At travelabulous, Kirk and I both carry the title of co-founder. We’ve decided that it’s unnecessary at this stage to name a CEO – mainly because our roles and responsibilities are so intermingled (though I also happen to think it douchey to assign yourself a C-level title in a company of 2-4 people).

However, earlier this month, I finished reading Ben Horowitz’s The Hard Thing About Hard Things. The book is great: extremely useful for startup founders, especially because it covers so much ground. Most (all?) of the material in the book can be found on Ben’s blog, but I enjoyed the satisfaction of reading it end to end in the order that the author intended. One of things the book discusses in detail is the selection of a CEO – why you should, and how.

On why – Ben believes that shared command is bad in almost all cases, and I tentatively agree with him. In the early stages, it’s working for us to loosely assign responsibility areas like “Design”, “Business” and “Technology”. We will want to formalize it eventually to avoid decision confusion among the growing team.

On how – this is how Andreessen Horowitz evaluates CEOs. In short, it comes down to:

  1. Does the CEO know what to do?
  2. Can the CEO get the company to do what she knows?
  3. Did the CEO achieve desired results against an appropriate set of objectives?

Today, I don’t believe I meet a16z‘s criteria for being CEO. While I’ve stepped out of my normally non-anticipatory, non-futuristic self to dream about the vision for travelabulous, I believe Kirk is better at both articulating the story in an inspiring, exciting way, and making decisions with limited data at high speed (and reversing them when wrong). This is something I am continually working on – acquiring and utilizing cojones, so to speak. There is rarely time to gather what would feel like “enough” data to me, but time spent dawdling is definitely time wasted, because the future will not wait for you to make a decision in order to become the present.

I am a people person, so I feel that the second point is where I am strongest. I am on a mission to surround myself with driven, smart, humble people – and, as we know, A players really like to work with other A players. While we have made mistakes in this realm already, I feel confident now that we’re building the right team. Lost time is a bad thing for a startup, of course, but not understanding the concept of sunk cost is worse; goes to the making decisions point earlier, too! We have the benefit of being a small team, so everyone can easily get things done. This is something we will strive to protect as we grow through non-hierarchical organization structures like Holacracy, open values as at Buffer, and a culture of freedom and responsibility like at Netflix.

Then there’s the whole measuring results against objectives thing: the main mistake we made here is that we hadn’t really set objectives for ourselves early on. We are fixing that now by building out the team and backlog (hat tip K), understanding our financial needs (hat tip A) and gearing up for an Alpha launch (stay tuned!). Then, only time will tell.

Clearly, both I and travelabulous are works in progress – together, we grow!