The Office

This past week I was speaking with the founder of a startup that’s been around for roughly five years and raised tens of millions in venture capital. It had been about six months since we last spoke. I was regaling him with tales of Paul and my bunk bed, recent mistakes we’d made in hiring a freelancer and our imminent plans to re-engage companies to turn Treatings into one of those businesses that make money. All things readers of this series (Hi Mom!) are tired of hearing about. About five minutes into our conversation, he abruptly asked, “So, are you happy?”

“Yes, I am,” I said, then quickly caveated. “I mean of course we haven’t proved that Treatings is a viable business, and my lifestyle is transitory, but I’m enjoying the process and learning a ton.”

He replied, “Sounds like you have a great, easy-going attitude. I’m jealous. I’m always paranoid and can’t relax when there’s so much left for us to do.”

I found this exchange interesting, not because of what he said, but because of how I felt about it. I took his comment as a backhanded compliment, like, “Being easy-going is a nice trait to have, but not necessarily if you’re trying to build a world-changing business.”

I felt a bit defensive. I didn’t want him to think I’m Mr. Nice Guy, content despite the tenuous state of Treatings. Later I thought, is being patient and accepting of the startup journey so bad? Maybe I should have whacked him upside his head with my phone to show him how bad ass I can be.

No startup founder wants to say they’re satisfied with where their product is, and for good reason. There’s always more to do, and complacency kills companies. I have been embarrassed by just about every product iteration we’ve released, but I’m happy with our trajectory. Maybe a better word than “happy” is “at peace.” We’ve made innumerable mistakes that we hopefully won’t repeat, but we’ve learned from them. So, how to be even-keeled and reconcile impatience with the state of the product with acceptance of the disorderly journey of a first-time entrepreneur?

When Paul and I hit roadblocks with Treatings, which is every day, our first line of defense is looking outward to see what we can “borrow” from others. We’ve modeled our professional networking framework after online dating sites, the messaging is informed by text message interfaces and our business model is inspired by employee referral programs. That got me thinking, should I also model my behavior after successful startup founders?

I’ve found that many of the most celebrated entrepreneurs could be placed into one of two buckets: the paranoid and gladiators. Of course, many founders could be classified as both. While the paranoid are primarily driven by trying to stay ahead of potential threats, gladiators are chasing towards those threats.

Aaron Levie, CEO of Box, operates at a frenetic pace with the mantra that “only the paranoid survive,” anxious that he could be disrupted at any time. His opts for sneakers as part of his daily uniform because they “help [him] walk faster.” He’s said, “I don’t have time for nonwork stuff,” and that seems to have worked out pretty well for him.

Travis Kalanick, CEO of Uber, is a poster child for the gladiatorial approach. He’s been quoted as saying, “You have to be a fighter, you have to be a warrior, and if not, you should go do something that is a little less disruptive. I’m bringing it, I’m not sleeping. If the other guy is sleeping, I am going to kick his ass.”

The point is not that these attitudes are bad. Quite the opposite. Aaron and Travis are impressive entrepreneurs who have managed to build incredible companies from the ground up in part because of their personalities. But glorification of the lifestyles of a handful of founders has created a culture where startups are often equated to war and founder bravado can air on the absurd. Francisco Dao commented on this trend in his post, “Hustle and Flow,” ridiculing founders who say things like, “you can sleep when you’re dead.”

When I hear founders make comments like that, it reminds me of a Michael Scott quote in “The Office.” When asked, “What do you think are your greatest strengths as a manager?” he replies, “Why don’t I tell you what my greatest weaknesses are? I work too hard. I care too much. And sometimes I can be too invested in my job.”

Generally accepted abuses of personal health, like lack of sleep, a poor diet and no exercise, are proudly worn on the sleeves of many entrepreneurs as accomplishments. I’m interested in accounts of entrepreneurs who go about it differently, being intensely focused on building an amazing product and business while also maintaining a balanced life.

I aspire to be an exemplar of the laid back entrepreneur. I want to be known for my obsession with Treatings but also able to admit to not losing sleep (because I do sleep!) over inevitable speed bumps without losing credibility. The only problem is that this doesn’t make for a gripping story… and I’m not successful.

Oh ya, and when I told Paul that the inspiration for this post was feeling defensive for being categorized as easy-going, his response was, “I mean… I don’t think you’re that easy-going.”