Exclusive: Pinterest unpins employee tax bills

March 23, 2015, 9:18 PM UTC
Pinterest Said To Be Raising Funding At $11 Billion Valuation
The Pinterest Inc. application (app) is displayed for a photograph in the Apple Inc. App Store on an iPad Air in Washington, D.C., U.S., on Thursday, Feb. 19, 2015. Pinterest Inc. the online scrapbooking company, is seeking to raise funding at a valuation of about $11 billion, according to a person familiar with the matter, continuing the soaring values of a group of high-profile technology startups. Photographer: Andrew Harrer/Bloomberg via Getty Images
Photograph by Andrew Harrer — Bloomberg via Getty Images

You are free to leave.

That was the message from Pinterest to its employees last week, during an all-hands meeting at the company’s San Francisco headquarters. But this wasn’t the sort of announcement that caused tears and frantic searches for cardboard boxes. Instead, it was followed by audible sighs of gratitude.

Fortune has learned that Pinterest told employees that if they have been with the company for at least two years and choose to move on (or who are terminated), they now can hold onto their vested stock options for another seven years (post-departure) without exercising them. By doing so, Pinterest has removed a massive tax liability that haunts the dream of many successful startup employees.

Here is how we described the broader situation last summer:

Early startup employees often take stock options in lieu of higher salaries. It’s a transaction covered in optimistic capitalism, with the employee betting that today’s worthless paper eventually will be valued higher than a few thousand greenbacks. And so the employee goes to work, in an effort to realize that vision.

But there is a big catch.

If the employee leaves the company after his options vest, he usually is required to exercise the options within a few months or else they are terminated. And exercising the options can create a big up-front tax bill.

The capitalist solution to this, of course, is for the employee to exercise the options and then sell some of the stock – either on the secondary market or back to the company – to cover the IRS demands. But many of the hottest startups are refusing to cooperate.

Pinterest, which recently raised new funding at an $11 billion valuation, is among those that has largely refused to cooperate (save for a tender offer back in October 2012). But, unlike many of its peers, Pinterest has spent time working on a creative way to solve the tax dilemma.

“The principle we’re operating under is one of fairness,” explains Pinterest co-founder Evan Sharp. “If you’ve made an important contribution to Pinterest, you should be able to keep that value. And that shouldn’t just be for people with enough cash to satisfy their tax liability.”

The big question now is if other Silicon Valley “unicorns” will follow Pinterest’s lead.

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