The five most common struggles of entrepreneurs
Kerwin Rae

After coaching thousands of businesses over the past 20 years, I keep hearing the same problems popping up.

It appears no matter how different our industries are, entrepreneurs everywhere are dealing with some pretty common challenges.

So, no matter what your business model, where you are, how big your company is, I’ve listed the five most common challenges I hear- and how to deal with them.

1. Sales

Learning how to sell is one of the most valuable things you can do for your businesses- and it really is the key to endless cash.

I tell all my clients that desperation and neediness will kill your sales game. When you head in too eager, its an instant turn off for customers because it shows you don’t have faith in your product or that you’re a bit snake-oily.

When you recognise that you’re being needy, there are three things you can do to fix that.

The first step is to enter into any situation wanting nothing– be okay with any outcome. This instantly makes you more attractive because you’re not giving off a subconscious air of desperation.

Next, focus on your strengths– you don’t want to be in a sales environment floundering around and grasping at straws. Don’t make stuff up or try to make your product fit the consumers needs, that’s desperate and you’re gonna make yourself look like an idiot. Why would they trust someone that’s just gonna tell people what they want to hear?

Finally, you’ve got to be willing to walk away. This counts extra if someone is disrespecting you as a sales person. It’s just not right to force your product on someone that you know won’t benefit from it, and letting people walk all over you in the hopes they’ll give you money is a sh*tty way to do business.

Set a high standard for what you accept, and you’ll instantly become more desirable.

2. Planning

Too much to do and not enough time is another famous start-up struggle.

Some of us end up juggling a day job while we work on our business.

A lot of us have families and young kids that really need time with us.

Then there’s just the plain old crunch-time that comes with being a business owner. To-do lists out the wazoo, deadlines all over the place, and sometimes no team to help you.

No matter what sticky situation you find yourself in, a good strategy is to plan your time like me and my clients do.

Once a year, me and my team set out the company’s priorities for the next 12 months. Big, hairy, audacious goals, as I like to call them. This takes about two days for me and the team to review last year’s goals, and set new ones for the coming year.

Then every quarter, we meet and choose which priorities need to be executed first. We call these our quarterly Tactical Operating Priorities (TOPs), every single one of which is assigned to a team member. For example, one might be for “ Publish one Unstoppable Podcast episode every week (Owner: Mattias)”.

We review these monthly to see how we’re tracking; cross off ones that are completed, note any changes in personnel and remove TOPs that might have become redundant. By keeping track every month, it allows us to pivot accordingly and offer support where required to ensure things get done.

Then every Monday, everyone sets out five goals they want to accomplish this week. Every single one of these goals is linked back to one of the quarterly tactical operating priorities. Stuff like recording a Podcast episode, interview for a new hire, hitting a specific sales target, solving world hunger- you get the gist.

Then every day, break that down even further into three tasks. It might be setting up the cameras, going through resumes, making 20 dials- something small so that every day and every week you’re consistently chipping away at big, strategic things.

3. Marketing

You could be an absolute gun at sales, but if you haven’t got enough leads then you’re gonna struggle.
Conversion rate could be 100%…but that doesn’t mean much if you only had two leads per year to start with.

If you’re not generating enough leads, then your issue is with marketing- thankfully we can solve that issue with the right tools.

See, there’s so much marketing clutter around that consumers have no idea who to trust. Seeing an ad means nothing because there’s ads everywhere.

The mere exposure effect is when someone sees you or your brand enough times that they trust you out of familiarity. But with all the ad clutter around, the number of times they need to be exposed to your brand before trusting you is predicted to be 20-25 right now.

If you advertise to the same customer 25 times, they’re not gonna trust you, they’re gonna hate you.

So the way you get customers familiar with you without pissing them off, is by exposing them to helpful content. I mean educational, inspiring, funny, motivational- stuff they go out of their way to look for.

It is a must to get your business across Facebook, and ideally Instagram, Twitter,LinkedIn and preferably every other platform as well.
Then, think about your client, and what would be helpful for them.

An infographic about how they can solve a common problem they have, the inspiring story behind how your brand started, or a funny meme related to your industry.

This is how you market to consumers, in a more organic and trustworthy way.

After they’ve seen a f**kload of your content and begun to trust you, that’s when you put a product in front of them and convert them into a lead so that you can solidify the relationship.

4. Leadership

One thing I will shout until I’m blue in the face, is that leadership is not a title- it’s a behaviour.

Anyone in my company can and does demonstrate conscious and humble leadership every single day. Regardless of “rank”, age, or seniority.

As a leader, it’s my responsibility to enroll my team in the purpose of what we’re trying to do , ensure we’re living by the values, and thank them for their commitment to the mission.

As a leader, sometimes you’ll be tasked with the all-too-common issue of how to motivate your team.

Some pretty traditional techniques are what I like to call “if…then…”. By this, I mean things like “if you do a really good job, you’ll get a carrot. If you do a bad job, you’ll get the stick”.

These are pretty ineffective.

Even when you’re just rewarding someone, studies show that people eventually lose motivation. One famous experiment was rewarding kids for doing artworks. The kids who hated art stayed hating it. The kids who didn’t really care started liking it, then hated it. Then, the kids who already loved art? Well, they ended up hating it too. Go figure.

What I prefer to use is unexpected surprise rewards, in combination with the powerful tool of social recognition.
Thank your talent by name, thank them publicly, and thank them randomly.

If you make it routine, it becomes less meaningful because people start to expect it.

For example, a lot of you might know my filmmaker, Mattias.

Mattias, if you’re reading:

Thank you so much for stepping up and taking on extra duties while we had a few people on leave. Because you went above and beyond, things are running really smoothly and I really appreciate it.

A public announcement of directed gratitude like this in front of your team has a profound effect, go try it and see for yourself.

5. Mindset

A lot of people have trouble identifying this as their biggest hurdle, but it really is the make or break of business.

Your mindset is the biggest determinant of your success.

Not how many competitors there are, not how many customers you have, it’s all within you.

I can give two people the same piece of advice. One will go and make tens of millions of dollars, and the other will sit around complaining that the advice doesn’t work because they’re not a billionaire yet.

The only difference, is the six inches of real estate between their ears.

As an entrepreneur, you need to accept full and total responsibility for the outcome of your business.

When we blame other people, all we end up doing is giving away our power. The success of your business is down to the decisions you’ve made. The people YOU hired, the money YOU invested, the content YOU posted (or didn’t post…).

Stop making excuses, and start recognising your power- for better or for worse.

It’s only once we reclaim our biggest mistakes, that we take back the ability to do something about them.