Tips on Building a Business From a Homeless CEO : Under30CEO Tips on Building a Business From a Homeless CEO : Under30CEO
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Tips on Building a Business From a Homeless CEO

| May 23, 2011 | 4 Comments

locationless entrepreneur

Remember when the internet was supposed to free us from our offices and desk jobs and allow us to hang out on beaches (where there was apparently no wind or sand to damage hardware) and do our work while we all lived mobile, stress free, well tanned lives? That promise never really came true, in spite of what all of those late nineties commercials had us believe. The truth is, most of us still go to the office. The only difference is that now, through email and texting, the office can now follow us home. Some could argue that the digital age, instead of liberating us from work, has tied us to our work closer than ever before by invading our homes.

I think the best move is not to try and work from home by getting rid of the office. It’s getting rid of the office by getting rid of the home.

There’s a new breed of entrepreneur out there, and it’s the locationless entrepreneur. But unlike the traveling salesman of the past, who was also locationless, the locationless entrepreneur travels where he or she wants to travel. I have been making money off of multiple online business and been permanently traveling for the last few years. Obviously, this isn’t for everyone. People with kids, marriages, or people who are scared to go out into the world and explore need not apply. But for those who want to see the world and aren’t willing to be forced to choose between career building and life experiences, the life of the locationless entrepreneur is the solution that allows you to live both realistically and idealistically, responsibly and imaginatively.

As fun as traveling all over the world and making money sounds, the fact of the matter is that it takes hard work and organization. Here are a few tips I’ve learned from my experiences as a locationless entrepreneur that have made the process run a little smoother.

First of all, communication is absolutely key. As multi-faceted as communication technology is these days, people still want to be able to call you on the phone. Hearing a voice is comforting. This is the first major obstacle of locationless living. There are still very few worldwide calling plans that are feasible and reasonable. You are going to have to do most of your communication by email. This means stay on top of things. You want to respond to things quickly and efficiently, giving the impression of stability. Google Canned Responses is just one of many methods to use. You want people to think you are in an office even when you’re using the wifi at turkish hookah bar. Be extra communicative, and if there are going to be delays in delivery or services, be up front about it and let people know. That way at least it looks like you are on top of things and see issues coming instead of getting caught off guard.

Secondly, be careful with outsourcing. Books like “The 4 Hour Work Week” give the illusion you can outsource everything to India and never work again. Although many things can be outsourced, remember that you can’t outsource at the expense of your product or service. Only outsource to people and groups you trust. Remember, at the end of the day it’s your business. Also, remember there are talented young people in the U.S., usually recent college graduates, who are desperately looking for work. You might not be able to use them forever, but hiring some of these talented youngsters for freelance work is a great way to take advantage of unused talent while outsourcing.

Thirdly, remember that just because you’re in an exotic locale doesn’t mean you have to work in an exotic space. When traveling you are constantly surrounded by new opportunities. Often times, these are distractions. You need to get work done to keep this lifestyle working for you. Find some boring space to work. You wouldn’t believe how much more you get done sitting in an empty room with gray walls than staring out over your computer onto a beach. Being able to separate work and play is important, because the natural lines that separate the two are pretty much erased if you’re a locationless entrepreneur.

And finally, remember that you don’t need to invent the next Google to be locationless. The history of the internet is filled with sexy ideas that may have generated initial interest but ultimately failed. You don’t have to reinvent the wheel. There is nothing wrong with proven models, and with the internet there are always clients if you know where to look. Lots of people try to start coffee shops and fail. The plumber always has business. Don’t try to be too hip or cool.

I am Jason, a location independent 23 year old traveling throughout the world, working 20-odd hours a week running 3 web-based businesses. You can find my blog at and on Twitter @LocationLess

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Category: Personal Branding, Startup Advice

  • Virtual Business Assistant

    This is a really good post on how to manage business.  #1 ‘communication is absolutely key.” is good one and really true.

  • Anonymous

    Very interesting read! Thanks for sharing tips and the experience here. 

  • Christi

    I disagree fiercely about people with marriages need not apply. If we say that, then we are totally ignoring what creativity can help us to do design our lifestyle. I can understand it better if we spoke about people with children maybe should not opt for a locationless office or home. It all depends on who you are married to. There are marriages where couples enjoy living a type of lifestyle where they can go anywhere they want and work from anywhere. When it comes to kids..that is harder to do, but doable if you are a “family” man or a “family” woman..meaning, you see yourself including your kids in your travel and life discoveries while traveling…those that are suited for your family to experience together.. Look at how some kids had to move around due to either the father or mother being in the it has been done before. Some parents homeschool their kids, so that is a solution to help make this lifestyle doable and exciting for the whole family There are ways around the obstacles that can normally block a person from living this kind of lifestyle….you just have to be creative enough to think how to do it. The world we live in now allows us to get away from living the strict traditional career, 9-5 lifestyle…so, even parents have more options on what they can or can not do as a career and still raise healthy kids. Why not interview someone who is a young entrepreneur living this lifestyle who is also a parent who is making it work.

  • Jacqueline

    As a virtual business concierge aka virtual/personal assistant, I agree with domestic outsourcing. I encourage entrepreneurs to outsource the tasks that will enable them to maximize time and work on core business activities.

    Do what you can. Outsource the rest!