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  • 3 Mistakes I Made as an Entrepreneur That You Need To Avoid Like the Plague

3 Mistakes I Made as an Entrepreneur That You Need To Avoid Like the Plague

Ari Page March 25, 2026

I became an entrepreneur at a relatively young age after my mother immigrated here in pursuit of the American Dream, and then I went on to build a multimillion dollar business from that idea.

As much as I’d love to say that everything went as smoothly as that first sentence might indicate, nothing could be further from the truth. I had no formal education in running a business and I had no mentors in the beginning. Hell, I started off as a ship-fitter before launching my own business. So unsurprisingly, I made a lot of mistakes along the way. 

Those mistakes were painful, costly, and time consuming, but they were also incredibly valuable. But on the other side of that coin—you don’t need to make the same mistakes to learn the lessons from them.

So in this article, I’m going to share three mistakes that I made as an entrepreneur that you need to avoid like the plague. Doing so will help you become more successful, more quickly, while facing fewer headaches along the way.

Let’s jump into it…

Delegation without direct oversight

It’s easy to fall into one of two extremes—all or nothing, when it comes to delegation.

Those who fail to delegate never end up scaling their business as large as they’d like because there’s only so much they can do by themselves.

But those who delegate without effective oversight face a different problem. A larger one, in my opinion. And that problem is the fact that they lose significant control over the direction of their business.

When I made this mistake, I was going through a lot in my personal life, and I trusted my team, so I figured I could let them handle things without any oversight which would allow me to focus on handling my personal challenges.

I was wrong.

Things started to fall apart after a while. They were telling me a far better story than what was happening in reality. Performance and outcomes were either misunderstood or exaggerated. Critical KPIs and looming business risks were overlooked. And revenue began to decline steeply.

Look, I still love and trust my team, and at the end of the day, the responsibility for these failures ultimately rests on my shoulders as the leader of my company. I don’t think these issues were driven by malice or dishonesty—I think they were just doing their best to do their jobs, but they veered off course amidst the chaos that exists in every business.

It’s important to remember that as a leader, the buck stops with us. It’s on us to make sure our team understands their tasks and our expectations, but it’s also on us to make sure we keep tabs on their performance and provide guidance along the way to keep them on track.

This ensures that your company achieves its goals with less course correction needed, less revenue lost, and fewer headaches.

Failing to personally maintain affiliate relationships

One of the biggest revenue drivers in my business is affiliate relationships. The way this works is that other businesses with an established following, which includes both their clients and their audience elsewhere, like social media, an email list, or events they host, will promote our company to their audience in exchange for a cut of the revenue from the closed sales from leads they sent us.

Side note—if you want to learn more about affiliate marketing, I wrote a pretty comprehensive article on the topic here.

That being said, despite the importance of this marketing channel for my business, I failed to maintain our affiliate relationships. 

I started to take them for granted, not from the perspective of not valuing them, but rather from the perspective of knowing that we were giving them a huge opportunity and lots of revenue within the partnership, but overlooking the importance of maintaining the personal aspects of the relationship.

Look, you could consistently provide tons of value in multiple ways, but if people feel like they’re just a number to you on a personal level, that relationship will eventually crumble.

Getting comfortable and taking my foot off the gas

Early in your entrepreneurial journey, it’s easier to stay focused because you have no choice but to grind. But once you start to scale and your revenue exceeds your immediate needs, it’s pretty easy to start getting complacent.

Your company gets to a point where it’s consistently generating a certain amount of revenue and you start to take that as the baseline. It becomes expected. And from there, many entrepreneurs start neglecting growth, improvements to their internal systems and processes, and innovating on their products or services.

That’s a recipe for failure, and it usually goes unnoticed until it’s too late. When times are good and you’re making plenty of money, the underlying problem is buried by surplus cashflow, but all it takes is for you to lose a few clients and the problem becomes as obvious as if someone had pointed a spotlight on it.

The reality is that business is always a series of ups and downs and we have to be acutely aware of exactly where we are at any given time. Beyond that, we need to be intensely proactive in identifying our situation and consistently pushing towards growth. This is critical because if a business isn’t actively growing, then it’s losing position to those that are.

So we need to keep tabs on what’s going on around us at all times, but this can be tough because we often give ourselves far more grace than we would give others. We’ll tell ourselves, “I’m not getting complacent, I’m just focused on this thing right now,” completely ignoring the fact that the “thing” we’re so focused on is actually not going to impact our goals in any meaningful way. 

That’s why it’s important to have a circle of advisors around us willing to be brutally honest with us about what they see. Some of these people might be employees, but our fellow entrepreneurs are often much better suited because they have an outsider’s perspective and their job doesn’t depend on you liking what they tell you.

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Tampa Bay Business & Wealth (TBBW) is the leading source of Tampa Bay business news, telling the stories behind the region’s biggest companies and the leaders shaping Tampa Bay’s economy.

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