Hey all, Dan here again.

I’ve struggled a lot with how to write this post. I’ve known for quite some time that I wanted to put pen to paper (or fingers to keyboard, I suppose) about what working with my best friends has been like, and how, ultimately, I feel about it. Turns out it’s kind of tricky (at least for me).

I started with a fairly typical Hacker-News-Headline-Baiting post called “Why You Should Work With Friends”. But as I was writing it, I realized that everything I was saying about my friends / co-workers was about how smart, capable, and great at their jobs they were. None of which had anything to do with them being friends. So that was kind of fruitless.

I went back to the drawing board. Michelle suggested writing the post as a response to Founder’s Dilemmas, which lays out a bunch of very cohesive arguments in favor of and in opposition to working with friends and family. I loved this idea and wrote it up. The result was a piece which basically went like this: the author of Founder’s Dilemmas is totally right but none of the negative things will happen to us because we’re too awesome.

Again, that was a blog post not worth posting. I got frustrated.

So I tabled the idea for a while. Luckily, we had a big push to get our expanded beta release out the door, so I was appropriately distracted by Lots and Lots of Code.

We finished that work last Tuesday. And it just happened to be one of those Amazing San Francisco Days where the weather is perfect. The beach wasn’t too cold for shorts and a t-shirt. The sun was glorious. And it stayed warm Even. After. The. Sun. Went. Down. For those of you who don’t live here — that basically NEVER happens. Douglas Adams reminded us to always bring a towel — people who live in San Francisco always remind each other to bring a jacket. We’ve been trained.

Oops, sorry for the digression. Back to my story. We finished our work and decided to take the afternoon to celebrate and enjoy the weather. We packed some beer and wine, hopped in our cars, and headed off to Fort Funston (aka Doggie Heaven). We parked, and a short hike later, we plopped down on a bluff overlooking the Pacific.

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I popped open my tallboy of Coors Fat (what? don’t judge me), everybody else pulled out their craft beer (snobs), and we cheersed (it’s a word, shut up). And then we did something that, I think, only a company full of best friends can do. We had three hours of Introspection Time.

Let me take a step back and explain what Introspection Time is. Every company moves forward at breakneck speed, even the oldest of corporations. There’s so much momentum at your back that it’s remarkably easy to just keep your head down and be pushed along. But it’s a recipe for disaster. If you don’t pop up from time to time to reflect on where you were, where you are now, and what path you took to get from there to here, you’re doomed to repeat past mistakes.

Introspection Time is where you put on the brakes, pull over, and just talk about what’s been going on. What you’ve noticed, what’s been bothering you, and what you’ve loved.

I think any company, with suitable leadership, can benefit from this sort of process. But Keen, which consists of five of my best friends and me, takes it to the next level. The ways in which we can be open and honest with each other are truly remarkable. We say things to each other that would certainly be unusual (if not forbidden) between co-workers in a typical employee-employee relationship. But rather than being weird, or causing friction in either our personal or professional relationships, it focuses us. It energizes us. It makes us feel like our voices matter, that the people we work with truly care about us, and that we’re free to care as much as we want right back.

I met somebody recently who I introduced to my friends. After hearing about how I also work with them, they asked, “… don’t you ever get tired of them?” I paused for a minute, because I know that you’re supposed to. But I don’t. That’s the truth. I’m truly lucky to have this job, and even if we suck and tank horribly and Keen dies a messy explosive death, I’m so grateful to have had the opportunity to work with some of the people I care about most.

In the end, I’m not for or against working with friends. Founder’s Dilemmasdoes an admirable job of exploring the complications involved in doing so.

What I am for, unequivocally, is that you should Work With People You Love. And I love Ryan, Micah, Kirk, Michelle, and Kyle. It’s sometimes incredibly hard. Disappointing them is way worse than getting negative feedback from some random co-workers. Remembering to be respectful and serious (rather than our default mode of shit-talking and goofiness) can definitely be a challenge. And while I think we do a great job of it, there are still those moments where it’s tough to separate work conflict from personal conflict.

But, the beautiful and terrible truth is that those shitty things pale in comparison to the moments where I look around our cool little office and see my Friends working incredibly hard to build something together with me. Something we’ll share forever, even if the business itself winks out.

-Dan
@dkador or dan@keen.io

P.S. Think I’m full of shit? Please share your stories of working with friends and loved ones. Good and bad are both welcome.

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