Walter White Buckley III grew up in a prominent Philadelphia-area family. His father ran a money management business called Buckley & Meuthing and his grandfather ran Buckley Brothers, also a money management firm. Buckley attended Episcopal Academy, an expensive private school, for kindergarten through high school. He then attended University of North Carolina at Chapel Hill, grading with a B.A. in political science. While in school, Buckley was motivated more by sports than business, starring on the North Carolina soccer team. His coach recalled "He played with wonderful, physical, reckless abandon", leaving it all on the field.
Buckley co-founded a medical supply company called Centralized Management Systems, which was sold in 1987. He spent the next three years working as a Commercial Loan Officer at CoreStates Financial Corporation before joining the venture capital firm Safeguard Scientifics. From 1991 to 1996, Buckley was the Vice President of Acquisitions at Safeguard. There, he oversaw the acquisitions of a number of companies including ChromoVision, Diamond Technology, Video Server, and XL Vision.
Buckley and fellow Safeguard executive Ken Fox noticed an emerging market in e-commerce business-to-business, or B2B as it would become known as, and left Safeguard in February 1996 to found their own venture capital firm, Internet Capital Group (ICG). The pair asked Safeguard head Pete Musser for $5 million in funding, but he insisted on investing $15. By May when initial funding completed, Buckley and Fox had raised $40 million to start ICG, twice what they had hoped for. In addition to Safeguard, major investors included Comcast, Compaq, and BancBoston Ventures.
Buckley served as the company's president from March 1996 to December 2001, at which time he became the company's Chairman, a position he continues to hold as of 2015. He has served as the CEO since its founding. By the height of the dot-com bubble in early 2000, ICG had invested $1.4 billion in 61 start-up firms, leading Business Week declared that "Buckley put B2B on the map". As dot-com excitement began to fade, Buckley refocused the company to find strategic partnerships with traditional industry leaders. For example, a joint venture with DuPont called CapSpan in early 2000.
ICG went public in August 1999 at $12 per share. Publicly traded on the NASDAQ, ICG reached $212 a share in December. Representing a market value of nearly $60 billion, that made ICG the third largest Internet company by market capitalization behind only AOL and Yahoo. Buckley held about 4% of the stock at the time, making him worth more than $2.5 billion on paper. The figure was short lived, as the price had been driven purely by speculation – few actually believed it was worth that much. In February 2000, insiders were legally allowed to sell and some did so, but the stock price remained above $100 as retail investors bought up insider sales due to dot-com excitement. When the dot-com bubble burst a few months later, ICG fell sharply. Buckley, who sold very little of his own stock, remained optimistic. "We have never been more confident of what we're building," he said in November 2000. "The market doesn't know that, but it will." The stock continued to fall, eventually dipping below $1 a share by September 2001.
ICG survived the crash, and changed its business model. Instead of taking small stakes in many companies, it would invest in a few "core" companies at a time, usually as majority owner. This allowed the company to have much greater control over the operations of its investments. By September 2014 when the company changed its name to Actua Corporation, its stock was trading in the upper teens again and was worth approximately $700 million.
Buckley is a Director of Candide Media Works, Channel Intelligence, e-Chemicals, iCueTV, Internet Healthcare Group, iSky, OneCoast Network Holdings, PaperExchange.com, PrivaSeek, Procurian USA, Sky Alland Marketing, Syncra Software, and Who?Vision Systems. He is a member of the board for Arrowroot Capital and Cross X Platform. He is on the advisory boards of the Carolina Entrepreneurial Initiative, the Kenan-Flagler Business School at University of North Carolina, and the Starfinder Foundation. Previously, he was a Director at BravoSolution US, Breakaway Solutions, and Cortera.
Buckley is known for a "coach-like style" of management that encourages teamwork and camaraderie.
In 2000, Business Week named Buckley as part of the eBiz 25. Also in 2000, he was named the Entrepreneur of the Year by Price Waterhouse, and received the Entrepreneurial Excellence Award from the Greater Philadelphia Venture Group. Buckley's cash compensation is $450,000 per year. He has averaged about $2 million in total compensation since 2008 including stock options.
Buckley is an avid runner, often traversing a long, rocky hill near the Actua headquarters.
In 2015, Buckley and his wife donated $350,000 to the presidential candidacy of Chris Christie.