The Right Way to Monetize a Blog (With Lessons From Wait But Why)

make money writing

There was once a time when if you wanted to live as a creator—as an artist—you needed a wealthy patron who was willing to sponsor and encourage your work.

In many ways, creators still need patrons to support their work today. But the "patron" now consists of the many people that make up a creator’s audience—their biggest fans.

YouTubers, writers, cartoonists, musicians, artists—creators of all kinds—are in an amazing position to build a business around the large and loyal audiences that consume their work. From merchandise to endorsements to speaking engagements to book sales, there’s ample opportunity for these creators to monetize their creativity.

So I decided to find out how Wait But Why, one of my favorite blogs and one Elon Musk loves to read, built a business on top of their content.

Wait But Why is a unique website, fuelled largely by long-form content with a sarcastic-yet-thoughtful tone, that’s amassed over 371,000 subscribers and brings in millions of visits a month with its one-of-a-kind content. Tim Urban, the writer and illustrator behind most of the site's content, covers everything from the future to philosophy, from artificial intelligence to procrastination and whatever interests him at the time.

Tim takes complex or abstract concepts and make them easy to understand and enjoy despite a word count that often pushes into the tens of thousands in an era where some say we have shorter attention spans than goldfish.

It's this style, depth and commitment to excellence that's enabled Wait But Why to land itself on the first page of Google for competitive search terms like "procrastination"—truly an example of 10X content: high quality content without equal in terms of the organic traffic, backlinks and engagement it brings.

10x content

But what's most interesting is how these entrepreneurs took an audience-first approach to building a business—a business that sets Tim loose to do what he loves with the support of his audience.

To understand how they monetize Tim's unique brain and the content that pours out of it, I talked to Andrew Finn, Co-Founder of Wait But Why, and the man who handles much of the blog's business side. 

For more on building your own blog-based business, check out How to Start a Blog That You Can Turn Into a Business.

To start, how did Wait But Why come about?

To start, how did Wait But Why come about?

Tim and I have been business partners for almost 8 or so years at this point. Tim and I grew up together, and we’ve known each other since Kindergarten.

We have another company that we started called ArborBridge, a test prep and tutoring company. And that’s what I still do 90% of the time.

Tim had always been writing a blog on the side, and it started to get really good, especially when he introduced stick figures. He’s always had this creative side that he wanted to itch, and we got to the point in our other business when it didn’t need both of us. So we decided to take a gamble, and have Tim stop working on the test prep company, write full time and see what happens.

Tim has a pretty special, creative brain. So we were pretty confident that, if he were to do it full-time, something good would come out of it. Though we weren’t sure what.

Because we had this other company, we were never forced to do things like sell crappy ads. We could afford to take our time for a couple years getting the website established without having to worry too much about monetization, which is probably a luxury many content creators might not have.

At what point did Wait But Why start growing its business side?

We had the store from the beginning. But we’ve just been kind of chipping away at it.

We knew we had 2 or 3 years when the site didn’t need to make money. But then there came a time when it it was like, “This site needs to stand on its own.”

We turned a bunch of posts into an eBook, started up with Patreon, added merchandise and other things.

But it’s only really been the last year that it’s come together.

Wait But Why as a business is still very, very undeveloped at this point. The goal right now isn’t to make as much money as possible. It’s to make as much awesome stuff as possible and the business will eventually take care of itself.

Tell me more about Patreon— the website that makes it easy for creators to get paid

Patreon was a big breakthrough.

We weren’t sure about Patreon at first. We didn’t think anyone was going to just give us money.

But then there was the guys at Kurzgesagt—this cool video platform, they’re called In a Nutshell now—who recommended it.

I think part of the reason it’s worked out well for us is that high alignment with our audience where they know we’re not trying to sell them a bunch of stuff, we’re not trying to put ads everywhere—we’re just trying to make really cool stuff and share it with them.

If we did ads on our site AND we did Patreon, people would probably have told us to go screw ourselves.

What are the differences between “content marketing” and building a business on top of a content site?

At the end of the day, I think it’s about figuring out, is your business the content or is your business the products being sold? Where’s all your attention going to go?

Content can go much further than products—if that’s the game you’re in, there’s plenty of ways to make money.

I think the difference for us is we were building a brand of content. The business was always the content and writing happened to be the best way to do it for us.

Because we’re entrepreneurs too, one thing we thought about was, “Is this fundamentally a good business model?”

Well, it is for two reasons:

  1. It scales infinitely because of the written word and the internet
  2. You can have a monopoly on it if your voice is authentic, if there’s that “something” no one else can copy.

Tim had this other blog for 6 years that he wrote on every once in a while. It was really funny, but only two thousand people or so read it.

There’s a real difference between being a casual writer who’s just “pretty damn funny”, and someone who spends every day thinking about his writing and what’s next— doing that same funny post, putting several more hours into it and even some money into promoting it.

That’s the difference between Tim as a casual blogger and Wait But Why.

What kind of challenges do you face building a business around content?

It’s always about the brand’s promise.

What’s the promise you’re trying to make to the audience? What the voice you’re trying to reach them with? Who are you to your audience, what are their expectations around that?

We tried to be super authentic, super honest, and not cheesy. And selling things can be kind of cheesy if you don’t do it right.

If we ever sell anything on the advertising side, it’ll be something we already really like and actually pay for ourselves. We’d work out an arrangement so everyone gets a good deal, creating a win-win situation with the audience. That’s always the tension around monetization for a business like this.

The other thing is finding your niche. Do you swear or do you not swear? How honest are you about your religious views? Do you do these things that might turn off large groups of people?

I think the best way is to be 1000% authentic and find the people who are looking for that.

How do you source products for the Wait But Why store? What are your best-sellers?

We have a company that we work with in North California called Brand Marinade and they do all the merchandise stuff for us—they even do short runs on t-shirts so they’re super nimble.

The plush toys we do ourselves. We got them designed and shipped from China.  

Comparing apples to apples, in the t-shirt department, the best-sellers would be stuff related to the procrastination post, which are also the posts that get the most engagement.

The plush toys do well, too, which are these pretty rad little dudes.

wait but why

The things that tend to be life-oriented tend to get people the most jazzed. I don’t think people are going to buy stuff on artificial intelligence as much as something that resonates with them personally.

The other day, I went out for dinner and saw a guy wearing one of our Social Survival Mammoth shirts, which was pretty cool to see out in the wild.

wait but why


How important is frequency when you’re producing content?

I actually don’t think frequency is that important.

Asking someone to read something is a huge task for them. I think it’s more important that, when you get their attention, you deliver on your promise.  

At the very beginning for us, it was a few posts a week for the first year. Then it was one post a week. Now it’s just off the rails.

I’m sure frequency matters for some sites. But there’s so much stuff out there that’s just mediocre. I think it’s more about being aligned with whatever your promise is.

You can do 5 posts a day if you’re trying to satisfy that part of a person’s brain that’s like, “This is like crack. I need more of this.” Or you can say to your audience, “I know this thing is long but I promise it’ll be really good because I spent a lot of time on it.”  

What’s worked well for Wait But Why when it comes to getting the content in front of people?

Facebook has been the best channel.

Promoting via Facebook is a good way to give your content the kindling it needs to get it going.

At the end of the day, it’s The Law of Large Numbers. If you can write something that’s awesome for 10% of the people who see it, maybe 5% of those people might share it.

With an audience of 100 people, that’s 5 people who might share it, and that probably won’t be enough for it to reach critical mass. So, if you can get it in front of 1000 people instead—and if it’s awesome—it’ll be more likely to spread.

It’s worth spending a little money to get there if you need to.

It’s also generally good to do some syndication, especially early on when you’re doing a lot of brand building. We’ve been syndicated on sites like Quartz, Gizmodo, Jezebel. etc.

How does Tim deal with negative comments as a creator?

Tim has pretty thick skin. He has much, much thicker skin than I do. Whenever I post something in my section of the site, every once in a while, I start crapping myself.  

Tim also had a blog for 6 years before he started this, and I think he worked out a lot of the kinks before he found his voice.

I think you need to understand that the internet is full of humans, and if enough humans read what you write then some are not going to like it, some might even get pissed off if it’s controversial, and there’s not much you can do about it.

Our readers tend to be pretty smart, high-brow people, so negative comments usually are not an issue.

Tim works really hard to make sure he’s at least technically correct about what he’s writing about. Someone might disagree on his interpretation but it’s not going to be about the facts.

Something crappy might happen, some people might leave some bad comments, and you think it’s the end of the world.

But then 3 months later, everyone’s moved on. It’s like that article doesn’t exist.

wait but why

So much of life is just a head-game with yourself: “I’m having this feeling. Why am I having this feeling? Is that a feeling worth having? No, probably not. Let’s work through this.”

At what point do you think creators should consider developing avenues to monetize their work?

When we started, it was like, we’re going to write some stuff. And if it’s awesome, the world is going to tell you it’s awesome and it’ll spread. If it’s just ‘really good’, then it probably won’t and you just have to accept the fact that you’re just ‘really good’ and not amazing at this.

Because an A grade to the internet is just nothing. Like it doesn’t matter. There’s a million people on the internet creating content and doing things. It needs to be an A++ to be relevant. People will spread stuff that’s an A++ because they want to.

If your extra 10 hours is going to monetization as opposed to creating content, and that means you’re only putting out A content, that marginal amount of effort is what makes the difference between 10x and 100x.

You’re better off getting as big as possible first, to really build your following of fans—your super fans. Once you do, there’s tons of ways you can monetize.

It’s kind of like the standard internet company business model where it’s like: Acquire users, grow and get bigger, then you can figure out how to make money later.

  • Step 1 is to create something that people give a crap about.
  • Step 2 to 10 is to repeat step 1 as many times as you need to.

If you haven’t gotten to the point where people would actually give a shit if you went away, then you haven’t gotten far enough.

What would you recommend to anyone looking to build a business around an audience?

Find your niche. I think especially with how large the world is, how large the internet is, if you can stick to your authentic voice then it’s awesome—no one copy that.

If you can be everything to a small group of people, it’s better than being “meh” to everyone.

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If Buzzfeed went away tomorrow, I don’t think people would really care for more than half a day before moving on to something else. But Jon Stewart going off the Daily Show, or your favorite author— like the Game of Thrones guy—kicks it and doesn’t write the next book, it’s soul-crushing.

The best ones are automatics—it’s like, “If you write it, I’ll read it.”

What are some of the tools that helped build Wait But Why as a business?

There's just so many tools:

I can't imagine someone trying to do this 15 years ago. One or two people can start building a small company today and actually make it.

Key Takeaways for Creators and Entrepreneurs 

Today's creators and influencers have audiences that are willing to give them something more scarce than their money: Their attention and their trust.

If you have an established audience—a real one that loves what you do for them—you're arguably in the best position to build a lasting business.

That's why building an audience with content has become a priority for many businesses looking to develop a brand that resonates with their customers, to replicate what many creators are naturally gifted at doing: being authentic, interesting, and attractive to the right people.

Whether content is an extension of your business or at the heart of it, authenticity and the desire to truly serve an audience is what'll pay you back in the end. 

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