What Is It Really Like to Run a Company?

Starting a company is the cool thing to do these days it seems. If you watch TV for any length of time you’ll inevitably see that VistaPrint commercial that glorifies new businesses and makes it seem as though its everyone’s dream to start one. Then there are the GoDaddy commercials that, if you didn’t know any better, would have you believe that having a business means you get a website and then customers charge in to shove money down your throat. Its also cool to not start a business. No, businesses are lame. What’s cool is starting a “startup” which to me has become a synonym for “an unrealistic business idea that involves a website and the word ‘viral’ that can only be profitable through investment and/or a buyout”. I have to roll my eyes any time I hear someone say they started or work for a startup. Everyone wants to start a startup or a business and have these dreams of what its like. I’m here to crush your dreams and tell you its nothing like what you imagine.

What is starting a company really like

Well, first off, if you’re starting a startup then you’re fucked. You’re totally doomed and I assume you’re taking someone else’s money so you can play house and call yourself a CEO or co-founder or some shit like that for a while. If you’re starting a startup you’re basically on a vacation from life. This article doesn’t apply to you. This is about people who are starting real businesses.

A real business is profitable because there are real people out there that want to give you money for the value you’re providing them. A business can be a technology company. Yes, it really can. I am the co-founder and CTO of Aplo, LLC, a health insurance technology company. We build software for real people that actually want to pay for what we’re selling. We’re not relying on someone else’s money to give something away free for a while in hopes that either more investors will give us outrageous sums of cash or that a larger company will buy us out. No. See, we’re from the midwest. Here in Chicago we do things a little more like 37Signals and a lot less like… I don’t know… just go look up all the failed companies in the TechCrunch archives. That’s how we’re not doing things. Anyway, I’m here to tell you what it’s like to run a business, not what I hate about the Silicon Valley bubble that’s getting ready to burst.

It’s the most fun you can have while killing yourself ever

Running a company is an up-at-dawn, pride-swallowing, nightmare of a job (that quote’s been adapted/blatantly stolen from Jerry Mguire). You really do get up at dawn and have about 30 minutes to yourself to have some coffee and watch the Today show before you have to jump on your first conference call of the day. If you’re lucky you get an hour to wake up.

After you’re sufficiently awake you meet with key employees to see how things are going, address problems, and set the direction of future projects. As a CTO I’m responsible for making sure that the code being written is in line with our big picture goals as a company. At this early stage I write a lot of code still but one of my jobs is to gradually teach others how to hold our software in their heads and slowly take over my role as a developer.

Then you’ll probably talk with your partner (notice I didn’t say co-founder. I could have because that’s what he is but that sounds too startup-y to me). You’ll tell him or her what your concerns are for the day or the week, maybe ask a few favors, maybe be asked to do some favors, and generally get in sync for the day. Then its off to work.

I work for about an hour and sometimes I come close to crying. Yep. I almost cry sometimes. Because running a company is not a vacation. You’re under constant pressure to put out work that’s just beyond what you think you’re capable of. You’re always pushing your limits and challenging yourself to do everything more and better than you ever knew you could. Do this every day for months on end and tack on all the responsibilities that should be spread across about 20 employees and you’ll just start to understand the pressure you’ll encounter as the owner of a business.

You’ll likely work from about 8am to 11pm on a slow day. Some days you get to stay home or at your office all day and work from there. But there’s nothing relaxing about it because you’ll have about a thousand phone calls and emails to answer as you’re trying to put out a product. We should have employees doing that but we need to make enough money to hire employees skilled enough to wrap their minds around your industry and your goals as a company.

Then you’re going to get sued. It’s inevitable that someone is going to sue you. The only variable really is the number of entities trying to sue you at once. Your goal shouldn’t be to avoid lawsuits because it won’t happen. Your goal should be to get sued the fewest number of times instead.

After that you’ll burn out and have panic attacks because you’re not sleeping or eating. But just before you completely lose your mind you’ll begin to laugh. A lot. Everything will be funny, you’ll stop caring about things that used to worry you and then suddenly, the moment you realize this, that’s when the first panic attack hits.

Some will say that this isn’t what should happen. They’ll say its not healthy or some hippie bullshit like that. Well this ain’t California. Out here in the real work you work your ass off until you come close to death so that you don’t have to work so damn hard when you’re so old that you really are close to death.

It’s worth it

Running a business is not for people who want to play house. It’s not for the guys who want to parade around with slick business cards spending other people’s money while taking every opportunity to tell whomever they meet that they’re the C-Whatever-O of some shitty company. It’s not for people who want to do fake work that makes them feel important but does nothing to make you money. It is gratifying. Building something that’s real that helps real people is worth all of the shit you will encounter. Talking to those people will make it all worth it even when they’re angry at you because you’ve disappointed them. The entire thing is something I wouldn’t trade for the world.

But it’s not for you. Listen to me. Almost everyone who reads this and wants to be in business for themselves isn’t ready for it. Its not what you think it is. And no matter how many people like me write about what it’s really like none of us can truly explain what its like. Kind of like giving birth. I can ask lots of women what that feels like but I won’t know until I do it. But I can’t do it even if I wanted to because I’m a male. But now I’m just taking this too far.

Don’t start a company. It sucks. You won’t like it. But it’s awesome.

Business, Web development

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