NEW YORK -- About a year ago Mary Ann Naples had a holy-cow moment. If she'd been a cartoon character, she would have smacked her forehead until stars came out.
She was standing atop an escalator at Book Expo America, the publishing world's spring jamboree in New York, surveying a convention hall of sullen faces. Many of the 30,000 booksellers, publishers, authors and agents were looking like well-heeled passengers on a leaky cruise ship.
The rise of digital books and online retailing was upending book publishing's business model. Publishers facing higher costs and less revenue were signing fewer authors; advances and royalties were declining; and bookstores were vanishing, leaving big American cities such as Laredo, Texas, without a single one.
And not least among the sky-is-falling signs, it was tougher to persuade a book editor, here in America's publishing capital, to buy lunch, never mind underwrite a book party for an established author.
Although everyone agrees stories need to be told and distributed -- most still through words in the form of sentences that make paragraphs that make chapters -- the industry remains uncertain about future ways to turn a profit.
Naples' escalator epiphany was that authors couldn't rely on publishers and agents to sort out the future. They had to harness the Internet on their own, to find new ways not only to draw audiences but also to keep them, and make money at it too. She'd observed how musicians were sidestepping the major labels by using online tools to connect with and sell their music directly to fans.
"There's something through direct selling that can make a difference in an author's career," she remembered thinking that day.
A year later, the Ivy League-educated Naples made a leap. After 20 years of birthing books -- first as an editor and later as a literary agent -- she joined OpenSky, a tech start-up in lower Manhattan that is developing an online platform for established authors, bloggers and celebrities to sell products they believe in and can endorse right off their own websites.
The site, which goes live this week, has so far signed up 1,000 such "tastemakers" and a slew of suppliers, and is designing tools to connect them with one another and shoppers as well as take care of all the messy details of commerce like warehousing, sourcing, shipping and billing.
A cookbook author, for example, not only sells books through OpenSky but also hawks a favorite barbecue sauce and grill. The author pockets 50% of the profit, with the rest going to OpenSky and others involved in the transaction.
This spring at Book Expo, instead of bearing a nametag that said "literary agent," Naples' read "retail." And this time, standing atop that same escalator, she thought book publishing's future looked a lot rosier.
In fact, it is still divided among pessimists (hoping to retire before the industry is unrecognizable), nihilists (contemptuous of books on paper and copyright laws) and optimists (eager to reinvent a digitized literary landscape).
Naples has decided to throw in her lot with the optimists.
Her recurring challenge at Book Expo, however, was to prove to literary pals that she was still in the same business they were: publishing. After one of those hair-tearing panels with big shots debating whether e-books hurt authors, Naples ran into moderator Simon Lipskar, a literary agent.
"You're doing the smart thing," Lipskar said, half-teasing, half-serious, "getting the hell out of this business."
Looking New York chic in a simple gray dress and dark brown clog boots, Naples gazed at Lipskar through the tools of her trade -- dark, heavy glasses that dominate her face. (They're like something you'd expect to find on the nose of Henry Kissinger, not a 43-year-old freckled woman with a voice that hints at an inner Lauren Bacall.)
"Simon," she said, "I am still in this business. I'm just helping authors develop their brands.... A little less editorial work, a little more positioning."
In between seminars and schmoozing, Naples pitched OpenSky to a series of publishing contacts. Most, like her, were reinventing themselves. She met with a former book editor who'd become a publishing "coach"; a savvy blogger with the title "chief executive optimist"; and a 56-year-old Boston publisher and his 24-year-old former intern, who were expanding their business with parenting and cooking websites.
David Hale Smith, a Texas literary agent, was about the only one who hadn't morphed roles since Naples last saw him. After they sat down at a table near that escalator, Smith immediately handed her a copy of a client's newest novel: "So Cold the River" by Michael Koryta. Smith mentioned that it's set in an old hotel in central Indiana known for its Pluto Water, believed to have healthful effects.
Naples lit up: "If [Koryta] was on OpenSky, the novel could be tied to a promotion of the hotel. He could have a button on his site for readers to buy the book and the water." (OpenSky would find a supplier to bottle and ship it.) She described other commercial possibilities: a sneak-peak download of a chapter of his next book, a "webinar" with him discussing his stories.
"It's a way for the author to add value to what he's offering readers and make deeper connections," Naples said. "You're not sending them elsewhere to buy things you recommend. The customer is your customer, you get the e-mail addresses, you get to engage with them any way you want."
Smith seemed interested: "I like that the authors get to have their own handcrafted storefront."
It's hard to imagine the long-deceased Jane Austen leveraging "Pride and Prejudice" into a matchmaking business or the more recently deceased crime novelist Stieg Larsson peddling the preferred coffee of his highly caffeinated main character, Mikael Blomkvist.
Naples acknowledged that not every book can be tied to a product or experience. But she described how many nonfiction authors who put thousands of hours into writing books and blogging never get the opportunity to tap into the commerce that grows out of their work. She pointed out author and food blogger Michael Ruhlman, an early recruit to OpenSky, who hears from thousands of readers wanting to know, for example, what knives he uses.
"He can now recommend something he loves and make a profit," Naples said.
Naples has exchanged 20 years of publishing "cred" for this Internet start-up because in her view technology, properly used, doesn't have to spell the end of the book world she has treasured.
"I still love the smell of old books from libraries, but now I'm platform agnostic," said Naples, who carries around an iPhone, iPad and laptop in her briefcase. "I read on any device, anywhere, all the time."
Naples grew up in suburban New Jersey in a family that had two nicely stocked bookshelves but was not literary. She was so excited by one of the first books she read, "My Friend Flicka," a 1941 novel about a boy and his horse, that she wrote to the author, who shocked her by writing back.
"After that, it was books, all the time," Naples said.
After topping off an undergraduate degree from Cornell University with a master's in English literature from the University of Virginia, Naples considered teaching until an employment agent told her that if she took a job at a Manhattan publishing house she'd earn $13,000 a year but spend her days reading. In 1990, she landed a position as assistant to the editor in chief of Doubleday and later went to Hyperion and Simon & Schuster.
"From the first day I knew this was the world for me," she said.
Over the next eight years Naples edited 100 books, including a first-novel sensation, "Fall on Your Knees" by Ann-Marie MacDonald, and Kathleen DesMaison's seven-step plan, "Potatoes Not Prozac: Solutions for Sugar Sensitivity."
Naples came to understand the serendipity, alchemy and sheer luck that went into a bestseller and watched as publishers became increasingly reliant on such hits while backlists languished. She also became more interested in lifestyle and inspiration books, and one day had an inspiration of her own (yes, another holy-cow moment) to become a literary agent. In 1998, she co-founded Creative Culture Inc. with a friend with similar literary tastes. Naples' husband, a filmmaker, was her entrepreneurial role model.
Last year, not long after her epiphany, a client asked Naples to look into OpenSky. She met founder John Caplan, former head of modeling agency Ford Models Inc., and was taken by his focus on helping "creative people monetize their passion."
"That seemed like a revolutionary idea," Naples said. "There used to be so little an author could do to make sure a book was a success except hope and wait for the publishing houses' backing. But they just had such a limited window of interest."
OpenSky's headquarters on West 18th Street is in a neighborhood where Silicon Alley overlaps with the publishing industry. But the vast open space, with bright blue walls and exposed ceiling pipes, feels a long way from the book-filled suites where Naples once toiled as an editor and agent.
Never mind having separate offices -- few people even have assigned desks. Rather, most mornings roughly two dozen OpenSky employees claim a work space by laying down a laptop.
Naples insists that she loves her new world, where music is always blaring and almost no one, except she, is over 40 or knows much about the marketplace of books.
"I come to work every day equally excited and scared," she said. "I've kind of made it a mission every day to imagine new possibilities for authors to have new streams of income."
She paused, plucked a blueberry from a small box on a bare desk, and smiled. "The world is changing and authors have to find ways to eat."