Define: Lifestyle Entrepreneur

Lifestyle Entrepreneur: a business owner who builds a business doing what he or she’s passionate about, earning enough money to live the lifestyle she wants.

The goal of a Lifestyle Entrepreneur is simple:

  • Earn $100,000+ a year with a Lifestyle Business doing what you love

Let’s break that down:

  • Earn $100,000+ a year: this is what you need to earn to cover your cost of living, have a good life and save money anywhere in the world. Sure, you’re not going to be buying Lamborghinis with this money but that is your choice. After $100k, you have the choice to work harder and go for the car, or you just enjoy your life as it is.
  • With a Lifestyle Business: owning a Lifestyle Business is the only way to get there. As an employee you aren’t in control of your agenda. As any other kind of entrepreneur you are gambling life now on a future event.
  • Doing what you love: your “North Star” of happiness. Work doesn’t become work anymore. And, if you get paid to do what you love, why would you ever want to sell out? Whereas the goal of a traditional Startup or Traditional Entrepreneur would be one day to “exit” the business, the goal of the Lifestyle Entrepreneur is different. The goal of a Lifestyle Entrepreneur is to keep playing the game.

Why Become a Lifestyle Entrepreneur?

  • You’re tired of the BS of working for someone else
  • You want more creative and financial freedom in your life
  • You feel you have more to give but aren’t able to express that skill in your current setup
  • You want to put a dent in the Universe and make a difference in people’s lives
  • You value experience over things
  • You seek adventure and challenge
  • Because life is only once…
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The Goal of the Lifestyle Entrepreneur

A lifestyle entrepreneur starts by defining their ideal lifestyle then builds a business that fits into that vision. This is a technique I picked up from Tim Ferriss in The 4 Hour Workweek. The traditional entrepreneur does it the other way round: they build a business then shoe-horn their lifestyle into that vision as an afterthought.

Happiness: our goal goals

Socrates called happiness “the goal of goals”.

Everything we do – building businesses, earning money, helping charities, traveling the world, recording music. Whatever it is, it comes back to happiness. For us and the people around us that count.

So, with that in mind, why do we build lifestyles where we are so busy that happiness becomes a bonus rather than our focus?

As a Lifestyle Entrepreneur, I’ve tried to step outside the rat race and learn how to create a lifestyle that puts happiness at the top of our needs pyramid. Then, and only then, engineer a business that makes that happen.

This is what I’ve learned.

Happiness is not rocket science

At the end of the day, this is what it’s all about isn’t it?

I wonder why we make it so difficult all this time, this searching for happiness.

I tried everything – yoga, meditation, veganism, making money, losing money.

I discovered that happiness wasn’t a state, but a verb.

What I mean by that is that being happy isn’t something that happens as a result of how you are thinking or feeling, but the result of what you are doing.

If you want to be happier, do more of what makes you happy.

happiness My Story as a Lifestyle Entrepreneur lifestyle entrepreneur grahamdbrown

Happiness starts inside

When you’re an adult, happiness isn’t your default state.

As a child, yes. Look how simple pleasures like feeding the ducks or chasing a plastic bag in the wind can make a child happy. But, as a grown up, we learn to fear what others think.

Matthieu Ricard, author of “Happiness” says that to become happy, we must train ourselves. Think of all the crap that life throws at us in any given day – problems, crises, the opinions of other people. Your goal is to fly, to be happy. But, this crap is gravity. If you don’t beat your wings, the crap will drag you back down to earth.

So, happiness is a verb that requires constant work.

We all have some things that we like to do, that make us happy.

Could be baking cakes with your kids, making music, going for a walk along the river, watching opera or exploring the backstreets of a foreign city.

Whatever it is, these are verbs, actions, that make us happy. And to be happy we need to practise them regularly.

And these actions don’t start with other people:

  • What your friends will think when you rock up in your new sports car
  • Reaching 10 million twitter followers
  • Looking young and glamorous like those girls in “Sex in the City”
  • Getting promoted to “Vice President”

The rat race has us in a bind, a belief system that happiness comes from the outside.

When we escape, we realise that happiness is internal and starts with ourselves.

So, now we know that, how can we be happier in life?

Being a Lifestyle Entrepreneur Means Doing More of What Makes You Happy

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I had the lifelong goal of completing the Ironman triathlon

But, I didn’t want to just complete the Ironman, I wanted to complete one of the toughest Ironmans in the world – Lanzarote, in Las Canarias off the west coast of Africa. Rather than just enter the race, we moved to Lanzarote and lived there for 18 months, alongside professional and elite triathletes who came to the sunny island to train.

Ironman Triathlon Challenges:

  • 2012: Ironman 70.3 UK
  • 2013: Ironman 70.3 Lanzarote
  • 2013: Ocean Lava 70.3 Lanzarote
  • 2014: Ironman Lanzarote
  • 2017: ITU Yokahama Japan
  • 2017: Ironman 70.3 Japan

Lifestyle Business = Freedom of Choice

Bob Dylan once said that “a man is a success if he gets up in the morning and goes to bed at night, and inbetween he does what he likes.”

That’s what we all want. Choice.

Choice means we can build the business around our dream lifestyle rather than shoehorn the lifestyle into the business as an afterthought. Too many CEOs and founders end up with businesses that make them unhappy or ones that they feel they are losing control of when too many people get involved in the decision making.

What’s it Like Being a Lifestyle Entrepreneur?

(Our route map: 5 year adventure traveling the world)

Screen-Shot-2017-05-11-at-19.08.34 My Story as a Lifestyle Entrepreneur lifestyle entrepreneur grahamdbrown

The best example I can share with you is my own story.

I am a Lifestyle Entrepreneur. For many years I was a traditional startup entrepreneur growing profitable businesses. It wasn’t until I exited my last business in 2012, sold up and traveled the world for 5 years with my family did I realize what was possible.

In that time we traveled to and lived in Hawaii, Fiji, New Zealand, Cyprus, Fuerteventura, Andalucia, Lanzarote, Florida, California, Okinawa and Kanagawa in Japan.

Currently Living In:

  • 2011: London, United Kingdom
  • 2012: Tauranga, New Zealand
  • 2013: Lanzarote, Spain
  • 2014: Okinawa, Japan
  • 2015: Malaga, Spain
  • 2016~ Kanagawa, Japan

What a Boundaryless Lifestyle Teaches You:

  • Freedom comes from stepping outside your comfort zone
  • Opportunities exist between borders
  • The similarities between you and me as entrepreneurs, regardless of our nationality, are bigger than the differences between us and people born in the same country
  • Your identity isn’t tied to a location, a creed or some myth, but who you want to be
  • It ain’t necessarily so…

Lifestyle Entrepreneurs: A 2nd Wave’s Coming of Age

For many years, being a Lifestyle Entrepreneur was seen as 2nd best by the macho startup community.

But, today that image is changing thanks to:

…we are witnessing an emergence of a 2nd generation of Lifestyle Entrepreneurs who are making very good money doing what they love.

Not only are they in control of their business and their work, they have time to do more of what makes them happy – whether that’s time with family, time to travel the world or time to do something crazy, like an Ironman triathlon.

Here’s why I believe being a Lifestyle Entrepreneur is the ultimate choice for anyone who wants to bring back more time, freedom and creativity into their life.

How is a Lifestyle Entrepreneur different to a Traditional Entrepreneur?

grahamdbrown-comparison-e1496210821339 My Story as a Lifestyle Entrepreneur lifestyle entrepreneur grahamdbrown

Lifestyle Entrepreneurs are a new class of business owners who unlike Traditional Entrepreneurs put Lifestyle at the top of their needs pyramid. Traditional Entrepreneurs defer their Lifestyle needs today in the hope they can enjoy a better lifestyle tomorrow.

Lifestyle Entrepreneurs are the cubicle escapees of Tim Ferriss’ 4 Hour Workweek, the Accidental Entrepreneurs of The $100 Startup and the Lean Entrepreneurs of The 7 Day Startup.

If you love entrepreneurship, but don’t love how it’s done… this is for you.

Wait… what did I just say, “don’t love how it’s done”?

What am I talking about?

Well, let’s start our story with Henry Ford, because he’s one of most (if not the most) celebrated entrepreneurs of all time. Ford’s management style is a legacy that shapes businesses and business thought to this day.

We’re all familiar with the anecdote where Ford tells the press,

“You can have any color… as long as it’s black”

There’s a reason behind that. Turns out that black paint dries quicker than any other color. Ford automobiles were black because they could build them faster and cheaper.

When we build businesses today, the ghost of Ford looms large behind us somewhere:

  • Automation and process
  • The ruthless quest to drive down cost and expand
  • Innovation

You see, I think it’s time to put Uncle Henry aside… He’s done his job for “Traditional Entrepreneurs”. I’m talking about all those people who secretly harbor a desire to be like him, the apex predator of their industry, changing the world for generations to come.

All that process, cost management and innovation… we don’t really enjoy that. In fact, we don’t enjoy institutions, organization or any kind of management. That’s not us.

New Ways of Thinking About Entrepreneurship

The Lifestyle Entrepreneur is a new class of entrepreneur, a class that has come into the fore in recent years thanks to the internet and thanks to a whole series of exciting and game-changing books like:

These books have redefined what it is to be a Lifestyle Entrepreneur and, importantly, what’s possible.

Lifestyle Entrepreneur: Not 2nd Best Anymore

I am a Lifestyle Entrepreneur, although it’s a term I struggled with for many years because it was always seen as second best to “true entrepreneurs” (which I’ll talk about in a minute). But that’s not true anymore. In fact, many Lifestyle Entrepreneurs are both happier and financially better off choosing this business model over the alternatives (salaried life and traditional entrepreneurship).

Why is a Lifestyle Business a good idea?

Lifestyle Entrepreneurs build their Lifestyle Business in such a way it is semi-automated:

  • That gives them the luxury of time (unlike salaried employees and traditional entrepreneurs).
  • Lifestyle Entrepreneurs also should make enough extra cashflow in their business to invest that cashflow into an investment business that makes money while they sleep. This is a core investment strategy taught by Robert Kiyosaki in Rich Dad Poor Dad. It’s also a key difference and a benefit from a traditional entrepreneurial “exit”. In this model, the Lifestyle Entrepreneur isn’t gambling his or her future on whether or not their business gets acquired. The Investment Business gives more control and certainty.
  • When your overheads are low, you can choose how to use your time. You can say “no” to the stuff, the people and the work that doesn’t get your heart beating faster. You can do more of the work that inspires you and, importantly, makes you missable in the eyes of your customers.
  • When you have time, you have choice, and that’s what it’s ultimately about.

5 Myths About Lifestyle Entrepreneurs

Myth #1: Lifestyle Entrepreneurs don’t earn much money

Like all entrepreneurs, there are successful and unsuccessful business owners. While in the past, this may have been partly true for Lifestyle Entrepreneurs, with the advent of the internet and access to the right business models such as those taught in these 5 books, nothing’s stopping you. I define Lifestyle Entrepreneurs as business owners who want to make 6 figures + annually doing what they’re passionate about. Not a bad lifestyle is it?

Myth #2: Lifestyle Entrepreneurs are Digital Nomads

Sure, Digital Nomads are a step in the right direction but the vast majority are freelancers working for the man. There are 2 key differences between a Digital Nomad and a Lifestyle Entrepreneur. Firstly, the goal of the Lifestyle Entrepreneur is lifestyle not nomadism. It’s also doesn’t have to be digitally based, but that’s a side issue. Secondly, and most important, the Lifestyle Entrepreneur has a system that moves him or her towards financial and creative freedom. This is what you’ll find in these 5 books – build a Lifestyle Business that creates cashflow, reinvest that cashflow into an Investment Business. This is a critical difference and it’s what many Digital Nomads need (but don’t know how) to reach the next stage of their journey towards freedom.

Myth #3: You Need Money to Start a Business

Chris Guillebeau wrote the $100 Startup to show you that this really is a myth. You don’t need much money at all these days. Dan Norris wrote the 7 Day Startup to show you that you can launch a business with minimum time and money. If you change the way you think about business, you need much less money than you think. That’s what I teach in this book – break out of the old-school 20th century mindset of launching big businesses and focus only on what’s necessary.

Myth #4: You Need to Jump Into the Deep-End

If you didn’t have to give up your work, would you start the business anyway? Guess what, here’s the good news. You can start your Lifestyle Business on the side. Thanks to the internet and the available business models for Lifestyle Entrepreneurs you can launch a business in the evenings or weekends. This is a low-risk model for getting into the game and one available to everyone who wants it.

Myth #5: You Need a World-Changing Idea

You don’t need one. Here are 2 reasons why. Firstly, some of the best businesses are built on average ideas. They don’t create the next billion dollar app but instead, they solve a problem that people like you have on a daily basis. Simple solutions to simple problems creates great Lifestyle Businesses. And Secondly, it’s not about the ideas but the execution. As I teach in this book, the best way to start a business is to stop worrying whether your idea is good or not and just launch. A lousy idea with great execution beats a great idea with lousy execution everyday. As long as you can do something which moves someone enough to go “wow, I’d like that”, you have the opportunity to create a successful Lifestyle Business.

Is Being a Lifestyle Entrepreneur for You? (7 Examples)

You Now Your Challenge Potential Solution
#1 Professional photographer Your challenge is you have a valuable skills but never enough time to develop it into something you can really get passionate about. You’re always running around chasing the next job or responding to client requests. You have the ability to create powerful experiences for a group of people willing to pay good money. There is a growing market out there for people who want to go on tours, a business that you can excel at, a business that satsified your wanderlust. But, don’t waste time waiting for the perfect time to get started, start small with a “Minimum Viable Product” as taught in the 7 Day Startup and you can launch this low-cost and low-risk.
#2 Self-employed app developer Currently you have 2 regular sources of work – inbound client requests that pay the bills but aren’t very exciting and that pet project you want to change the world with but takes time and money (you have neither) Stop worrying about that next billion dollar app and start developing apps that generate casfhlow in the short term. Who is the tribe you belong to and what kind of problems do they have on a daily basis? Are you a surfer or a anime geek? Develop low-cost and lean solutions for your tribe that can get quick feedback into the app stores and help you grow. These fans will be your best marketing department and help you scale at minimum cost.
#3 Affiliate marketer You’re an expert at turning web traffic into money but you’re always fighting change and surprises that spring out of the network. If only you had more to time to invest in something outside of the world of affiliate marketing that could generate your a side income. Your biggest challenge is time. What is the 80% of your results and which 20% of your efforts do they come from? How can you double down on these efforts and reduce your workload to free up a little time to start re-allocating your cashflow wisely. Can you diversify out of affiliate marketing into consultancy? Can you productize your knowledge (people are always asking you for help so maybe this is a good starting point). Create excess cashflow and start investing that into an investment business that can build your financial and creative freedom long term
#4 Creative agency owner You are fantastic at what you do but that comes with a price. You’re forever torn between clients and your family. Whether it’s pitches, presentations or conference speaking, everyone wants a piece of you. The more you want to grow your business, the harder it gets. The frustrating part is that as your revenues grow, your profit remains static, eaten up by an increasing number of staff and expanding cost base. You’re building a monster that needs constant feeding but you know the hard truth that 80% of the value from your agency comes from YOU. You are the one that clients want. You are the one that lightens up the room with your insight. Rather than dilute down your value-add by implementing management structures and taking on extra staff, how can you cut down on the low-value work? Are there clients you can say NO to, to free up space for the other stuff? Can you productize your agency offering to create a passive income pipeline while you’re active on client work?
#5 Self-employed app developer Currently you have 2 regular sources of work – inbound client requests that pay the bills but aren’t very exciting and that pet project you want to change the world with but takes time and money (you have neither) Stop worrying about that next billion dollar app and start developing apps that generate casfhlow in the short term. Who is the tribe you belong to and what kind of problems do they have on a daily basis? Are you a surfer or a anime geek? Develop low-cost and lean solutions for your tribe that can get quick feedback into the app stores and help you grow. These fans will be your best marketing department and help you scale at minimum cost.
#6 Digital nomad You already made a choice. You packed your belongings and traveled the world. You spent some time in Chiang Mai, Thailand learning new skills. You got restless and moved on. You made “some” money but you never managed to achieve that dream you were sold with the “laptop on the beach”. You began doubting your own skills and wonder whether you can actually do this at all. Fear not… You face the problem many entrepreneurs encounter when starting out. They key is the direction in which you take your journey. Rather than try and scale up your income through freelancing you need to be conscious by the manner in which you grow. You should build a minimal base of freelancing income that covers your overheads but no more. The marginal gain of that extra income is small. So rather than chase extra income, use that time to start building your Lifestyle Business. Use your freelancing income to bankroll the project and give yourself enough burn time for the business to grow as it needs. Using the models I teach in my book, you can do this low cost and low risk.
#7 Salaried Employee You are earning good money but this isn’t what you’re on this planet to do, there’s some greater challenge out there waiting for you. You feel you can’t risk your career or commitments to do this right now. It’s a thought that keeps bugging you but you keep putting it off until “someday”. Of all these scenarios, you have the most to gain from becoming a Lifestyle Entrepreneur. You know that too. Your challenge isn’t being sold on the benefit of working for yourself it’s the where, how, what, when etc. The good news is that you don’t have to jump in at the deep end to start your business today. You can start your business on the side – weekends and evenings – and build it low-risk. If it doesn’t work out, you lose nothing. You can carry on as you are. If it does work out, you get to that wonderful point in your life where you have choice – where you can earn MORE from your Lifestyle Business from your salaried work. That opens up so many possibilities to you. Not only can you decide to go full time but you also insure yourself against change. What if your boss turns round one day and tells you you’re being fired? What if you get asked to moved to another office? Without a safety net you become desperate. A Lifestyle Business protects you from these unforeseen life events.

Why is now a good time for Lifestyle Entrepreneurs?

  • The wealth of books like these 5 books that helped me become a Lifestyle Entrepreneur.
  • Customers are increasingly demanding more human experiences from brands (hence the rise of brands like Starbucks over McDonald’s). Just look at how airlines fare in the media these days. Big companies are suffering from diseconomies of scale. This need for humane brands combined with transparency and vulnerability means people are willing to forego their preconceptions about what a company or brand should be e.g. big offices, large complement of staff etc and in its place get a more direct, personal relationship. That means a Lifestyle Entrepreneur can compete with a big brand, not on the basis of scale but on the basis of being more human. 
  • The growth in radical business models that has emerged as a result of that perfect storm of ideas i.e. lean startup, lifestyle entrepreneurship, digital nomads, location independence and the internet. These include: dropshipping, affiliate marketing, internet marketing etc.
  • Unlike some traditional startups and big companies, Lifestyle Entrepreneurs can operate under the radar and connect with customers without being seen for as long as they need to. This is a powerful advantage. You can go out and make mistakes without public scrutiny. You can stay small, agile and lean while the big guys struggle with bureaucracy and committees.
  • You can start a business for less than $100. Yes, it’s possible. Chris Guillebeau wrote a book about it. That means you don’t need investment. Stay lean as long as possible. You shouldn’t be borrowing money or getting investment until you need the capital to scale (and that’s an option rather than the default path for a lifestyle entrepreneur too). You don’t need a business plan, an office, a team, job titles or lawyers. You can shortcut all the crap associated with starting a business that complicates everything and slows you down. In fact, you don’t need a business until you have customers, which means if it doesn’t work out, you have little to lose.

My Lifestyle Entrepreneur Strategy

lifestyle-entrepreneur-strategy My Story as a Lifestyle Entrepreneur lifestyle entrepreneur grahamdbrown

Here’s how you do it. It’s no secret, it’s not rocket science and I’m happy to teach it to you.

Think you have plenty of time to start building the lifestyle of your dreams? Think you’re going to reach retirement in good shape? There’s a 50% chance that you’ll never make it.


Adventure is the mindset you need to become a Lifestyle Entrepreneur. Adventure is why you’re here. It’s the spirit of Lifestyle Entrepreneurship.


Authority is the system you need to create to become a Lifestyle Entrepreneur. Authority is the mechanics that turns your skill into money. It’s how you’re going to do it.


Action is the daily habits you need to learn to become a Lifestyle Entrepreneur. Action is what you’re going to do on a daily basis. It’s the fuel that keeps the engine of your Lifestyle Business turning over.

Lifestyle Design: Ask “what if?”

What would it take to have that lifestyle?

In most people’s cases, the tail wags the lifestyle dog. They fit lifestyle around their work. It’s never fulfilling and often stressful. Most people save up money for their 2 weeks in the sun to decompress from 50 weeks of hard work.

But if you consciously started out by putting “lifestyle” at the top of the pyramid and then re-engineering work around that primary need you can be happier.

And the good news is that today, with the advent of the internet and the growing availability of business models suited to this setup, being a Lifestyle Entrepreneur and being successful is more than possible. Lifestyle Entrepreneurs can make far more money than salaried employees, engage in more fulfilling work and have more control over their schedules to do more of what makes them happy.

This is a “what if?” question that is core to becoming a successful Lifestyle Entrepreneur.

Bob Dylan wrote that “a man is a success if he gets up in the morning and goes to bed at night, and in-between he does what he likes.”

A successful Lifestyle Entrepreneur makes a conscious decision to design a life where he or she is able to do more of what makes him or her happy.

Let’s say that happiness, as in my case, is endurance sports like triathlon and cycling. Living in London, both the weather and traffic conspire to make that a challenge. So, what do you do? You end up working harder, making more money. And what do you do with that money once you get it? You spend it on “stuff” to make you happy. But, that “stuff” like cars and clothes never really makes you happy.

Adventure makes me happy. Business is an adventure. Some years ago, I sold my shares in a profitable business and decided to travel the world. Why? Because travel made me and my family happy. We lived for 18 months in Lanzarote, Spain – part of the Canary Islands 200km off the west coast of Africa. Why? Because with its 3000 hours of annual sunshine, brutal hill climbs and virtually non-existent traffic, Lanzarote is a mecca for endurance sports athletes.

The journey to happiness starts by asking, “what if I could have a lifestyle where I can do more of what makes me happy?”

Why Wait to Live Your Dream Lifestyle?

81% of people said “travel the world” when asked what they’d do if they won the lottery.

Why gamble your dreams on winning the lottery? (This also applies to Traditional Entrepreneurs who build businesses hoping they can sell it in future)

What if you could live your dream lifestyle NOW rather than wait until you’re 65?

What if you could live the millionaire lifestyle without having a million in the bank?

With the right strategy, you really can go experience the world. Life is so much more than 2 weeks in the sun every year.

OK, are you ready for the bad news?

Look at the following table and find the scenario most like you now.

% Probability you will DIE, become CRITICALLY ILL or DISABLED by retirement age (65 yrs)

You are RISK %
20 year old female (non-smoker) 53%
35 year old male (smoker) 54%
45 year old male (non-smoker) 46%

(Source: Canadian Institute of Actuaries)

If you are gambling your whole life on your retirement, your chances are the same as flipping the coin. How insane is that? But, that’s the insanity most people are living without realising it.
There is a 50-50 chance you won’t make it to retirement on your own terms (alive or in good health).

Can you risk working hard for your whole life only to never get to enjoy it?

Here’s the GOOD NEWS.

You can start living today as if it was the rest of your life.

You can take back control and start living on your own terms.

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