It was the summer of 2000. The NASDAQ had peaked, and while things weren’t yet in free fall, it was clear that Internet-related companies had some major stress in front of them. Brad had spent a week on the East Coast totally maxed out in 18-hour days at numerous companies in which he was an investor. We had a relaxing weekend planned with longtime friends in Newport, Rhode Island, and Brad was looking forward to catching his breath.

A town car picked up Amy at Logan Airport and then swung by an office park in the Boston suburbs to pick up Brad. He came out of the office on his cell phone, dragging his luggage, and somehow managed to get in the car while continuing the conversation. He waved a quick hello to Amy and continued talking. The driver took off on the 90-minute drive to Newport.

About halfway there he finished his call. He hung up, turned to a moderately annoyed-looking Amy, and said a more enthusiastic hello. We chatted for a few minutes and his phone rang again. He answered immediately and launched into another conversation that lasted until we got to our friends’ house.

It was late Friday afternoon in Newport on a beautiful summer day. We settled into chairs in our friends’ backyard with a drink. Brad pulled a pile of paper out of his bag and set it in front of him. Smartphones weren’t very smart in 2000, and Wi-Fi wasn’t ubiquitous yet, so he often dragged around a bunch of stuff he had to read and used “downtime” like late Friday afternoon to grind through ...

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