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So, if I understood correctly, they had a liquidity event where people could cash in their options/shares, and people did. They seemed to expect this expense, IIUC they even took on capital (Series I funding) to make sure they can afford it. The loss is not due to bad financial performance at all (the article mentions increased sales by 30%). Hats off to Stripe for making sure that their employees, who had to sit on their options, had a chance to finally cash in on the success of the company.

(If my understanding is correct, the title is quite misleading, because it makes it sound like Stripe was struggling. When in fact they flexed their muscle by taking on cash to hand to their employees).

As someone who’s held worthless equity in 6 or so startups this sounds amazing
I got screwed on options once. Never again.
Yeah, still trying to figure where’s the problem for Stripe
This title appears to be clickbait. They had a “one off” liquidity event that accounted for the doubling of employee costs, meanwhile their revenue is growing rapidly according to this article.
I really don’t get how anyone can find writing misleading headlines fulfilling in any way.
Clickbait? It's what happens when self-annointed "journalists" don't understand / practice actual journalism. It persists because no one stands up to say, "You're not a journalist. You're a hack."