Keith Trowbridge, “The Father of Timeshare,” Tells All in New Biography

Keith Trowbridge’s life has been a roller coaster ride, starting at ground level and painstakingly rising to dizzying heights, then taking a series of harrowing twists and turns, soaring upward and diving down, rising again, and at last coming to a level place. In Time to Share, the new book he wrote with Barbara Hill Freeman, the acknowledged “Father of Timeshare” starts at the beginning and traces his wild ride. There’s tragedy, comedy, and drama, love and hate, rags and riches. It’s a primer on real estate development. It’s also a cautionary tale.

A natural-born storyteller, in Time to Share Trowbridge introduces us to the people, places, and circumstances that shaped him. It’s an inspiring, and at times shocking, story that begins in Sarnia, Ontario, with a large and colorful extended family, all part of a centuries-old farming and fishing dynasty. A childhood that might have led to menial work in a Canadian oil refinery instead fostered his innate qualities of determination and perseverance. He made good…and then some!

The first in his family to attend college, he excelled in every way, gathering honors, enjoying exploits and activities, and gaining experience, first at Bowling Green State University (BGSU) and then at the University of Michigan, where he earned a Ph.D. All this while marrying in his junior year and having a young family to support.

And support them he did, by ingenuity and the sheer force of his personality. Starting small, he began buying housing and renting it to his fellow students. He learned the ins and outs of the real estate business and came up with ways to parlay one success into others. At the time, it was just a way to make ends meet; but it set the stage for future ventures and adventures.

Even though his father had transformed himself, rising from a life of poverty to the ranks of million-dollar-sales stars in the Canadian life-insurance industry, Keith decided he wasn’t cut out to sell insurance. Instead, he pursued a career in institutional research in the rarified world of academia. Positions at BGSU and Michigan led to a spot at the forefront of planning every aspect of Florida International University (FIU) in Miami during preparations for its inaugural year.

Along the way, he met people who influenced him to turn his full attention from academia to real estate. In the early 1970s, he decided that Sanibel Island, Florida, was the place to start. With its popularity due to its climate, tropical beauty, beaches loaded with exotic shells, and great fishing opportunities, Sanibel seemed the perfect spot to build a motel. After doing his research, putting in an enormous amount of effort, and raising financing, an oil embargo that made the relatively remote island an untenable vacation spot also made the motel project go bust.

Trowbridge rolled up the motel plans for the last time and turned his attention to other properties on the island, including condominiums. His instincts were sound, but again circumstances got in the way. Still, he came out ahead. Slightly.

It was then that he invented vacation ownership or interval ownership, which is now universally known as timeshare. This was the very first instance where buyers were able to purchase – not rent – a week at a resort and know that it was theirs year after year. Of course, he had to convince potential owners that this was not only a good idea, but also a “real” thing. His marketing methods as he recounts them in Time to Share were ingenious and often hilarious.

Trowbridge formed the Captran corporation that grew by leaps and bounds, right along with the vacation ownership business. He built or repurposed resorts on Sanibel, Fort Myers Beach, and elsewhere in Southwest Florida. Then he spread out to other areas of Florida, ski resorts in the Western U.S. and across Canada, and the islands of the Bahamas and Caribbean.

Everything was going well until a lawsuit blindsided him and forced him to declare bankruptcy. After that disaster, he again found ways to rebuild his business. Over his long career, he’s made fortunes, lost fortunes, and made them again. He’s resilient and perceives failure as a challenge.

For the past twenty years, Trowbridge has been at the helm of Executive Quest, the “headhunting” firm he founded to match timeshare resorts with candidates for high-level positions world-wide. Recent placements are in Egypt and Viet Nam.

Long a legend in the real estate industry, Trowbridge now looks back on an exciting life, first as a boy setting his sights on something better than he was given, and then as an exceptional student and leader, head of a large and fascinating family, mover and shaker on Sanibel, where he was a resident for thirty years, restaurant owner, conservationist, avid fisherman and boater, and even briefly a movie producer. He also drops a few names of famous people he’s met along the way, John F. Kennedy and Ted Turner among them, and tells about his experience being interviewed by Jane Pauley on the Today show. It’s all part of how he spent his “dash,” the time between his birth and today: 1937-

Trowbridge’s co-author is Barbara Hill Freeman of Sanibel and Maine. Little did she know when she and her husband purchased two interval ownership weeks on Sanibel in 1983 that one day she’d write about “The Father of Timeshare.” Her background as an award-winning reporter and feature writer – “an exceptional journalist” according to Time magazine veteran editor Ray Cave – was helpful during the weekly interviews with Trowbridge over the course of more than a year. Freeman is the author of The Spare-time Gardener and co-author/photographer for a comprehensive coffee-table book about Coastal Maine Botanical Gardens, where she was director of communications.

Time to Share is available in paperback (232 pages with 83 photos) at, Sanibel Historical Museum & Village, MacIntosh Books & Paper, and at book signings in Southwest Florida. A Kindle edition is available.