The Suitcase Entrepreneur: Create Freedom in Business and Adventure in Life

The Suitcase Entrepreneur: Create Freedom in Business and Adventure in Life

by Natalie Sisson
The Suitcase Entrepreneur: Create Freedom in Business and Adventure in Life

The Suitcase Entrepreneur: Create Freedom in Business and Adventure in Life

by Natalie Sisson


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Now in its third edition, The Suitcase Entrepreneur teaches readers how to package and sell their skills to earn enough money to be able to work and live anywhere, build a profitable online business, and live life on their own terms.

After eight years of working in the soul-crushing bureaucracy of the corporate world, Natalie Sisson quit her high-paying job and moved to Canada, started a blog, and cofounded a technology company. In just eighteen months she learned how to build an online platform from scratch, and then left to start her own business—which involved visiting Argentina to eat empanadas, play Ultimate Frisbee, and launch her first digital product. After five years, she now runs a six-figure business from her laptop, while living out of a suitcase and teaching entrepreneurs worldwide how to build a business and lifestyle they love.

In The Suitcase Entrepreneur you’ll learn how to establish your business online, reach a global audience, and build a virtual team to give you more free time, money, and independence. With a new introduction, as well as updated resources and information, this practical guide uncovers the three key stages of creating a self-sufficient business and how to become a successful digital nomad and live life on your own terms.

Product Details

ISBN-13: 9781501178177
Publisher: Gallery Books
Publication date: 09/05/2017
Edition description: Revised
Pages: 272
Product dimensions: 5.50(w) x 8.30(h) x 0.80(d)

About the Author

Natalie Sisson is a global adventurer and digital nomad who is on a mission to create freedom in business and adventure in life for herself and other entrepreneurs. She has worked with thousands of clients to design a profitable lifestyle business they love. She has inspired millions of people through her popular blog, podcast, and lifestyle video series, as well as through events, retreats, and speaking engagements. Originally from New Zealand, Natalie has citizenship in the United Kingdom and permanent residences in Canada and Los Angeles. She has travelled to sixty-nine countries and has lived on five continents. After mastering her marketing and business development skills for eight years in the corporate world, Natalie went on to cofound a technology start-up in Vancouver in 2008, which is now the number one fundraising application on Facebook. She’s been featured in Yahoo Finance, The Guardian, The Age, New Zealand Herald, Huffington Post, Forbes, American Express Open Forum, Mashable, Visa Business Network, and Social Media Today. She is the author of The Suitcase Entrepreneur.

Read an Excerpt

The Suitcase Entrepreneur
Life is either a daring adventure or nothing.


My working day is a little . . . different. I don’t go to an office. I rarely if ever go to meetings. Although I run my own business that allows me to travel all over the world, my schedule is mine to do with as I choose.

And I don’t choose boardrooms, clock-watching, time-card stamping, or those endless gray meetings in gray boardrooms with gray, desperately unhappy people.

Since you are reading this, then I bet that’s not the life for you, either.

Instead, you might want to spend your days like I do: cycling through Africa, throwing yourself off the Victoria Falls Bridge, Zambia, riding a motorbike through the hills of Thailand or hiking the famous W Trek in Patagonia.

Instead, you may want to spend them reading a book in a hammock in your garden, playing with your children or pets, or spending quality time with your partner and then heading off to a midafternoon movie, followed by dinner and dancing.

That’s what I do, and all while my business works for me. The good news is, you can do the same. You can run a thriving online business from your laptop, from anywhere in the world, on your own schedule. Let me show you how.

I choose freedom as my highest value in life. I do everything in my power to have more of it. This means that every single decision I make is based upon staying true to this value. If it doesn’t fit, I don’t do it. BG.

In pursuit of freedom I became a homeless vagabond (or a world citizen) and lived out of my suitcase full-time. I had no address and no home base, but I had the ability to truly live life on my own terms.

Now that I have my own property and 2.5 acres of land, I have a different type of freedom, which I relish. A loving partner, chickens and an adorable dog, a local community and adventure and nature on my doorstep, as well as regular travel.

While this is very different from the life I led, it is just as freeing, for very different reasons. I choose freedom on a daily basis.

There are two types of reactions when I tell people what I do.

The first is “Wow! That sounds amazing. I’d love to be able to do that one day.”

The second is “Are you crazy?” followed by “How do you live out of a suitcase? How on earth do you manage that?”

So am I crazy? Perhaps a little—I’ll let you be the judge.

I grew up in New Zealand, one of the most beautiful countries in the world, where my European parents had settled after a world tour honeymoon.

I spent my childhood outdoors, playing sport. Dad worked hard so we could enjoy as many vacations as his job—as an insurance salesman—would allow.

I started to travel with the family at the age of two. By the time I turned six, I ended up having to repeat a school year because our family had taken too much time off to travel.

Fast-forward to when I was twenty-seven and was still struck with the travel bug. In fact, I found myself with a strong urge to leave New Zealand . . . possibly indefinitely. I packed my bags in February 2006 and spent the next three hundred days living out of a suitcase.

In fact, I’ve been almost permanently in a state of pack ever since.

I started by traveling across Southeast Asia and ended up arriving in London, England, on my twenty-seventh birthday, where I stayed for two and a half years. Since then I’ve also called Vancouver, Buenos Aires, Los Angeles, Amsterdam, and Berlin home (even if just for a few months).

On top of all of these nomadic pursuits I have managed to build a successful online business and a movement of Freedomists at that I’m privileged to lead.

If you’re wondering how on earth I achieved this, then know that it all comes down to one simple philosophy: a true desire to live my life the way I want to, no matter what. This true desire is what people are missing when they detail all the reasons they can’t possibly live the life they want.

My way of living hasn’t always been like this. I spent close to nine years of my life chasing the corporate dream, working my way up through high-paying jobs in marketing, brand management, and business development across a diverse range of industries in both New Zealand and Europe. Working for someone else really taught me important lessons about what works and what doesn’t, especially from an operations and management perspective.

Looking back, I always chose roles where I was offered a lot of scope and flexibility to work on my own initiatives, and where I was able to take charge of making them happen. This was a good thing because I hate authority. Most managers realized this quickly, but not before they had hired me.

I am a self-motivated person and often started in a defined role only to turn it upside down. A nine-month contract with a global pharmaceutical company saw me travel all over Europe, working with key opinion leaders and local sales teams, but also saw me reinvent its entire brand positioning including the core message, the marketing, and the communication strategy. This bull-by-the-horns approach earned me a lot of respect and a big bonus.

By June 2008, though, I had had enough of the nine-to-five. My high-level job in London, where I was at the time, pushed me over the edge. On paper it looked amazing: great pay, head of a brand-new department, the ability to build my own team. But it was with an old-school firm that was archaic in its thinking, smothered in bureaucracy, and drowning in office politics. My lack of progress was slowly killing me. I was battling against the very people who had hired me to do the job!

So less than a year after starting that particular job—in fact just after I had received a raise and a solid performance review—I quit. My friends thought I was crazy, as I’d just bought a house in London, too. But I was sick and tired of working in organizations where I had no freedom to make a real impact or to influence the outcome.

Less than two weeks after quitting in London, I bought a one-way plane ticket to Vancouver (Canada), represented New Zealand at the Ultimate Frisbee Championships, and started a new life.

I had invested most of my final salary payout and pension plan into my property in London, but had enough money left in the bank for just a few months of living costs in Vancouver—one of the most expensive cities in the world.

If you’re going to make a significant change in your life, consider making a big move, like taking a trip to a different part of the world or at least to a new location within your country. This helps you to get out of your comfort zone and take a different perspective. After all, if you do what you’ve always done, you’ll get what you’ve always got.

After my nine-to-five experiences in the corporate world, I was determined to start my own business in my own way and so was hitting up every networking event available in order to make strong connections. As luck would have it, I met my future business partner—Daryl Hatton—at one of these events.

Our respective loves of marketing and technology brought us together two days later, when we discussed his idea to build a social fund-raising platform. He told me that when I said, “I’m a homeless unemployed bum and I want to start my own business,” he was sold! (Well, that and my solid background in marketing and business development, which complemented his technology background perfectly.)

When I ask people what it is that they do better than anyone else, I often see them pause and think. If you want to take advantage of all the opportunities available to you, you have to know what it is that sets you apart: your “Special Sauce.”

You may be excellent at building relationships or founding teams or making the complex seem simple or breaking large projects down into manageable chunks. You may “just” be really good at listening, talking, or socializing. All of these talents can be your strategic advantage. But more than that, you need to be able to communicate this clearly and effectively to everyone you meet, in a heartbeat. The better you can define what your unique ingredient is and how it can be applied in the situation you’re in, the more opportunities will come your way.

Daryl and I joined forces in September 2008 and formed ConnectionPoint Systems, right about the time I was starting to get a little desperate for funds, having been in Vancouver for two months, burning through my savings. We set to work creating FundRazr, which—due in no part to me—is now one of the top fund-raising applications on Facebook, with more than a million users.

While Daryl was a seasoned entrepreneur, I was thrown into the deep end. My time was spent getting a grip on the world of alpha and beta releases, speaking the language of developers, figuring out how to make money when “freemium” was all the rage, and understanding the world of angel investors so that we could actually survive on our current burn rate (how much cash you spend each month when building a company from scratch).

My way of dealing with being in the male-dominated technology industry and understanding the entire spectrum of being involved in a start-up was to blog about it. It was a cathartic experience for me to write about all that I was learning, on a weekly basis. I set up a WordPress site, bought the domain name, and set about learning all I could about blogging.

Meanwhile, our team worked on the standard start-up diet of long hours, little sleep, and too much caffeine. We were strapped financially, which meant the pressure was on to ship our product to market as soon as we could.

After an intense period of building our application and finding investors, both Daryl and I started to realize that I was more into my blog than our start-up. Eighteen months after starting this company, and with Daryl’s blessing, I left to pursue my own thing.

The trouble was, I had no idea what that thing was.

Even if you’re naturally risk-averse, throw yourself in the deep end if you really want to change your current circumstances. Nothing makes you move heaven and earth to get what you really want more than being forced into it. Don’t be afraid to quit your job or your current business, even if there are a million reasons (aka excuses) to put it off until next month. Each day you do that, you lose another day of your ideal life.

Also, don’t have an attractive backup plan. As Seth Godin states, if you have a backup plan, you’ll always defer to it. So simply focus on the outcome you want, not the alternatives (which may look far more appealing, like real income and job security).

So there I was. I had a blog that was read only by my mum and two friends and a strong desire to work for myself. I also had very little money to my name, so I managed to set up my new Canadian company for under $100.

The next six months were the toughest—and most formative—of my life. I went without any income and on two occasions could barely pay my rent. I was terrified. When a friend came to visit from New Zealand, I broke down in tears. I was so relieved to see someone who understood me and what I was going through.

My friend believed in me. He’d seen me progress up through the ranks of my corporate career and had witnessed my persistence and dedication to training for nine months to win a regional body-sculpting competition back in 2004. I needed someone to have faith in me at this tough time, as I wasn’t sure I had enough in myself.

Around this time my parents invited me to fly home and live with them or to consider getting a job again. The mere mention of that second option made me more determined than ever to make a real go of building my business.

Then one day a friend in Vancouver threw me a lifeline. She’d seen what I’d achieved during the time I’d lived there and referred me to her client, a Groupon-like start-up, who were in need of a social media strategist. We had several meetings to discuss how my experience in building FundRazr using social media could help them build their platform.

I’d sent them a proposal for $2,000. I’d never charged that much in my life, but I aimed high for two reasons. One reason was that I’ve always enjoyed the process of negotiation and was adept at punching way above my weight back in the corporate world; the second was that I had only $18 left in my bank account. There was no way I couldn’t win this opportunity.

One thing you have to get a handle on when starting any business is charging what you’re worth, based on the value you deliver to your client. This is one of the most challenging areas for entrepreneurs, especially when they’re starting out and in need of money. But trust me, if you start off by lowballing your prices, it becomes very hard to raise them. You also have to factor in your own overheads—administrative and running costs.

In my third meeting with my potential clients, I decided it was crunch time. I had to clinch the deal by restating why I was exactly what they were looking for. Luckily, they agreed. They wrote me a check for 50 percent up front, and I ran across the road to bank it right after we shook hands. My rent was paid, and I could sleep another night with a roof over my head.

Despite this small win, things didn’t get immediately better. I was still worried I’d have to give in and get a job. There was nothing consistent about my revenue and I had no idea about my long-term plan.

Yet I had learned something invaluable for the first time in my life—I could charge people for my existing knowledge. I could monetize ME.

So I pushed through that tough period, with several sleepless nights, and instead of giving in, I relied heavily upon my growing reputation in Vancouver as a social media “expert”—which simply meant I knew just enough more than others to charge for it.

People tell me all the time that they don’t feel good enough at something to make a business out of it, that they’re not expert enough, and they have no real skill set that they can monetize. That’s a load of crap.

Everyone on this earth has a sweet spot: the intersection between what you’re good (or great) at, what you enjoy—or better yet, love—doing, and what people will pay you for. This doesn’t mean you have to be an expert. You just need to know a little more than the person who needs and is willing to pay for your help.

Next I decided to host a social media boot camp. I tapped heavily into my existing networks, and to my surprise, I managed to sell out not one, but three workshops in a row!

I charged $1,500 for a two-day course and made over $15,000 in less than a month!

So what did I do once I’d established myself in this industry? I promptly left town.

I left everything I’d built up in Vancouver to live in Argentina for five months.

Once again my friends thought I was nuts.

But the thing is, like many world travelers, I have trouble staying in one place. Once I feel I’ve established myself somewhere, once I’ve made the right contacts, experienced the culture, and feel like a local, I tend to want to move on to the next adventure.

After a two-month stint in Los Angeles, staying rent-free at my friends’ grand house in Manhattan Beach (it helps to have true friends in high places), I was flying to Buenos Aires and the land of empanadas and tango.

Here’s the thing, though: I did capitalize on what I’d learned by turning the content from those three workshops into my first-ever digital online program, which launched in November 2010. I did as much active learning as possible to get up to speed with how to launch a product online, including marketing, membership sites, sales pages, launch sequences, and webinars.

Despite losing my voice and being just able to speak on my first-ever webinar, I managed to make one sale of $297 with the thirty people who attended live, and several more after. In hindsight, that was a lousy result, but in my mind I’d officially done it. I’d launched a product that people actually wanted to buy, and had made my first few thousand dollars online. That was all I needed to prove to myself that I could turn my own thing into a business.

It’s crucial that you maximize your existing capital and repurpose what you’ve already got to create further profits. Be resourceful and hustle. Take what you’re already doing and turn it into a number of spin-off products or services. You’re a writer? Great! What about writing guides for wannabe writers and selling them on Amazon? Or holding in-person writing workshops, recording those, and packaging those audios into an online self-study course?

One fine evening in 2010, in a hotel in Las Vegas, the Suitcase Entrepreneur brand was born. I’d been at a conference where I’d spent the entire day answering the same questions: What’s your name? What do you do? Where do you live?

Naturally people were fascinated that I lived nowhere. A few people labeled me the traveling entrepreneur until Matthew Goldberg, who’s now a good friend of mine, said, “Oh, so you’re kind of the Suitcase Entrepreneur.”

My face lit up, and I knew he was bang on. That’s exactly what I was, and he suggested I go and buy the domain name straightaway.

Once I had that name, my brand was born and I was able to get clear on what I was doing, whom I was helping, and what I could offer. I wrote my bestselling BYOB Build Your Online Business guide after getting a great response for writing a blog series about building a business online. I updated my social media program and relaunched it.

What’s more, I created and launched a high-end mastermind and coaching program for women entrepreneurs with Natalie MacNeil, creator of She Takes on the World, listed by Forbes as one of the the Top 100 Sites for Entrepreneurs.

After our first $40,000 launch (more than the entire year’s salary I made in my first ever job), we knew we were onto something, and this was the audience we wanted to help the most.

During this period I’d become a contributing author for Forbes when they picked up an article they liked on my own blog. I also wrote several guest posts for huge authority sites (those that get a lot of traffic and people linking to them), and was appointed as a Nike Make Yourself movement ambassador, as well as having my blog posts syndicated directly on Visa Business Network’s site.

I started offering coaching on my site in 2011 and doubled my prices in the first few months when I realized there was more demand—and it was harder work—than I thought but very rewarding. All of this resulted in my first six-figure year in business.

That is just a taste of how the journey of this Suitcase Entrepreneur business started. Let’s round this out with the adventure and travel side of life to show you the full picture.

To paint a picture of what living the nomadic lifestyle is like, take a look at some examples from my own life. I have:

Been declared a fiscal nomad and am proud to be a resident in three countries, own two passports, and have three international bank accounts

Traveled to seventy countries on five continents to date, and many of those several times over

Acquired mobile SIM cards from the United States, New Zealand, Namibia, the United Kingdom, Malaysia, Kenya, Canada, Germany, and South Africa and counting

Spent close to seven full months of my life in airports, getting to and from whichever destination I’m off to next

Done my best work on these modes of transport, especially offline, and written a book (hey! you’re reading it) on planes, trains, and boats

Taken a fifty-four-hour trip door to door from Wellington, New Zealand, to Madrid (I can’t sleep on planes)

Made money in my sleep through selling digital products and programs available 24/7

Coached clients while sitting on a beach, in an airport, and in a small Slovakian village in the mountains

Bought four properties in my real estate portfolio in New Zealand and Portugal so far that I live in, host, or rent to my Freedomist community

Life is meant to be an adventure. Remember: you have all the time in the world to grow up. I have no intention of growing up, but until such a time that I have to, I’ve done things like this:

Crossed the Myanmar border illegally by mistake and got chased out by locals with rifles

Tried to joke around with a security guard in the Sydney airport, saying I had explosives strapped to my chest—don’t ask, silly idea

Cycled 6,500 kilometers (4,000 miles) from Nairobi, Kenya, to Cape Town, South Africa, in 2012, raising over $12,500 for charity

Won a gold medal in Ultimate Frisbee at the 2007 World Beach Championships in Brazil, and played at World Championship level on four different continents since 2006

Broken a world record for dragon boating across the English Channel in 2007 with, among others, Kate Middleton, the future Queen of England

Completed a yearlong experiment in 2004 to get really lean (10 percent body fat), eating lots of chicken and broccoli and working out seven days a week, to win a body-sculpting competition, and then competing in the New Zealand Nationals

Along with travel, adventure makes you well rounded and ready to face most of the challenges that life throws at you. All of this makes you a better businessperson as well, because being an entrepreneur is one of the wildest roller-coaster rides you’ll ever experience.

There are many more adventures detailed in this book for you to learn from, too. Got your passport ready?

Write or record an honest conversation with yourself or a good friend about what you really enjoy doing, what you’re naturally good at, and what people you could help today by combining those things into an offering. Brainstorm as many avenues as you can in twenty minutes.

Work out (with a trusted friend or mentor) whether these are in fact logical and feasible, and rank which ones you’d prefer to do in order of priority.

Better yet, head to my free companion course at to download my sweet spot template and exercise to work out which opportunities are best for you to take to the next stage and turn into a business you love!

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