Jones was the builder and the owner of the Aspen Highlands, one of the four ski areas of Aspen, Colorado. Aspen Highlands had its beginning in 1956. Jones owned the land at the base of the mountain and became interested in developing it after the Forest Service suggested it would be a "great place for a ski area." Jones first offered the opportunity to Aspen Skiing Company who turned it down. He then hired Dick Durrance to do a feasibility study and to design a lodge. Jones went ahead with the project on his own, and laid out a well-balanced set of ski runs: 25% beginner, 50% intermediate, 25% advanced. Jones financed the project by selling the lumber from the cleared ski runs and using low cost labor. When the area opened in 1958 it had three lifts, including the world's longest single section double chairlift and eventually grew to over 50 trails. The base area of Highlands Mountain is located 1½ miles from the village of Aspen.
Throughout his ownership, Aspen Highlands and founder Jones remained at odds with the local rival Aspen Skiing Company, which owned and operated the three other ski areas Aspen Mountain, Buttermilk and Snowmass in Aspen, with Jones owning the remaining independent ski area, Aspen Highlands. In 1979, Jones sued the Aspen Skiing Company, alleging violations of the Sherman Act. Aspen Highlands and Aspen Skiing had, for several years, cooperated to sell an "all-Aspen" ticket that allowed a skier to visit Aspen Skiing's three mountains and Aspen Highlands. However, the rival companies were unable to agree on a means to administer this program and distribute proceeds. In 1978, Aspen Skiing decided to discontinue the all-Aspen ticket, and to instead sell only the ticket to the three Aspen Skiing mountains. Aspen Skiing also refused to sell Aspen Highlands any lift tickets to the Aspen Skiing mountains, thereby preventing Aspen Highlands from offering its own multi-mountain package. The issue made it to the US Supreme Court and was decided as with Jones winning over $10 million in treble damages.
Halls of Fame
In 1998, Jones was inducted into the Aspen Hall of Fame and in 2000, he was inducted into the . At the induction ceremony, the Colorado Hall of Fame noted:
Whip's vision and marketing ingenuity proved invaluable when he had to compete with the larger Aspen Ski Corporation... His innovative marketing lured many a skier to the Highlands with the promise of fun. Many Coloradans remember with nostalgia the wine and cheese parties, flips on skis, and the opening of Steeplechase near the top of Loge Peak--a steep, avalanche-prone slope that gave expert skiers a taste of adventure.
In 1992, after the longest continuous ownership of any ski area in Colorado, Jones donated the Highlands to Harvard University. The $18.3 million gift remains one of the largest donations the University has ever received. The proceeds endow the "Whipple V.N. Jones Cornerstone Scholarship Fund" and the "Whipple V.N. Jones Professor of Economics Chair" once held by Andrei Shleifer and currently held by Xiao-Li Meng.