“I wrote time and billing software and case management software,” he says. Stack soon branched out on his own to take his computer know-how to other law firms. “And I computerized the entire law practice.” “Then IBM came out with the first real PC,” recalls Stack. In 1980, as a student law clerk, he computerized the products liability division of Nurenberg, Plevin Heller & McCarthy Co. When Charles Stack graduated from Case Western Reserve University law school in 1982, he was already familiar with computers he owned the fabled Radio Shack TRS-80 Model 1 - the first true personal computer. This time, his plan includes remaining the market leader. His latest venture,, sells software components online, and Stack believes it will change the way businesses acquire and build their software applications. All of which made the transaction seem rather familiar to Stack, who has spent the last 20 years a step ahead of the mainstream and a step behind the big money.īut in the mind of this reclusive entrepreneur, that is about to change.Īfter quietly undermining the foundation of the retail book trade, Stack has now taken aim at the software business. It was an unquestionably profitable payday for Charles Stack - but nothing compared to the $32 million that Amazon’s IPO attracted just a month after the sale. (At the time, its sales volume apparently had already been eclipsed by the months-old, though Stack has never revealed any meaningful clues about the finances of his businesses.) Instead, he sold the business in 1996 for $4.2 million to the company that has since become Cendant Corp. But Stack’s entrance into the world of Internet finance came before the impossibly high multiples achieved by one high-tech stock after another. If his goal from the start had been to take the enterprise public, Book Stacks today might be the premier online book store. The selection eventually reached more than 500,000 titles under Stack’s ownership, but for all his vision about the impact of the Internet on consumers, Stack failed in one critical area: He didn’t anticipate the excitement it would generate in the financial community. To feed my own habit,” says Stack, whose own bookish personality is more like the reference section than, say, new fiction. “My dream was to have a bookstore that had every book ever published. Several minutes later, Stack understood what the technology meant for his first customer, who had a computer that read ASCII text aloud and a Braille keyboard for input.Ĭharles Stack may have been the first true online retailer, but his venture was grossly undercapitalized and outmatched by those who followed. He waited through an abnormally long pause, and waited still more as the answer appeared on the screen in front of him, one painstakingly typed letter at a time:Ī…s… … a… … b…l…i…n…d… … p…e…r…s…o…n…, the response began. Instead, he prudently typed the more open-ended message: “Why do you like this service?” Stack had spent a year painstakingly programming the BBS for ease of use - an unusual nicety at the time - and he wanted to ask the customer what was taking so damn long. “Finally, we broke in on his session and told him he was our first customer.” “We couldn’t stand it anymore,” Stack says. But a mix of excitement and frustration got the better of him. ![]() The minutes dragged the staff waited for the visitor to make a purchase Stack tried not to interfere. “I remember watching this person typing very, very slowly,” Stack recalls in an uncharacteristic chattiness. Stack and his staff huddled around a single monitor to watch the historic transaction unfold. “So we sat there and watched the modems, with the ringers turned up loud.”Īfter a week of nervous fidgeting, a modem finally hissed and lit up. “BBS technology lets you watch the guy navigate through the site,” Stack explains. Then, day after day, Stack and his small staff passed time at the office, waiting for someone - anyone - to see one of the ads and dial the phone number that would let their computer log on to the bookstore. He first got word out about the bookstore by placing ads in magazines dedicated to the esoteric world of online bulletin board systems - BBSs in computerese. What Stack remembers most about that first online sale was the waiting. Stack courageously ventured into those inhospitable waters in 1992 when he founded the world’s first online bookstore - Book Stacks Unlimited - long before the World Wide Web existed. It’s not a stretch to call him the Ferdinand Magellan of e-commerce, exploring the very edges of the online world at a time when the Internet was text only, security encryption was still military technology and people trying to sell stuff were as welcome as a 16th century Spaniard in the Pacific. Charles Stack may be the first person to ever sell a book on the Internet.
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