[Preface: The above is a pic of Necker Island, Richard Branson's private island. Would you like to join me and Richard Branson on Necker for a week of mentoring? Here are the details on how you can get an all-expenses-paid trip. It'd be great to meet you.]

The following is a guest post by Breanden Beneschott, co-founder and COO of Toptal, a marketplace for top developers. I have no affiliation with the company, but I found Breanden’s story fascinating.

This post covers how he traveled through 20+ countries while building a company, experiencing the best the world had to offer. His how-to instructions include travel tools, shortcuts, and all the non-obvious systems you’d expect from a great engineer.

For context and to kick us off, an excerpt from Breanden’s email to me might be helpful. Edited down a bit, here it is:

We started Toptal 3.5 years ago from my dorm room at Princeton (I think a week after I met you briefly in Ed Zschau’s class [TIM: I guest lectured there], where I decided to do my final paper on the company). By the time I finished school six months later, Toptal was doing well with clients and engineers all over the world. We decided to move to Eastern Europe and keep practicing what we were preaching, in terms of scaling a company via a completely distributed team. Doing so allowed us to funnel nearly all profits back into growing the business (and live like kings for next to nothing). We are now approx 60 team members and 1000 engineers (e.g., top-100 Rails contributors, guys from CERN, university professors, etc.) working with thousands of clients (e.g., Beats, Zendesk, Artsy, JPMorgan, etc.) with virtually zero restrictions when it comes to location.

People constantly ask me how I manage to travel and work the way I do. I had always hoped outside (non-Toptal) people would see this post and be inspired to join us or pick up and travel while working on their own big ideas.

BTW, I do expect that comments will highlight the ambiguity of the “growing hundreds of percent year over year” statement. We’ve very deliberately avoided most press until now, as we didn’t want to build a company based on PR, and we’ve never publicly announced our revenue. Right now we are well north of XXM/yr [TIM: I replaced the actual number with XX but, suffice to say, they have 9-figure acquisition offers and term sheets] and growing like a weed, but few non-core people know that. So do you see any tactful way of preempting those sorts of comments?

Yep, I do. I could include your email like I just did.

Now, on to the details. This is a good one, folks, so keep reading.  Breanden’s tips apply mostly to the mobility and travel pieces of the puzzle; if you’d like additional business-building tools, I highly suggest this article on rapid testing (in a weekend), this article on hacking Kickstarter, and this post on all aspects of marketing and PR.

Enter Breanden

[The following is based on my personal experience as a traveling engineer and founder. Feel free to contact me any time at breanden [at] toptal [dot] com.]

I’ve lived and worked remotely in approximately 29 countries since I finished school three years ago. I’ve been running Toptal, a venture funded company growing hundreds of percent year over year—all from my laptop, phone, and tablet.

Croatia · Bosnia · Italy · France · Switzerland · Germany · Austria · Georgia · Romania · Serbia · Slovenia · Spain · Ukraine · Morocco · Brazil · Canada · Paraguay · Argentina · Uruguay · New Zealand · Australia · Hong Kong · USA · England · Turkey · Chile · Slovakia · Czech Republic · Lebanon

I don’t have an apartment. I don’t have a house. I don’t have an office.

I hate the cold, so I summer hop.

Everywhere I go, I meet great engineers who end up becoming invaluable parts of Toptal.

I encourage everyone in Toptal to travel, and a lot of us do. Some of us travel for week long “breaks” throughout the year, and some of us live out of a suitcase like me. Few of us ever stop working for a full day.

I’m writing this because…

I was repeatedly asked if I had some sort of guide or checklist for traveling/working the way I do. Especially for first-timers, the idea of adventuring while working can be daunting. There are a lot of details to consider, and I’ve learned a lot from my own trial-and-error.

The more I thought about it, the more I realized a guide like this was actually missing.

The 4-Hour Workweek was great, and I like Tim Ferriss a lot. But what if you want to work more than 4 hours a week? I like working crazy hours. I don’t want a lifestyle company. I want to solve hard problems. I want to build something big and give it my all.

I want a book on how to create a billion-dollar company while becoming a fighter pilot. (I’m trying to build a world-changing company while becoming a professional polo player.) That would be inspiring. But until it comes, maybe this post will be helpful to a few people.

Why travel?

Because it’s unbelievably awesome.

Now is the time: it’s feasible like never before. You can put in a full work day no matter where you are. If you’re standing in line for airport security, you can listen to The Changelog. If you’re in the Hungarian countryside, you can work perfectly via 4G. If you’re flying across the world, you can work from the moment you buckle in to the moment you stand up to get off the plane. The airport will have WiFi to push a commit if your plane didn’t. You can travel while producing some of the best work of your career, and you will grow with every new stamp in your passport.

The secret benefit: avoiding burnout.

I don’t take vacations. I don’t want to work hard to build a company that makes lots of money so I can piss off and go on holiday. I’m at a start-up. I’m a part of it, and it’s a part of me. This is a marathon, and there will be a winner. Traveling and working allows you to go non-stop. There is no burnout. There’s no staring at a clock or calendar waiting for the EOD/weekend/break. You’re refreshed weekly, and you can hone your focus and structure your time so you are a cross functional superstar who never stops learning.

Playing polo (often with Toptal developers) in Argentina. Total cost for sponsorship: 400 pesos (~$40) for t-shirts.

Length of travel

I usually stay in places for ~3 months. Why?

It fits under the constraints of the typical tourist visa.

More on that in a second.

It gives you time to relax and focus in between the stressful travel sessions.

Power trips of 9 countries in 3 weeks are for students on holiday. You need to be able to stop traveling and focus on work.

It gives you time to really explore and get to know a place and people.

There are almost certainly local tech meetups, and there are likely to be other Toptal engineers wherever you go now as well.

You can really try local culture.

Learn to play polo in Argentina. Practice capoeira in Brazil. Go to trance festivals in Europe. If you don’t know where to start, join Internations and go to expat meetups.

It helps with costs.

Trips of this duration help you negotiate special medium-term deals on apartments, cars, vespas, etc.

Who to go with

A close friend/colleague

You can split costs for a lot of things like cars, hotels, etc. You can also split the research and push each other to do things you might not do yourself (like go out to new places, go on adventures, rent a boat, etc.).

Alone

Not for the faint of heart, but not everyone has the flexibility you do as a software engineer. If you don’t have anyone to go with, don’t let it stop you. With Internations and a network like Toptal, you can almost certainly go anywhere and immediately find people with lots in common.

A girlfriend/boyfriend

Can be by far the most expensive option, but it’s probably the most rewarding and fun. Nothing brings compatible people together like adventure. However, nothing drives incompatible people apart like stress, so be careful. The other thing to consider is whether your significant other will also be working during your travels. If so, that’s tremendous, and you are very lucky. If not, that can be very hard. The added costs of having a dependent aside, you don’t want to be in a position where someone resents you for constantly working during what they’ve misunderstood to be a vacation. Luckily there are many interesting careers in addition to software engineering that are now doable remotely (e.g., executive assistant, translator, designer, tutor, entrepreneur, etc.).

What to take

Backpack

Always a carry on. Pretty much always with me.

Laptop

I use a