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172 Replies to “How to Travel to 20+ Countries…While Building a Massive Business in the Process”

  1. I made this dream into a reality 10 years ago. Been running two companies and traveling for work and fun every month. 40 + countries and counting. Although, I’m not married, don’t have any kids and never date self obsessed controlling women(Americans) foreign chicks are so much more laid back and up for anything. I don’t like hippies.

  2. Well, why to take an extra gps if you can travel with your phone? And iphone 6 charges quite fast, you can do it in 1 hour in a cafe or a bar while talking to the barwoman. And for 3 months stays i wouldn’t take toiletries with me but instead buy most of them there..

    Nice article !

  3. It’s amazing what we can do with the support of the Internet. I’m getting ready to begin traveling and managing my business from abroad. This is my dream.

  4. Breanden – I host a travel podcast (aptly named the Travel Stories Podcast) – I KNOW you have some good stories. Let me know if this interests you 🙂

      1. Having a portable business that you can take anywhere in the world is important, and is something I am working on, and being able to accept any payment method you like is freedom also.

  5. I’m considering spending a year in New Zealand while continuing to run my business, which is internet based. I’ve heard some conflicting stories on internet quality and speed issues. Have any of you had any recent experience with this there? Any suggestions?

  6. This… is awesome!! haha, thank you 🙂 …today I feel less alone by living out of a suitcase with no-fixed-abode. The only bit missing for me is a lucrative business, but I continue my learning every single day and get the odd web development/cafe job here and there (as well as anything else I can pick up).

    The great thing about a minimalistic lifestyle is that there are also very low expenses, so I can live on much less. I know there is a place and a niche for me in this world and all will come to fruition eventually.

    Thank you for this great list of resources and tips. My vision is also to continue travelling, but staying in places for 2 to 3 months at a time. Aside from the frequent loneliness, it’s an amazing lifestyle that I cherish and enjoy.

    Now I’m going to have to lookup Toptal 🙂

  7. Great article! Historically I never really had a desire to travel that much but over the last couple years that has changed dramatically. I definitely think 3 months a is a good timeframe and have enjoyed being in new environments as well as meeting new people.

  8. I like your advice on passports, take a picture and email it to yourself. It is very handy when you lose your passport. Lost my passport a few years ago in France and wished I had some sort of backup. I am now using Passcovers which gives you a passport recovery card and also allows for passport image upload.

  9. What’s the health insurance for entrepreneurs? Tim, what should we use or does the world need to create it? If it’s already out there, please let me know.
    My dream insurance:
    – Just need it for ‘major’ health issues (aka Large Deductible $5K+)
    – Get to go to the doctors I want
    – Happy to pay for the doctors visit fee in full, especially if that gives me freedom to choose where I go
    – Would like tests/xrays/bloodwork/etc mostly covered AND to know the price before I approve it. An app that can tell me what I will owe before I say yes to it, or the doctor being able to tell me.
    – Prescriptions – It seems like the pharmacy can get me just as good or better prices self pay than with my current healthcare. But whatever makes the prices consistently fair. Happy to just selfpay for prescriptions if that makes the insurance cheaper.

  10. Great and very informative article! My wife and I plan to travel around Europe for a year, while working remotely as freelancers and also might setup a business in some of the EU countries. We learnt a lot from your article and experience! Thanks a lot!