"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."
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."