The Desolation of The First Time Entrepreneur

Thomas Brag
3 min readFeb 18, 2015

Four things to know before you start your first business

“So what? That’s it? After two years… we’re just done?”

“I think it’s time we open our eyes, we weren’t ready for this…”

After two years of uphill struggle as 20-year-old first-time entrepreneurs, we gave up. Even though we had “failed” plenty of times within those two years, this was the first time it truly felt like failure.

During our journey however, we learned more than we could have ever imagined, mostly by realizing how little we actually knew. We ended up meeting countless struggling first-time entrepreneurs just like ourselves; some succeeded but most did not. Here are some things we learned, hope it might be useful to some.

These four things will inevitably happen:

1- You worry about what your friends think instead of your customers

When you start a company, usually the co-founders are the only ones who know how things are really going. And the answer most times is:

“Not so good”

Your friends ask you how things are going and you start worrying more about what people are thinking about you and your decisions rather than what your customers are thinking about your product. That’s not good. Screw what your friends are thinking, their lives probably suck too at some unfulfilling 9–5, they’re just not talking about it.

2- You know nothing, but you don’t know that

If you are starting a new company, chances are that there are already hundreds of people trying to solve the same problem. Too many first time entrepreneurs don’t do their research (including us). A simple Google search can give you answers. However, doing this is scary and can quickly get discouraging. You start to find more and more companies building the same thing you are, but don’t get discouraged; you might have just saved yourself months of trial and error. Look at what they are building, try their service, find the problems with it and then fix it.

3- Too many things to think about

Some people start a company thinking “I’ll be my own boss”. The truth is: as Phil Libin (Evernote) puts it: you will never be accountable to more people than when you become an entrepreneur. Your users, your employees, your investors, your partners, are now all looking at you for answers. The pressure is not always easy to handle. Find a mentor or other entrepreneur friends you can talk to.

4- You will start questioning yourself and you own ambitions

If you started a company, you must be somewhat irrational. A lot of things suck about it, yet so many things are also awesome about it. But the awesome things take time and we don’t emphasize that enough. According to Paul Graham, an average exit is 8 years… 8 years! Yet most people expect to succeed in a few months or a couple of years just because Instagram did it. Don’t look at outliers, look at the norm. Success takes time, hard work and obsessive focus on your product.

Get ready.

If you have friends starting their own businesses, send them this article and let them know: They’re not alone.

As a break from startups I now tell my stories by making comedy videos on YouTube (yes, big shift) you can watch them here.

Follow me if you liked this story, I’m going to be posting a lot more.

I post pictures on my Instagram and you can contact me on Twitter.

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Thomas Brag

I love to tell stories. Previously a startup founder, currently an amateur YouTuber: https://www.youtube.com/user/PracProcrastination