Duck Image Credit: Soraya Nukunkit
Duck Image Credit: Soraya Nukunkit

If you ask most founders why they wanted to start a company, you’ll likely find that a big part of it had to do with building a team. The notion of creating a place where people can have fun, build a career, and create something great rings true. The culture that develops within a startup (at least in my experience) is one of the primary sources of pride for a founder. In fact, when people ask me how I feel about the whole experience, I usually say that I’m more proud of the team we built and the culture that developed than any of the success we had as an enterprise.

Stop Trying So Hard

I’ve been at companies where a conscious effort was placed on getting people to “hang out” so that a culture would develop. Most well intentioned attempts at building a culture tend to backfire because they feel forced. For example, I contend that the phrase “fun run” is a contradiction in terms, and should not be used as a way to unite employees and boost morale. Similarly, I don’t believe that bowling is ever okay for an offsite, though this may be my personal bias based on my tendency to get a strike on the first frame followed exclusively by gutter balls.

What We Had

Even former Context Optionalites who have gone on to wildly successful and well known startups talk about the good old days at CO. And it’s not just in retrospect that we had something special. I distinctly remember standing next to Kevin (because we were dressed as conjoined twins) at a Context Optional twin-themed party shaking our heads and asking, How did this happen? How did we become this place where people have so much fun?

It’s hard to pinpoint ways in which the culture at CO was good. There are countless examples, but they all sound contrived if you weren’t there. There was the “Mission Hipster”-themed party, where one guy showed up at our venue in the Mission wearing a full mariachi getup, claiming he misunderstood what “Mission Hipster” meant. There was our mascot, the rubber ducky, which came about when we needed an extremely cheap giveaway for our table at Facebook’s F8 conference and then took on cultural significance over the years. Our overly aggressive “Go EF Yourself” t-shirts we wore to an ill-fated GitHub dodgeball match shortly after being acquired by Efficient Frontier. Our annual awards ceremony featuring duck trophies hand sculpted by our own Mary-Anne Brannigan. The cheapo offsite at the (then) rat infested ghost-townish Metreon. Our “Pajama Day” policy, where each employee could declare “pajama day” once during their tenure at the company. While pajama day was only declared once, it was a fun and very cozy day.

But these are all things any company could do and still not have a “good culture”. I think what truly made it a good culture was the respect the company had for individuals, their ideas, and their development.

How It All Just Happened

I wish I could say that, due to the high importance we placed on culture, we had a plan from the beginning. The reality is that the culture at CO came from the employees, not the founders. Our role was letting it happen.

Example: I’m not big into happy hours. I didn’t really even like the bar across the alley from us. But when a few employees made the case for a company-sponsored happy hour, we agreed to provide the credit card as long as the people proposing the happy hour would take care of the details. Happy hours became a cultural institution built upon our laziness.

The biggest contributor to the culture, more than the low budget events and opportunities to drink, was the degree to which individuals could thrive in their own way. From the beginning, we hired people we wanted to work with, even if their skill set didn’t line up perfectly. We became pretty good at finding the right role for them. Sometimes it was across functions — Our first Business Development hire primarily did Sales, then approved contracts, then worked remotely from Kazakstan, then ran Strategy. His role evolved as the company did. Other times we recognized emerging leaders and people moved up in the organization very rapidly.

The result was that people (from what they’ve told me) felt like Context Optional was a place where good work was rewarded, there was a large degree of flexibility to find something that was a good fit for you, and if you proposed an idea to Kevin or Scott, they’d let you do it as long as you took responsibility for it.

The secret to developing a good startup culture turns out to be doing nothing, but supporting everything (except for Naked Tuesdays, which we vetoed). Give people the resources to put things together and ownership of it, and they’ll feel more of a connection than a forced bowling event or “fun run”. I mean seriously — running with your coworkers? For fun?

Sidebar: Hiring Out of Necessity Destroys Culture

Since we were cashflow driven, we never had a huge hiring push because we couldn’t afford it. While we occasionally got desperate and claimed we’d take anyone with a pulse who could read a Ruby tutorial, for the most part we operated in an “always hiring good people” mode. Sometimes the projects had to be understaffed for a little while as we waited for the right hire, and sometimes new hires went without a project for a little while as we got a little ahead of ourselves.

I’ve seen every other approach to hiring go wrong at other companies. The “hiring push” that comes with raising a large round or using open reqs at any cost while they’re still open, has a dilutive effect on culture — you just can’t indoctrinate a large number of people rapidly, and you tend to lower your standards. The “talent over personality” approach leads to a motley bunch of smart people who don’t work together. Several times, we had the opportunity to hire someone who would make a big difference politically — they were well connected, came from a competitor, or had a strong background. But we passed if we didn’t like them or they just didn’t strike us as smart… which sounds obvious but is kind of hard to do if you think this person will come with a competitive advantage.

Hire people, not resumes.

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