INTRODUCTION

In 1937, a British literary critic named Cyril Connolly sat down to write a book around an unusual question: How does an author create something that lasts for ten years? Connolly’s view was that the mark of literary greatness lay in standing the test of time. With the specter of world war looming on the horizon, the idea of anything surviving in an uncertain future had a kind of poignancy and meaning to it.

The book that Connolly wrote, Enemies of Promise, explored contemporary literature and the timeless challenges of making great art. It was also an honest self-examination of why Connolly, himself a talented writer, hadn’t broken through commercially with his previous work. By no means a mainstream book, Enemies of Promise was still a provocative inquiry into the important questions that artists have always asked themselves and one another.

Considering the author’s belief that he was qualified to determine what contributes to lasting work, we are faced with an interesting set of questions: How did his own work do? How long did a book about lasting end up surviving? Was he able to hit the mark he’d set? Could Cyril Connolly, like some literary Babe Ruth, actually end up sending the ball where he had called it?

While it never became a trendy cultural sensation, this unusual book ultimately endured through wars, political revolutions, fads, divorces, new styles (which became old styles and were transplanted by newer styles), massive technological disruption, and so much else. It lasted first for a decade—in 1948, ten years after its release, Enemies of Promise was expanded and given its first reprinting. The book got the same treatment in 2008, some sixty years later, and here we are again talking about it today.

Connolly managed to do what few artists can do: He made something that stood the test of time. His words still hold up and are still read. Cyril was quotable in his day and he’s quoted today. (Most famous are acrid quips like: “There is no more somber enemy of good art than the pram in the hall” and “Whom the Gods wish to destroy, they first call promising.”) The book has far outlived him and almost everything else published around the same time, retaining for Connolly a cult following decades after his death. And most impressively, given the subject matter, this success wasn’t some accident. Clearly he consciously sought this—and achieved it. Today, all this time later, his theories about the creative process remain relevant, at least to me, since they were the inspiration for the book you’re reading right now.

Is that not the kind of lasting success that every creative person strives for? To produce something that is consumed (and sells) for years and years, that enters the “canon” of our industry or field, that becomes seminal, that makes money (and has impact) while we sleep, even after we’ve moved on to other projects?

The novels of James Salter have been described as “imperishable.” A translator of the dissident writer Aleksandr Solzhenitsyn once observed that the man’s writing possessed a certain “changeless freshness.” One of Bob Dylan’s biographers has pointed out that even though many of the musician’s songs were written about momentous events in the 1960s, the music holds true and has “transcended his time.” What phrases! What a way to express what so many of us would like to achieve. Not only us writers or musicians, but, in their purest form, every entrepreneur, designer, journalist, producer, filmmaker, comedian, blogger, pundit, actor, investor—anyone doing any kind of creative work—is attempting to do just that: to have impact and to survive.

Yet undeniably, most of us fail in that effort. Why? First, we must grant that it’s really hard. Backbreakingly, you-might-end-up-in-a-nuthouse-if-you-think-about-it-too-much hard. Though I suspect that’s not why most creatives fall far short of making work that lasts for even ten minutes, let alone ten years. The truth is that they never give themselves a real shot at it. They fail because, strategically, they never had a chance. Not when almost every incentive, every example, every how-to guide they look to, even the cues they take from well-meaning fans and critics, leads them in the wrong direction.

It’s hard to see how it could be otherwise when the top “thought leaders” and business “experts” deceive us with shortcuts and tricks that optimize for quick and obvious success. Creators resort to hacking bestseller lists, counting social media shares, or raising huge amounts of investor capital far before they have a business model. People claim to want to do something that matters, yet they measure themselves against things that don’t, and track their progress not in years but in microseconds. They want to make something timeless, but they focus instead on immediate payoffs and instant gratification.

During the creative process, too many are led astray by shortcuts. We claim to want to be more than a flash in the pan, but at no juncture do we stop and consider how to increase longevity and shelf life. Instead, we use whatever is hot, cool, trendy, and selling well as our benchmarks. As a result, we have to produce more, market harder, sell out worse. It’s a treadmill, and it’s getting faster by the day.

No wonder people think creative success is impossible. With this short-term mindset, it more or less is.

A Better Way, a New Model

In every industry—from books to movies to restaurants to plays and software—certain creations can be described as “perennial.” By that I mean that, regardless of how well they may have done at their release or the scale of audience they have reached, these products have found continued success and more customers over time. They are the kind of art or products that we return to more than once, that we recommend to others, even if they’re no longer trendy or brand-new. In this way, they are timeless, dependable resources and unsung moneymakers, paying like annuities to their owners. Like gold or land, they increase in value over time because they are always of value to someone, somewhere. In other words, they are not simply perennial; they are perennial sellers.

Take The Shawshank Redemption, for example. As a movie, it underwhelmed at the box office—never playing on more than a thousand screens and barely clawing back its production budget in gross ticket sales. But in the years since release, it has brought in more than $100 million. There are minor actors in that movie who receive $800-plus checks every month in residuals. Turn on your television this weekend and you will probably find the movie playing somewhere on some channel.

There is a restaurant right next to the Staples Center in Los Angeles called the Original Pantry Cafe that is open twenty-four hours a day, seven days a week, every day of the year . . . and has been since 1924 (it famously doesn’t even have locks on the doors). Known simply as the Pantry to its devoted regulars, it has amassed over 33,000 consecutive days (and over 792,000 consecutive hours) of selling breakfast food and the occasional steak. Most mornings there is a line outside to get in. The only thing that’s changed in ninety-three years are the prices, grudgingly increased due to a century of inflation. A few blocks away, there’s Clifton’s Cafeteria, a restaurant that’s been serving diners since 1935 (and that partly inspired the whimsical personality of Disneyland). On its wall is the longest continuously running neon sign in the world—lit without fail for over seventy-seven years.

My favorite band growing up was the heavy metal group Iron Maiden. Despite getting little radio airplay, they have managed to sell more than 85 million albums over the course of a four-decade-long career. Even today, they regularly sell out shows of 30,000 or even 60,000 seats all over the world.* How can they beat Madonna in Spotify streams (her top five songs at 110 million streams vs. Iron Maiden’s top five songs at 160 million streams)? How do they do it? How does that happen?

Not that selling actual music is the only way to be perennial in the music business. Have you ever seen a drummer playing Zildjian cymbals? If you’ve watched Dave Grohl (Foo Fighters and Nirvana), Keith Moon (The Who), or Phil Collins, you sure have. That company was founded in Constantinople in 1623. Zildjian has been making cymbals for four centuries.

Fiskars, the scissor company, has been around since 1649. The high-end candle company Cire Trudon has been around since the seventeenth century. Trudon may have made its name supplying candles to the court of King Louis XIV and later to Napoleon, but it’s still a growing company—Trudon opened its first New York City retail location in 2015.

Here’s what’s even crazier: Chances are those companies will still exist in ten years. Whatever changes I will have to make to this book in later editions, I have little doubt that, barring some tragedy, the Pantry, Shawshank, Iron Maiden, and Zildjian will still be going strong. They are examples of a phenomenon known in economics as the Lindy effect.* Named after a famous restaurant where showbiz types used to meet to discuss trends in the industry, it observes that every day something lasts, the chances that it will continue to last increase. Or as the investor and writer Nassim Taleb has put it, “If a book has been in print for forty years, I can expect it to be in print for another forty years. But, and that is the main difference, if it survives another decade, then it will be expected to be in print another fifty years. . . . Every year that passes without extinction doubles the additional life expectancy.”

In other words, classics stay classic and become more so over time. Think of it as compound interest for creative work.

Brilliant financial minds have grasped this reality of the creative industries for some time. In the 1990s, the investment banker Bill Pullman created an investment vehicle that allowed owners of the rights to valuable songs to raise bonds based on the future income streams of those perennial assets. Today they’re called “Bowie Bonds,” since the late David Bowie raised some $55 million off the royalties of his back catalog.*

In 1986, an entrepreneur named Ted Turner bought the movie studios MGM and United Artists for a little over $1.5 billion. Just three months later, struggling under the debt of the two studios, he decided to sell the companies off in pieces, a big chunk of them right back to the person he’d bought them from in what looked like a huge loss. In fact, it was one of the most brilliant moves in the history of the entertainment business. Turner kept MGM’s film library and the television rights to classic films that included blockbusters like Gone with the Wind but was largely made up of a block of solid films like Network, Diner, Shaft, and The Postman Always Rings Twice. Combined, these films would produce more than $100 million a year in revenue, and when Turner would go on to launch channels like Turner Network Television (TNT) and Turner Classic Movies (TCM), they would play nonstop. He built a multibillion-dollar empire on perennial sellers—not only right in front of people’s noses, but while those people were turning up their noses at him. “What do you want with a bunch of old movies no one watches anymore?” they scoffed.

The brilliance of it is that perennial sellers—big or small—not only refuse to die or fade into oblivion; they grow stronger with each passing day. The works of Homer and Shakespeare, along with hundreds of other dead playwrights and philosophers—despite all being available for free online—still sell hundreds of thousands of copies per year. Star Wars isn’t suddenly going to stop making money—in fact, the profits from the franchise are actually now accelerating, some forty years after conception. Nor is every “classic” a towering work of staggering genius. In 2015, catalog albums in the music industry—titles at least eighteen months or older—outsold all new releases for the first time in the history of the music business. The albums your parents grew up listening to, that record you liked in high school, the steady climbers that are just getting going after a slow start—they moved more units than all the chart-topping artists and hot singles combined.

A year and a half—that’s not so long. Compared with what George Lucas or Shakespeare has done, ten years doesn’t seem so long either. So why does it seem to be so hard to do? Why do so few seem to even try? And is this reluctance—or deliberate ignorance—not an opportunity for those of us who are fascinated by these artistic outliers to set out to create our own?

A Lifelong Fascination

When I was a teenager, everything I liked was old. My favorite bands had released their first albums before I was born and were still going strong decades later when I came around (and thankfully, the ones that are still alive still are). I remember picking up The Great Gatsby in high school for the first time and being shocked that something intended to be so timely—about the Jazz Age—could, more than a half century later, still feel so timeless. Even the movies I found myself watching and rewatching weren’t in the theaters; they were on television—the so-called classic films.

Early in my career, I was a research assistant for Robert Greene, whose historic masterwork, The 48 Laws of Power, didn’t hit the bestseller lists until a decade after its release. It has since sold more than a million copies and has been translated into dozens of languages. I would suspect that a hundred years from now people will still be reading it. The first book I worked on was I Hope They Serve Beer in Hell, by controversial blogger Tucker Max. It received a $7,500 advance from a small publisher after being rejected by almost every other imprint in the business, yet went on to sell an upwards of 1.5 million copies and spend six consecutive years on the bestseller lists. A perennial seller and then some—the book celebrated its ten-year anniversary recently, and still moves roughly three hundred copies week in and week out.

I later became the director of marketing at American Apparel, where the company’s bestselling styles were not new trendy fashion pieces but its classic T-shirts, underwear, and socks. The founder once told me his goal was to make clothes that people years in the future would still be buying in vintage clothing shops. It was this focus on well-made staple products, combined with creative and provocative marketing, that helped American Apparel sell hundreds of millions of garments in its two decades in business.

All of this was my education in the art of the perennial seller—how they work, what goes into them, and why they matter, from both a personal and a business standpoint. I applied this knowledge in the creation of my own company, Brass Check, which has carved out a niche pushing clients toward creating and marketing work to last. Authors we’ve worked with have sold more than ten million books, spent seven hundred weeks on bestseller lists, and been translated into close to fifty languages. Our past media clients, including outlets like the New York Observer and Complex, have become quiet traffic behemoths. One of the startups I advise is a vinyl record club—the definition of a business model (and, surprisingly, a medium) that has endured.

I’ve even tried to apply this contrarian thinking to my own writing. I don’t believe I have created masterpieces that will last a thousand years, but I humbly submit that longevity has been the aim of my work. I’ve tried to model my own books on the perennial mindset and have started to see the results of those efforts. You wouldn’t know it from the New York Times bestseller list, but in the years since they’ve been published, my books have sold more than four hundred thousand copies in more than twenty-five languages and continue to sell steadily day in and day out. These works may go out of print someday, but every morning that they stick around increases their chances through another evening.

How to make something last—whether it’s for a few months more than the average or for a century—has been my lifelong fascination. It’s also become a question central to my livelihood. Is there a common creative mindset behind work that lasts? How is it different from work that’s popular one day, gone the next? How do such creators think about the vocabulary used to package their work? What kind of relationship do they have with their fans and followers? Is there a pattern to perennial sellers that we can learn from?

These questions are what led me to research and write this book. In the pages that follow, we’re going to examine these questions in many forms, from many industries, from many eras. Not just the incredible amount of work that goes into the creation of works that stand the test of time. But how to position them. How to market them. How to build a career around them. And how to avoid falling for the seduction of short-term notability to focus on the real brass ring: long-term success and renown.

In my quest for answers, I’ve spoken to everyone from Craig Newmark of Craigslist fame to legendary music producer Rick Rubin to Jane Friedman, whose company Open Road publishes for the estates of timeless authors like Thomas Wolfe, Isaac Asimov, and H. G. Wells. I interviewed agents, marketers, publicists, entrepreneurs, business owners, and academics about how to make things that last. And I tested some of my findings within my own company, often with surprising results.

A Decade? A Century? That’s Impossible!

Makers of great work are intimidating. It’s easy for us to look at them and think: They are better than me. They’re special. The gods must have smiled on them. Only geniuses can achieve that level of success, and only flashes of inspiration from the muses can spur it. It’s all about the right person at the right time in the right place.

The number of people in the entertainment industry who have told me some version of “You could never do that today” while discussing certain classic shows and works of brilliance is both heartbreaking and mystifying. How uninspiring is that? How fatalistic and defeatist? Surely one way to ensure that creating amazing, lasting work is impossible is by convincing everyone that it cannot be done on purpose.

I’ve seen too many clients do it too many times to know that longevity isn’t an accident. Anyone who studies the history of literature, film, or art can see that while luck is certainly an important factor, perennial success is also the result of the right decisions, the right priorities, and the right product. There are too many commonalities among perennial sellers across many different mediums and industries for luck to be the only factor. With the right mindset, the right process, and the right set of business strategies, you can increase the likelihood that your work will join the ranks of these classics. Their success can be your success.

Yet, too often, the approach of the average creator is to hope to get lucky. On top of that, we focus on all the wrong metrics for measuring our success and, in the process, actually diminish our chances for longevity. Making a beloved classic that lasts for a hundred years may seem like a tall order. Fine, put that aside. What if we start by just trying to make something that lasts longer than average?

Cut flowers can outlast movies that people have poured millions into. Investors dump businesses and businesses shed products faster than a deer sheds its antlers. The average NFL lineman has a longer career than a book is given time to find its legs.

Let’s start by rejecting those flawed assumptions from the outset. Let’s start by internalizing the best practices of those who’ve achieved intermediate and lasting success so we can give ourselves the best chance of joining the lofty perch of those who have made something truly perennial and timeless. Let’s be truly ambitious.

To that end, this will not be another marketing book—though marketing will be an important part of it. Instead, this book examines every part of the process from the creative act to creating a legacy. It will teach you:

I personally love books, and a lot of my clients and readers are authors, so there will be a lot here about books (not a bad industry to study, by the way, with over $70 billion a year in revenue). But the ideas put forth in this book are in no way limited to authors.

We’re all selling ideas. Whatever the form, the process is the same. And if we get really good at it and we think about it the right way, our idea can sell forever, an infinite number of times.

That’s the dream. To matter, to reach, to last.

So let’s go get it.