Issue link: https://nebusinessmedia.uberflip.com/i/1541563
4 0 C T I N N O V A T O R S , 2 0 2 5 and $100 million from outside investors, including Microso co-founder Paul Allen, financier George Soros and cable television executive John C. Malone. e company's "name-your-own- price" model changed how consumers purchased airline tickets. Priceline's March 30, 1999, initial public offering was a sensation. e stock, priced at $16 per share, closed the first day at $69, giving the company a $9.8 billion market value — the highest first- day value ever achieved by an internet company, the New York Times reported at the time. Walker quickly became a billionaire, with Forbes estimating his net worth at $1.6 billion in August 2000. At its peak, the stock reached $165 per share. But the dot-com crash hit hard. Walker stepped down as Priceline's vice chairman in late 2000. By October 2000, his estimated net worth had plummeted to $333 million, according to Time magazine. Yet, Walker's legacy endures. Today, Priceline (now part of Booking Holdings) is a highly profitable, multibillion-dollar public company serving tens of millions of customers. From Queens to Connecticut Born in Queens, New York, Walker grew up in an entrepreneurial household. His father Arthur was a real estate developer, and his mother Jeanette — who fled Europe at age 6 to escape Nazi persecution and later became a golf and bridge champion — instilled in him a fierce competitive drive. Walker's inventive streak emerged early. At 9, he created and distributed his own newspaper. At 13, he undercut the canteen's prices by selling candy to kids at summer camp. e entrepreneurial bug had bitten hard. Aer his mother died when he was 18, Walker attended Cornell University, where he majored in industrial and labor relations, graduating in 1977. During college, he became an expert at the board game Monopoly, even serving as president of the Ivy League Monopoly Association. He co-authored "1,000 Ways to Win Monopoly Games" with future Cornell President Jeffrey S. Lehman, which drew the ire of Parker Brothers, the game's manufacturer. e company threatened legal action. His early business ventures included at least one failure. During a leave of absence from Cornell, Walker started a weekly newspaper — the Midweek Observer — in the college town of Ithaca, New York. Publishing giant Gannett ran his paper out of business, leaving him in debt. Walker married Eileen McManus in 1982. McManus, a former personnel executive at IBM, is currently a trustee for Cornell University and board co-chair at e Harvey School in Katonah, New York. ey have two children, Evan and Lindsey, and live in Ridgefield. Outside advantage In the 1980s, Walker founded Catalog Media Corp., which produced and distributed mail-order catalogs for national retail clients. ere, Walker was joined by a recent Wesleyan University graduate, Jon Ellenthal, to help build a distribution channel for catalogs in Walden bookstores across the country. e two would continue working together on ventures for more than 30 years; Ellenthal is now president of ApiJect. Catalog Media's breakthrough came when Walker was invited to a meeting with Jim Barksdale, then the No. 2 executive at shipping giant Federal Express. FedEx was seeking new revenue beyond documents and parcels, and Walker spotted a niche in catalog shipping. At that time, catalogs typically ceased operations in late November because customers believed post-anksgiving orders took six to eight weeks to fulfill — making holiday delivery impossible. Walker proposed a flanking strategy: instead of competing with UPS purely on cost or speed, he persuaded catalog companies to promote "FedEx delivery guaranteed" throughout their materials, implicitly extending the ordering window to Dec. 21. e effect was dramatic. Catalogs added several weeks to their peak selling season, and FedEx went from tens of millions of dollars in catalog revenue to more than half a billion dollars over five years, Ellenthal said. "It really unlocked new benefits for everybody involved," Ellenthal said. "Benefits to the catalog company — they sold more. Benefits to the consumer — they didn't have to go fight the traffic at the mall on Dec. 14. And certainly benefits to FedEx, who was able to compete using their brand as a marketing asset rather than just a shipping asset." e FedEx success demonstrated a pattern that would define Walker's career: finding novel approaches by looking at problems from outside the industry. "Innovation comes from an outsider, because everybody inside the industry is vested in doing things how they've always been done," Ellenthal said. "Jay is a student first, and he's certainly a student of human behavior. He understands the essential role of storytelling in human communication. And he also understands that big breakthroughs are possible when you look at problems from a very different vantage point." Disrupting magazines In 1991, Walker partnered with serial entrepreneur Michael Loeb to create NewSub Services, later renamed Synapse Group, which changed how Americans subscribed to magazines. e innovation was deceptively simple: converting magazine subscriptions from fixed-term contracts to open-ended services that continued until customers canceled — similar to how newspapers and phone service worked. When subscriptions became perpetual until canceled, customer lifetime value doubled, which allowed magazines to invest in better customer service and richer introductory offers, Ellenthal explained. Synapse further forged alliances with credit card companies, embedding free magazine offers into monthly billing statements — eliminating the friction of mailing payments. By 1998, Synapse had sold 30 million subscriptions with sales approaching $300 million. e company was acquiring more customers for major publishers than the publishers were acquiring themselves, Ellenthal said. In 2006, Time Warner fully acquired Synapse for an undisclosed sum. Ellenthal observed: "Everything Jay builds has never been done before. … Being first can be quite lucrative." A new challenge Walker calls ApiJect his most difficult venture yet, in part because health care is a high-friction, regulated industry that defaults to the philosophy of "do no harm." at means change is slow, and risk is high. Continued from previous page Glass walkways and spiral staircases wind through The Walker Library of the History of Human Imagina- tion, Jay Walker's private collection. The space features rare books, historical artifacts and displays cele- brating human innovation, including a 1957 Russian Sputnik backup and a 17th-century atlas containing the first maps to depict the sun at the center of the universe.