How Does This Whole "Writing Online" Thing Work?

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Some careers have clear, well-defined paths to success. If you want to make partner at a prestigious law firm, for example, you need to crush the LSAT, attend law school at Yale/Harvard/Georgetown/something similar, clerk with a top firm one summer, secure an offer, spend a couple of years doing grunt work, then climb the ladder from there.

In finance, the IB analyst to PE/HF/VC route is tried and true. In consulting, you can spend 3-4 years at McKinsey, Bain, or BCG, get your MBA (sponsored by your employer, of course), return to your employer, and resume the climb to partner.

Pursuing one of these careers is like hiking Mt. Kilimanjaro. While it certainly isn’t easy (you are competing with some of the most ambitious high achievers on the planet, after all), the route is known and well-documented. If you do your research, you’ll know exactly what you’re getting into. You may not win the game, but you will know how the game is won.

Writing is not a well-defined path. There is no metaphorical “ladder to success” for the writer. Some writers make good money from their craft, but most never make a dollar. A large part of that is because content creation is subject to power laws: the top 1% of creators capture 99% of the revenue.

However, there is another variable at play: aspiring writers don’t know what they should be aspiring to.

Sure, Tim Ferriss, Mark Manson, and James Clear built massive, million-person audiences from their blogs. But how did they go from zero to hero? And beyond that, how do writers in the middle, those with smaller, still valuable audiences, support themselves?

Over the last six months or so, I have fielded dozens, maybe hundreds, of inquiries asking variations of two questions: 1) “What do you do?” and 2) “How does that actually work?” And I get it. From the outside, none of this makes sense. You write stuff, people read it, you… make money? Wut.

As I was updating my notes for my Newsletter Playbook course, I realized, “Damn, I should probably just publish a blog piece about this already.”

So that’s where we are today. Hopefully, this piece will answer everyone’s questions about how this whole writing thing works.

Vamos.

“Alright Jack, so how do you actually make money from a free blog?”

At the most basic level, I sell ads. You have probably noticed that at the top of pretty much every blog post, I have a “Today’s Young Money Is Sponsored by… !”

Well, all of those “sponsored by’s” pay money to be sponsors. And a lot of variables affect pricing:

Who is your audience? Are they high earning? Are they an engaged group? Are they niche? Do you have a strong open rate? Click-through rate? Did the advertiser run a campaign before? Was it successful? Was it a flop? How well can you negotiate? And most importantly… What are the general market conditions? (CPMs, CTRs, and other metrics matter to an extent, but the biggest variable impacting pricing is how much a typical advertiser is willing to spend to advertise at that time.) For example, in early 2021, sponsors were throwing obscene amounts of cash at different marketing campaigns. (I should have started Young Money two years earlier, seriously missed the bull market on that one.)

Throw all of these questions and variables into a box, shake it up, then pitch a price for your ad slots.

Now you’re probably wondering, “Okay, how much money do you make from ads?” The answer is “it depends,” but I have been able to consistently fill my calendar at ~$1,000+ per primary slot, and I send two articles per week. For reference, I have ~33,000 readers, a 50% open rate, and a decent Twitter and Linkedin following that drives additional page views.

But that’s just for primary ads.

I also have a “Jack’s Picks” section at the bottom of my posts, where I plug interesting things I’ve read and/or listened to over the last week, as well as affiliate deals (if you buy something I linked, I get a percentage of the revenue) and secondary ads (I charge a reduced price for the smaller ad slot.)

A typical post has one primary sponsor and one affiliate deal, and I try to schedule everything at least a month in advance so they’re locked in.

Sounds simple, right? Not exactly. There’s actually a lot more to it than just copying and pasting ads.

I usually write the ad copy, or at least heavily modify some pre-existing copy to better fit my tone. I have to send insertion orders (IOs) and invoices, report engagement stats (opens, clicks, whatever), follow up for unpaid invoices, and stay in touch for potential future campaigns.

These are unglamorous, tedious tasks. They are also an essential part of the process.

“Where do you get the sponsors from?”

All over the place, really. Sometimes I DM folks on Twitter, especially if a CEO, founder, or marketing leader from an interesting company follows me. Typically, if someone likes my content, there’s a decent chance that they are somewhat interested in running a sponsorship campaign, or at least testing one ad. Sometimes folks DM or email me after coming across my page. I leverage Litquidity occasionally (I edit his newsletter with 230k readers, more on that later), and a 3^rd party company, Ad Astra, places some of my ads too.

So yeah, that’s how I make money from this blog, in a nutshell. However, a blog is much more valuable than the sum of its ad slots.

“Okay… what do you mean?”

It’s not just about the content, it’s about the opportunities that stem from the content.

Young Money isn’t the only thing I write, though it is the reason that I landed my other gigs. Litquidity hired me to edit and help write ad copy for his daily finance newsletter, Exec Sum, as well.

How did I get this gig? I DM’d him on Twitter, sent him my finance blog, and said that I wanted to help with Exec Sum if he was interested.

Turns out, he was. The reason that he gave me the time of day? My blog provided proof of work that I knew what I was doing. It showed that 1) I was disciplined enough to consistently hit “publish” and 2) I had a decent understanding of the newsletter game already.

Once you’ve published 50+ pieces of content, you have a solid library to pull from. And then when you see an opportunity like I did to work with someone else, you have a valuable reference to leverage in your pitch. Every single day we encounter new opportunities, and written content is an insane competitive advantage.

And you don’t always have to pitch yourself to others. If you stay in the game long enough, opportunities will come looking for you.

People have reached out to me via email and Twitter and paid me for consulting calls. I’ve been offered a variety of contract gigs, from copywriting to ghostwriting (more on this in a second). And my reach has continued to expand as my articles have circulated Twitter and Linkedin and text messages and email chains.

More people = more opportunities. And if you’re a good writer, people will pay very good money for your help, because good writing is hard.

Back to the ghostwriting thing. A strong social media presence can help you build an audience of hundreds of thousands of followers. An audience of that size is invaluable. But churning out the content needed to build that audience is arduous. And some folks will pay top dollar for your help crafting that content.

I haven’t done any ghostwriting (yet), but I do have friends making hundreds of thousands of dollars ghostwriting for various clients on Twitter and Linkedin. The one thing they have in common? All of their inquiries originated from someone reading and appreciating their work.

It’s not just about monetizing your writing itself (though that is nice), oftentimes it’s about leveraging your content to help you land new opportunities.

So in summary, I wrote a free blog, and that free blog landed me a gig with a larger newsletter, plus dozens of other opportunities, and once that free blog hit a critical size, I started selling advertisements. But there are other ways to make money in this content game, too.

“Tell me more.”

On platforms like beehiiv and Substack, you can put your content behind a paywall. If you have 1,000 readers willing to pay $10 per month for full access to your work, you can make $120,000 per year. Not bad, no?

The one problem with paid subscribers is that your audience grows slower. I prefer greater reach at the expense of short-term revenue, but the recurring revenue from subscribers (not to mention the extra time freed up by not having to sell ads) would be nice.

If your audience is valuable enough, companies may actually pay you for featured content as well. Packy McCormick has made a name for himself as one of the biggest writers in the tech space, and 1-2x per month, different companies pay him to write “sponsored deep dives” about them in his newsletter, Not Boring. They want exposure to his audience, and they are willing to pay for him to publish a 5,000+ word business breakdown.

Your content might just land you a full-time job too.

Morgan Housel used to write for The Motley Fool, and then he was hired by Collaborative Fund, a VC, because their CEO liked his work. While Morgan is a partner at Collaborative Fund, his sole job responsibility is to write his blog. The reason? A lot of people read his stuff, and all of that exposure is valuable for a venture capital firm that wants to increase its brand awareness.

As you can see, there is more than one way to win this game.

“So what’s the catch?”

The writing game is hard. Realistically, you have to be willing to publish at least 1x per week for a year+ without making a dime before you hit any significant breakthroughs. Oh yeah, and your content has to be high quality every single time, because you are competing with the rest of the internet for the ever-decreasing attention spans of your would-be readers.

Publishing 2,000-4,000+ words per week isn’t easy. Publishing 2,000-4,000+ words per week with nothing to show for your efforts, for months on end? That’s kind of insane.

But we all do it anyway. That’s just how this whole game works.

- Jack

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Jack's Picks

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• Once again, if you are interested in our Newsletter Playbook course, check it out here.

• Intelligencer’s Eric Levitz wrote about why adolescents seem depressed despite the fact that the world has never been better.