Feature / December 13, 2023

The Definitive Guide to Starting Your Own Media Company

How to throw off the corporate shackles and launch an independent news outlet.

Kelsey McKinney and Aleksander Chan
Goodbye, bad corporate thing that you don’t run, Hello, good indie thing that you DO run. (Details of thing TBD.)
This, but better: Goodbye, bad corporate thing that you don’t run, Hello, good indie thing that you DO run. (Details of thing TBD.) (Clockwise, top right: Underwood Archives / Getty Images; Justin Sullivan / Getty Images; AP)
PLEASE DO NOT DO THIS

So you want to start your own media company.

This is a bad idea. We are qualified to say this because we have done it. As founding members of two new, worker-owned media companies (Discourse Blog and Defector Media), we are begging you not to do this. Maybe open a bakery, or open a dog sanctuary, or even go back to law school! If it is too late for you—if you (like us) did not heed this warning and stuck by your silly little dreams of making the media ecosystem a healthier, more interesting place—then at least don’t repeat the mistakes others have made before you.

You might have noticed that very few of the upstart publishers of the social media age have survived: Just in the past few years, companies like Bustle Digital Group have either closed entire publications (RIP again, Gawker) or, like HuffPost, merged into the holdings of BuzzFeed (which itself has shuttered its news division). Things aren’t much better in legacy media: The Washington Post is owned by one of the richest men in the world. Yet even though the paper’s operating costs amount to pocket change for Jeff Bezos, reporters at the Post still face near-annual rounds of layoffs and buyouts.

In all likelihood, you’re among the thousands of journalists who have been canned in the past couple of decades as the Googles, Apples, and Facebooks of the world ate everyone’s lunch (and then some). The insane idea of starting, running, and, God help you, living off the money you make from the media company you built yourself has its own appeal when the typical routes to a livelihood keep disappearing. Is it really a saner option to get back in line for one of the 12 jobs left in journalism—only to get laid off two years later?

Or maybe you’ve survived the layoffs and are making ends meet in your incredibly shrinking newsroom, with dwindling resources to do the work of two (or three or four or 16) people, and have reached your breaking point. Perhaps you’ve been toiling for far too long as a permalancer, subsisting on contracts from a publisher who never seems to be able to bring you on full-time. Or you’re freelancing, watching all the places you used to pitch die slow and painful deaths, taking with them the trickle of income you had left.

We started our own media companies after our newsroom was sold to private equity—chop shops for businesses, but the suits wear $800 down vests—and the workers were either let go or forced to endure a torrent of bullshit that eventually compels you to quit. We’re here to tell you that what we did might have seemed insane—but it was worth taking the leap. Here’s what we learned.

TO BEGIN, YOU MUST FIRST BECOME CURSED

The real key to starting your own media company is to become as traumatized as possible by the media. Our journey with the evils and dangers of the industry began before either of us could legally drink. In the early 2010s, we worked together at a college newspaper that (in retrospect) projected a metaphorical blinking red sign that read “Do not go into journalism” on every wall of the basement we worked in. The college newspaper did not have enough money. The pages of the print edition were chopped every quarter. We paid our staff writers nothing. We worked full-time, many of us piling up personal debt just to work there in between classes. This, we thought, was “paying our dues.” It turned out to be the perfect preparation for the burgeoning new-media industry!

After graduation, we made our way to New York. We worked and wrote for various blogs—from Gothamist to The Awl to Fusion.net—that are now dead or mere husks. We lived through the pivot to Facebook, the pivot to video, the pivot to uniques, the pivot to Google News. None of these pivots made our writing any better or our mental health any stronger. The pivots themselves were bad business—for journalism, if not for the platforms. The companies we worked for lost money. We were laid off (more than once). Every single workplace we have ever shared has gone down in flames. The last jobs that we held at the same company were at Gizmodo Media Group (later G/O Media) in 2019: Aleks at Splinter and Kelsey at Deadspin. We made a joke about how we’d be lucky if it lasted a year. Within six months, both of our sites were dead—Splinter after being bled dry, stripped of resources, and thrown off a cliff overnight, and Deadspin after C-suite editorial interference so egregious that the entire staff quit en masse.

We recommend this process. Not only will it cost you thousands of dollars in therapy bills, but it’s a great crash course in how not to run a media company. Who needs an MBA when you can watch a lot of doofuses with MBAs drive perfectly profitable companies into the ground? You can’t buy that kind of experience, but you will in fact pay for it.

You will need so many more things than you’ll realize, but to get started, you really only need two things: (1) an idea for what you want your company to be, and (2) friends.

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Does the idea need to be “good”? Hopefully! Would it help if you had a distinctive approach or point of view to differentiate yourself? Sure. Mostly, though, it has to be a framework you can see yourself living with for (ideally) a long time. How do you get an idea for what your company should be? Please return to step one. The terror of working in the industry (or even reading anything from a major newspaper or one of the few blogs that still exist) will show you how many holes there are in the media ecosystem. Surely one of them is interesting enough for you to try and fill. Defector chose sports, and Discourse Blog chose politics and birds, but we are sure there’s an audience of readers out there for any topic, be it books or fine art or pickleball or brain surgery.

Now about those “friends”: They should be people you are comfortable owning a company with. We chose to form our companies with the coworkers we knew well from having worked together for years, almost all of whom we are trauma-bonded to. That’s beautiful.

When you know everyone’s deal, it can be easier to reach consensus on difficult decisions. You do not have to do it this way. But think hard about who you want to put your name next to on official documents that say: “WE OWN THIS BUSINESS AND ITS PROBLEMS TOGETHER.” Don’t just think about who you want to be a part of the big party you want to throw for surviving five years—think about who is going to make you feel comfortable and secure when you’re forced, in your first few years of existence, to survive both a pandemic and a global recession, too.

BUILD A FOUNDATION

Now that you have your idea and your pals, get everyone together and start talking. Take notes. You don’t have to figure everything out to get started, but you should talk about the big-picture items: What is our media company called? What do we stand for? Who does what? When do we want to launch, and how?

As you make your plans, figure out your timeline and decide who is responsible for doing what and when. Focus on the truly structural elements, to start with, and resist getting bogged down in the day-to-day details like posting schedules or headline conventions. That all comes in due time. For now, concentrate on the big picture.

This will involve more discussion than you realize, and there will be disagreements. It could take a few weeks or even months to reach a consensus. Something we’ve found helpful is trying to make decisions from a place of active solidarity, where everyone can be OK with an option even if it isn’t their first choice. But getting to that point requires some amount of fighting and debate. You might be seeing friends in a new light (business owners), and that might be very different from how you already know them (weirdo journalists). Some people might decide this isn’t for them.

But everyone should try and be honest about what their limits are. This is when you get everything out in the open.

LEARN ABOUT MONEY

OK, so you have an idea, and you have friends. You’re an innovator, even. You are the future of the media business! Good start, but famously, businesses need money. How are you going to pay for all this? How will you turn a profit? Subscriptions? Ads? Car washes?

Should you find yourself in the enviable position of being able to start your own company free of conflict and rich in capital, then by all means, go ahead. But if you are not the progeny of the elite, then you may have noticed: Writers and editors aren’t usually paid particularly well, at least not compared with the people who laid them off. To choose to work in media is to trade the ability to buy a new couch for the knowledge of what every single meme means.

So you’re likely not flush with cash. There’s a good chance you’ll have to work evenings and weekends launching your new company, probably without any money at first. This could be prohibitive for many people, and it certainly wasn’t easy for us. We helped build Discourse Blog and Defector Media between freelance assignments and day jobs. In short, we still have to make ends meet, silly dreams and all. For a lot of us, these sites are not yet our only source of income. You need to be prepared for the fact that even if you do manage to get your company going, it might not make enough for you to live off its revenue alone. Only you can decide whether the risk is worth it.

PLEASE, FOR THE LOVE OF GOD, DO NOT TRY TO DO THE BUSINESS YOURSELF

After watching a ton of dreary men in gingham shirts and khakis destroy the companies you love, it is easy to believe that businesspeople don’t do anything and aren’t helpful. This idea has a lot of potential, until you begin asking your fellow writers and editors if they know how to look up how much they have in their 401(k), or even if they know how to navigate a spreadsheet. One major decision you have to make as a company is whether you are going to file your taxes as W-2 employees or W-9 employees or K-1 employees. If you don’t know what those terms mean, you can’t do this on your own. You need to pay some businesspeople to help you. Not everyone with an MBA is so bad!

One option is to try and persuade someone who knows anything about money (fundraising, tax codes, business shit) to join your janky pirate ship full-time. This may work, but it may not. It is worth a shot, because one businessperson is worth 82 bloggers. Do not tell them this. They will get a big head. Also, you can’t afford to pay them that difference.

But at the absolute minimum, you will need a lawyer, to prevent you from getting sued; an accountant, to prevent you from getting sued and keep you from giving the government every single dollar you make; and someone who understands how things like paychecks and invoices work.

Unfortunately, finding this person will also require you to do something called “decision-making matrices.” Don’t worry—the MBA-havers will know what this means. It’s just a framework that will help you decide what powers people have within the company and what checks exist on them.

It is important not to repeat the mistakes of the rich dudes who came before you. Do not take money from venture capitalists. Do not seek riches beyond your wildest expectations. This is journalism, after all! No businessperson (or team) can do magic. No media company can scale itself to infinite profit forever. At their absolute best, profitable media companies will make ends meet. The ideal situation here is enough stability to allow everyone to quit their second job. That’s the best-case scenario.

THE PART YOU KNOW HOW TO DO: GET POSTING

It is a media worker’s dream to have full power over what your website looks like. There’s no one imposing restrictions on your work! There’s no dude who just bought the company asking you if you’ve considered posting about the start time of the Super Bowl! No, Josh, we hadn’t considered doing the exact same thing as every other company!

There is no Josh here at your own media company. There is only you.

Still, the power to post what you want is daunting: The website becomes an empty document, taunting you, reminding you how much opportunity and beauty could exist if you just stopped being so scared. It is helpful, we have found, to set boundaries to work within. The infinite space of the blank page is too intimidating. You have to figure out what you want your main focus to be, what tone you want that coverage to carry, how often you want to publish, what time of day (or night) you want to publish, and what you think readers will want.

Writing, editing, planning, publishing—you know, those tasks everyone always complains about doing—is the easiest part of this process. This step (the second-to-last on this long list) is the easiest because you already know how to do it. This is the part of your job that’s second nature, which is why it comes so late in this handy guide. It is easy to get bogged down in these fun questions instead of doing the active work to set up your company to succeed. But don’t worry: You can fight about what to post, and when, and with what frequency for the rest of your company’s existence! How lucky!

NOW YOU HAVE TO DO IT!!! AND NOT JUST THE WRITING PART. ALL OF THE PARTS

Planning is important, but planning past the point of productivity is procrastination. No amount of planning can save you from launching your website with a typo in a headline, or only realizing later that no one knows how to obtain health insurance.

There are so many steps before this one that it could be easy to never get here. You must roam through the terrible halls of your brain for weeks, maybe months or years, to find your good ideas. Your friends might be busy. Your money problems might feel insurmountable. But at some point, you must declare it good enough. No starting position will be so good that it can prevent failure. You must face the terror of being seen. You must launch your website and try. No more dilly-dallying.

Very quickly, you will realize the true benefit of working for a major media company that could lay you off at any time: isolation from tiny problems. Sure, the big companies will restrict your freedom of speech, refuse to give you cost-of-living raises, try to police what you do in your personal time, edit your work into a bland shell of what it started off as, and one day at random kick you out of Slack as a signal that you’ve been laid off before they even call you—but at least when you work for a corporation, it is someone else’s problem when the homepage isn’t working on your smartphone, or a button doesn’t work, or the entire site is suddenly taken over by a pop-up ad without any warning. Unfortunately, all those problems are your problems now. You are the one who has to help your colleagues find health insurance. You are the one who has to figure out how to get people to subscribe, troubleshoot when not enough do, and make plans to try and reduce the dreaded “churn.” Everything is your job now: the blogs and the backlash and the W-9s or W-2s or K-1s or whatever.

We tried to warn you at the start. We tried to tell you that this would be miserable and difficult and suck up every single minute of your free time. But if you’ve gotten this far, you may be a lost cause like us. You may have a silly little dream, and all you want to know is: Is it worth it?

Of course it is.

Kelsey McKinney

Kelsey McKinney is a writer and co-owner at Defector and the host of the Normal Gossip podcast.

Aleksander Chan

Aleksander Chan is the publisher and co-owner of Discourse Blog and the former editor in chief of Splinter.

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