Caught In The Webb

How to Throw a Legendary Holiday Party Without Pissing Off Your Investors

This man is a professional

Holiday season is here, and that means your startup needs to have a holiday party! I was just hanging with some Midwestern, non-techie friends of mine who work in “normal” jobs, and they were all going on about how they all skip their office holiday parties. They’re the cool kids after all, and, as they say “I spend enough time with those people at work. I don’t want to spend my personal life with them.”

But startups are crazy backwards land, and you basically live and breathe and poop and shower with your coworkers. So you’re going to holiday party with them too. This isn’t a recommendation from me, it’s a practical fact. I mean, really. You probably go out drinking with your coworkers two to three days a week already, at minimum. So it seems safe to say you’re going to have a holiday party with them, even if it’s just the five of you drunkenly realizing at 2 a.m. that oh hey, this could be your holiday party and woooooooo!

It’s actually kind of an interesting logic puzzle. If you and your startup cohorts go out practically every night together already, what makes a holiday party different than any other night of the year? Santa hats play a part. But really, the question should be turned on its head: “If we’re going to have a holiday party, what do we do to make it special?”

And so I am here to help you. I have thrown a fair number of holiday parties in my day. Some have reached the status of legend. Some failed miserably. The have ran from 10 to 1,000 people. Here’s what I’ve found that works. Read More