Re: In 2012, when Butterfield was convinced he’d failed, Braccia was steadfast, said Bradley Horowitz, who put some of his own money in the game company. That’s probably because Braccia recalled what happened the last time Butterfield made a bad game. It morphed into a popular photo-sharing site called Flickr, which Yahoo! bought for around $25 million in 2005. Braccia, Butterfield and Horowitz all worked together at Yahoo.

So it worked twice for Butterfield and I think it deserves exploring. Maybe this is the pattern:

1. Find a smart technical person you trust and fund their dream project with excess cash.

2. Don’t freak out if it flops- set up an expectation that if it flops, use the leftover cash to make a more generally useful tool/service.

Maybe the first dream project is always expected to fail, but it is necessary for releasing some sort of creative pressure, building trust, and learning how to communicate honestly between investor and innovator. If it produces unicorns more often, vcs should be happy to fund the first flop as it somehow prepares the perfectionist to ditch their grand visions and get back to making something dirty that works, but doing it of their own volition instead of feeling trapped.

To clarify: it’s boring to work on a flop— to put in more effort and not get any positive feedback. I think the natural reaction is to try to take things you learned, abandon the flop and try to work on something new. And in this wanting to start something new comes more openness to creating something that gets positive feedback quickly — not making a perfectionist monument because you already tried that and felt the pain. I don’t know if there is an expression for the feeling to be liberated to make something that is not “important” according to your own aesthetics... getting over yourself?