How Does It Feel To Be A CEO?


Most articles I read on startup companies discuss the process of building the product, acquiring the customers, or scaling the team.  However, I’ve been thinking about the way startup CEOs feel while they’re building their company as opposed to what they do. One side of the story is the energy and excitement of building a company. All CEOs believe the juice is worth the squeeze. However, sometimes the squeeze can be hard.

So much of what we read is nearly romantic in nature, for example, the creation of an MVP, the pursuit of the customer, or product-market fit. Fit? How many startup CEOs wake up every morning feeling like they ‘fit,’ or have found ‘fit,’ or, for that matter, even know what ‘fit’ means?

Consider the word optimize. What percentage of startup CEOs feel like they’re ‘optimizing’ on a daily basis?  I know a large number of CEOs use the word. But, when they say optimize, how frequently do they really mean “search,” or, “fixing stuff that doesn’t work.”

I don’t know of a framework or process that helps startup CEOs understand how to manage “how it feels” to run a startup. I find that interesting because much of the time it’s harder to feel good while being a CEO than it is to do a good job being a CEO.

In my experience with dozens of startup CEOs, here are some of the thing they feel on a daily basis when things get tough:

  • Fit is bullshit Most of the CEOs I know would never admit to feeling ‘fit.’ Growing a company means constantly pushing it and its employees into unfamiliar territory.  Companies and people feel out of place in unfamiliar territory until they adjust. CEOs spend more time feeling out of place, than fit.
  • Never the hammer, always the nail In a startup, shit flows uphill and that leads to the CEO. There’s always a set of issues a CEO can’t share with anyone.  It’s his cross to bear and he works through it as best he can.  He takes it home at night and it keeps him up and unfortunately, it’s rarely a constructive issue.
  • Simplicity is a unicorn “If one more person tells me to focus on simplification, their life is going to get really complicated.”
    There’s nothing simple about building a startup.  A CEO figures out how to make buying pen and paper a complicated decision.  After all, he could spend that $25 on nine google adwords. Simplicity might be the most frustrating word in the English language to a startup CEO.  (Ok, that’s not true, everyone knows that ‘Pivot’ holds that distinction).

If you’re a startup CEO, I suspect you’re going to feel these things at some point. Turns out, product management processes and analytical data on your customer funnels do little to help you manage these feelings. Startup CEOs should be prepared for these feelings and have a process to manage them, just like they have a process for managing everything else.

Here’s my suggested process:  make something small, everyday.

In my experience, making something is one of the most cathartic exercises that can instill a feeling of accomplishment. The key is to keep what you make small. Don’t set out to make a grandiose change or strategic artifact. Keep it small and if possible, social. Don't worry about whether or not the task is the job of the CEO. All CEOs started as something else and many of them are parlaying their original craft into a business. Revisit your craft, it's ok to do so for 20 minutes a day. After all, you're the CEO. Do some data entry with the team, wireframe an idea and share it with your team, call two customers and document their success and share it with your team.  20 minutes, get in, get out, look at what you made and pat yourself on the back for the result. The result will be a small demonstration of simple, optimized, fit. By the end of the week you’ll have 5 results you've created. By the end of the month you’ll have 20.

Personally, I dig into helping our portfolio companies create their financial models by playing in Excel. I know there are others that can do that, but I do some of it because for now, it's my thing.

All CEOs believe the little things matter in their businesses. Take some time to do one little thing a day that guarantees you'll enjoy how you feel about your business.