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Why I Choose to be Rich and Homeless

How much could you pack in a single suitcase? Thirty-six-year-old Natalie Sisson manages to fit her entire life in one bag.

For nearly four years, Sisson has been homeless. But it’s not what you think. The New Zealand native travels the world, living out of her suitcase and running a business from her laptop. She doesn’t have a permanent residence and calls herself ‘The Suitcase Entrepreneur,” also the title of her blog and book.

“People think that I’m either crazy, a little bit strange or they think it sounds fantastic,” she says. “I like to think of myself as a citizen of the world. Wherever I place my suitcase, that’s kind of my home.”

She identifies as a new breed of worker, the “digital nomad,” someone who works exclusively online and isn’t tied to a single geographic location.

“I have about eight revenue streams. My blog brings in some form of advertising and affiliate marketing. I have digital products and programs for sale. I do coaching, and it’s all online through Skype,” she says.

Sisson estimates she saves as much as $2,000 a month because she doesn’t have typical living expenses, and she keeps her travel cheap by rooming with locals or friends. “I’d like to think that this lifestyle is actually pretty cost effective. A lot of people think travel is really expensive but when you don’t have all those extra payments like mortgages etc. you can stay in places quite cheap,” says Sisson.

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Back in 2008, the entrepreneur found herself frustrated with her corporate career in London, despite a recent promotion. “I quit my job after my big pay raise. I had just invested in a property in London, so my friends thought I was nuts. I decided to leave the country and go to Canada,” she says.

Once in Vancouver, she worked on a tech startup with a business partner she met at a networking event. She became fascinated by the industry, especially how few women were in the field. “I started a blog to talk about my experience and used it as a way to interview some of these women in technology,” she says. “I realized probably about six months in that it was becoming more of a passion than the business that we had built.”

Fast-forward to today, she’s transformed that blog into a six-figure business, appearing at speaking engagements and teaching social media marketing and online entrepreneurship to others through live events and workshops.

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To date, Natalie’s traveled to 66 countries, visiting 15 in 2013 alone, with her longest stay in Berlin for two months. She holds passports in two countries and has permanent resident status in a third. Plus, she has bank accounts in four countries and has collected 17 SIM cards for her mobile phone. But her jet-setting lifestyle isn’t without challenge.

“It’s really difficult to maintain relationships in a deeper way, in deeper connection so I really use tools like Skype and video to connect with family and friends back home and I also make a point of trying to visit my really good friends,” she says.

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This year, she plans to slow down, by her standards, anyway.

“Now that I’m wanting to settle a little more and spend more time in each place, I would definitely love to find somebody who’s up for an adventure and for moving around as well,” she says. “I think this year I might hit a few less countries than normal… maybe around ten.”

Special thanks to Viceroy New York and Il Baretto for making this video possible.