You’re more than the Fucking Janitor: Thoughts on Startup Leadership

Last month, I had the honor of participating in the inaugural Foundry Group portfolio CEO summit where we had an enlightening discussion on leadership. To kick-off the conversation, one of the other CEOs volunteered the story of a time he felt he failed as a leader: he had a disagreement with some of the engineers on his team about the complexity of a given feature; and when their conversations reached an impasse, he took matters into his own hands and coded the feature himself.

I found the most interesting part of the ensuing discussion to be the disagreement over whether this CEO’s act of digging in and coding the feature himself was a leadership success or failure. We didn’t do a formal survey, but the group appeared to be divided into two camps: one that felt he should have focused on solving the communication and process (and possibly staffing) issues that prevented his team from executing as he desired; and the other that saw value in the example he set by showing he was capable of and prepared to do what he asked of others.

Earlier this week I read Zach Bruhnke’s excellent post You’re not the CEO – you’re the Fucking Janitor, and it took my mind back to that discussion about what good leadership looks like in a startup. My answer: it depends. It seemed to me that the folks at the summit who felt this CEO failed by doing instead of managing were leaders of more mature companies, while the ones who admired his leadership by example tended to be running earlier stage startups. As someone running a company that had recently raised our Series A and was growing from a team of 5 in January to 14 today, I found myself agreeing with both sides of the debate.

For a boot-strapped or even seed-funded startup, I think Zach’s post is spot on. The “CEO” in Zach’s story is a total douche, and my business cards say “Co-founder” precisely because calling myself the Chief Executive over 4 of my friends made me think of Yertle the Turtle. My dad always told me “the fish stinks from the head”, which is just his graphic way of saying great leaders lead by example. In my relatively short leadership career thus far, I’ve taken this to heart and always jump at the opportunity to do things myself.

In addition to the mutual respect and motivation Zach mentions in his post, one of the greatest advantages I’ve found in this approach is the intimate understanding a leader attains of how things are done within their team. Across the many failures of leadership I’ve observed (I was at Yahoo! for 4 years 😉 ), there’s a recurring theme of the leader being too removed from the actual doing. Especially in the technology world, the means of production can be just as important as the output. I can’t tell you the number of product and business leaders I’ve dealt with who treat engineering like a commodity instead of a potential competitive advantage. You only need to look to the world’s most valuable company to see what great supply chain management (i.e. caring how the sausage gets made) can do for your business. And when you’re a software company, every architectural decision your team makes has a bearing on essential business considerations like performance, reliability, time-to-market, and agility in responding to new threats and opportunities. That’s why awe.sm is, above all else, an engineering-driven organization (and looking for even more great engineers 🙂 ).

But in a later stage company, the leadership challenge is greater because you need to figure out more scalable ways of achieving these same goals. There was one particular line of Zach’s post that stuck out for me in this regard:

If you want to be a CEO in the sense that you dream of then you should remember to be the Fucking Janitor too.

A couple months after raising our Series A, I was washing dishes in the office and caught myself feeling self-satisfied because here I was, CEO of a company that had just raised millions of dollars, doing the dishes. I thought about my dad’s smelly fish saying and how he’d be proud of me. Then I thought about our investors and what they’d think of this…and it struck me they’d be pissed. Here I was, CEO of a company in which they’d just invested millions of dollars, doing the dishes instead of the dozens of other things only I could be doing to make their investment successful.

In the few months since then, my leadership focus has shifted. I still do the dishes when it’s my turn; when AWS shits the bed at some inhuman hour, I’m in our IRC room doing what little I can to help; and I always want to understand the gory details about why we made one architectural decision over another even if I wouldn’t know how to implement either of them myself. I am proud to continue to be a colleague to my team above all else. But leadership in a larger organization requires more than that. Our goal is to achieve on a scale bigger than what one person can achieve alone, and that means the leader needs to lead not just do. Doing is good, but when it turns you into a micro-manager or takes you away from leading, it can be counter-productive.

Delegation is hard. I’m finding delegating well to be much more challenging than doing things myself. Leading purely by example just requires effort and a willingness to do things that aren’t fun or glamorous, and as the leader you’re usually the most incentivized to get those things done. But effective delegation requires much more than mere will, it is a skill set developed with patience and learning and painful trial and error. It requires finding great people, training them in the skills you need them to have, motivating them to share your goals, empowering them with the resources and information to be successful, trusting them to do their jobs, and then giving them feedback on how to improve. I have come to believe my primary job as a leader is to enable the members of our team to deliver what the company needs from them, and that’s a lot harder and even less glamorous than being the Fucking Janitor.

Why I’m excited about @getmoreclarity from @danmartell

Ironically, Dan Martell is one of the most genuine friends I’ve made in the startup world. I say ironically because he is a caricature – the guy literally uses hashtags when he speaks :-). But none of that can take away from how legitimately passionate he is about helping others, in particular other entrepreneurs.

Dan doesn’t talk about it much, but his path to the #leanstartup celebrity all his Twitter followers know today was a pretty long and unglamorous road compared to a lot of today’s entrepreneurs (including myself). Though he doesn’t remember it, Dan and I first met on the Internet back in 2009 when I was trying to do some early content marketing for awe.sm and he was, as always, building his personal brand by explaining how he got to 595 Twitter followers (how quaint! 😉 ). At the time, I believe Dan was still living in Canada having sold the professional services business he had built over years of unglamorously quotidian hard work, and, like me, was trying to break into the Silicon Valley in-crowd. I wrote him off as YASMDB (yet-another-social-media-douchebag), albeit one with amazing hair and actually pretty good advice, and forgot about @danmartell.

About a year later, awe.sm got its first “office” in San Francisco courtesy of some desks Klout was subletting in their space, where Flowtown was already subletting a conference room. Over the following 2.5 years I got to know Dan as we worked side-by-side there and later at the new office we moved to with Flowtown and Plancast. In such close quarters for such an extended period of time in such often-times stressful circumstances, you learn a lot about anyone. And what I learned about Dan is that his enthusiasm and passion and child-like love of startups are unimpugnably genuine. But in Dan’s case, I found myself learning a lot not just about him but from him as well. I learned from his example as well as his mentorship, with which he was always generous to everyone – those of us in the office just were fortunate enough to have access to the firehose. He has one of the best product senses I’ve ever seen because he has the rare ability to assume the veil of ignorance of a real user. And his belief that creativity and hard-work (aka #hustle) can solve any problem enables him to turn whatever challenge you bring him into an opportunity.

Even though we’ve talked about it several times over the last few months, what Dan is doing with Clarity.fm wasn’t truly clear to me until today when I started reading the (impressive) press coverage of their launch. Until this morning, I saw it as Dan building a product to solve a pain point Dan had and thought enough other people have to make it a viable business. Then I read the following quote Dan gave in the TechCrunch post:

For the first years of my working career, I was still living in my native Canada and I was desperate for advice. I emailed the minister of my province there, he respected that I was a young entrepreneur, and he introduced me to three guys that had built hundred million dollar companies. That was the reason that I moved to San Francisco in the first place,” Martell said. “I know that getting the right advice at the right time can dramatically change an entrepreneur’s life.

Only then did I realize this isn’t purely a convenience product for Dan, it’s a passion product. And when an entrepreneur and product person as talented as Dan is passionate about something, you know it is going to be great. So that is why I’m excited Clarity is being built by Dan.

As for why I am (and I think you should be) excited about Clarity in general, my friend Hunter says it better (and more concisely) than I can:

So if you’re an entrepreneur seeking advice, check out Clarity and don’t bother with Mark Cuban, go straight for this guy.