5 awkward situations you’ll have to navigate as a first-time entrepreneur

We’ve talked a fair bit about Business start ups and Entrepreneurs recently, so we’ll taper it back a little from here on in. But here’s a little heads-up for the future business men and women amongst you:

1. Being completely clueless


You’re not going to have all the answers as the head of a new company. Not only will you have to take on unfamiliar responsibilities, but you’ll also have to make quick decisions with little time and information to go on. You’re not going to be an expert in everything so trust your team around you who do have the knowledge and expertise, but make sure you have the final say on important calls!

Awkward DBA 2


2. Admitting you’re wrong

So, you’re going to make mistakes. As the company leader, those missteps can affect everyone else’s hard work and create awkward situations no first-time entrepreneur wants to be in. Projects might have to be redone, timelines revisited, sales may be lost and product design might have to go back to the drawing board.

When you realize you were wrong, own it. Don’t belittle the mistake, or blame someone else. It’s how you react that’s important. Make sure you learn from your mistake, and move on with enthusiasm. Once bitten and all that…

3. Constantly having to raise money

One of the biggest issues new companies face is cash flow. In order to keep your new business growing rapidly, you’ll have to raise capital. Then do it again. And again.

You’ll have to get comfortable with asking for investment. It’s not always easy, and you’ll have to have a certain element of ‘right place, right time, right investors’. Raising money is hard, but it’s a necessity if you want to make it big.


The first trick is knowing your audience. Grab their attention and focus them on the conversation. They hear pitches all day, every day and you need to stand out. Nail down your pitch, know your business inside and out. Keep it simple!

And finally practice, practice, practice.

Pioneers Festival Investors Day


4. Disagreements with investors

Once you get the money in the bank, it can lead to another sticky situation: deciding how to use it. And chances are, your investors aren’t always going to agree with you.

When disagreements with investors do arise, you’ll need to hear them out. After all, they were the ones that gave you the money, and if they’re on the board or are a trusted and experienced voice, you’ll likely learn a lot. But that doesn’t mean they’ll always be right.

You’ll have to learn to pick your battles. Should they start talking about taking the company in a direction you don’t believe in, or suggesting changes that aren’t aligned with the core mission, or that go against the core analytical understanding of the biz, it’s time to stand your ground.

Remember, they likely only want what’s best for the company too! And when talking with them, speak their language. Facts and figures. Don’t give them an inch!

5. Letting someone go

Being a first-time entrepreneur means that you are now responsible and in control of your team’s employment. When an employee doesn’t work out or the budget dictates cuts, it’s up to you to make that hard call. And with a small team and the inherent closeness that creates, letting someone go can be incredibly difficult.

Above all else, the company must come first. So if someone on the team is impeding success due to poor performance, misalignment with core values, or holding a less necessary position, you’ll be the one charged with making the tough decision and delivering the news.

Provide context, and always keep in mind that this is a human being with a life, and that they deserve your consideration, respect, and to be heard. But also keep it relatively short and to the point to minimize pain for everybody. It’s unlikely that this task will ever become easy, but knowing it’s the best decision for the company — and often for the individual impacted — will help keep everyone involved on the right track.

If you want your company to make it in the long-run, be ready to get out of your comfort zone. You’ll come out of it on the other side a better manager, a better leader, and with a stronger company.

That’s all your questions answered then! Might as well crack on with that idea you’ve got and get looking for investors! First things first, a Business course. We’ve got them here, take a look today.


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