Learning A New Space

A lot of the world’s great entrepreneurs focus their careers on one specific domain, dedicating themselves to building the world’s best [INSERT SECTOR HERE: insurance claims processing software, oatmeal stout, sliding bevel] company.

Not me. I find most businesses fascinating. To me, the process is the product. The act of creating the company gives me the juice. Just being around great people and making it all work. (You can tell because I’ve done software AND software.)

So when my original idea for my current company didn’t stir up interest from potential customers (and hires), I tried not to get my panties in a bunch. My cofounder Erik and I went back to the trough for more ideas. The most important thing was to find a place where we could be the best. Getting too attached to one idea would be a problem.

Being deep in mobile development software, Erik brought a new idea around the large-scale development of mobile apps that was a perfect fit for him given his background. We followed the breadcrumbs on the idea and got a lot of positive responses from folks in the know. Just one catch: unlike my original idea which I understood well, I was a bit out of my league on this technology.

I would have to dig in and learn a new space.

Homer's Quest

How I Approach It

I’ve always been a business leader, not a technologist. My strengths are strategy, leadership, sales, marketing, product positioning, blah, blah, blah. My weak point is engineering depth.

A CEO doesn’t need to be an engineer–and sometimes too much depth can be a problem–but too little understanding will be a train wreck. You need to be very willing to learn and eat your own dogfood, but you also need to hit the right level of knowledge. Think about it like the earth’s makeup:

  1. Crust (the “what”): At this level (common to many salespeople), you get the main concepts, but not why they were created or how they work together. You can speak about the topic but usually need someone else to jump in and help with questions.

  2. Mantle (the “why”): You can speak intelligently about the concepts and design decisions. You understand the entire architecture, but you don’t go deep on the constituent parts. Like owning a house, you should know why you have a roof and how it is constructed to fit with the rest of the house and when it needs replacing, but you don’t need to know what type of flashing was used or the shingling technique.

  3. Core (the “how”): You get how the whole enchilada works together at every level (what, why and how) and can go wherever the conversation goes. People who build the product exist at this level and can answer any question, but there’s a risk of getting too deep (which can hinder decision-making).

As a CEO, I strive to live at the mantle. I like to know how everything fits together and to be able to speak the language, but going too deep in one area will take away from my big picture perspective, thus making it hard to make the best decisions. And it’s probably an indication I’m spending time on the wrong stuff.

How It’s Going So Far

There’s a scene from a classic Simpsons episode where Homer is trying to help get business for a friend’s bowling alley. He does some research. First you see him reading “Advanced Marketing.” Then “Beginning Marketing.” Then he’s looking up “Marketing” in the dictionary. That’s how I felt at first.

But I’ve kept on it. I’ve started coding for iOS and Android, learning Swift (Apple’s new dev language), researching complex computing concepts, taking online classes in data management and structures. And pitching people over and over. It’s like an immersion program for a foreign language – study hard and try it out on real people. You have to risk having egg on your face to make progress.

It can be frustrating. My partner’s knowledge flowed like wine while I was like a bottle of Heinz 57.

But gradually things start to change. It actually starts to become fun. And it starts working. Before you know it, you can chew the fat with the best of them.

So, my advice for CEO’s like me: dig in deeper than your comfort zone. But not so deep you lose perspective. And use middle school geology and food metaphors whenever you need to make a point and/or are on a calorie restriction diet.

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