This Is the Secret to Business and Artistic Success

One of the strangest things about business to me has always been how damn far everyone is from the products they create and the customers who use them. 

You have a problem with a product you bought and you call customer service, but you’re not actually talking to an employee of the company who made it—you’re talking to a customer service contractor, who is employed by an agency that runs third-party customer logistics, who in turn was hired by the company you purchased from (if in fact you bought direct, instead of through a retailer). 

Whenever companies are investigated by labor activists, the story always follows a similar path of intermediation: Shoe Company X outsourced to Manufacturer Y who outsourced to Factory Z who in turn used slave labor to make shoes not just for Shoe Company X but for all their competitors too. 

“We had no idea that the workers were being treated so poorly,” a spokesperson for the company explains, who is often a crisis PR flak, not an employee. What’s more, they are usually not totally lying. Neither the company, nor their spokesperson.

Even my profession—books—is illustrative of this phenomenon. You walk into an independent bookstore in your town and purchase a book because you like to “support authors’’ or “support local small business.” But what actually happened is this: you bought a book from a shop, who in turn bought their books from a large distributor like Ingram (est. annual revenue of $2.4 billion), who in turn bought their books from a publisher like Houghton Mifflin Harcourt (market cap of nearly $1 billion), who in turn had acquired the book from the writer. In the business of books, the creator and the customer (i.e. the author and the reader) are several steps removed from each other. Even a multi-billion dollar behemoth like my publisher, Penguin Random House, sells the vast majority of their books to Amazon, who in turn uses a complicated algorithm to decide what to show to customers, and what to charge them.  

This has always struck me as weird, as well as ethically fraught. On top of that, it’s also felt like bad business to me. We say marketing is important, that knowing your customer is key, but then businesses hand responsibility for those areas off to a bunch of contractors? And then use their insights and choices to decide what to make next? Imagine a sports team who doesn’t do their own scouting, player development or coaching! Who doesn’t interact with their own fans!

How can you do a good job of making stuff for your customers if you don’t have a relationship with them? The short answer is, you can’t. Publishers are quick to tell authors about what audiences like and don’t like, but where are they getting this information? Not from the source, that’s for sure! 

When I was in marketing, I loved talking to people with the same job at other companies and in different industries. Or, not really the same job, because the “Director of Marketing” at most companies is often supplemented by an outside advertising agency, a creative agency and a PR agency. Like The Bobs in Office Space, I’d ask my own version of their question: What would you say you do here? 

As the flywheel of my own books has begun to spin faster and faster—nearing 4 million copies sold—I have become increasingly less satisfied with this intermediated status quo. I remember once talking to an author who had sold a million copies of a book that was published seven or eight years previous. Ok, I asked them, what kind of email list have you got? They started telling me about how many contacts were in their Outlook. Meaning: They didn’t have an email list at all. They’d sold a million books… but that relationship was Amazon’s to own (or in their case, Borders, which had existed when their book came out).

Since my first book was published in 2012, I’ve made sure the last page of the book asked readers to send me an email to sign up for my list. Hundreds of thousands of people have done that. I have entered many of their emails into my list personally. Their names have passed from my eyes through my fingertips into my customer database. I have heard what they liked and don’t like about the books. I have seen what’s worked and what hasn’t. I have gotten to know them.

Of course, I have social media, too (you can follow me on Instagram, Twitter, TikTok and YouTube). But in the last several years, I’ve decided that those communication channels were not sufficient. I needed to be in the business of transacting directly to my readers, as well.

I had Tobias Lütke, the founder of Shopify, on my podcast recently and we talked about the power of a platform like his, one that allows people to become their own retailers. In 2017, with, we opened our own store. We started with a print, then moved on to challenge coins and then online products and a premium leatherbound edition of The Daily Stoic too. Since we launched, we’ve directly sold to north of 100,000 customers. Or rather, to a whole football stadium worth of “true fans” who we now have a relationship with. 

Imagine standing on the 50-yard line of the Big House at the University of Michigan, packed with people to the very rim of the stadium, and knowing you’ve sold something to every single face staring back at you. It’s an immensely powerful feeling. 

Mostly though, it’s a liberating one. I’ve said before that I spell “success as a-u-t-o-n-o-m-y,” and this fits with that philosophy. I don’t want other people telling me what to do. I don’t want to be dependent on other people either. Yes, I work with a traditional publisher on my bigger books, but by choice.

Early in the pandemic, I started working on a fable about Stoicism that came out of stories I was telling my then 3-year old son. After I had finished the outline of the idea, I went to my publisher—who had done 10 books with me at that point—to see if they wanted to work on this one. They came back with terms that just made zero financial or creative sense for me. Part of me was frustrated, but I also believed that they had given me a great gift. Now I could do The Boy Who Would Be King myself. 

I did it faster. I did it cheaper. I did it with complete creative control. I even got to print it in the United States. In its first week, it sold more than 5,000 copies without a peep of external marketing or PR, just an email and a social post to my own fans, sold through my own store. It would have been enough to debut on any of the major bestseller lists—but of course, it didn’t appear on any because those lists had no way of tracking it. 

But what do I care? Well, let me tell you. I care about the fact that something I care about got into the hands of people who care about it. 

Isn’t that the whole point of art? Isn’t that the true basis of sustained (and sustainable) success in business?

Fewer middlemen. Fewer impediments. No delays in getting to market.

I did a talk for a fashion company a few weeks ago. When they started, they did 90% of their sales through retailers and 10% direct-to-consumer. That ratio has flipped as they have grown, based on the CEO’s strategic plan. Imagine if that hadn’t been the plan? They would have been destroyed during the pandemic, when physical retail was largely shut down or severely sidelined. And even without something like a pandemic, by going direct-to-consumer, they improved their margins, as well as the quality of their product… because, you know, they actually knew who their customers were and what those people liked. And by cutting out all those middlemen they could take the savings and apply it to the substance of the product itself.

Nobody knows what the future holds, that’s true. I will continue to traditionally publish many of my projects. My publisher helps me do things I can’t do and I help them do things other authors can’t do—which is why we choose to work together. Even right now, I am working on a distribution deal to get The Boy Who Would Be King sold through other stores. 

Still, I’m not sure how anybody goes broke working directly—as much as possible—with the audience and market they serve. Are there efficiencies that come from outside contractors and manufacturers? Of course. Are there great opportunities selling through other people’s platforms or stores or audiences? Obviously.

But if you’re not also cultivating a direct line to your people, what are you doing? Being arrogant and reckless is the answer, in my opinion. You’re gambling that the middleman will always need you, you’re gambling that your intuition will always land with the audience. You’re also giving up autonomy and creative freedom, too.

I’ll conclude with a great passage from The 50th Law by Robert Greene, as it defines the imperative for all creators perfectly:

Your goal must be to break down the distance between you and your audience, the base of your support in life. Some of this distance is mental—it comes from your ego and the need to feel superior. Some of it is physical—the nature of your business tends to shut you off from the public with lawyers of bureaucracy. In any event, what you are seeking is maximum interaction, allowing you to get a feel for people on this inside. You come to thrive off their feedback and criticism. Operating this way, what you will produce will not fail to resonate because it will come from the inside. This deep level of interaction is the source of the most powerful and popular works in culture and business, and a political style that truly connects.

Written by Ryan Holiday