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Common Pitfalls of Entrepreneurship

Published 02/21/2019

For this chapter, we spoke with Allison Chandler from Trendying, a constantly updating clothing line based on the trending topics of the day.

Gunner Technology: Talking about common pitfalls, and please don’t take offense, but we hit a lot of them together with Trendying.

Allison Chandler: No offense taken. The whole thing was a big learning experience for me.

GT: And in large part for us too. One thing that sticks out for me is the pitfall of too many cooks in the kitchen, which we’ve discussed at length.

AC: Absolutely. We had a lot of voices in the room, a lot of voices with super strong opinions too, and it was hard to tell people their ideas had to wait. There were a lot of tough decisions and early on we weren’t really making them, we were just kind of going with everything.

GT: And that’s a huge danger and something we’ve seen all the time, but you really stepped in there and became that leading voice who heard everyone, but also made those tough decisions when they had to be made.

AC: Yea, I remember a really heated – I’ll call it a discussion – where there were sort of two competing directions for the line to take. And at some point you just need to pick the one that you feel is the right one and go with it. And maybe you’re wrong, but at least you’re moving.

GT: That’s a great lesson, and hey, it worked out, right?

AC: So far, so good!


We’ve worked with so many entrepreneurs at this point that we have a pretty long list of things to avoid. A lot of it is stuff folks don’t want to hear, but these are hard-earned lessons from the trenches. Ignore these warning at your peril!

Too Many Cooks in the Kitchen

One major problem that afflicts entrepreneurs is having too many cooks in the kitchen. What does that mean exactly? It means there are too many folks with seemingly final say on product decisions.

Once you have more than one person trying to drive the direction of a product or service, you’re already in trouble. If you have 3 or 4 (or a dozen), you’re basically cooked.

The problem is human nature. Everyone thinks their vision is correct and no one wants to hear that they’re wrong. Plus, with stakeholders, people feel like they’ve invested resources into the idea and feel like that’s earned them some final say over the vision.

You can’t let this happen.

Dictatorships rightfully have a negative reputation in civilized society, but in business, they can actually be a boon. What you need at the end of the day is someone (anyone, really) to have final say over design and development decisions.

If you ignore that, and have too many cooks in the kitchen, have fun spinning your wheels for the next couple years while you try to make everyone happy.

I Fought the Law and… the Law Won.

It seems silly to have to even say it, but it has to be said: don’t break the law. We’ve worked with so many entrepreneurs at this point that a few have fallen through the cracks. What we mean is that we’ve accidentally worked with companies who were, it turns out, breaking the law.

It’s tough to know when companies are doing so because you’re largely at the mercy of them to be up front and honest with you as far as the rules and regulations go. You can’t have your legal team do double duty – redoing all the work that the legal team of your partners did.

And we take legal very seriously. We only ever work on the up and up at Gunner Technology, but sometimes people lie to you and misrepresent their companies and their legality. That’s sort of the nature of the beast.

What we can say, however, is that if you know that someone is breaking the law, run away. Do not get involved with a company who is breaking the law. Don’t even get involved with folks who are at the edge of legality. It’s just not worth the risk.

A Classic Catch-22

Here’s the problem you’ll most likely run into: you need users for your idea to take off, but you won’t get users until your idea takes off.

Consider a social network: it’s only useful if a huge number of people are using it, especially friends and family who are on it, but your friends and family won’t be on it until a huge number of people are using it. There are probably a couple dozen (or hundred) social networks launched every month that completely bomb because they don’t have a plan for increasing the number of users.

So what can you do? Foremost, you can create a product that people actually want to use. That’s the best step you can take to increase usership. Beyond that, however, you basically need concrete plans.

As we’ve discussed before, you need a marketing strategy and a development strategy and a design strategy. You have to build your product in such a way that it gains as many users as it can (if the number of users is critical to the success of your idea, which it usually is).

Stop Moonlighting

Finally, one major failure we’ve seen again and again is entrepreneurs keeping their day (or night) job. We’re all for working hard, but at some point, if you’re really invested in your idea, you have to give up the safety of your current career to pursue your dream.

We’ve worked with so many entrepreneurs who held onto their day jobs like the edge of a cliff over an ocean. But sometimes you have to just let go and take the plunge.

In fact, if you have any goal of growing your business into something massive and truly world-changing, then you absolutely must stop moonlighting.

Commitment is key with entrepreneurship. In addition to the other methods of failure we’ve touched on earlier, the most important thing you can do is go all in on your idea. You only go around once, so why not?!