While at Dartmouth in 1980, Winebaum started his first business, Same Day Fish Company. He spent summers throughout high school and college working on fishing boats and started a fish processing and distribution business delivering fish and lobsters to restaurants and supermarkets throughout Northern New England. He started his professional career at Fortune magazine in 1982. He then moved to Time magazine in 1983, and U.S. News & World Report in 1985 where he was instrumental in the turnaround of the magazine and in the development of the series of special issues, including . He and his wife Cindy started FamilyFun magazine with their own funds in 1991. The magazine was an instant hit and was named one of AdWeek’s Hot 5 list of magazines for 1992. Winebaum sold the magazine to the Walt Disney Company in 1992. While at Disney, he founded FamilyPC magazine in 1994. Also in that year, he put together the business plan for The Walt Disney Company’s Internet initiatives which he went on to lead. He was named President of Disney Online in 1995. As president of Disney Online, and later as Chairman of Buena Vista Internet Group, he oversaw all of Disney’s Internet businesses, including Disney.com, ABCNews.com and ESPN.com. Winebaum left Disney in 1999 to co-found eCompanies, an Internet incubator and venture fund, with EarthLink founder Sky Dayton. It is a privately held company, and while it reportedly struggled for a time when the dot-com bubble burst, it ultimately launched and funded several successful companies. The businesses that came out of eCompanies include LowerMyBills.com, which was purchased by Experian in 2005, JAMDAT Mobile, which went public and was then purchased by Electronic Arts, Boingo Wireless, which went public in 2011, USBX which was purchased by Imperial Capital, and Business.com which was purchased by RH Donnelly in 2007. Winebaum was CEO of Business.com from 2002 until its sale in 2007. In January 2010, Winebaum founded Brighter.com. Brighter is an online resource that delivers price and reputation transparency and access to tens of thousands of top rated dentists at competitive prices, making quality dental care affordable for millions of Americans. Cigna acquired Brighter in December 2017 and as part of the transaction Winebaum became Cigna's Chief Digital Officer,.
Other activities and awards
Winebaum serves on the board of directors of Gigya, Vision to Learn, Child Obesity 180, and was Founding Chairman of Seven Arrows Elementary School. Jake was named E&Y's 2018 Technology Entrepreneur of the Year in Los Angeles,. Jake's expertise and contributions to the Internet industry have been recognized by the Los Angeles Venture Association which inducted him into its Hall of Fame in 2010, Time magazine, which awarded him a place in the Top 50 Cyber Elite, and Wired Magazine, which named him one of the Wired 25.
Family and leisure
Winebaum remains a competitive athlete in endurance cycling and running events and Masters ski racing. He has competed in the Leadville 100, Transalp Challenge mountain bike races, Tour Transalp, and Everest Challenge road bike races multiple times, and placed 6th in the 2008 National Masters Ski Championships. In 1986, he married Cindy Weston, daughter of G.I. Joe inventor Stanley Weston; they have 2 children.
