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Stripe’s Early Stock Awards Could Boost IPO Plans – The Information

Stripe founders John and Patrick Collison have indicated that the payments software pioneer, valued at $95 billion in its last fundraising, is in no rush to go public. And few tech firms want to test the choppy public stock markets. But a fresh listing could solve a looming problem for the 13-year-old startup: Stock awards to some of its earliest employees expire next year.

Some of the company’s early employees in South San Francisco, California, have 10-year stock options that expire next year, according to two people with direct knowledge of the matter. If these original Stripe employees exercise the options before they expire, they will have to put up cash to pay a large tax bill based on the private value of Stripe stock. Stripe could arrange another secondary offer to buy these loyal employees’ private stock, money the employees could then use to pay their tax bills. Alternatively, an IPO or direct listing would allow Stripe’s employees — as well as investors — to cash out. Airbnb faced similar pressure on stock awards in 2020, the year it went public after an unprecedented drop in travel.

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