Maverick Traveler

Location Independence, Geo Arbitrage, Individual Freedom

How To Succeed And Thrive As A Solo Entrepreneur

Although I’ve complained about the soulless feeling I get whenever I’m back in New York City, there’s one thing this city has that many other cities lack. While other cities and places where I’ve lived such as Kiev, Vilnius, Rio de Janeiro and even places like Bali are fantastic for relaxation, soul-searching and finding the meaning of life, New York City is about nothing of that sort; the Big Apple is all about the hustle.

The hustle is everywhere. It permeates the air. Everyone is rushing somewhere, creating something, building something, thinking about something. Of course, many people are busy for the sake of being busy (ie, the 9-5 sheeple), but they don’t concern me: I’m more interested in the self-made entrepreneurs who seem to be all over the city. Case in point: I’ve been frequenting random coffee shops all over the city and almost every time I met an entrepreneur who was heavily focused on building a new product or service.

The best part about being surrounded by other entrepreneurs is that it motivates you to work harder. Ever since getting back to NYC for the holidays, I’ve become much more productive and even completed a couple of long-overdue projects that were languishing on my to-do list for over a year.

As I’ve recently explained, America is a heavily consumerist society. Everyone seems to be talking about either about products they’re replacing, products they’re using now, or products they’re planning to buy next. I bought my sister an Amazon Echo for her birthday. And she loves it. Now, she’s using it to order more stuff on Amazon. While it’s a nice product, it’s hard to not wonder if the whole thing is really Amazon’s trojan horse, a way for consumers to buy even more products, both quicker and easier.

An army of entrepreneurs

Living in a consumerist culture with Amazon’s two-day prime shipping has its upside as well: they reduce friction. When looked from a pure consumer mindset, they allow you to purchase goods quicker. But, when viewed from a producer mindset, they allow you to acquire useful tools transform yourself from a mere mortal to an entrepreneur quicker and more effectively.

For example, let’s say you want to create youtube videos either to increase marketing reach for your own existing brand or as part of a brand new brand. It’s not that hard. For around $400 you can purchase a decent entry-level camera that takes excellent video, slap on a $100 lens, a budget $70 lightning kit, and for around $500-600, the quality of your videos will be better than 99% of the people out there.

Of course, you’ll also need to learn the right skills to create great videos, but that can be fixed by enrolling in a few courses, taking live workshops or hiring a marketing consultant. Creating quality and engaging content is no longer some secret that only “few” people know—it’s a commodity that anyone with the desire can readily learn.

This is nothing short of astounding. Can you imagine creating quality video content 30 or even 15 years ago? Back then, it was something that only huge television networks were able to do, but now anyone can spend $500 and have a decent video studio where they can produce high-quality content.

All of this is happening as a result of the democratization, decentralizing and commoditization of several key things. First, you have the commoditization of quality products. Quality creator gear such as laptops, cameras or high-quality microphones has become super affordable thanks to the economies of scale. Since almost everyone in rich Western countries can afford a $500 camera, it’s also having a further downward effect on prices, and manufacturers are motivated to create new and better technology at a quicker pace.

Second, thanks to the Internet, the way people create stuff is being democratized. YouTube and other platforms are enabling everyone to become a creator, essentially an entrepreneur. I don’t watch regular network TV and, although I do have Netflix, I generally spend more time on YouTube consuming content from regular guys like you and me rather than a movie produced by a huge Hollywood studio. Thanks to the Internet, everyone is a click away from becoming an entrepreneur.

And, last but not least, as the result of the first two, more people are becoming motivated to carve out their own path and become entrepreneurs. This means that more and more people are choosing to step up their game and ascend to the next level, and thus need products and services created by other entrepreneurs just like them. It’s a win/win for everyone involved.

Compressing time

As an entrepreneur myself, I’m always on the lookout for new products and services that can help me become more productive and increase my output. Just recently, I picked up a new camera. Although the iPhone usually suffices, I wanted something nicer for YouTube videos as well as for other business projects.

Since I’m a completely new to photography, I spent hours and hours on YouTube learning all there’s to know about operating a semi-professional camera. I also purchased a couple of great courses on making quality videos. Although I’ve learned my camera’s endless settings mostly inside out, there’s one thing I still can’t do: take great pictures. I know how to focus my camera and set proper exposure, but I just can’t create a great shot even if my life depended on it.

Unlike learning the camera’s manual mode, taking great pictures is obviously something that will improve only through experience and endless trial and error. But I don’t want to go through the painful process of trial and error. I know that if I spend even a day with someone who has tons of experience, I will learn many useful things that will otherwise take me months and even years to learn on my own.

What I really want to do is compress the one thing that I’ll never get back: time.

So, I had a random thought the other day: wouldn’t it be a great idea if a pro or amateur photographer does a workshop in New York City and teaches me street photography. The idea would be for me to walk around with another human and take pictures all over the city. That way I can spend time with someone who knows what they’re doing (thanks to years of experience) and learn lots of valuable things. And I would be more than happy to pay that person for their time a fixed price. Being able to compress time is a true superpower.

This would be a win/win for both parties. I would compress my time and learn a valuable skill. The amateur photographer would earn a little cash on the weekend that he would otherwise not have. Then, he could use that cash to compress his own time. And I would leverage my new skill to make someone’s life easier and better.

Entrepreneur’s greatest weapon: specialization

This brings to another important point: to become successful, you must specialize in something. Being the jack of all trades is nice, but you can’t make a dent in the universe if everything you do is merely average; you must also carve out a niche and do it better than most people.

Specialization either means an arduous process of trial and error, where you’re learning all the general skills that you need to master your specialized skill, or you just focus on the one thing that you feel you do better than others (and you enjoy) and bring in very smart people who’re good at other skills that you need to make your own skill shine.

Many years ago, I was stubborn and preferred to do everything myself. I was essentially a jack of all trades; I could do a bunch of different things decently and some better than others, but I didn’t have a single skill that really defined me. So, I became an expert in everything. I learned Photoshop, video editing, programming, server administration, security, and tons of other things. I also thought myself marketing, advertising, copywriting, writing and a bunch of other things. As a result, I could do a bunch of new things, but everything I did was average at best.

Nowadays, I would never spend time mastering things that aren’t part of my core skillset. Thus, I wouldn’t touch things like design, Unix administration and even programming with a ten-inch pole. Working on these things just distracts me from working on the things that move the needle and make difference. Now, I just focus on what I’m good at and delegate everything else to people that are good at other things.

That’s why in any given year, I typically spend several thousand dollars on various courses. Quality courses allow me to ramp up a skill very quickly instead of spending hours and hours on sites like YouTube watching random videos.

Talking to smart people helps too. Throughout my travels, I’ve met lots of self-made men, men who were running six- and seven-figure businesses. Sometimes, even a thirty-minute conversation over lunch helped my businesses substantially. When I can’t find a smart guy, I hire one. The consultations I’ve done in areas where I was stuck with an expert was easily one of the best ways I’ve spent money.

I also mentor aspiring entrepreneurs once or twice a year. It’s a program where I teach you everything I’ve learned, fully customized for your specific situation and objective. Since I don’t do it very often, the waiting lists are almost always full. I once received an applicant who seemed very interested, but after I forwarded him the program structure and enrollment fee, he declined. He decided he’d rather learn it via trial and error. Nothing against that approach, but knowing what I know now and possessing the experience I possess, I would never embark on something that might take me years and years of fruitless trial and error. It’s always more pragmatic to buy experience instead of wasting time.

Once upon a time before the Internet, entrepreneurship and things like location-independence were either very difficult or just not viable. If you wanted to start a business in 1960, you’d have walk door-to-door to sell your wares or cold-call a ton of people. That kind of hustle certainly wasn’t for everyone.

Nowadays, not only are people actively looking for products to make their lives easier and better but building those products and finding customers for them similarly requires nothing more than a few clicks. We’re in an era where everyone is a potential builder and creator of value and everyone is a potential consumer of that value. The key is specialization. Acquire the right skills, focus on what you excel at, and bring in other smart people to fill in the gaps.



  1. Hey James,

    If you’re in NYC and talking street photography and learning how to take great shots, have a chat with Goldmund (

    I’m sure you’ll both have a lot to share with each other and he seems like a genuinely good guy.

  2. Thank God for the Internet. One reason is my amazing blog on WordPress. The other is starting my membership website. I am happy that I do not have to spend the rest of my life in constantly working at crappy jobs, dealing with crappy people, and earning crappy (which means low quality) pay.

    Like James, I also am willing to hire experts so that my website would be superb and ready to attract many customers.

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