Uncommon profile: Natalie Sisson – Candid confessions from a suitcase entrepreneur

Common: Dreaming of a life of travel while working for yourself.

Uncommon: There are a lot of people who fantasize about traveling the world and working from anywhere on their own schedule. Few people actually do it. Natalie Sisson is one of these adventurous, risk-taking souls. But, according to her, she wasn’t always this way.

We crossed paths on an entrepreneur retreat in the middle of the Costa Rican rainforest in 2009.  After learning more about her background and her renewed passion for entrepreneurship, we stayed in contact and I’ve been observing her already impressive list of adventures only grow in number. Today, I’m reaching out to her all the way to Buenos Aires—her newest hotspot (well, for a little while anyway).

KH: In a few sentences, what’s your life story and how did you end up working full time from Buenos Aires?

NS: I’m a Kiwi entrepreneur, passionate about getting more women into business, travelling the world, and playing Ultimate Frisbee. I left New Zealand in 2006 to go and live in London for 2.5 years. Following that I moved to Vancouver, Canada, to play in the World Ultimate Frisbee Championships. I was determined to start my own business after almost 10 years working in the corporate world of brand marketing, product management, and new business development.

Over a giant cheese platter and glass of wine I was fortunate enough to meet my future business partner. A few weeks later we started FundRazr.com – a Facebook payments application. It was such an amazing experience to take an idea and create an actual business out of it.

The technology startup world was also something I became enamored with – fast pace, fast fails, and ever changing landscapes. During this time I started my blog to chart my entrepreneurial experiences and to use it as a platform to interview other women in the technological world since there was such a lack of them at the time. Before long, my blog had taken on a life its own and only became an even bigger passion for me. As an addiction of sorts, I decided to begin working on it full time in late April 2010.

In late December I moved to Buenos Aires to learn Spanish, enjoy my summer, and prove that I could run my business from anywhere. This constant travel became a new addiction. My mission is to live somewhere new every few months. Impossible? Surprisingly, it’s very possible. Thanks to the many online tools I use, the growth of social media, and outsourcing, I don’t need to be tied to one location.

KH: You are passionate about the title, “entrepreneur” – what does it mean to you and why is the concept so important?

NS: In reality, it means a lot of hard work. It’s not easy to live the life you always envisioned – and for me, it’s one where I choose my own adventures and work from where I want, when I want.  Finally, I get to choose my projects and who I work with.

Entrepreneurs also have the ability to create a better world for others by bringing their ideas and innovations to life. Leaving a legacy is what drives me more than anything.

KH: You’ve become known as the “Suitcase Entrepreneur;” what’s the story behind the name?

NS: While at a conference for women entrepreneurs last year, every time I introduced myself I was asked where I live. My answer was always “I live out of my suitcase.” It got such a great reaction that it just stuck. A copywriting friend suggested `The Suitcase Entrepreneur’ and to buy the domain, which I did. The rest is history.


KH: What are 3 false assumptions many people have about running an online business and/or blog?

  1. “It’s easy”: Running an online blog and business is one of the most challenging endeavors I’ve ever undertaken. I don’t have a side business to support my way of life – my blog is my only income.  I simply create valuable products and programs to sell to my community and the rest of the world.
  2. “It costs very little”: Initial costs can be low by using a free WP blog theme, hosting it, and having some basic design work done. But when done professionally, it takes much more time and money than one would typically expect. Design, hosting, and copy costs add up quick. Then there are certain online services and software programs to purchase. On top of that there are courses to take to continue “upskilling.” There is always so much to learn!
  3. “You have to be a technical whiz”: It’s not true at all actually. I’ve developed a lot of new skills and do a lot of my own “backend” work, but I’m certainly no coding genius.  I know my limits and outsource the rest so I can focus on what I do best.

KH: What is the most surprising reward of being a “Suitcase Entrepreneur”?

NS: For me, it’s definitely the adventure and the support I get from everyone I meet. This tells me I’m doing the right thing. There are always days when I feel like it’s all too difficult, but then a wonderful email arrives in my inbox from someone I’ve inspired and how they started their own business and moved to a new country.  It makes it all worthwhile – the community engagement is my fuel.

KH: What is the greatest challenge of being a “Suitcase Entrepreneur”?

Where do I start? Moving around so much can be taxing in itself, because once you establish some roots and meet some great people, it seems that it is also time to move on.  This can be hard when you’ve made some great friendships.

From a business perspective it’s dealing with a variety of things: unreliable wifi, no office to work from, different time zones, and access to local or international services. But the challenge is also part of the fun.  There is always a tradeoff.

KH: What does it take to be uncommon among the countless bloggers online today?

NS: I’d like to think things have partly worked out for myself after more than a year, but I’m constantly testing and experimenting. I’ve learned that you first need to define and target a very focused niche market and then add your personality to it. To stand out you must commit 110% to providing value, insight and humor on a regular basis. The most successful people have not tried to be everything and do everything. They’ve positioned themselves as an expert in just one thing and built a community around that.  Also, it doesn’t pay to try to copy others. It helps to be aware of what other leaders are doing, but you must chart your own path. Be unique; be yourself. People can spot authenticity immediately.

KH: What should every online entrepreneur know to be most effective?

NS: How to streamline your day to make sure you’re being the most effective you can. When you don’t have an office to go to, a team to hold you accountable, and consistent working hours, it’s really easy to waste a lot of time. It’s not a matter of working all day; it’s a matter of working for results. I love using tools that keep me in check and ensure I’m making the most of my precious hours. Chrometa, for example, tracks everything I do online and shows me how to make the  most of it.


KH: Why did you write your latest ebook, `The Ultimate Toolkit for the Evolutionary Entrepreneur’?

NS: Simply because I adore how these tools and technology can help people save time and money while making their lives easier. I’ve seen way too many people spend lots of money trying out new services and then never actually using them. In most cases, it’s because they don’t have a grasp of the bigger picture and don’t fully understand how the tools can work together to enable a more streamlined way of working.

I also know that it can be overwhelming to keep up with the new tools on the market and understand the jargon. Since I rely on these tools, many people started asking me for suggestions so I decided, after much testing and reviewing over the years, that I’d share my knowledge and recommend the best tools that can save you time and money.  I outline one free and one paid tool/service for each of the most critical areas of business. I know entrepreneurs don’t have time to sort through 25 different tools that manage finances, so I created one comprehensive toolkit.

KH: How have the tools in your ebook helped you?

NS: Well, I couldn’t run my business without them. I store all my important documents securely in the cloud, I hold Skype calls with team and clients for free from anywhere, I track my time and my team’s time, and I manage multiple projects online that transcend borders. They have allowed me to do more for less. I’ve also spent lots of money initially investigating each tool and wasting a lot of time using the wrong tools (hence my desire to write this book).  As Kent mentioned in his last post, it’s all about creating the right systems so you don’t get stuck doing things that eat up your valuable time.

KH: Any parting advice?

NS: I know I’ve referenced the topic of passion a lot, but you can’t just run a business on passion alone. You’ve got to have guts, determination, and a whole heap of courage. A sense of adventure definitely helps too – to boldly go where no one else has gone before (Star Trek had some golden nuggets to share).  And finally, you just need to take action. One step is all it takes to get started. You owe it to yourself and the world to share your gifts. So quit talking about doing that and just do it!



Stay uncommon,

Thanks for reading. Hope to see you in the comments section below. For new & different content, let's meet here:

Facebook | Twitter | LinkedIn | Instagram


Note: If you’re interested in starting an online business – or just about any small business – check out Natalie’s Ultimate Toolkit for the Evolutionary Entrepreneur She’s giving Uncommon Life readers 20% off the book this week. Just use the code featuredtool. I don’t benefit if you purchase her book other than seeing you thrive. Learn more here.