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Person

Keith Rabois

Venture capitalist and general partner at Khosla Ventures, known for early stakes in startups such as Square, Stripe, and DoorDash.

Known aliases

  • Rabois

Current stories

investConfirmed7 publishers

Dragoneer leads $1.85 billion into Ramp at no more than 30 times annualized revenue

Ramp raised $1.85 billion in a primary round at a $60 billion valuation, led by Dragoneer Investment Group. At annualized revenue above $2 billion the price is at most 30 times sales, for a company that says its cash flow is positive.

Perspective Coverage

8 publishers
Builder
Builder 24%
Operator
Operator 28%
Investor
Investor 48%

Reality

Evidence58
Adoption75
Hype gap+25
Incentives72
Confidence68
leadershipOne report1 publisher

Khosla calls portfolio company Factory 'second tier' in a fight over a board observer's move to Cognition

Vinod Khosla publicly sided with Cognition against Factory AI, which his firm helped fund in a $200 million round last month. For founders who share investors with a rival, the episode argues for writing observer access and investor conflicts into the contract.

Reality

Evidence55
Adoption
Not scored
Hype gap+5
Incentives75
Confidence55
leadershipOne report1 publisher

Factory says its board observer spent weeks talking to Cognition before joining it as revenue chief

Factory CEO Matan Grinberg says he terminated board observer Chris Degnan for weeks of talks with Cognition, the $48 billion rival hiring him as revenue chief. Degnan and Cognition deny wrongdoing, so the fight turns on when an observer owes a board notice of talks with a rival.

Reality

Evidence40
Adoption
Not scored
Hype gap+30
Incentives80
Confidence40
investOne report1 publisher

Airwallex waits out a 2026 calendar already carrying $132bn of equity supply

The payments company says it will be IPO-ready by December and that this is still not the time, and against roughly $132 billion of large offerings already on the year's tape, its $650 million of private funding looks like the cheaper trade.

Publishers:fortune.com

Reality

Evidence42
Adoption47
Hype gap+14
Incentives74
Confidence46
productOne report1 publisher

Rippling shipped the product it was sued over the moment both suits vanished

No settlement, no money, no fees. Runlayer's year-long design partner released a rival MCP gateway the same night the litigation ended, and that is the lesson for founders.

Publishers:techcrunch.com

Reality

Evidence58
Adoption24
Hype gap+18
Incentives62
Confidence55