The Marginalian
The Marginalian

Rejection as Creative Catalyst: A Lesson in Entrepreneurship from New Yorker Cartoon Editor Bob Mankoff

“Serious cat people, like first-rate art critics, are chivvied by passion into perspicacity,” Anthony Lane wrote in the introduction to the impossibly delightful Big New Yorker Book of Cats. Incidentally, the same can be said of both cartoonists and entrepreneurs, but especially of entrepreneurial cartoonists.

In his new memoir, How About Never — Is Never Good for You?: My Life in Cartoons (public library), titled after his cartoon-turned-pop-culture-classic, Bob Mankoff, who founded the New Yorker’s wildly successful Cartoon Bank and has been the magazine’s cartoon editor since 1997, peels the curtain on how he reverse-engineered the machinery of a successful cartoon and turned his side project into a trajectory to the top. Embedded in his story is a testament to the power of self-education, tenacity, and the gift of seeing rejection not as a deterrent but as a springboard for entrepreneurship — something we’ve seen again and again in the psychology of failure and mastery.

Mankoff, who dropped out of his psychology Ph.D. in the 1970s to pursue a career in cartooning, decided to educate himself in the intricacies of the New Yorker aesthetic by spending countless hours at the New York Public Library, which he calls his “cartoon college.” There, he closely studied every single issue of the magazine since its inception in 1925 to understand what made cartoons work. This self-initiated learning was something Mankoff modeled after his father, an erudite man with little formal schooling who had educated himself at the New York Public Library — a heartening testament to the power of alternative education. He encapsulates his learnings from his systematic ethnography of the New Yorker cartoon:

I later learned that The New Yorker doesn’t call a cartoon a cartoon. The material of interest is referred to as a “drawing.” And because it’s a drawing, not a cartoon, it doesn’t necessarily have to be funny. Interesting is enough, if you’re as interesting as William Steig or Saul Steinberg. But whatever the form or content of the cartoons, the one common thread that ran through all of those I studied in the New York Public Library was that they made the reader think. You had to be a participant in the experience, up-to-date on the latest trends and buzzwords, aware of the world around you, and possessing a mental flexibility able to appreciate different comic visions, techniques, and talents.

Mankoff adds a note on his two greatest influences, Saul Steinberg and James Thurber:

Steinberg appealed to my rationality and Thurber to my whimsicality. Steinberg’s cartoons didn’t cause an outward laugh or even an inward one, but they made my mind smile. Each one was a philosophical mediation in ink.

Thurber, for him, provided two different kinds of inspiration:

First, his flavor of funny wasn’t like the traditional gag. His captions didn’t make sense of the image. Instead, the caption made what was going on stranger and, if you were on the Thurber wavelength, funnier.

Thurber’s jokes were not the type you “get” in that classic way where you suddenly put two different frames of reference together and therefore are able to understand why the former Mrs. Harris is up there on the bookshelf. And trying to figure out where the midgets came from or, for that matter, why they made you giggle, wasn’t going to get you anywhere. It was go-with-the-flow humor in which you enjoyed absurdity by giving yourself over to it.

That approach appealed to my wacky side and encouraged me to, well, have a whack at it. My absurdity was different from Thurber’s because weirdness by definition, if truly weird, needs to be idiosyncratic.

What was especially intriguing about Thurber, a man who knew how to transmogrify the absurd into the humorously philosophical, was his apparent lack of drawing skill in the traditional sense, which offered a kind of assurance for Mankoff:

Look, if the requirement for admission to The New Yorker was that I would have to draw as well as Addams, Arno, George Price, “Watch out, Fred! Here it comes again!” or Charles Saxon, well, that was going to be too high a bar for someone who couldn’t even make the Music and Art honor roll. But Thurber’s drawing ability was considerably less daunting. It looked amateurish by any academic standard, including that of my old high school. In fact, to get into M&A I’d had to submit a portfolio that included drawings of the human figure, and if those figures had looked anything like Thurber’s homunculi, I never would have been admitted.

But arguably the most interesting aspect of Mankoff’s career was how he came to found the magazine’s now-legendary Cartoon Bank, a simple but at the time incredibly innovative online database from which one could license a cartoon or buy a print. In 1990, when the web as we know it was but a half-conscious infant, Mankoff came up what he thought was a “million-dollar idea” — to do for cartoons what stock-photo houses had long been doing for photography, making cartoons available for licensing to publishers and general-public fans alike. He originally thought he’d populate the bank with cartoons published in The New Yorker — it seemed like a simple, brilliant, win-win proposition.

Alas, the magazine rejected it, which neither surprised Mankoff nor deterred him:

I was just a cartoonist with an idea, and The New Yorker was quite comfortable rejecting ideas from cartoonists—it did just that by the hundreds every week. This experience with rejection gave me an idea for Plan B. The New Yorker was getting many more cartoons than it could possibly use. No matter how funny your batch was, necessity demanded that most of it be deemed not funny enough. Why not create the Cartoon Bank from all the cartoons The New Yorker was rejecting every week? That would amount to thousands every year.

While some of the rejects, Mankoff points out euphemistically, “fell short of great,” the majority “weren’t half bad, a quarter bad, or bad at all” — in fact, they were pretty fantastic, which makes sense even as a purely statistical probability: Some of the best cartoonists in the world submit a total 500 cartoons to The New Yorker per week, of which the magazine prints, on average, only 17. Driven by the belief that the remaining 483 couldn’t all be “stinkers,” Mankoff decided to forge forward with the Cartoon Bank idea — a concept that would not only help the cartoonists themselves by giving their work wider exposure and enabling them to make money from the rejects, but would also help The New Yorker in the long run.

But bringing the idea to life would take two things: an understanding of cartoons, both creatively and commercially, and some computer skills. Fortunately, Mankoff had both — not only that, but also had incredible foresight about the future of social technology. In 1982, more than two decades before Facebook was born and even before Mark Zuckerberg was conceived, Mankoff drew the following cartoon:

The Cartoon Bank idea was also very much shaped, as most cultural innovations, by the available technology at the time. To think that Mankoff pulled off what he did in that context gives one pause amidst the modern technologies we take for granted:

MacPaint wasn’t good for drawing cartoons, but once you had drawn one, it was good for tinkering with it. Now if only you could draw the cartoon on paper and get it into the computer! Trying to stuff them into the disk drive didn’t work, but I discovered an early handheld scanner that you would drag across what you wanted to scan. It wasn’t wide enough for cartoons; you needed two passes to scan one, and then the software would stitch the image together.

As scanners got better and Macs more powerful, I began storing all my cartoons on the computer. From this it was not much of a leap to think that I could store all my friends’ cartoons, too, and sell them, which is how the idea of the Cartoon Bank was conceived.

From that point on, a lifelong pattern emerges in Mankoff’s story as his creative and entrepreneurial journey becomes largely propelled by women. First, his wife, Sarah — a business entrepreneur herself — not only supports Mankoff unconditionally as he pursues “what many thought to be a hairbrained scheme” (how’s that for a homonym pun), but she also teaches him the practicalities of running a business. Meanwhile, Mankoff was busy convincing the other New Yorker cartoonists of the project’s value. By 1997, seven years after its conception, that derided “scheme” had come to life and quickly proved to be a brilliant idea. But Mankoff needed one last push — it was still a catalog of rejected cartoons rather than an official archive of The New Yorker’s licensable drawings.

This is when another pivotal woman enters the scene: Media mogul Tina Brown had just been hired away from Vanity Fair to helm The New Yorker, and Mankoff set out to sell her on the Cartoon Bank idea. In one of the most intriguing asides in the book, especially given the context of Brown’s media stature today, Mankoff writes:

At a luncheon Tina held for the cartoonists, she told us … that she thought the Cartoon Bank was “a million-dollar idea.” All of this was exhilarating but also frightening. Here I was on the cusp of becoming an overnight success at the age of fifty. I had luck and Tina on my side, so what could go wrong? Everything, I feared. What Queen Tina wanted, Queen Tina got, and as long as I was golden, that boded well. Right now, Tina was blowing hot, but she could just as easily blow cold, and then off with your head as well as your headline. Golden boys, under Tina, could turn to lead very quickly.

But Brown was, and is, above all a shrewd businesswoman, so the Cartoon Bank was a go:

By 1997 the Cartoon Bank was up on this newfangled thing called the Internet and was among the first, if not the first, to, in today’s jargon, “monetize” cartoons.

And yet the Bank remained an archive of rejected cartoons — that is, until a third woman steps in: Deputy editor Pam McCarthy, who had come to The New Yorker along with Brown from Vanity Fair, became a champion of the project’s potential and set out to convince, Si Newhouse, the owner of The New Yorker, to buy the Cartoon Bank and expand it to include not only rejects but actual published cartoons.

Once the offer was on the table, Mankoff agreed to sell his baby on two conditions — that he would remain president and that he would be made cartoon editor of The New Yorker — the latter was a bold proposition, which he didn’t think the magazine would buy but when, by fluke or politics, then-editor Lee Lorenz announced his retirement a few months later, Brown immediately gave Mankoff the coveted job. He writes of the change with just the right balance of good-guy self-consciousness and entrepreneur’s confident ambition:

Look, I was very grateful to Lee for having brought me into the magazine, but not so grateful that I didn’t want his job. In other words, I was an ingrate. It wasn’t that I thought I could do it better, but I did think I could do it differently, by evolving the tradition, bringing in new comic sensibilities, and using the combined positions of president of the Cartoon Bank and cartoon editor to make cartooning more economically viable. So when push came to shove, I guess I did think I could do the job better.

I actually didn’t expect them to meet the second condition and I knew they wouldn’t, but I felt it couldn’t hurt to have my ambitions, both for myself and the expanded nature of the job.

Lo and behold, they did, and Mankoff became the magazine’s editor in 1997, seven years after he envisioned the Bank of Rejects — the once-fledgling idea that went on to become of The New Yorker’s most successful offshoots. In a New York Times article about Mankoff’s new position, Tina Brown was quoted as not only extolling his “edgy, contemporary kind of humor,” but also his role as “a passionate curator of and defender of and promoter of the art of cartooning.”

But the tragic nature of business is such that once creative venture tips into a scale large enough to tickle the commercial interests of those involved, those interests begin to warp the integrity and heart of the venture — a perilous pattern of which E.B. White admonished in 1976. What was originally primarily a way to get cartoonists exposure and help them make a living from their art now became a showcase for Condé Nast’s products. Mankoff notes wryly:

The fun stopped for me about ten years into it, when the focus shifted from the Cartoon Bank to using the online platform to promote Condé Nast’s photos, covers, and illustrations from other magazines, such as Vogue, Vanity Fair, Glamour, and Golf Digest. Nothing wrong with doing that from a corporate point of view, but from a personal perspective it was clear that someone who has no interest in fashion, never reads celebrity profiles, is unglamorous, and agrees with Mark Twain that golf is “a good walk spoiled” wouldn’t be a good fit to head such an entity.

So Mankoff stepped away from the Cartoon Bank — because, as Kio Stark memorably put it, “a gracefully executed quit is a beautiful thing” — but remained cartoon editor of the magazine. It’s a position he still inhabits with his singular sensibility and inexhaustibly refreshing kind of humor — he, who educated himself in the ethos of cartooning at the public library and who took himself to the top of a legendary cultural institution by scrapping together its rejects and sculpting them into a crown jewel.

In the rest of How About Never — Is Never Good for You?, Mankoff goes on to explore how he found his voice as an artist, what role luck and timing play in success, what makes a successful New Yorker cartoon, and how to win the magazine’s coveted caption contest. Complement it with the wonderful Blown Covers, a collection of rejected New Yorker covers we were never meant to see.

For a teaser-taste, see Mankoff’s fantastic TED talk exploring the anatomy of a New Yorker cartoon and touching on Arthur Koestler’s seminal theory of how humor and creativity work:

Published March 27, 2014




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