12 Mistakes I Made My First Year as an Entrepreneur

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Making entrepreneur mistakes is part of being a business person. I could spend several hours talking about each one, but I made my top 12 mistakes as a businessman during my first year in business.

Entrepreneurs are often in a hurry to grow their business, making mistakes that can cost them time and money. We want you to avoid these missteps by learning from others’ experiences with this blog post. Read on for the top 12 biggest mistakes we see business people making all too often–and how you can learn from their errors!

#1: I almost quit.

I almost quit. 

Hands down, the dumbest entrepreneur mistake I made in my first year of successful business was that I almost quit.

I almost believed myself when I said I couldn’t do this.

I almost believed that I wasn’t cut out to become a business person.

Also, I almost believed it when people said, “you’re not good enough to be a businessman.”

Almost. And I almost quit during my first year. Had I gone through with that, then it would’ve been the biggest entrepreneur mistake I could ever have made.

#2: I wanted to become CEO too early.

I wanted to become CEO too early.

Allow me to explain. I tried organizing way too much, way too soon.

There’s only one way to be a businessman: you have to sell something.

Before most business people can graduate to becoming CEO or President, they have to be salesmen first.

The most important thing is to sell, sell, sell. Like Mark Zuckerberg, Jeff Bezos, and Elon Musk, some of the biggest names in the online business are all successful because they have products that they sell and are popular in the business news.

So my biggest businessman mistake was trying to be a business owner when I should have been a salesman instead. I should have been out there and learning how to make a living—by selling my product.

#3: Taking advice from too many people.


Taking advice from too many people.

If you’ve ever been pregnant or been with someone pregnant, know that everyone wants to share their advice.

They do this because it’s what worked for them. Everyone has their own opinion! And that’s okay. It’s not right or wrong. It’s simply their opinion.

The problem lies in the fact that it’s easy to take too much advice from too many people.

And this exactly what happened during my first year as a businessman. My mind was on a million different things, and it wasn’t productive. Even worse, I was also getting advice from some of the wrong people.

Here’s an example. When I was 20 years old, my first mentor was involved in nine different sales companies, each selling a different product. According to him, that’s the way to do it (with multiple income streams and all that).

However, I realized that that’s not the right way. And guess what? It’s still not working for him today.

Instead of seeking the advice of every “successful” person out there, it’s better to find people who are already living the life that you want.

Get their advice and their input on their mistakes when they were in your position at the phase in business you’re currently in.

#4: Not knowing how to ask for advice

When transitioning from employee to entrepreneur, there is a hidden challenge: hiring employees don’t usually ask for advice. They just get told what to do, and they do it.

The employee mindset doesn’t value asking for ways to improve. It’s become so easy just to quit when you don’t like it anymore!

Once you become a businessman, your mind needs to shift from being told what to do to and asking for advice on business person mistakes.

Learn to seek out advice. But as explained in #3, this advice on mistakes as a businessman creates and has to come from the right people.

#5: Using force versus influence.


Using force versus influence.

An entrepreneur mistake I made a lot during my first year was that I forced too much on my clients, staff, sales team, everyone. I was using force when I should have been using influence.

In effect, I was managing the success of the people around me instead of leading them.

You have to set an example of success. It’s with this example that you can effectively lead your team.

Doing this also takes a massive load off your shoulders so you can concentrate on growing your business instead of getting bogged down by the nitty-gritty.

#6: Living the dream too early.

Using force versus influence.

You can imagine how it was when I started my business and started making money. I bought a brand new car with huge payments. I bought drinks for everyone. I partied hard. I spent $10,000 I didn’t have in just one weekend in Vegas.

That was a rookie businessman’s mistake. Never forget that the goal of your business is to stay in business. When you stay in business, you have the opportunity to grow it. Otherwise, you have nothing.

Don’t repeat these startup mistakes. Living the dream when you haven’t earned it yet can backfire in a BIG way.

#7: Trying to sell too many products


Let me tell you a story. I chose the financial industry by joining Morgan Stanley Dean Witter & Co. My first day on the job was on September 10, 2001. It was the worst time to enter finance as the tragedy of 9/11 happened the very next day.

The market tanked by about a thousand points. Nobody wanted to buy stocks and mutual funds. Nobody wanted a financial advisor. The market kept crashing, and trust in it was at an all-time low.

Fear, panic, war. These were the things on everyone’s minds. And then I started seeing mortgages start climbing. Before I knew it, negative amortization was the next big thing.

I got tempted to get in on this. Everyone in LA wanted in. There’s nothing wrong with it as those who actually did it made a lot to spend money—more power to them. But for me, I chose to stick it out in finance.

In just a week, one of my competitors completely overtook me. His secret? Mortgage, mortgage, mortgage. So I decided that a mortgage was the way. But he was also into escrow. He was also into real estate. He was also into the title.

He said we have to become like banks. We have to do property and casualty too. We have to do tax services.

I see this business person’s mistake all the time. Please don’t fall for it. Focus your efforts on a single product. That’s what’s going to work.

#8: Thinking that I already knew it all.


I became a businessman when I was just 21 years old. Back then, I thought I already knew everything that I needed to know to succeed. What followed was that I hit rock bottom—and it was the best thing that could’ve happened to me.

I firmly believe that everyone needs to experience two major things in their lifetime: a huge heartbreak and a very early and very significant failure in my own business.

These things teach you that you don’t know everything yet. Even Socrates, on his deathbed, said that all he knows is that he knows nothing.

If one of the greatest minds in human history could say such a thing, then what more the rest of us?

The top priority is that we remain coachable and that we keep learning from others. This has been working well for me. It would be a mistake to let my successes get to my head!

#9: Partying too much, too hard


There’s no way around it. I love to party. I loved Thursdays because it was ladies’ night. I frequently went to Dublin’s, and I can’t remember how many times I’ve been kicked out. It was a great place. The same goes for Miyagi’s.

We went to all these clubs in Hollywood. You name it. We’d check it out. We partied like crazy. I mentioned Vegas, right? We would party every night from Thursday night to Sunday night.

I would get up on Friday morning to go to work, thinking it’s going to be just fine. After all, I’ve had three Red Bulls to keep me going. Right? Nope, it didn’t work that way.

I needed to be focused.

Let me tell you something. All the great things about parties—the drinks and the girls—it became boring real quick. Said, there’s no real substance behind it.

The bigger players don’t party like that. They OWN the nightclub. They don’t party with the people in the club. They own the products that the people pay top dollar for.

It’s a mistake that’s way too common not to be mentioned. Stay focused on the real prize, and don’t get distracted by the girls and the flashy lights.

#10: Acting like a boss, not an employee.


Acting like a boss, not an employee.

Maybe you’ve heard that most people say that they can do whatever they want now that they’re entrepreneurs.

That’s a huge mistake. With an attitude like that, you’ll definitely fail.

When you switch from employee to businessman, you’re missing one thing, and that’s a boss who will tell you what to do.

If you weren’t a boss as an employee, you might find it challenging to be a business person because you’ve never done it before and didn’t know the process.

Many successful business people fail because they don’t have anyone to hold them accountable for their actions.

Avoid this entrepreneur’s mistake. Learn to be accountable for both the successes AND failures of your business.

#11: Working without a schedule.

I cannot stress this enough. As a business person, you need to have a schedule, and you have to stick to it. If you don’t, you have to punish yourself for it.

During my first months, I didn’t have a schedule. I showed up whenever I wanted to.

The thing is, as a businessman, you need a schedule. You won’t be working from 9:00 am to 5:00 pm. You’ll be working from 7:00 am to 10:00 pm!

It is an entrepreneur’s mistake to think that you become a businessman to work fewer hours. In reality, you become a business person to work twice as many hours.

#12: Not having a Business Model Plan.

In the beginning, I had no clue what a business plan was. I had no business idea on how to write a plan. Back then, we didn’t have Google to search for the answers.

In your first year of business, you may not need a successful business plan. But it would help if you still had a plan or process.

It should include actionable items.

I will make 200 calls today. Also, I will give away 100 new business cards today.

I will network and connect with 50 people using social media.

Then, I will read for an hour per day. As you can see, these action plans have everything to do with disciplines and developing skills.

It would help if you had a plan for those.

There you have it. Those were the 12 mistakes I made in my first year in my sustainable business. You can bet that there were a lot more, though!

Other Things to Know

Many business people often make the biggest mistake of trying to do everything themselves. They want to build their product, manage customer relationships and still have time for personal life–but this is impossible. Business people need a team that can delegate responsibilities to stay on track with goals.

Creating a Business Model

Creating a Business Model

The second most common mistake we see successful entrepreneurs making is not establishing clear boundaries from day one between work and home life. It’s easy for your family or friends who don’t understand entrepreneurship to get frustrated when you’re always working, but if you let them know ahead of time what it takes, then there won’t be any surprises! Creating boundaries helps a business person feel more grounded, which will help keep burnout at bay too.

Fighting the Urge to Spend Money

If you’re a business person, there will be times when it feels like more money will keep flowing in. But those days don’t last forever, and eventually, your bank account is running on fumes again. It’s easy for business people to believe they have a bottomless pit of funds because that sometimes what their company seems like–but you’ll need all the cash saved up when things start slowing down.

A Successful Business vs. A Failing One

I also learned the hard way that a successful business is not one where you’re working 24 hours per day. It isn’t easy to keep up with every aspect of your company when all your time becomes work time, even if it feels like there are lots of opportunities for growth and more learning experiences on the horizon.

Keep Thinking About A Business Idea

Having business ideas is the key to keeping your brand relevant. You want to be up and coming into the new-age digital marketing world and ahead of certain trends. With this in mind, keep watch on another great idea that successful companies have used and branch off of that with your own.

What is the single biggest mistake that you think many entrepreneurs make?

Mistakes I made that were the most costly to my business were primarily focusing on too many tasks at once, burning myself out, and not completing any of them well.

Also, not delegating enough when I was first starting a business to do all work instead of dividing it up amongst team members who were fully capable of doing it. Keep in mind. Success doesn’t happen overnight. These same mistakes can happen time and time again. Just make sure your marketing plan prepares for it.

Final Thoughts

Starting a business and marketing plan has never been easier, but that doesn’t mean success. If you want to avoid the biggest mistakes of other business people start and have your own success story, make sure you plan for all scenarios before taking any action.

Hopefully, this article has helped you and other future new business people to achieve success. Make sure to remember, as a new entrepreneur, to invest in a successful startup, have enough money, find your target audience, always accept new clients, and watch out for the common mistakes of other many entrepreneurs. Check out Lead Advisors for your marketing and business needs!


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