Wiz founder: Leaving Microsoft ‘most horrible decision ever’

Of course, upending his life to embark on his own project coincidently during lockdown proved nerve wracking. “It felt like the most horrible decision ever,” Rappaport said at Fortune’s Brainstorm Tech conference this week. 

Part of the problem was that Rappaport was departing a role and company that he truly enjoyed. “I was on the mothership,” Rappaport said. “I truly, I love Microsoft. I had a great job, great impact on security,” he continued. 

Even so, Rappaport was feeling like it was time for a change. He had done everything he needed to do at Microsoft, after all.

“My first flight back from Redmond [Washington], I wrote on a napkin a list of what I wanted to do at Microsoft, what was important for me to accomplish,” he told Forbes. “When I finished the napkin, I left the job.”

Ready for his next adventure, he went on to co-create and become chief executive at Wiz, a cloud security company. The only problem? No one wanted him. “Nobody picks up the phone, nobody answers us,” he explained to Fortune of his time trying to get Wiz off the ground in the heat of the pandemic. 

But the timing was surprisingly serendipitous. He said in hindsight, “if you pinpoint a time in history, probably March 2020, that’s the time to start a cloud security [company].” In part, they were not inventing the wheel but refurbishing it, taking cues from tech companies that had laid the ground before them. 

“The advantage that we had is learning from the mistakes of the others,” he said.

What felt like an error in judgment has paid off tremendously for Rappaport. Alphabets’ Google Cloud business is said to be in “advanced talks” to acquire Wiz for the price of about $23 billion, according to The Wall Street Journal. Rappaport declined to  comment on said deal while at Fortune’s conference but referred to it as the “23-ton elephant in the room.”