Stripe Faces $3.5 Billion Tax Bill as Staff Shares Expire (2)

Stripe Inc., one of the world’s most valuable startups, told investors it plans to use money it receives in its latest round of fundraising to help cover a roughly $3.5 billion tax bill.

Using an illustrative valuation of $55 billion, the payments giant said it is looking to raise about $2.3 billion to cover tax withholdings in the first quarter, according to an investor document seen by Bloomberg News. It plans to withhold an additional $500 million and $700 million in taxes later this year and next year, respectively.

The company also expects to use $600 million of the ...