Startup, Standup, and the Importance of Being Funny

Yes. Ha-Ha Funny


For the last few years of my startup journey, with wisdom behind me and old age in front of me, I've been more of the mind that startup must be fun in order to be successful. So when one of the young(ish) dudes I'm mentoring told me that one of his goals for the next six months was to do 20 minutes of standup at an open mic night, my day immediately got 100x better.

And look, I don't mean to oversimplify the concept of fun when I talk about startup. I'm not talking about shoehorning beer Fridays or a ping-pong table into the culture at an early stage. In fact, those two examples themselves are played and silly.

Beer Fridays are stupid. There's no better way to lower productivity and open all sorts of liability windows than plopping a keg into the middle of your workspace at noon on a Friday. Plus, I've always been of the mind that drunk is drunk. If I'm going to have a beer, I'd much rather have six than two (be responsible, kids), so I make sure of things like not having to drive and, you know, not having any laptops around.

And there's a startup I get to walk by sometimes (trying to keep this anonymous) where they have a ping-pong table tucked into the corner of their office, where it's sat since they've been there. I've never seen even so much as a sign that anyone has ever played a game -- the table halves have always been askew, you know, not completely flush. But I'm assuming said startup thought it was mandatory to make their place a fun place to work.

Startup culture is deeper than that, it should permeate every seam of the fabric of the company.

That begins with the founders and extends all the way through the organization. Sure, I know some startups and forward-thinking companies aren't fun. Everything I hear about Amazon tells me it's an awful place to work. Google, from what I know, is like an IBM of mandatory procedures and protocols disguised as a theme park of whimsy.

But man, why do we make startup so damn boring?

Maybe I've just been through the ringer enough times to have come to the realization that life is too short to spend it in a cubicle staring at financials. I mean, I'm just as hardworking as the next entrepreneur -- maybe more so, as I'm constantly doing something entrepreneurial -- like, I've learned to eat ice cream entrepreneurially, you know, for the kids.

But maybe startup spends so much time filling the heads of its participants and potential participants with stories of grueling labor, dismal workdays, and impending failure and doom that we've sucked all the fun out of it.

Part of me would rather look at Hollywood for startup advice over Mountain View. I mean, if you're going to take on that much risk and huge responsibilities and trying to change the world and what not, maybe Han Solo should be your spirit animal instead of boring-ass Steve Jobs or Elon Musk.

No disrespect.

Automated Insights, in our first few years, was the funniest place I've ever worked. In fact, I had something called the "Funny List" which was a semi-mock running top 10 (or however many employees we had at the time), ranked by how funny they currently were, and we usually opened our meetings by reviewing that list.

OF COURSE THAT'S STUPID! I'm not an idiot. But during the dog days, when we were working on big projects with insane deadlines and crazy hours, sense of humor was the one thing that kept people from losing their minds.

Not to mention the creativity it unleashed -- in everything from what we put in the product to how we marketed the product. Not everything was a joke, but we started to develop timing and rhythm and were always aware of where the limitations were when considering our own success. If you can bomb during a meeting, you can bomb during a launch.

I study funny. I read books by and about comedians. I watch documentaries. I'm aware in my writing of rules like funny is better in threes, punctuation and presentation are part of the communication, and less is always better than more.

I know big words. I know buzzwords. But I also know how to communicate, and I know which words and how they're said will flip the switch to get my ideas into your brain. I know that more than half the time the message is not nearly as important as how it's delivered.

Every entrepreneur should know this. You can't sell new and world-changing ideas without being able to communicate those ideas in a fashion that gets those ideas a little closer to reality for people who aren't you.

Humor is your best weapon and fun is your most productive environment.

So as dude makes his way to the stage to pray he doesn't bomb in front of his first audience, I'll be there, and I'm honored and I feel lucky that I get to be there from the beginning. And I'm jealous because I don't have enough in me to do the very same thing (I'm much better on paper, this piece notwithstanding).

But maybe I will. I mean, in startup, you're always learning. And maybe some of that wisdom I've developed over the last 20 years can be turned into observational humor.

I can get 20 minutes out of 20 years, right?