Harry Braverman wrote about the ‘degradation of labor’ — capitalism demands that the infinite human potential for creativity is degraded so that it can be more efficient, compliant on the factory floor. I propose in my unpublished and unreadable dissertation, ‘upgraded labor’ — the illusion of creative work as an escape from that mechanization and extraction of labor; a cruel illusion because it promises autonomy yet always slightly out of reach.” This is how Chan writes convalescing at home, dizzy on Naproxen. I, completely sober, was reminded instead of Winnie the Pooh:

“Now then, Pooh,” said Christopher Robin, “where’s your boat?”

“I ought to say,” explained Pooh as they walked down to the shore of the island, “that it isn’t just an ordinary sort of boat. Sometimes it’s a Boat, and sometimes it’s more of an Accident. It all depends.”

“Depends on what?”

“On whether I’m on the top of it or underneath it.”

“I think you could have a picture of my face next to this paragraph.” I wrote back.

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I don’t think we’re taught to consider our position in relation to our Boat. On top or underneath, we’re only told to want more of it, especially when it’s an Accident.

This is one of the pathologies of the startup industry (and capitalism in general) — how we’ve been conditioned to believe that we should always want more. We should want to achieve more, to have more money, more status, more power. No matter the cost. No matter how our actions alienate us from each other, our work, and ourselves. Even worse is the expectation that we should want to want more of any of these things. Our modern narratives are myth-making examples of people who took more. There are whole industries and experts devoted to instructing us in new and more efficient means of acquiring more. And if somehow you free yourself from underneath all this more, you confuse the freedom for loss. At least, I have. But I don’t want that anymore. What I want is precise. I want to be a hands-on creative again. I want to pursue projects outside of Cut without feeling guilty. I want to make work with integrity, to earn a living doing so, and to be present for my friends and family. What else is there? After all, the earth may survive for another four billion years, but we’re all going to be dead way before then.

Today, I caught up with a friend of mine, Jake. Thirteen years ago, I made a music video for Jake’s band, Minus the Bear. It was the first video I ever made. It was also the piece that got me the job where I met the person who would back me into making Cut years later. A year ago, Jake’s band broke up. Now here we were. How symmetrical.

Over a lunch of breakfast foods and beer we shared our scars. Jake started to count on his fingers. “First it was awful. Then okay. Then pretty bad. Now it’s good and sometimes really boring. And bad again.” His phone rang.

“It’s my boss. I have a boss now. I have to take this.” He stood up and wandered over to a corner of the restaurant. A minute or so later he sat down.

“But I thought you wanted to break up the band for awhile.”

“I did.” He said, without hesitation or explanation.

“Are you happy?”

Jake paused and looked up at the ceiling. I couldn’t tell if he was searching for the right words or if I had introduced him to a question he hadn’t asked himself yet.

“What are you going to do?” I asked.

“I don’t know. I could write a children’s book. I have all these stories I tell the kids. I have one about a girl that has a backpack filled with beans and she has wings attached to the backpack. And if she eats enough beans her farts allow her to fly.” I nodded my head and agreed with him that it sounded promising. Kids do like farts.

He pointed to his shirt. It said Gig Harbor Audio. The logo was of a pentagram overlaid on top of a picture of the last supper.

“I thought I could open up a hi-fi shop, so I took a job at one a couple of days a week to see how it works. I used to wonder, how many customers are there really for hi fidelity audio systems that cost over $10,000? The answer is, not many.” He laughed.

“So, it’s a front.” I offered jokingly.

“Yeah, maybe.” He shrugged. “The owner does a lot of consulting work for Eastern European countries.” I pictured Jake as an unwitting accomplice to an international money laundering ring.

“But now Steph and I are talking about starting a kiwiberry farm.” He said it like a question. “I’m not even sure what a kiwiberry is. But apparently it’s a vine? Do you know about this? It’s a vine with berries, I guess? We could grow them in the San Juans where the climate is good for producing these ki-wi-berries…” each syllable then word tumbled out of his mouth individually in a way that seemed to surprise him. “…for the kiwiberry consumer? Whoever that is.”

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