How Okta's CEO convinced his wife in 2008 that he should leave Salesforce to start a company

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In the middle of the recession, Okta co-founder Todd McKinnon wrote a detailed presentation about why it was time to leave Salesforce for his new start-up.

McKinnon resigned from Salesforce around Thanksgiving 2008, and then joined up with co-founder Frederic Kerrest, who'd also previously worked at Salesforce, in early 2009. The pair quickly moved away from application monitoring and shifted to identity management, with the idea that if workers were going to be using all these applications in the cloud, IT managers needed a way to keep everything secure and sanctioned.

"People seemed like they needed it sooner," McKinnon said, in an interview. A year later, they changed the name to Okta, a meteorological term that refers to the amount of cloud cover at a given time. The company outpaced even his best expectations, going public in 2017 at an initial valuation of $1.5 billion. Okta is now one of the cloud success stories of the decade, poised to close the year at about $575 million in annual revenue, up 44% from a year earlier, though rising sales and marketing costs mean the company is still losing money. The stock is up more than seven-fold from its 2017 IPO, including jumping 89% this year.

While McKinnon saw the trend towards cloud apps well before it was obvious, any number of things could go wrong. Microsoft, which was developing what would become some of the most popular cloud apps as part of Office 365, steadily got more into cloud-based identity management. There were also products available from legacy providers like

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