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What Defector Staffers Learned From One Year Of Being Small Business Owners

Illsutration shows Applegath's Vertical Machine, a newspaper printing press, in operation, from an advertisement in the Printers' Register Supplement, 1870s. (Photo by Kean Collection/Getty Images)
Kean Collection/Getty Images

One year ago I bound myself, arm-in-arm, to 18 of the others who'd also walked off a job they loved, and we formed a new vertebra in the backbone of the American economy. We became small business owners.

Because of the absurdity of this transition, the eye-rolling reverence given to nebulously defined small business owners, and the straightforwardly modest ambitions of Defector, I began to occasionally amuse and regularly annoy those around me by referring to myself as a Small Business Owner. Getting my neighbor to take out the building's trash cans while I'm away? I am closing business deals. Teaching a new coworker about all of our moronic Slack jokes? I am a job creator. It was then and is now a good bit. The delta between what I do (post stories like "The Tennis Ball Hit Him In The Penis") and what the small business owner is imagined to do in the annals of the American Mindset (uphold our shared values of enterprise and self-sufficiency or whatever) is quite wide.

But in the time between when Tom Ley assigned me this blog and its publication today, something sweet happened and the irony-to-sincerity pipeline did its thing. Defector only works as well as what we put into it, and as silly as the bit that started this blog was, there is some meaningful reflection to be done about what it means to build something together. So here is what the staff of Defector learned from one year of practicing the success/deals business lifestyle.

Barry Petchesky

I have learned how much motivations matter. At the Old Site, your and all the other writers’ motivations were clearly to be a bunch of little blog gremlins making life difficult for me. Doing typos. Whining at all hours for edits. Refusing to learn how to use an en-dash. “Accidentally” spending $400 on a premium Getty photo when we only had the standard subscription, and “accidentally” doing it several times. But I got it. It sucks when the person or persons getting wealthy off our labor was a series of weirdo wannabe media titans/faceless corporations/evil dorks with bad hairpieces. We took pride in our work, but fundamentally we were the product, not the producers.

Now it’s all different, since nobody but us stands to gain or lose from the blogs being good or bad or $400 more expensive for a photo that quite frankly wasn’t all that much better than the regular ones on offer. And I think that shows, speaking in my role as editor. The blogs are thoughtful, because the writers care about their work. The blogs flow freely because even you goblins are smart enough to realize that readers want them. The blogs are unhinged, in a good way, because there’s no one to piss off but ourselves.

It sucks mondo ass that, in the media industry, there’s basically no paycheck that’s not ethically compromised in some way—except that’s not true! It’s not! We’re living proof that you can find a way to do the work only for yourself and for the readers, and because of that it becomes the most fulfilling work there is.

Maitreyi Anantharaman

I’m still surprised by how well this has gone, so I guess I’ve learned that small businesses really can be run humanely, democratically, and sustainably, all at once. At the same time, from Defector's initial challenges/expenses, I’ve learned that for a country so starry-eyed about entrepreneurship, we could make it way easier for small businesses to be run like cooperatives and not the unsafe, poor-paying despotisms they often are. Transitioning away from employer-provided health insurance to a universal public system is one idea that comes to mind. I expect this suggestion to be taken seriously now that I’m the most pandered-to person in American politics: the midwestern small business owner. Someone make Nuts and Gum next.

Ray Ratto

After a year of this great steaming nonsense, I can safely say that being one of lots of owner/operators definitely lacks the kind of fun-filled worker oppression we all imagined would come with being moguls. No mass layoffs over the phone, no changing the locks overnight, no salary or benefit cuts, no agitating against union organizers, no e-mails saying Employee X has been transferred to the Iqaluit office.

Frankly, it makes a body wonder when all the corporate hijinks we were promised is  supposed to start.

In truth, though, this is nothing like top-down America, where the intermediate goal is to stand on the skulls of one's enemies to get closer to the ultimate goal of standing on the heads of one's friends. This is more Crabwalk America, in which the forward motion is either side-to-side or slightly diagonal, and whatever hierarchy there is is responsible mostly for large-scale hamster-herding (like the Birthday Soiree) and turning 96-word sentence/thickets into 76-word sentence/rhododendrons (the day-to-day scythework). Indeed, if there are titles here (and ignore the masthead; that's just there for tax avoidance reasons), it is much closer to The Cat In The Hat than anything else. Comrade Ley would be Thing 1, Comrade Wang Thing 2, Comrade Anantharaman Thing 3 based on a rough alphabetical and experiential order though Thing 22 to cover the Original Quitters and vital add-ons, and finally Comrade Darling as Thing 24. There is a particular delight in that last one, as she sounds a lot like the name of a Blackadder character if only Rowan Atkinson had been born Russian.

(For the record, I am Thing 23 at least by my count, as I was a freelancer at the original slagpit and thus was neither harassed by the lizards of the old regime nor had the honor of walking off the job with my pitmates. I am thus more bullshevik than bolshevik).

In the year since, I have learned that when everyone has the same sized piece, a lot of the posturing of who gets to be and know and do more than whom vanishes. I have learned that having an office is better than a Zoom call because only an idiot would go out after work to have a pop with the laptop. I have learned that living 2,900 miles away from the home office (and most of the home officers) means I have physically met only three of the other Things (to be specific, Things 10, 18 and 22), so most of my fellow oppressors are technically strangers. And frankly, in the final  analysis aren't we all?

And yet I enjoy and trust almost all of them implicitly (the one shall go unnamed for potential psychological damage and intraorganizational resentment reasons), and I am acute aware that everyone is in this for the same correct reason. I mean, if some spaceman/billionaire wanted to offer us $700 million for the site we'd leap at it, but said billionaire would be buying us, since we are also the product as well as the owners, which means we'd be working for someone else which is where this hamster wheel to hell began. Only we'd be lots richer; I'd cheerfully refuse to work for a moron oppressor with $30 million in my pocket. I'm kind of a happy-go-lucky whore that way.

But I digress. I have not yet learned as much as I should about the business end of our little scam-o-matic, which is why it is good to have Thing 2 as our corporate eyes and ears, and the technological skills required to be a modern blogger, which covers Things 1, 3 through 5, 7 through 22 and 24. I am still learning how friendship works with strangers when they are living through massive floods while we are living through enormous lake-eating fires.

Mostly, though, I am learning how to have what passes for the time of my life. I work for and with smart people who don't spend all day every day trying to prove it, and knowing that we're all in it together all the way down to the paycheck provides a level of satisfaction that no other job ever has. There have been marriages and births and lots of brilliant words and pictures of boats and bridges and dogs and Ottawa Senators and Remembered Guys, just like a regular company, but with none of the backstabbing that makes corporate life worth living. In sum, you should have all Thing/companions/fellow  bastards this good at some time in your lives.

Though if you have $700 million burning a hole in your portfolio ...  well, talk to Things 1 and 2. We're always open to screwing the proletarian dream for our own acquisitive ends.

Kelsey McKinney

What I have learned in my one year as a job creator and entrepreneur is to conquer and comprehend my greatest business rival: the P&L statements. But in all honesty, I don't think I realized how vulnerable starting a company is. While there's a kind of terror in presenting something to the world and saying, "Here is this thing that I think is worth your money," it's much more terrifying to have people believe in you? That sounds stupid, but I am constantly terrified of not creating enough or not doing this well enough. I get really sappy when I think about all the people who gave us money in a terrible year to make this. I want to do right by them, and I really hope we are. 

Giri Nathan

I learned that if you are a small business owner you can just kind of decide to do things correctly. Even if there exist deeply entrenched norms in your industry that are crappy, you can choose to not make your own business not crappy in those respects. And then, even after months of waiting nervously, as if having cheated the universe, you will find that you did not suffer any consequences for making your business not crappy. The other shoe never drops.

Chris Thompson

I intended to spend a couple days thinking seriously about this question, perhaps staring off into the middle distance with a somber, contemplative look on my face while wearing a clean and comfy sweater or something. Then my infant child painted her entire upper body in hummus, taught herself to crawl and somehow to sprint-crawl, and discovered a new sound which can only be described as “pterodactyl caught in trash compactor,” which means that instead of thinking deeply in poses suited for Dark Web Intellectual Magazine I have spent the last three days in a kind of depraved and sleep-deprived lunatic euphoria. I need a shower and a shave as badly as any human ever has; my clothes are filthy and rank; my home looks like a bomb went off in a Kids-R-Us. I haven’t stopped laughing for 72 hours. 

What I have learned from becoming a thought leader in the small business job creation space is that the experience of having an extremely alive infant child is exactly as joyful and magical as your paycheck and health insurance will allow it to be. I can’t even bear to think what brand-new life would be like for this tiny wonderful person, trapped in a sagging country home with a panicking out-of-work blogger and all the attendant radiating self-loathing, had I not achieved this super-duper-earned and legitimate stature as a self-made entrepreneurial-style innovator. Now she is shrieking the word “BLAH” at one million decibels and flinging yogurt on the ceiling and cackling maniacally, and I have to go.

Jasper Wang

Given I am a dreaded Man With An MBA, I imagine most people will, correctly, ignore my contribution. So I'll direct my comments only at other business-y types.

Defector Media LLC was formed some 14 months ago, and launched two months later. In that time, the most important thing I have learned is that it’s possible. It’s possible to effectively and efficiently operate a small business with democratic governance, decentralized equity ownership, narrow salary ranges, and an explicit acknowledgement that the business has no assets but its workers. It's possible to embrace the collective, to teach anyone to read a P&L, to adjust your relationship with the profit motive from “as much as possible” to “enough,” to explain to your friends that yes, the corporate bylaws are such that two-thirds of your coworkers could band together to fire you at any time, but if you do get canned, it would probably have been just and deserved. It's possible to live your personal values professionally. Many people in the U.S. worker cooperative space—some of whom I’ve had the pleasure to be in touch with this past year—have long known all of this to be true, but I needed to live it to really believe it.

I'm not suggesting a worker cooperative is an appropriate structure for every group of people, at every business, at every size, in perpetuity (Defector could self-destruct tomorrow over a Slack fight about whether a very sweaty summer is worse than a very cold winter). But I have learned that business-y types like me and you—an illustrative but very real you, a person with a traditional corporate background, who routinely complains about "late-stage capitalism" and gave money to Elizabeth Warren and likes TikToks with this audio but just can't quite figure out how to get off the corporate treadmill yourself—can use our skills to help build a more ethical company and a kinder workplace that we can be proud of at the end of the day. Even on those days when my entire job consists of answering customer service emails and approving invoices, I feel a sense of pride and fulfillment that was previously not what I came to expect from my professional life.

I do not want to be (too) sanctimonious here. Before I left my job to help start Defector, I had a healthy savings account, no children, no sick family members, and a spouse who made more money than I did. I have lived a blessed life that allowed me to take a reasonable professional risk, and my next job may be back on the corporate track. Defector is not fighting child poverty or creating vaccines; my favorite blog this year was literally about fake farts. Many people may not even understand what I'm getting at, because they have what is frankly a much healthier attitude towards their careers and have no expectation of extracting meaning from their day jobs. But some of you reading this are suffering from a chronic professional malaise, hoping for something more fulfilling before you somehow get convinced to chase that next promotion.  And I am certain you could do something like this, too. I am certain that thousands of people, just on the island of Manhattan, would be able to do my job adequately. I just happened to be the one to raise my hand.

So to you MBA types, go ahead and root for me to get fired over, say, an unconscionable opinion about beets. In the meantime, read this book, buy this shirt, and keep your eyes open. Who knows when your (other) favorite small business may convert to a co-op and need someone to read the P&L.

Justin Ellis

I wish I had some Brené Brown knowledge darts to drop on this, but I don’t. And obviously if I did I’d want to save it for when I can monetize the hell out. But the thing I’ve realized in a year of doing this is you have to put as much effort and care into relationships with your people as you would put into “business shit.” You have to be able to be a little vulnerable with people and trust them to do the same with you.

Basically you have to say, “I will not fuck you over because this is as important to me as it is to you,” in 100 different big and small ways every day. I don’t know if that makes sense. But when you’re not an arm of some giant, established global conglomerate, you’re accountable in a different way? I came into Defector as the outsider, the Season 6 new cast member brought on to the old franchise. And I literally met all of my coworkers in person for the first time on the day we celebrated one year. But I would not feel as devoted to Defector’s success without all the time we all put into getting to know and take care of each other. I hope that makes sense?

Lauren Theisen

I learned that if someone asks you what you do for a living, it's very difficult to say "I own a website" without sounding like an asshole.

Kalyn Kahler

It's a better way! When I worked at Sports Illustrated, we had three ownership changes in the five years I was there. Time Inc, Meredith, ABG/Maven. Each time we were sold, things got progressively worse. The budget and the staff were decimated, it felt like we were constantly pivoting to video, and autoplay videos took over the site rendering it unreadable. I always knew I would get laid off, and eventually I did. Then I freelanced at Bleacher Report and a few days after signing a contract to do reported features for B/R Mag, almost the entire B/R Mag staff was laid off. I wasn't even on staff there and yet I still couldn't escape the layoff cycle! It was exhausting trying to keep up with constantly changing visions. I joined the Defector staff in February and working here has taught me that there really is a better way to run a media company. All the complaints I tallied over my career elsewhere just don't exist here because we set up committees to design exactly how we want the company to function. There are no layers of bureaucracy to fight through just to make a suggestion about the business. 

I have learned to train my brain to stop caring about traffic numbers and page views or how many times per week I write something. Those measurables don't direct what we do here. It was hard to get myself outside of that frame of thinking, because so much of what I had done before was tracked and counted. We are writing for our subscribers here, not for the easy SEO pageviews, and that has challenged me to find different angles and to find my blogging voice. 

Luis Paez-Pumar

Things I've Learned From One Year Of Being A Small Business Owner/Job Creator/Self-Made Entrepreneurial-Style Innovator, Ranked

1. That there's nothing like the thrill of trying something new and with no safety net, only for it to work out
2. That I enjoy these idiots that I call my coworkers so much that seeing them exclusively over Zoom is enough to get me through a pandemic winter
3. How to run streams on Twitch, technical difficulties and all
4. That having a separate subscription tier for commenters can turn the worst feature on the internet into a wonderful home for discussions and truly terrible puns
5. That I am really good at trivia, but even better at portraying a wrestling heel
6. That this website can support blogs both incredible and incredibly stupid
7. That I can write about what I love with reckless abandon, worrying only that it's good and not that it's going to increase ad revenue that I will never see
8. That my food takes are objectively correct and, in fact, I am brave for sharing them
9. That Samer can recognize a fart, online
10. Getting hit by a truck transporting basil, parsley, oregano, things of that nature
11. That a lot of people on Twitch want me to "eat shit"

Drew Magary

This site runs almost exclusively on subscription revenue, which means that I'm writing for what is essentially a closed-off internet ecosystem. That means that I'm no longer obligated to write for the broadest possible audience, even though I desperately want to. I'm a shameless attention whore, so writing to go viral was something that suited me nicely and is now a difficult habit to kick. 

I can still strive for endless page views over at my other day job. But here at Defector, I've had to learn how to write without putting any pressure on myself to do a post that'll get linked by some famous asshole on Twitter or whoever. I'm still trying to rein in that needy child within me, to work for a more EXCLUSIVE client base. And in fact, there was a time early this year when I didn't think I was doing a very good job of it. I didn't find what I was writing all that interesting, and I wondered if I'd ever get the THAT'S A POST! kind of magic going back on inside my head again. 

But that's how you learn anything: by failing. By doubting. By questioning what you do. By sucking. I'm still wracked with some doubts here and there, but not nearly as many as I had before. That's because of both the Defector staff and the Defector readership. We've all bought into this shit together, which means we all believe in each other. Many hands make light work. I try my best to never forget that. Even when I'm yelling at Luis.

Dave McKenna

I’d weathered lots of business models in my decades of working for media companies. And all of them were already in the trash bin of history or headed there when we launched Defector a year ago with our untried but true cooperative ownership set-up. 

My first job in journalism came as a paperboy. I delivered the Washington Post for six years in the 1970s. I’m sure having that job in that era as a kid had something to do with how I ended up typing for a living for the next several decades. I started just as Woodward and Bernstein were doublehandedly making journalism cool by diving into Watergate coverage and forcing out the most powerful man in the world. I still have the “Nixon Resigns” issue, the most famous front page in the Post’s history, and it’s in the basement in the canvas Post bag I delivered it in. D.C. had been a multi-paper town, but the Washington Post had a virtual monopoly on my neighborhood and the entire market after Watergate. My pay as a paperboy came by collecting money each month from subscribers on my route. Good work and goodwill sold lots of newspapers. 

My first writing job came at Washington City Paper in the mid-1980s. Alternative weeklies were making journalism even cooler, by covering things the old-school dailies historically undercovered or ignored, like race and gender issues and punk rock. Free newspapers became a viable business model. The printed copies distributed all over the city brought in boatloads of money with edgy classified advertising the establishment publications wouldn’t take; many of these were “personal” ads considered radical at the time just because they acknowledged non-hetero romance. 

While at City Paper, I got sued for millions of dollars by Dan Snyder, the owner of the Washington NFL franchise. A billionaire vs. a $16.99-an-hour putz. There was nothing factually wrong about the story that inspired Snyder's suit. He just wanted me fired. Snyder got destroyed in the court of public opinion and abandoned the suit (10 years ago today, actually). Not to get too corny, but the First Amendment saved me, and my workplace. Nothing, however, could protect City Paper from the digital age. I stayed at City Paper for 26 years, long enough to see the onset of the internet and Craigslist ads, which killed the ad revenues of free newspapers and made their business model completely obsolete. I left after City Paper was taken over during bankruptcy proceedings by a hedge fund. 

Then I got hired by Deadspin, a publication of Gawker Media, a forward-thinking, internet-only news operation that was the alternative journalism of the day. Gawker made gobs of money covering the sorts of social and entertainment issues the local alt-weeklies once did on a national scale. Gawker depended on ad sales and clicks, and good work brought in lots of both. While I worked for Gawker, we became the first digital media company to unionize. But Gawker was put out of business by a lawsuit sponsored by Peter Thiel, a vindictive billionaire. There was nothing factually wrong about the Gawker story that inspired the lawsuit (a story I had no part in), but once again a rich guy didn’t like my workplace and tried using litigation to get revenge. The First Amendment should have protected Gawker like it did City Paper. But times had changed. The anti-media movement picked up lots of steam in the intervening years. Thiel succeeded where Snyder failed. The ruination of Gawker showed that no journalism business is safe. 

Deadspin was taken over by a private equity firm, like so many news outlets had been in recent years. The financial firm that got us happened to be headed up by a mean rich guy who behaved like a mean rich guy would. Rather than stick around while he ruined what we had at Deadspin, the whole staff quit simultaneously. Nobody had a job lined up as they jumped off. I felt lucky just to witness this unprecedented display of worker solidarity and activism up close, let alone be a part of it, and thought I’d finally done something that would have made my labor-loving parents proud if only they were still around. 

Journalism jobs had been going away for some time by then. I was pretty sure my days of getting paid to type were over and that my future was indeed the pasture. I was at peace with a “career” that went from “Nixon Resigns” to Deadspin resigns. Then the Deadspin diaspora started Defector, a cooperative operation, owned by the workers, as avant-garde as any of the forward-thinking places I’d already been blessed to be a part of. It’s too early to say our cooperative set-up is replicable enough to become an industry standard. But throughout our incredible first year, I saw that my job at Defector has similarities to the one I had as a Washington Post paperboy all those years ago. I only get paid if we collect money from subscribers. And goodwill and good work can still bring in readers and dollars. Same as it ever was.


David Roth

Mostly because of how they get talked about in our politics but also because of the people who self-identify as such that I've met in my life, I can't say that I ever wanted to be a Small Business Owner/Job Creator prior to becoming one. It felt like wanting to be a landlord, somehow, which again I think mostly has to do with the way that this identity is understood and performed in a culture that currently is built to create and serve Aspiring Landlord personality types—people whose whole identity is grounded in being kind of sourly and vengefully in charge of other people whom, just by dint of those people not being In Charge, our job creating protagonists regard as sort of minor villains or just faceless NPC types in their own hero's journey. What I did not anticipate was 1) how incredibly, beautifully liberating it would be to be free of having my professional and personal life be subject to people like that, and 2) how immediate and present that feeling would be just in the process of doing my own job every day. It's still a job, I still have to do stuff I don't necessarily feel like doing, but it is so different and so urgently different to be creating all this not just with people I care about and believe in, but to know that I am not doing it for some cretin who, to the extent he even knows who I am or what I do, thinks that what I do only has meaning insofar as it serves him. It is a good thing to create a job, I guess, and kind of a cool feeling to create your own, but until now I've never had a relationship with a Job Creator that didn't hinge on the implicit promise that the person who created my job could un-create it, and the realization that he almost certainly would as soon as his own interests required that. Maybe I have just had bad bosses, or just worked in a bad industry. I think both of those are true. But it's weird to feel this kind of attachment to a job, or a workplace. For reasons of self-protection, I've never felt that way before; I've loved my coworkers elsewhere, but I always knew that we were on borrowed time, and that we were borrowing it from someone I couldn't trust at all. The whole purpose of creating these jobs was that we wanted to do them, and keep them. That feels different, and good.

Albert Burneko

I dunno man TKTKTK, can I have a little more time to work on this.

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