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.

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.

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 MacBook Pro 15″ Retina.

Unlocked Smartphone
Get a local SIM card (usually a prepaid or pay-as-you-go for between $20-$50 at T-Mobile, Vodafone, etc., with a few GBs of data that you can top up as-needed) everywhere you go so you can always be online and never stress about what you’re missing. Don’t leave the store until you have the phone in your hands with working Internet. If you’re on an iPhone 5, you can almost always cut a micro SIM to fit the nano SIM and it will work just fine.

Tablet
You’re an engineer. Use Airdisplay to enable your tablet as a second monitor. It also makes it much easier to work on planes: I used an iPad Mini to write this post on a flight from LAX to Auckland, New Zealand.

GPS
I rent cars and explore places a lot, so this is key. I have a Garmin Nuvi. I try to download the maps before I leave to go to anywhere new.

External charger
iPhone batteries are terrible, and this saves the day.

Apple headphones
For work, I use the ones that come with everything Apple. They never fail, and I live on Skype. I see lots of people with more expensive systems and they constantly have problems. It’s pointless.

Ethernet cable
WiFi doesn’t always work.

Travel adapter
You’ll use this everywhere. If you ever find yourself without one, ask the hotel if they have an extra.

Sunglasses

New whiteboard marker
It saves the day at least a couple times a year, whether it’s because you’re collaborating in a co-working space and all the markers are dead or you need to work out something John Nash-style.

Pens

Passport
Take photos of this on your phone and also email them to yourself.

Insurance card
Take photos of this on your phone and also email them to yourself.

SIM card collection

Business cards

Thera-Band
Olympic gymnasts use these for resistance training. With 6″ of rubber, you can do a full body workout anywhere. When you spend long hours on your computer, you need to get up and exercise every hour.

Ibuprofen
For headaches and general aches and pains.

Dramamine
For motion sickness.

Probiotics
For digestion. Traveling can be stressful, and new foods do unexpected things.

Deodorant
Don’t let yourself expire. Like wearing boat shoes? Put a dab on your feet as well.

Toothbrush

Suitcase 1

Checked on flights. Leave your Louis Vuitton luggage at home. It just makes you a target, and your stuff will get stolen. Some people swear by expensive luggage, but I’ve used a basic 5-piece luggage set since I graduated high school in 2004, and it’s worked fine.

Clothes. You can figure out the basics but I usually carry the following:

• Dress shirt
• Dress shoes
• Gym shorts
• Running shoes. Running is a great way to explore places. [TIM: Bruce Lee had a similar philosophy while shooting films.]
• Swim shorts
• Flip flops. For gyms, pools, and beaches.

Toiletries.

• Shaver
• Toothbrush
• Floss
• Toothpaste
• Sunscreen

Suitcase 2

Aka the “toy bag”; also checked on flights.

Snowboards, polo equipment, surf boards, or whatever you need for your specific trip.
It sounds strange, but always make sure your stuff is clean. Some countries (like New Zealand) are very protective, and if there’s dirt, sand, grass, hair, etc. on your stuff, they may take everything and sanitize it for you (in God knows what) at the airport, or even confiscate it.

Where to stay

Try NomadList for selecting a city.
The data here does not match my own experience in many cases, but, overall, it gives a pretty good overview of some of the important aspects you’ll want to consider for each location you choose.

Airbnb is what I use most, but it’s a PITA [pain in the ass] for medium-term stays.
I see a need in the market for medium-term rentals. If you know of a better solution, please let me know! Unless you’re booking far in advance (something I find impossible), you’ll find Airbnb places might be available for a month straight except for one or two weekends where you’ll have to either temporarily move out or find another place. Don’t get too comfortable. I’ve had success asking the Airbnb hosts if they have recommendations on medium-term housing. They often have friends with unlisted places or can make special arrangements for you (like getting an apartment ready that they weren’t renting at all before… and since you’re there, you can check it out before you commit). Once you’ve stayed with them via Airbnb, you’ve earned their trust a bit, and they’re usually very helpful.

You need great Internet.
So, for now, Antarctica is out. But most places are totally fine (and often better than in the US). However, you have to do your homework. As a traveling software engineer, you can never be unavailable due to bad Internet. Buy a pay-as-you-go SIM first thing, but still be sure to explicitly ask every host/hotel/realtor etc. what the Internet speeds are.

Here’s my standard message when making an inquiry on Airbnb:

Hi {{name}},

Your apartment looks amazing. Any chance it’s available tonight for two people?

Also, as engineers, we do a lot of our work online, so we really need stable and quick internet. Do you know the speed of your connection (e.g., 10Mbs/2Mbps)? If not, would you mind running a little test (just google “internet speed test” and click the first result) and letting me know?

Thank you so much for your consideration.

Best,
Breanden

Every hotel will say their Internet is great, but you can usually find reviews about how good their Internet really is on Tripadvisor (and by Googling). Sometimes specific rooms at a hotel are ok while others are not. Do not get into a position where you can’t have a clear Skype call because you listened to a clueless receptionist.

You can also try All The Rooms and HomeAway.
All The Rooms is an aggregator of many house/apartment/hotel websites. HomeAway is similar to Airbnb. Some of these sites are better than others in each city.

Kayak and Hipmunk are good for hotels/rental cars.
However, you can usually call the hotels directly and negotiate better rates and upgrades.

Always ask for a better room or free upgrade when you check into a hotel.
You’ll get something about 50% of the time.

Similarly, always try to negotiate a special weekly or monthly rate on housing and cars.

Don’t stay in hostels.
You’re not a kid. You’re a professional, and you need dedicated time to focus on work.

How to pull it off

The longer you wait, the more expensive it is.
That said, I hate planning, and I find that last minute usually works out fine. Worst case scenario: you’re uncomfortable for a little while (red eye flight, stuck in traffic while it’s 900 degrees, etc.) but you end up with a funny story and an adventure.

Rental cars (above)
If you’re American, learn how to drive a stick shift before you go overseas. They are much cheaper to rent, and it’s often impossible to find an automatic.

Rewards programs
Use TripIt or SuperFly to keep track of and redeem your rewards. They will build up over time.

Money
I always try to carry a few hundred USD. It’s easily exchanged whereas others currencies aren’t always. Before you travel, you’ll also need to call your banks and let them know in which countries you’ll be using your debit card. Otherwise they may block it after your first transaction, and you’ll have a mess to untangle. Also, be sure to download a currency converter app so you know how much things cost; and when you need more cash, pull it from an ATM instead of an exchange in order to reduce fees.

Skype number
Get one and add credit to it so you can call clients, hotels, etc. any time. It’s also wise to have it forward to your current mobile number so your clients and colleagues can call you when they need to.

Lost a charger or adapter?
Ask the hotel desk. They usually have a box of them that other guests have left behind.

WiFi
Check Foursquare for free WiFi hotspots. Rewards lounges usually have a WiFi network. Restaurants often do as well… just ask for the password. Many gas stations like Shell and OMV have open and fast WiFi as well.

Time zones
Always use something like World Time Buddy to easily double check time zones. Do not get into a position where you’re missing team calls because you forgot daylight savings time or you did the mental math wrong.

When to go

Any time you want.

Visas

As I mentioned earlier, most countries permit a three-month stay under their tourist visa. (Specifically, 90 out of every 180 days.)

Most counties are very easy to go in and out of.
The worst is always the US where I’m treated like a terrorist virtually every time I enter or leave. (I refuse to fly into Seattle–Tacoma International Airport ever again). For many countries (in my experience, as an American), all you need to do is show up at the border not looking like a criminal, and they will give you a tourist visa as you go through the airport. In some countries like Turkey, you’ll have to pay a small fee (~$20). In others, you need to fill out paperwork beforehand and pay a larger fee (e.g., Argentina and Brazil). I carry a printout of a recent bank statement and copies of my return tickets (if I have them) just in case a customs agent asks to see them (and some countries like New Zealand require them).

Always check visa requirements before you travel.
I like using CheapoAir’s tool. If you have questions, call an embassy.

This sounds obvious, but don’t overstay your visas.
While most countries are pretty forgiving (you pay a fee on your way out/in and you can’t come back for a while… if you’re caught at all), it’s not worth the stress (and waiting in that line feeling guilty and terrified is freaking stressful). If you love a place and want to stay longer, find a recommended lawyer on Internations (just post a question asking for recommendations) and ask what it takes. For Europe, it’s pretty easy (at least in my experience as an American). You can go to a lax country like Hungary and pretty easily get a 1-year visa, which is then good for anywhere in the Schengen Zone.

Misc.

Communication with clients.

If the technical ability is there, then now it comes down to communication and reliability. I always tell engineers and their clients that if I were to take each into a separate room, they need to always be able to give identical answers to the following three questions:

1. What are you working on now?
2. What were you just working on?
3. What will you be working on tomorrow?

Maintaining that level of communication and transparency is not difficult in an office, but it’s also not difficult when you’re remote. Always be connected and proactive.

Always lock your suitcases with TSA approved locks.
I’ve had lots of baggage get lost and several misc items get stolen.

When flying, always check the rates for business class.
If you’re checking multiple bags, sometimes business class can be cheaper because the bags are free.

When you’re on long flights, get up and walk around every couple hours.
You don’t want to die from a blood clot.

Attitude

Shit will happen. Try to let it go immediately.
You don’t need to (nor can you) plan every last detail when you travel, and you don’t need to follow every rule. Sometimes you need to wing it. Be impulsive. Seize an opportunity to jump on a train to Oktoberfest with a group of brand new friends. Invite the girl you can’t stop thinking about to a wild weekend in Turkey. Go to Georgia and party like Russia might come back tomorrow.

That’s when awesome happens. Welcome to Toptal.

###

QUESTION OF THE DAY:  What would you add to the above recommendations? Please share in the comments by clicking here!

Posted on: October 4, 2014.

Please check out Tribe of Mentors, my newest book, which shares short, tactical life advice from 100+ world-class performers. Many of the world’s most famous entrepreneurs, athletes, investors, poker players, and artists are part of the book. The tips and strategies in Tribe of Mentors have already changed my life, and I hope the same for you. Click here for a sample chapter and full details. Roughly 90% of the guests have never appeared on my podcast.

Who was interviewed? Here’s a very partial list: tech icons (founders of Facebook, Twitter, LinkedIn, Craigslist, Pinterest, Spotify, Salesforce, Dropbox, and more), Jimmy Fallon, Arianna Huffington, Brandon Stanton (Humans of New York), Lord Rabbi Jonathan Sacks, Ayaan Hirsi Ali, Ben Stiller, Maurice Ashley (first African-American Grandmaster of chess), Brené Brown (researcher and bestselling author), Rick Rubin (legendary music producer), Temple Grandin (animal behavior expert and autism activist), Franklin Leonard (The Black List), Dara Torres (12-time Olympic medalist in swimming), David Lynch (director), Kelly Slater (surfing legend), Bozoma Saint John (Beats/Apple/Uber), Lewis Cantley (famed cancer researcher), Maria Sharapova, Chris Anderson (curator of TED), Terry Crews, Greg Norman (golf icon), Vitalik Buterin (creator of Ethereum), and nearly 100 more. Check it all out by clicking here.