Mistakes I Made My First Year as an Entrepreneur

Your fear of failure keeps you playing small, so much smaller than you're capable of, and so much smaller than your dreams. And as long as you allow your fear, your worry about the mistakes you will or might make, slow you down, you will always play it safe. Whenever you are doing something that you don't know how to do, that you've never done before, when you are in that situation, your fear of failing or your fear of making a mistake, it'll be screaming at you and trying to hold you back.

It's not about failing. It's about not giving up. The best entrepreneurs, those heroes you have? They have failed time and time again. They just didn't stop. When I look back at starting my company 13 or 14 years ago, I made so many mistakes. It happens to all of us, no matter the industry. No matter your experience as an entrepreneur. You will make mistake after mistake after mistake. But we have the chance to learn from each other.

So I want to share with you the 10 mistakes that I made early on, that I normally wouldn't talk about, that I normally wouldn't want anyone to know about. But hopefully, you can learn from and you will not make the same mistakes yourself.

1. I thought if I built it today, they will come

We all believe somehow that if we just have a good enough product, a smart enough offering, if we're just good enough when we start, people will show up, they'll take notice, they will want the product, it'll somehow breakthrough. I feel foolish for saying it. But when I started, I somehow thought it was enough to build a website or to do some simple marketing, or to be sharper, smarter, and have a good product.

It's not like the world is waiting for you. It's not like you're going to open up your business or start selling something and everyone's gonna be like, “Finally, you're here. I've been waiting this whole time for you!”. There are competitors. There are other services, there are other products; just because you opened it doesn't mean that, just like that, you're going to get some sales, you're gonna get some deals or be able to make it happen. Because you're not going to break through just by showing up.

2. Taking marketing seriously

When I started my business, I had no money. I had no clients. And so it was very hard for me to justify and rationalize and even be comfortable spending a ton of money on marketing. I just didn't have the dollars. And so with entrepreneurs who are in startup mode, those who don't take marketing seriously lose years and years and years. I know you may not have the resources, but you have to take marketing seriously, right from day one.

3. Looking at the competition

There are two ways to look at the competition. You can either look at them and say, “I am going to crush you. I'm going to build something better than you because you guys suck”. Or you can look at the competition and get completely depressed. “They have a team bigger than me. They've products and services and budgets and marketing campaigns. And everything about them is so much better than me”.

If you're trying to beat the competition, you're really just going to end up copying them. Because you don't know what you don't know, you haven't learned, you haven't spent the years there, you don't know how to actually beat them yet, you're just going to copy them. And on this side, if you get all down about yourself, you're going to beat yourself up. But they didn't start with that. They started where you're starting now; they have years and years on you. So you comparing your tiny little startup company to someone who has tons of head start and budget and everything else will do nothing but leave you feeling sad and depressed. Stop focusing on the competition and focus on what you do and make it better.

4. Becoming a CEO of nothing

Titles don't matter to me, but they matter to a lot of other people. You can be the president, you can be the CEO, you can be this C suite or that C suite or whatever you want to be, but if you don't really have a team, if you don't really have a brand, if you don't really have a company or resources or investors or budget, it doesn't really matter what your title is. Being the chief officer who manages resources, when you don't have any resources will slow you down. You have to hustle and put in the hours and the work. But what you can't do is get caught up in your persona or thinking that your title should bring certain benefits to you.

5. Being desperate for the sale

I hit a point in my startup where four months in, I realized I was running out of money. You better believe that motivated me, that kicked me in the butt. And so I went out and I got a business coach, and the business coach gave me one of the greatest lessons even though I'm running out of money.

I'm five months away from bankruptcy. I need to walk into every meeting and every conversation like I have a million dollars in my pocket because if I am desperate for the revenue, or the money or the sale, it is going to cloud my thinking. It's going to cloud my judgment. I'm going to make bad decisions. I'm going to take on projects or do work or sell things that I just never intended. I'm going to ruin my name, my reputation, and everything. So you literally know how desperate you are for the money, you need to walk into every conversation, into every meeting, like you have a million dollars of cash in your pocket, and you want to help them, you want to do good work, you want to make the sale, of course, but you don't need it. You're not desperate for it.

And that puts you in a better position for negotiation, leverage, because you can walk away at any point.

6. Spending more time thinking than actually doing

In a startup, it's really easy to get caught up thinking that you have to have everything thought out. If you have a plan, you have to have a strategy, you have to be able to figure out how everything is going to click together in a few years. And meanwhile, you're not getting the revenue, you're not getting the sales, you're not doing the work that you need to do today to even stay open today or in a few years.

You can literally lose everything and go bankrupt in 12 or 18 months while you're busy planning what your business will look like. How you work and think through strategy feels like progress. It feels safe. There's no risk. It's just all on you. But you guys spend less time thinking and more time doing, focusing on marketing, sales, getting that product out, getting the investors in, you hustle through and get yourself to a position where you're at least even open at your three or your five-year mark, and you worry about that stuff later, just focus on making it happen.

7. Being impatient

All entrepreneurs are impatient. We want things to happen. We want them to happen quickly, and we want them done well, but things take time. And so I thought by year one, I would have certain things. It took three years to get there. I thought that I should have a bigger team, a better team. I should have more clients, I should have a bigger brand. I should be able to think the way that a $10 million company thought when I only had $60,000 in revenue. I was impatient. And that impatience made me put certain things at risk and made me make certain decisions. And more than anything, it just made me feel behind.

It made me feel like I wasn't doing a good job because I thought it would be faster if you were slacking. If you were slow, and you better learn to become impatient and kick yourself in the butt. But if you're like most entrepreneurs, you're already impatient. In which case, you need to give yourself some time to make it happen.

8. I didn't understand clients

I thought I knew what people wanted. I thought I understood what I was selling. I thought I understood pricing and what people were buying, but the only way to really be able to understand what clients want and know what the right prices are, and get a sense of what they're really buying, is by spending time with them. Spending time talking with them, listening to them, asking them questions, and it is super tempting when you're in startup to not want to talk to clients until you're ready.

You know you want everything to be perfect or you get the sale and then you disappear. You're busy delivering on the sale. So you never check-in. You never talk. You never do any of those things; companies and startups who spent an insane amount of time talking and working with clients learn faster and will be in a better position to succeed because they truly understand what clients want.

9. Wasting time wishing I had investors

Every entrepreneur, the whole history of time, always wishes they had more money. A bigger team, more dollars, more capital, more runway, we all wish we had more money all of the time. It never goes away.

And so you know, in year one I was thinking that if I just had investors and if I just had this capital, here's how I would use it. And here's what I would do with that time and that energy, focusing on selling my business and packaging in such a way I can bring investors; but this way of thinking distracts you from actually making a company that can sell to customers and in your two or three or five years, thinking, “Oh, if I just had these dollars, I could superscale, I could scale a lot quicker, I could put them to work this way”, also distracts you from the really creative ideas that will come to you naturally when you're backed into the corner, and you have to make it work.

So the more time you spend wishing that you had more money, the less time you actually have to come up with the creative solutions to make it happen even with no money.

10. Thinking more products or services is the answer

I fell into the trap of thinking more products, more services, more offerings, is the answer. And it actually just made my business much more complicated. So this line of thinking usually goes like this: “If I have $250,000 revenue with this product, if I introduced 10 products that have 2.5 million, right, and it makes sense because I could have all of these little products or these little services or these little businesses, each one of them will generate this type of income, maybe even passively. And when you combine it all together, look at how rich I am. Look at how much money I have”.

But what we fail to take into account is that each one of those businesses or products or services is unique in itself. And so when I started, we had all of these different things. And by year three, I cut down to just one, just one focus. And when I did that, my business exploded, it literally took off. By cutting back on being a generalist and focusing on an extreme niche, it actually helps people understand more about what I did. It helped me focus my operations, my investment, my staff, my marketing, on just that one type of client. And it allowed me to grow really, really quick. Every time I get tempted to think, “If I could do $1,000,005 with this one, what if I did three, boom, there's three times more revenue”, I'm reminded about how much more complicated my business will be, how much more marketing I’d need, how much more infrastructure I’d need, how these businesses may not complement each other. And really, what a distraction it is to have all of these different things.

Almost everyone who goes from one or two companies or offerings and then scales up over time, finds themselves cutting back on some of these things because you just can't focus on all of them, you can't make it work. So rather than early on thinking you can somehow grow through acquisition or grow through all of these products or all these services, focus on the one that's going to take you to the next level.

You are going to make mistakes along the way.

The secret is not giving up, but learning from these little mistakes, learning from the big ones even, and then always going one step in front of the other to make it happen. You do that, and you will find yourself building a business that others look at and think, “How the hell did they do it?”