How to Succeed on Substack (Probably, Maybe?)

A Practical Guide From Someone Who Has Technically Not Died (Yet) Doing It

One our readers commented recently that I must be ‘making a million dollars a month’ on Substack. I started laughing uncontrollably for the next several minutes.

This person said it with the casual confidence of a man who has never once operated a spreadsheet. “You’re a Substack bestseller,” he said. “You must be RAKING IT IN.” He used those exact words. Raking it in. Like I am some kind of financial leaf blower aimed directly at the internet.

I am not raking it in.

I want to be very clear about this before we go any further, Substack bestseller does not equate to NY Times bestseller. Because apparently the word “bestseller” means different things to different people and one of those things is “yacht.” I am not on a yacht. I am not even on a pontoon boat or even a free canoe I stole from abandoned-house-by-the-river’s yard.

I am in a motel room in upstate New York drinking something called Tropical Fantasia, which is a soda that does not appear to exist anywhere on the internet according to my research and which I am fairly certain the Russian owner of this motel is brewing in his basement as part of some ambitious side hustle that frankly I respect.

It tastes like someone described a mango to a person who had never seen fruit and then that person made a beverage. I have been here long enough that I drink it voluntarily now. That is what success tastes like. (Carbonated sugar water with fruit-like artificial flavor.)

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Here is what I actually know about building a Substack. I know it the way a man knows which dumpsters have the good stuff. Through years of unpleasant personal experience.

The Part Where I Disabuse You of Every Fantasy You Currently Have

The first thing you need to understand is that this is not easy. Not “harder than I thought” not easy. Not “takes some dedication” not easy. I spent three years working eighty-hour weeks in a roach-infested flophouse living on canned beans and rice. Not as a metaphor. Actual canned beans. Actual rice. Actual roaches (I called them roommates to cope). Three years of this before the operation started generating enough money to constitute what a reasonable person would call survival income.

And that was AFTER I figured out what I was doing!

More than half of what we bring in goes right back out the door. AI research tokens cost real money. Lily, my editor (who is 23, brilliant, and regularly prevents me from publishing things that would get us sued), costs real money. Research assistants to take my AI research and expand on it cost real money. The programmers to build our tools cost real money (I make them now to save money). The graphic designers cost real money (I do this more often than not now too for the same reason).

If you are picturing a bestselling publication as a money printer that runs while the owner sips drinks on a beach, please know that the beach in this scenario is a parking lot and the drink is mystery basement soda.

I could make significantly more money tomorrow if I put on a collared shirt and walked back into the corporate programming world. Easy forty-hour weeks. Benefits. A salary with actual numbers in it. I know exactly how to do this and I choose not to, which either speaks to my deep commitment to independent journalism or my complete inability to tolerate having a boss. Probably both. Definitely both.

Okay. Now that your expectations have been properly managed, here is what actually works.

Go Find the People Who Are Already Winning

The single most useful thing I did when I started was go to the Substack bestseller page in my niche and subscribe to every single publication on both the actual bestseller list and the rising stars list. Not to steal their content. To STUDY them. Find out what they are writing about. Find out which social media platforms they are active on. Figure out who their audience is and whether any portion of that audience might also be interested in what YOU are doing.

Then build an HTML page with links to all of their publications. Set up email notifications so that the INSTANT they publish anything, you get an alert. And then be the first person to comment. Every time. Tell them genuinely that the article was great (if it was great, and if it wasn’t great, find something specific that WAS good and say that). Then mention your Substack URL.

I did this every single day for TWO YEARS before I got my first paid subscriber. Two years. Every single day. If that sentence did not make you reconsider your life choices, keep reading.

The people who quit after three months and write posts about “why Substack doesn’t work” did not do this for two years. They did it for a week and then posted about their feelings on Notes instead.

Notes Will Not Save You But Writestack Might Help

Speaking of Notes, yes you should be posting there, no it is not the magic growth engine that every Substack marketing guide written in 2024 promised you. There are approximately nine million people on Substack Notes right now posting “great insights, check out my newsletter!” under other people’s posts and the entire thing is starting to resemble a digital multilevel marketing convention.

That said, Notes DOES work. It just requires you to actually be interesting, which is more effort than most people are willing to put in.

My friend Orel built a tool called Writestack.io that can help you analyze which of your notes are actually generating subscribers, automate reposting the ones that performed well, and generally take the guesswork out of figuring out what your audience responds to. You CAN use it for full automation but I do not recommend that unless you are specifically running a marketing account, in which case your soul is probably already beyond saving and Orel’s tool is the least of your problems.

Be Nice to People, Which is Harder Than It Sounds

Thank people when they comment. Thank people when they share your work. Thank people when they leave a like. This sounds obvious and I want you to know that Lily has to remind me to do this on a regular basis because I am, and I say this with full self-awareness, kind of an asshole.

Not a MEAN asshole. More of a “I spent forty years letting rich people and a genuinely insane father treat me like a doormat so now my default setting is ‘do not take any nonsense from anyone under any circumstances’” asshole. Which is a legitimate survival mechanism that does not translate especially well to community building on a writing platform.

Lily is considerably nicer than I am and the comment section reflects this. Be more like Lily.

Read the News Every Single Morning Like It Is Your Actual Job, Because It Is

I spend two to three hours every morning reading what everyone in my niche is covering. Not to copy them. To find the stories that I think will resonate with my specific audience that nobody else is covering the way I would cover it.

When I find something worth pursuing, I start doing AI-assisted research and then pass the materials to Lily and our research assistants for additional digging. After a few days we have what I can only describe as a mountain of data that I then feed into a local AI research system I built specifically for this purpose (the cloud AI data center people are not getting their hands on my research process, see also: our entire other body of work on why that matters). The local AI finds the key connections. Then I write.

Then I write for eight hours. Then I edit for another eight hours, or Lily edits it if she is available, which she sometimes is because she is a professional and I pay her. First drafts are terrible. Second drafts are slightly less terrible. The draft that gets published is the one where I have read it so many times that individual words have stopped making sense and I have to just commit and post it.

DO NOT publish garbage. Substack is full of people who spent twenty minutes reading a headline and another twenty minutes writing two paragraphs about it, and their readers know exactly what they paid for, which was nothing, because nobody paid for it. Your readers can tell when you did not try. Respect them enough to try.

You Need to Actually Enjoy This, Which is Also Harder Than It Sounds

Do not come to Substack to make money. Come to Substack because you have something to say and you are willing to say it for years before anyone pays you to say it.

I have lived in a men’s shelter. I have lived in a tent after the men’s shelter became untenable due to what I will diplomatically describe as a challenging resident population (meth addiction and recent prison release were well represented).

I lived in a roach motel room, then upgraded to a different roach motel room, then eventually achieved what I consider my current peak of residential accomplishment, which is a roach-FREE motel room with unlimited access to Tropical Fantasia soda (flavor: ambiguous, origin: suspicious, availability: exclusively this motel).

This is fifteen years of work. I have been threatened. I have been sued (case dismissed). I have been doxxed. I have been harassed in ways that required the involvement of law enforcement. I have lost count of how many paid subscribers I gained last year versus how many I lost, and I will tell you that the numbers are uncomfortably similar.

And I would not trade it for the corner office.

Not because this is glamorous, because it is not. But because I am constitutionally incapable of watching something wrong happen and staying quiet about it. That is the only qualification that matters for this job. Not a journalism degree. Not a platform. Not a niche. Just an inability to shut up about things that matter.

If you have that quality, you might make it. It will take longer than you want and cost more than you can afford and you will eat a lot of beans.

But someday, if you work hard enough, you too might find yourself drinking mystery basement soda in a roach-free motel room, technically surviving, and writing a guide for the next person brave or stupid enough to try this.

There is no meaningful difference between those two things.

And if you figure out what Tropical Fantasia actually is, I genuinely need to know.

Help keep the Wise Wolf howling.

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Here is what I want. I want a newsvan. Not a fancy one. Just one that starts reliably and has enough room in the back for camera equipment and Lily’s increasingly alarming collection of research notes. I want to give Lily a full-time salary and an actual office in an actual building where the soda comes from a vending machine and not a Russian man’s basement.

I want The Wise Wolf to become a real news magazine with its own website, its own design team, and an actual printed edition that gets delivered to your house through the United States Postal Service while that is still a service our government bothers to provide.

I want a lawyer who knows how to walk into a federal courtroom and make life uncomfortable for a dozen billionaires who spent more on cat food for their pet tigers last year than I have made in the last decade of doing this work.

None of that happens without you. This started as a labor of love and it IS still a labor of love, but it is also my profession, Lily’s income, and a small business with real employees who depend on it staying alive. All of that fails the moment you stop sharing our work and stop telling other people it exists.

So if you read something here that made you think, made you angry, or made you laugh despite yourself, please consider a paid upgrade if you can afford one, and share our articles even if you cannot. We are two people and a dream and a very suspicious soda, and we are genuinely grateful you are here.