Then why did shareholders choose to sell?

In choosing to sell they decided the risk wasn't worth the reward.

If you were in their position, would you have sold or held?

Maybe they thought an IPO wasn’t going to happen because the market would be in bad shape or there would be too much regulation there.

Maybe they were seeing the AI boom on the horizon and wanted the capital out now to deploy there. They wanted to chase AI not hodl some “old” pre-AI thing. A lot of people think AI is going to render the entire process of which Figma has become a key part obsolete. (I don’t.)

Those are two things I can think of to explain this behavior.

Also some people like to get out when they’re ahead. “The world is full of rich people who sold too soon, not rich people who sold too late.” This makes sense if you are generally pessimistic, which many are for various reasons.

The shareholders chose to sell because it was a decent/OK deal for everyone other than the users of the software/society at large.

I have no idea why they agreed to the deal, one imagines a bunch of competing interests ranging from late D, E, F+ round holders, to founders, to influential employees. By the time a company is selling to a mega-conglomerate (in effect, a holding company) for 20 billion dollars it's pretty hard to un-grind the sausage on how a bunch of competing incentives got resolved.

As a founder? Obviously I hold unless I know something is rotten in Denmark and it's about to collapse like a Michael Siebel sale to Autodesk. Are you kidding? I've got a startup so successful that I'm already a billionaire and my choices are:

- let it ride, be a star, chart my own course - go work for fucking Adobe lol

Yeah, easy one.

If I'm an early VC or a limited partner with some structural reason to need the cash before some accounting period ends or something? Maybe I want the sale. Maybe I own a bunch of Adobe stock and I want the consolidation. Maybe a lot of things.

Don't know why the deal got agreed to pending regulator approval. If I'm an already richer-than-God founder, or an employee who can either get full value for my shares or get Windsurf'd in some preference shenanigans, or most anyone else involved? Then fuck Adobe.