Life is Short. Have Fun.

There’s a lot going on in the world right now.

A lot of distractions. A lot of things to feel stressed about. A lot of armchair entrepreneurs telling founders to “just put your head down and build” (never mind that they’ve long since forgotten what it actually feels like to build).

Being a founder is never easy. I know firsthand — I’ve done it 4 times. It doesn’t matter if you’re building a high-growth VC-backed company, a slow-growth calm business, a consulting company, or something else…they’re all hard! It’s risky. It’s stressful. It involves long hours and sleepless nights. And that’s before throwing in curveballs like global pandemics, unprecedented interest rates spikes and geopolitical rollercoasters.

Life as an founder

But entrepreneurship can also be a hell of a lot of fun.

One of the things I try to do with my “founder journey” posts is to share simple tips to improve the entrepreneurial experience that are easy for even the busiest founders to adopt. 5 Easy Ways to be a Healthier Founder, Treat Yo’ Self and Find Your Recharge are recent examples of this. Today, I’m going to focus on fun.

I’ve previously written about the recent resurgence of hustle culture in certain corners of the startup world. Last week, Matt Munson published a post challenging what he sees as a false choice between “leading with heart” and “founder-mode”. Matt noted that, as a founder:

You can lead with heart and strength.

You can be decisive and deeply human.

You can care about your team and hold a clear standard.

His point is an important one, which I deeply believe in: the best founders don’t choose between high expectations and showing empathy for their teams. Nor should they face or force that choice on themselves. That’s where fun comes in.

But before I get there, I want to be clear in my belief that for many ambitious people, the simple act of being part of an intense, high-growth startup is fun. A few years ago, Tobi Lütke of Shopify made the following observation (which was shockingly controversial in some circles):

Tobi’s point was that working long, hard hours can itself be fun, if you enjoy the work and the people you’re working with.

But no matter how passionate about the work you are, and no matter how caring and brilliant the people you’re surrounded by are, it can still be exhausting. Which is where genuine fun comes in. The thing is, you don’t need to come up with grand plans to have fun. You just need to be open to taking things a bit less seriously. And the impact can be huge (both on you and on your team).

In the early days of Aster Data, we were working particularly long hours (often well into the night). There was an intensity to our work environment, such that when things went wrong — which they often did — people had a tendency to get pretty upset.

One day, one of the engineers brought in a stuffed animal of the “evil monkey” from the TV show Family Guy to the office. He declared that, going forward, the evil monkey would belong to whomever most recently broke the build.

Now, one could imagine that this could amp up the level of frustration when the build broke, but it had the polar opposite effect. Everyone found it so hilarious to have a giant stuffed monkey pointing at them that breaking the build went from an event that triggered frustration and arguments to a celebration of the “build monkey” being moved to a new person’s desk. That simple gesture of fun was a key pillar of the Aster Data engineering culture for years through to the company’s acquisition.

At DataHero, we had a similar level of intensity in the early days that would occasionally result in colorful arguments (particularly amongst the founders 😬). We eventually recognized that we had to button things up, but we didn’t want to lose the intensity. My long-time partner-in-crime, Gail Yui, proposed a solution: the “HR Jar” (aka a grown up “swear jar”). The implementation was simple, yet hilarious.

If someone used inappropriate language or an argument got too heated, anyone could yell out “HR violation!” and the entire company would immediately stop what they were doing. That person would then recount what just happened (e.g. “Chris just said that my idea was stupid”) and the rest of the company would vote on whether or not it was an “HR violation” (99.99% of complaints were voted to be HR violations).

Don’t ask about the zebra head

Over time, things got even funnier as there developed a trend of “prepayments” into the HR jar (people would proactively drop $20 into the jar before going to town on something that they were annoyed with). None of this related to actual HR violations, mind you. It was simply a fun way to defuse arguments. And when the jar got full? We would take the entire company out to the bar around the corner for drinks.

The observant reader will notice that in neither of these examples did the idea come from a founder. Rather, their success came from the fact that the founders were willing to adopt silly ideas proposed by the team. Being willing to support and incorporate grassroots “fun” into the company serves the dual purpose of making work more enjoyable and empowering the rest of the team. Easy. Simple. Win-win.

There are plenty of ways to incorporate fun into startups, from stocking games in the office to taking the team out to offsites to planned multi-day retreats. But in my experience, the biggest impact comes from adopting simple, silly ideas without overthinking it. Over time, those small injections of fun can change the trajectory of a company (and your experience as a founder).

Want another suggestion? Take the budget you’ve set aside for the next fancy team dinner and swap it for an impromptu cooking “competition”.