What it’s Really Like to Run a Startup

What it’s really like to run a Startup

Startups – tech companies specifically – have been idolized in recent years. 2020 has been no exception. Even with the pandemic sweeping the world, there have been multiple high-profile IPOs that have produced billions of dollars out of thin air.

Those stories can be inspiring for the nascent startup founder but the headlines are just a bright spot in an otherwise long and often dreary tunnel.

I run UsefulPDF – a bootstrapped startup in the document management and online signature space. Our direct competitors are unicorns with hundreds of millions of dollars in investor funding. Needless to say, it’s a competitive space. I want to share what it’s like to run a startup with tons of potential and stiff competition.

Too much free time and no free time

As a startup founder, I get to make my own schedule every single day. It seems like bliss – right? I can choose to do absolutely nothing on a regular basis or the minimum amount of work to get by.

Unfortunately, as a founder, your business is your baby. It requires attention and effort to nurture and if you don’t do it then no one else will. Everyone on your team takes their cue from you.

If you slack of then they will too. If you work hard then they’ll slack off a little bit less. On a more serious note, founders that actually want to succeed have little to no time for themselves. There’s always another fire to put out or initiative to launch.

Your head of marketing needs your opinion on this and the designer wants to confirm this iteration with you. Oh, don’t forget about the usability tests you need to review.

Even when the company gets larger and you have the ability to delegate major tasks, you often choose not to. No one can do it quite like you and that’s to be expected. You’re unique and so is everyone else you hire.

Just know this. In the beginning of your startup there will be a thousand things to do and only you to do them. When you achieve a bit of success. There will be ten thousand things to do and only a handful of people to do it.

You can get back your time if you’re determined but be ready to sacrifice in other areas. Such is life.

Mostly monotonous

A startup isn’t nearly as glamorous as the media and movies make it seem. In fact, it’s almost boring. The thing in business is that you experiment to find new ways and methods of doing things but you don’t throw out what’s working.

Only a small amount of your effort will be spent doing those experiments. The majority of your time and energy will be focused on doing more of what’s already working. That means going into the office in the morning, putting your head down to work, going home in the evening, and putting your head down to work some more.

Sure, you can try to spice it up by celebrating every milestone and win. In the end, it doesn’t change the fact that most founders aren’t jet setting around the world, vacationing in the Caribbean, or having lunch with their senator.

If you want to embark on this journey, be ready to spend the next decade doing more of the same.

Always thinking about the startup

Many people don’t realize that a startup is all consuming. It’s like a rounded 10 ton boulder perched at the top of a hill. It takes a massive amount of energy to start moving it because it’s not perfectly smooth, if you stop applying force, it’ll come to rest again.

Eventually, it’ll pick up enough energy so you won’t even have to push anymore. The boulder will keep moving with its own momentum and wreck anything that’s in front of it.

If that boulder is your startup, the energy applied is your attention and effort. It takes up your time when you’re working on it and when you’re not. You think about it in the shower. It crowds your thoughts when you’re watching a movie or TV.

It’s like a weight on your mind that you never truly lift. It’s not necessarily a bad thing but it can weigh down relationships. If you’re married, your spouse will constantly complain about you zoning out. If you’re dating then it probably won’t work unless they’re supremely understanding.

My wife has gotten used to it. I’m a lucky one. Many startup founders are unmarried or have gotten divorced because the company is the real love of their life.

This brings with it a sense of guilt. It’s difficult to truly concentrate on something that’s not relevant to your company. It doesn’t command the same kind of attention and consumption.

You feel guilty about doing things that don’t directly relate to growing the company.

- Binge watch Netflix on Sunday afternoon – how dare you?

- Take a few days off after a year to recharge – who gave you the right?

- And so on.

I was at my kid’s ball game. All I could think about were new strategies to grow the business. My wife noticed and scolded me. It didn’t help much.

Unimaginable pressure

If you’ve ever been a team leader, had kids, or have the responsibility for the success or development of another human being then you know what true pressure is.

Now, imagine that you’re responsible for making enough money to pay an entire team of people. If you mess up then they’re in a hard position and all of their families are in a hard position. Some of them may lose homes, cars, or some other calamity.

In addition to the people you employ, you have a responsibility to your customers. If your product fails, it’s your fault. Not the fault of Janet in quality control or James in development.

If you fail, everyone who has tied their rope to your car fails as well. This pressure weighs on you constantly and is part of the reason why thinking about your startup consumes you.

This life isn’t for everyone. It’s demanding physically, mentally, and emotionally. You can work for years and have little to show for it or you can take off like a rocket ship.

Don’t get me wrong. It seems like I have a nihilistic view about running a startup but I love it. Even the monotony is enjoyable to me – it excites me.

I wake up every morning knowing that I hold my fate in my hands. I know that I’m developing my skills and living up to the expectations that people have put in me. I may not be going as fast as some but I’m charting my own course and there’s nothing else in the world.

If you want to jump in headfirst, be my guest. Just know it’s harder than anything you’ve ever done or will ever do.