John Lindsay Jr. is changing his image.

Relaxing with a coffee at a Spring Garden Road restaurant, the entrepreneur, philanthropist and co-creator of downtown’s iconic Purdy’s Wharf development has traded in the regulation blue suit, white shirt and red tie for an open-necked, pink-and-blue striped shirt.

At 56, he said he’s now more focused on the information technology side of the family business and less on commercial real estate development. Going to a meeting these days, he says, clients do not expect him to look solid and respectable, like his buildings...

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