“By twenty-five, I had published my first book — which was an immediate and controversial best seller — and it had my face on the cover. A studio optioned the rights to create a television show about my life. In the next few years, I accumulated many of the trappings of success — influence, a platform, press, resources, money, even a little notoriety. Later, I built a successful company on the back of those assets, where I worked with well-known, well-paying clients and did the kind of recognized work that got me invited to speak at conferences and fancy events...

“But a story like this is never honest or helpful. In my retelling to you just now, I left a lot out. Conveniently omitted were the stresses and temptations; the stomach-turning drops and the mistakes — all the mistakes — were left on the cutting-room floor in favor of the highlight reel. They are the times I would rather not discuss: A public evisceration by someone I looked up to, which so crushed me at the time that I was later taken to the emergency room. The day I lost my nerve, walked into my boss’s office, and told him I couldn’t cut it and was going back to school — and meant it.The ephemeral nature of best-sellerdom, and how short it actually was (a week). The book signing that one person showed up at. The company I founded tearing itself to pieces and having to rebuild it. Twice. These are just some of the moments that get nicely edited out.”

This is how Ryan Holiday started his new book, entitled, Ego is the Enemy. As he mentioned, Holiday is not just an author. He has trained under writers like Robert Greene and Tucker Max, applied their processes and lessons to his own writing, and developed a keen awareness of the industry’s nuances and strategies.

This is the side of writing I’d originally wanted to explore, the part that goes beyond the book. The part which is much less clear, and less obvious, to aspiring writers. “The business side of things,” as some people might say. Because as writers, it’s only by understanding the business that we can give our work the best chances of surviving and thriving. And where better to have started talking business, than money.

As Andy Warhol wrote in his book, The Philosophy of Andy Warhol, “Being good in business is the most fascinating kind of art. During the hippies era people put down the idea of business – they'd say 'Money is bad', and 'Working is bad', but making money is art and working is art and good business is the best art.”

Holiday has his finances in order. He set up a limited liability company (LLC) to store revenue from his books. That includes his book advances, speaking gigs (his keynote fees currently range from $15,000 — $20,000), and book royalties (two of his three books have earned out). Through this LLC, he also invests in real estate and startups. “That’s much less cash flow, but over the long-term, will hopefully be lucrative,” he said.

Holiday currently is a partner of Brass Check, a creative agency, which generates north of 50 percent of his income. This additional income stream provided him with diversification. When Holiday negotiated with his publisher for a second book, he took a lower advance, in order to secure the deal before his first book was launched. “I was willing to take that loss because I didn’t need the book advance to pay my bills,” Holiday said.

While book launches are important to build initial awareness, Holiday believes that writers should focus on recurring sales of the book in the long run. “It’s not so much that lists really have anything to do with a book’s long-term success. But when the majority of books come out, they sell a vastly disproportionate majority of all their total sales in the first couple of weeks,” he said. The publishing industry, on the other hand, is supported by books that continue to steadily sell after their launch, almost indefinitely. “What you’re trying to create, as an author, is a portfolio or a catalog of intellectual property that sells over time.”

“Not only are there certain tax implications for that, but you’re creating an annuity,” Holiday said. “Every six months, I get a royalty statement from my publisher that has so far been larger than the previous one.”

At the time of this article, Holiday’s first book, Trust Me, I’m Lying, sold around 200 copies a week. His second book, Growth Hacker Marketing, sold around 200 to 300 copies per week. On average, his third book, The Obstacle Is The Way sold around 1,000 to 1,500 copies per week in the U.S. He addressed the importance of recurring sales, saying, “If [books] could sell that way over time, that becomes a significant source of revenue for an author. If you look at someone like Malcolm Gladwell, he’s probably selling 4,000 to 5,000 copies a week, every single week.” Those types of recurring sales “is what makes publishing or book writing potentially very lucrative,” said Holiday.

Yet, despite his thorough understanding of the marketing and the business of books, Holiday emphasized that many aspiring authors and writers still overlooked most important element: actually making a great book.

“The question that writers get asked the most by people who want to be writers is, ‘How do I get an agent? What’s the best way to market my book?’” said Holiday. “People ask these questions that are very tactical, and then they completely forget the larger, fundamental, questions of, ‘How do you make a great book?’ or, ‘How long does it take to make a book?’ or, ‘What’s the best method for developing your voice?’”

“It’s fucking hard to come up with not just a good idea and a good title, but to figure out how your arguments should be structured, what ideas to include and not to include, the right tone, and the core audience that you should be aiming at.”

“Those sort of questions ultimately matter a hundred times more than any single marketing decision,” said Holiday. “Every minute or hour you spend on the book, that has the biggest potential ROI for you. Taking your time, picking the right topic, picking the right ideas, testing the material, these are the things that are going to have the most resonance over time.”

“A book is a piece of intellectual property. That intellectual property can be leveraged in a lots of ways. You can create a YouTube series. You can sell it to a studio, who turns it into a film or a movie. There are different things that you can do. If you actually see it as intellectual property, it helps you understand it a little bit more.”

“I don’t think people totally get that. They’re more like, ‘Oh, I’ve gotta make a business card, because somebody said books are the new business card.’ They are, but if it’s not a good business card that’s going to hold up over time, it’s a wasted exercise.”

My conversation with Ryan Holiday was illuminating for many reasons. I came into the conversation expecting insights on business, but, as Holiday mentioned, the business of writing is never more important than the art. Authors get caught up in trying to sign a deal, and forget that the hard work is in doing interesting things and actually making a book.

This must be what Jay Z meant when he wrote in his book Decoded, “I've reflected some of that in my music because, to be honest, it was my mentality to some degree—when I committed to a career in rap, I wasn't taking a vow of poverty. I saw it as another hustle, one that happened to coincide with my natural talents and the culture I loved. I was an eager hustler and a reluctant artist. But the irony of it is that to make the hustle work, really work, over the long term, you have to be a true artist, too.”

Image by: Stockholm Public Library by Samantha Marx.