When I spoke with the entrepreneur Chris Whittle for the first time, this September, he was calling from his modest but tasteful saltbox home in Sharon, Connecticut, constructed in 1740. “It always amazes me that it was built before the revolution,” he tells me. “I really love it here.”
Whittle, now 77 years old, is often described as one of the great salesmen of his generation, so I’m not particularly surprised by his ability to make the best of a bad situation. He retreated to the $1.2 million house in 2023 to lick his wounds during the pandemic after losing nearly everything he had built for himself during the previous 40-plus years.
