Toast built a $30 billion business by defying Silicon Valley VCs

Chris Comparato, CEO, the Toast, Inc. IPO at the New York Stock Exchange, on September 22, 2021.

Source: NYSE

Not long after selling software company Endeca to Oracle in 2011 for over $1 billion, Steve Papa called Bessemer Venture Partners with a hot tip. He said three of his best engineers were working on something new that Bessemer, which had previously backed Endeca, would be crazy not to fund.

Kent Bennett, who’d been a junior associate on the Endeca deal, fielded the call. He told Papa there was some empty space at the firm’s office in Boston that his people could use. But Bennett knew he couldn’t get his firm, one of the biggest and most successful in the venture industry, to write a check to three engineers with an unspecified project.

“I said, ‘Well just send them over here and they can hang out here until they figure it out,'” Bennett told CNBC, recalling his conversation with Papa.

The three guys and some office space eventually became Toast, a…

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