I was never a natural salesman or even a businessman. Even today, after making hundreds of thousands of dollars online, I don’t consider myself to be one. Unlike some of my friends who are just born to sell, selling never came naturally to me.

But the life I wanted meant that I needed to learn how to get money from people in exchange for my products and services. And, in order to do that, I had to learn how to sell.

I simply had no other choice.

Over the past fifteen years or so (way before this blog), I’ve sold all kinds of stuff online that have netted me hundreds of thousands of dollars.

Here are some of the psychological hurdles you must overcome to be able to successfully sell anything online:

1) Don’t be afraid to ask for money

When I initially started out selling, this was the hardest thing for me to internalize.

The constant voice in my head went something like this: “Hold on a second. So, you’re saying that I can put some stuff online, and people will somehow find my website, and then, get this, actually pull out their credit cards and give me money? Are you serious? No way.”

Maybe it was because I was born and raised in a Communist country (Soviet Union) where selling and asking for money was a foreign concept. Or, maybe not, because I’ve noticed people in rich and capitalistic societies having similar mental blocks.

There’s another important benefit to selling: when you ask for money, you’re implicitly validating your product’s value and benefits to others. This is probably why many people shy away from asking money: they’re afraid of being rejected because they are worrying their work might not be worth anything.

Don’t be that guy. If you’ve done the work and solved someone else’s problem, you should feel entitled to a reward.

2) Don’t be afraid to charge more

The corollary to the first point is that you shouldn’t be afraid to charge more—in many cases, much, much more than what you initially think. That’s because people buy stuff based on value to them not on the value you think the product is worth.

Case in point: when I released my first video course, The Maverick Entrepreneur Bootcamp, I initially charged only $47. Then, I looked around and realized that similar courses are priced anywhere from $197 to $397. So, I went ahead and raised the price to $97.

The result? Sales more than doubled. That’s because people equated the course’s price to its heightened value. In fact, $47 is really a price point of an ebook with some bonuses, so charging that little for a high quality video course that teaches you how to easily make money is not only a bargain, but it’s actually sending the wrong message. It’s counterproductive.

Going forward, I plan to double the price to $197, which I feel is better aligned with the membership’s overall value and positioning.

3) Don’t wait until your product is “perfect”

Five years ago, I decided to build an application. I was living in Miami Beach at the time. So, instead of hitting the beach everyday like my friends (and pretty much everyone else who lived there), I holed myself in a Starbucks and began to feverishly code. A month later the app was ready.

But I didn’t release it. I felt it wasn’t ready. So I kept fixing it up, polishing it, adding features, tweaking the UI and design. I finally released it two months later.

It flopped. It sold a few copies, just enough to cover the cable bill. It was certainly far from a success, that I had envisioned it would be.

The crucial mistake I made was that I assumed that the customers needed the app to be absolutely perfect. But, instead, what the customers needed was a solution their problems.

In other words, what I considered “perfect” was purely subjective and had little connection to what the customers wanted. Perfection was a concept in my head and in my head only.

I’m not saying that you should release a product that’s crappy and full of spelling typos, bugs and technical glitches. The product must absolutely work. It must solve the customer’s problem. If it doesn’t work, then you shouldn’t release it. But if it works and is able to solve the customer’s problems and issues, then by all means get the thing out there.

4) Don’t be afraid to compete

I’ve always been a loner and chose to do things my own way. I’d stay away from crowds and areas of heavy competition chiefly for two reasons: 1) I didn’t feel I was worthy enough of competing and 2) I always thought that I could do something “on my own” better and therefore competition was unnecessary.

What I didn’t realize is that competition exists for a reason, a very good reason. It exists because there’s a high confluence of buyers and sellers. It’s like that popular restaurant in downtown where it’s almost impossible to book a table. Why did the owners of the restaurant decide to open it in an area where there’s heavy competition? Because that’s where there’s a lot of foot traffic and demand. That’s where the action is. That’s where the money is.

While you have limited space in the physical world, the good news is that on the Internet, there’s plenty of room for just about anyone. All it takes is a little tweaking of your product and you’ll have no problems finding that customers who’re not happy with a competitor’s product.

After all, tweaking your product in a busy market is much, much better than having a product with absolutely no competition—and sales. A fraction of any number is greater than the fraction of zero.

5) Don’t be afraid to hear a “No”

The number one reason people are afraid of selling is the same reason people are afraid to pretty much do anything: rejection. They’re afraid of being told no.

A lot of people think Internet selling is black and white: either the customer buys the product or not. That maybe true for lower priced items, but when you’re working your way into higher priced items, then things aren’t so simple. Often times, the customer wants to ask you question, think about the purchase, and think some more.

Ultimately the customer wants to be sold. So, you have to be persistent. Talk to the customer. Figure out why they aren’t interested or what you can do to solve their particular problem.

I’ve had many situations where initially the customer refused to purchase a higher-priced item, but then some time later decided to buy.

Besides, even if you get a ‘No,’ it’s not really the end of the world. Rejection makes absolutely no difference in the end.

6) Be shameless

One of the things I noticed is that people build a product, release it, but for some reason or another don’t really tout as much as they should. I used to be like this. I would build a product, a product that I believed in, a product I felt would solve people’s most pressing problems, but when I felt it didn’t quite attract the interest I wanted, I would back off and do something else. It’s almost like I didn’t believe in the product that I painstakingly spent so much time building.

That was the wrong approach. You must be proud of what you build and let others know about it. Be bold about the product’s claims in terms of solving the customer’s problems.

A big part of that is inherently polarizing. Does your product work better than someone else’s product? Don’t be afraid to say it. Be vocal. Create a conversation. Stimulate a reaction. Get noticed in a busy world.

For others to believe in your product, you must believe in it first and foremost. Selling is most effective when you believe in the product so much that you don’t really need to “sell it.” Let others know that what you’ve built has magnificently solved your problems and will do the same for others as well.

7) Don’t equate all marketers and salesmen with scammers and con-artists

When I used to work as a software engineer on a large (and famous) Internet company in Silicon Valley, I didn’t look at marketers and salesmen highly. Mostly because I thought that those guys were full of shit.

I mean, guys like myself are actually building stuff, so what the heck are all those other guys getting paid for? They’re all full of shit.

That pretty much summed up my ignorance about, well, how the world really works. While the stuff I was building was beyond awesome, apart from my dear mother and close friends, no one would ever find out it about—at least if it wasn’t for those guys.

To be sure, there are a lot of scammy marketers and salesmen out there pushing garbage like penis pills, pumps, etc. Just like in any area, there’s a lot of unscrupulous people out there trying to make a buck.

But these guys are super important. They make shit happen. They are the ones who make the masses aware of a particular products/services or even you. They make sure you exist. They are the reason you’re aware of products that help you in some way, shape or form.

Instead of simply discounting something that you don’t understand—an automatic human reaction—it’s helpful to step back and try to learn a thing or two. They might just help you to do something that you couldn’t do before.

Final thoughts

As someone with a very analytical brain, selling has been a foreign concept to me for most of my life. Mostly because I was antisocial and didn’t like to be around people. Instead, I found a refuge around computers, playing video games and building all kinds of applications in a dark cubicle in a place far, far away called Silicon Valley.

I now know better. Selling is a fundamental part of any business; in fact, it defines the business. If you can’t sell, you don’t have a business. It’s what separates the 9-5 middle class sheeple from self-made men who go on to make millions of dollars. It’s your ability to create something and persuade others that it’ll benefit them in some shape or form.

As soon as I decided I wanted to travel, I had to give up that refuge of building something and learn how to add value in different ways. Since I was no longer working at a company with a dedicated marketing and selling departments, I had to learn it all on my own.

The best advice I can give you is that you must view marketing and sales as a conversation between you and prospective buyers/customers. If you’re not talking, they don’t know you exist. The more you talk, the more you have a chance to be noticed and sell.

The good news is that all of this is merely a mindset switch. You must start to think differently. Once you realize that selling isn’t rocket science and is merely a conversation where value is exchanged, everything else will come together, and you’ll be able to do what you love and then be handsomely rewarded for it by people whose lives you’re improving. It’s really the missing link that’s standing between you and the life that you really want.


Are you interested in turning your ideas into a location-independent business? Interested in learning directly from someone who's done it before and has ten years of experience to back it up? In that case, check out the new program called Maverick Mentorship.

It's an exclusive, limited time program where you get to work directly with me on turning your passions and interests into a sustainable location-independent business.For more information, please see Maverick Mentorship


James Maverick

James Maverick

James Maverick used to work in a cubicle as a code monkey in Silicon Valley. Then, in 2007, he quit his job and a one-way ticket to Brazil. Ever since, he continued to travel, visiting over 85 countries and living in more than a dozen of them. He loved his location-independent lifestyle and has no plans to live in America.
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