Will Poole likes to joke that he picked the wrong time to leave Microsoft.
It was 2008, the global financial crisis was beginning to bite, and the world’s most profitable business, Windows, was the last thing anyone would walk away from.
But Poole had seen this cycle before. Downturns, he believed, were not moments to retreat.
He had lived this playbook as a young founder in the early 90s, selling his first startup at 23, then again during Netscape-era browser wars, and later while running a $13-billion division at Microsoft.
