Top 10 Business Books for Aspiring Digital Nomads & Lifestyle Entrepreneurs

Starting a business can be a life-changing event, for better or for worse. If you're sick of your day job and aspire to live a globetrotting 'digital nomad' lifestyle, or just a life without a boss, beware that the road is filled with landmines.

Before you consider quitting your job, I encourage you to proceed with caution and educate yourself as much as possible about the world of business and entrepreneurship.

To aid you on your journey and to help you weigh the risks, I've assembled a list of my favorite educational business books that have helped me on my ongoing and extremely challenging journey to create a successful lifestyle business. Happy reading, and I wish you the best of luck on whatever career or lifestyle path you choose! 

10) Tribes by Seth Godin

With the growth of the Internet and social networks, it's never been easier to connect with other likeminded people. However, with so much poor quality content circulating around the web, this doesn’t necessarily make it easy to grow a following. In Tribes, Godin discusses how the most successful movements and businesses created “tribes” by sharing powerful common interests and by leveraging a medium, such as social media, to communicate their message.

If you want your business or movement to gain traction, you need to follow a similar path,  creating and sharing a message that triggers strong emotions. Ever think about musicians that have fans that will follow all over the world and pay any price to see them in concert? Customers, like music fans, are price insensitive when their emotions are triggered. In building your brand, your aim should be to connect with your customers’ hearts not just their minds.

In creating the Blue Ocean Life Company, my goal is to assemble a “tribe” of people that are passionate about their desire to leave the corporate grind and reconnect with nature to improve their physical and emotional well-being. Whatever your cause may be, be sure to follow the principles laid out in this essential business book and you’ll be able to create a brand with a following that grows.

9) How To Make Friends and Influence People by Dale Carnegie 

This all-time best seller is a “must read” for anyone looking to get into sales or for anyone just looking to network. In reading this book, I learned how “soft” or “people” skills were among the most important skill sets I needed to perfect in order to become successful at sales or growing a business. As an example, I learned that something as simple as remembering someone’s name was extraordinarily important when it came to networking and something many people often overlook.

When bootstrapping my agency business, I applied the principles I learned from the book in relationship building and networking. I took a genuine interest in the lives of other people, learned to listen more attentively, while also learning to look at things from other people’s perspective. Before you venture off on your own, be sure you brush up these skills among many others that are mentioned in the book. Without these soft skills, your business will be destined for failure.

8) Zero to One: Notes on Startups, or How to Build the Future by Peter Thiel

Peter Thiel, who was one of the co-founders of PayPal along with Elon Musk, explains what the truly extraordinary companies have done to break the mold in this essential book for ambitious entrepreneurs. Some of the most successful companies in history didn't copy anyone else. They went from zero to one, not one to n. In other words, they were innovators, not imitators. Ever heard of Microsoft? They created the first PC operating system, and for that reason, they became a monopolistic powerhouse in the software space.

When creating the Blue Ocean Life Company, my goal has been to create a brand like no other before, one that goes against what most corporations promote in terms of lifestyle goals. If you are building your own brand, you should be trying to create something that is truly unique while leaving imitation to the masses. While you may not be able to create the next Microsoft like most of us, at least this book will give you the right mindset you'll need to pave your own unique path to success.

7) Winning the Customer: Turn Consumers into Fans and Get Them to Spend More by Lou Imbriano

This former CMO of my favorite sports team, the New England Patriots, talks about how you need to create fans of your business, not just customers, to breed ongoing success. True fanatics will pay anything to be associated with a winning brand (like the Patriots) while people without an emotional investment in your brand will move on.

Lou goes on to explain that when building relationships with B2B customers, sometimes you have to put the contract in the drawer to show them you’re willing to work with someone on a personal level. After all, behind every business are people with human emotions so showing goodwill to help builder stronger interpersonal relationships can only help your cause.

In creating the Blue Ocean Life Company, we are certainly trying to create a fanbase, not just a customer base. You should be trying to do the same.

6) The Relationship Edge: The Key to Strategic Influence and Selling Success by Jerry Acuff 

When I first started my own digital agency, my goal was to get my foot in the door at a large organization and upsell my services across the entire organization. In applying what I learned from this book, I was able to accomplish this goal, securing my first major account with a global enterprise that I have retained and grown for over 6 years now.

If your business model involves selling to large organizations, you'll likely learn that building genuine relationships across an entire organization, not with just one person, will be crucial to your success. Imagine what would happen if your one client contact decides to leave his or her job. There’s a strong possibility you’ll lose the business, so getting to know people across the entire organization is vitally important.

Most importantly, Relationship Edge proves that long lasting, interpersonal relationships are immensely more valuable than short-term, superficial business relationships that come and go. Read this book, and gain an ‘edge’ in business by learning to retain and grow client relationships for the long term.

 5) Purple Cow by Seth Godin  

If you're working with little to no marketing budget like I was, you’re going to have to take greater creative risks to “earn” anyone’s attention. You have to be unique, compelling, and sometimes unusual to stand out in a marketplace full of homogenous competition. Otherwise, no one will write about you never mind give you the time of day.  This is especially the case in saturated markets, or what they refer to as “red oceans” in Blue Ocean Strategy.

Have you ever heard for Scrub Daddy, the sponge with the smiley face, that was featured on Shark Tank? Just two and a half years after appearing on Shark Tank, this company generated $50 million dollars in sales. Every other sponge on the shelves looked the same. Scrub Daddy was a "purple cow," or something different than the rest of the herd.

In applying my learnings from both Purple Cow, I’ve tried to position the Blue Ocean Life Company with distinct and compelling qualities that I believe people in the media will want to write about or cover. Before starting going off on your own, be sure you have a plan for creating a "purple cow" of your own, otherwise, you'll blend in with every other business on the market.

4) The E-Myth Revisited by Michael Gerber.

If you don't have a business degree like me, you may be getting into business without the right frame of mind. There is a common belief amongst aspiring business owners that because you have a certain skill set, you are qualified to run a business. This couldn’t be further from the truth, however, as having a skill set is only part of the problem. Many people create a business to work in it, selling their skillset and performing all day to day functions, while remarkably successful businesses can run on their own. Working in a business will make you a prisoner to it while working on a business can set you free. Ever heard for McDonalds? They created the framework for the franchise or turnkey business model, allowing its owners to step away from day-to-day operations, selling its model to franchisees while becoming one of the most recognizable brands in history.

After years of trying to manage my digital marketing agency with no time off, I came to realize that the business I had created was the furthest thing from a being a turnkey business. Not having vacation time was defeating the purpose of creating my business in the first place. I wanted more time off, not less. In my most recent pivot, in creating a drop-shipping product-based business, my goal is to create a business that will free me rather than tie me down. If you have a vision for a certain type of business in mind, be sure you’re creating something can step away from, not one that will consume your life.

3) Blue Mind: The Surprising Science That Shows How Being Near, In, On, or Under Water Can Make You Happier, Healthier, More Connected, and Better at What You Do by Wallace J. Nichols

I had always loved the beach as a kid, but as an adult, I began spending more of my time in urban environments. I lived in NYC for 3 years, an experience I loved tremendously, but something about the concrete jungle seemed to compound my stress and anxiety levels.

After my agency business and partnership fell apart, I found myself broke and reluctantly moving back in with my parents who had recently moved to Cape Cod. During my days on the Cape, I oftentimes went to the beach during periods of high stress and anxiety. While it may have been because of bad decisions or just bad luck, going broke and spending more time by the ocean turned out to be the best thing for my well being. Surprisingly, my life-long anxiety symptoms started to alleviate as I spent more time at the beach, and I developed a hunch that the ocean had something to do with my progress.

To determine whether my hunch was more than just a old wives' tale, I started to research the topic on Google. I wanted to find out whether there was some science behind my theory that the ocean was actually beneficial to mental health. Upon doing multiple searches on Google, I came across Blue Mind, a revolutionary book that delves into scientific research that has shown that bodies of water have scientifically proven positive impact on the mind. According to Wallace J Nichols, author of Blue Mind, in a USA Today interview, “research has shown that being near, in, on or under water can provide a long list of benefits for our mind and body, including lowering stress and anxiety, increasing an overall sense of well-being and happiness, a lower heart and breathing rate, and safe, better workouts”  Beyond this, studies have shown that “ocean therapy” can actually reduce symptoms of PTSD.

While many people on Wall Street will laugh at the idea of creating a lifestyle business, most of these people don’t understand that your physical and workplace environment can have a huge impact on your mental and physical health. If they read Blue Mind, maybe they would understand and consider a career path that takes them out of the office and by a lake or the ocean.

 2) The 4-Hour Workweek: Escape 9-5, Live Anywhere, and Join the New Rich by Tim Ferriss

In the 4-Hour Work Week, author Tim Ferriss argues that people that follow the traditional corporate career path have it all wrong. He asserts that you should never trade your time for money at a day job while waiting to retire and travel the world at 65.  Instead of slaving away in a stuffy office, Tim advocates for "lifestyle design," a type of lifestyle entrepreneurship that lets you control where and when you work, allowing you to fit work around your lifestyle, not the other way around.

When I first left my full-time job, like many others, I aspired to be like Tim Ferris. What I did right was quitting a full-time job to do remote contract work, which allowed me to pursue multiple ventures and travel freely. What I did wrong was creating a service-based business that I wasn't able to automate or scale and was never able to take time off from.

As I am transitioning away from a services-based business, leveraging drop shipping for a new product-based brand, I now believe I'm inching closer to a lifestyle much more like what Tim Ferriss describes in his book. Although I haven't been able to follow Ferriss' blueprint exactly, his book taught me that I should move away from the "employee" mindset, in which people trade their time for money while being forced to work within the limiting walls of an employer.

Just remember as you start your own business, it should set you free, not tie you down, so you need to be constantly evaluating whether you are actually getting closer to achieving your goals or getting further away from them. If you are never getting time off, then maybe it's time to reevaluate your situation and change course.

1 ) Blue Ocean Strategy: How to Create Uncontested Market Space and Make the Competition Irrelevant by Renée Mauborgne & W. Chan Kim.  

Prior to reading Blue Ocean Strategy, I found myself going broke trying to sell digital marketing services in a hyper-competitive industry. As the book defines it, I was trapped in a “red ocean,” fighting a losing and bloody for profits. While reading this book multiple times, I came to realize something that had never ever crossed my mind before: that business wasn’t a zero-sum game. In other words, you could become successful without competing head-to-head.

The book goes on to give many examples of companies that focused on creating demand rather than competing for existing demand. In doing so, these companies created uncontested market space. Cirque du Soleil, a company that reinvented the circus, attracted new customers instead of competing head-to-head for the same existing circus customers.

If you're going off on your own, and like me, you're not seeking capital investment, then you are likely going be in the thick of a “red ocean.” Before moving forward, think about whether your business is going to be competing for existing demand or creating new demand. If it’s the former, you may be entering a market where there’s a race to the bottom in terms of profitability. While it may not be necessary to abandon ship now, consider the long-term growth opportunity within your industry while also contemplating ways to create “blue ocean” opportunities down the road.

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