We love catching up with people and companies who have the same vision as Teleport. A little while ago, we came across Startup Diaries – a team hitting the roads on a mission to discover alternative working models from Santiago de Chile to Sao Paulo. We asked Fabian, one of the team members, to bring us up to speed about Startup Diaries and what they’re up to.

Tell us more about Startup Diaries – what is the core idea behind it and what are your main goals when it comes to the project?

Startup Diaries was started in effort to explore the future of the Nomad Company, to understand how people can balance growth and freedom from location. When I first started Helpando.it after leaving a very lucrative yet time consuming position with a top global startup, I knew that I wanted to push my boundaries further. I wanted to see how far I could take the idea of a “company” in a connected, global economy.

So I decided to take our company across South America, from bottom to top, over 18,500km, to test the idea of a mobile office. Our mobile office is actually a Land Rover Defender that we affectionately refer to as La Oficina. This is how Startup Diaries took shape. It’s a project we started to document our travels, struggles, and conversations with people who are also redefining how we work.

Who’s in your team and what are their roles?

Our entire global team unfortunately can’t all fit in our moving office (or our headquarters). I’m also sure quite a few of them wouldn’t want to have spent 6 months driving around with us. For now, travelling in La Oficina, are Dominic, our talented accounts and project manager, Vinh, our office and content manager and myself, CEO & Founder of Helpando, responsible for first client contact and data migrations.


(Right to left) Dominic, Vin, and Fabian posing with La Oficina

We also count on a remote team of 7 people, with people in Canada, Russia, Romania, Spain and more depending on the day.

You’ve defined yourself as a “nomad company”. Could you explain the term in a bit more detail? What are the differences between a company nomad and a freelancing nomad?

The biggest difference is the long term vision. The most common digital nomad story is “pay to play”, work to make just enough money to be able to pay for the next day, week or leg of the journey. There are careerists, those who take it seriously and maintain a long term pipeline. But it’s exceedingly rare for the freelancing nomad to actively pursue growth, right? As a Nomad Company, though saying we work 9-5 would be a misnomer, we have meetings (easy when you’re driving around all the time), structure and most importantly, a cohesive focus on the growth of the company and brand. It does mean that eventually we might outgrow our 3-4 person vehicle – we’ll have to deal with that later.

Where did the decision to hit the road come from? Were some employees hesitant as to whether this would work or was it an unanimous agreement?

I was and have always strived to be location independent. I went from Berlin to Congo in an old Mercedes a few years ago, combining fundraising with music and a crazy bet (for each 10$ donated to social projects, I needed to find a person to sing a song with me). I’ve also lived in several different countries (including Chile and Spain). So the foundation was there.

I had serendipity line up in my favor when I asked a good friend what I should do with my life and he answered “Buy this Land Rover” and included a link to the car we’re driving around in now. I had the idea of the car, but I didn’t really know why. At that time time I was in Brazil for the World Cup and long story short, I ended up meeting Ed, who showed me the innovative side of the city I was in at the time. He insisted on showing the innovative and creative side of the city. I was blown away by these ideas and thought that it would be fascinating to explore and showcase how South America is full of innovation hubs, and people who are redefining how we work. And all the while, while exploring the great continent, I would test the idea of running a nomad company.

It should go without saying this isn’t for everyone. Imagine spending 6 months on the road with anyone? Even your significant other? Now try thinking of doing it with your your co-workers. There’ve been plenty of moments of doubt. In the end it was a great experience for all involved. We all learned an incredible amount, personally and professionally. And perhaps most importantly the bottom line, especially professionally, has exceeded our expectations. We proved to ourselves that the idea of a nomad company is very viable.


La Oficina, setup for the night by one of Chile’s wild beaches.

Why did you choose South America for your travels?

Let’s get the obvious out of the way – It’s cheap! Especially gas. But also food, accommodations, and of course nightlife. South America is spectacular! Beaches, deserts, volcanoes, jungle, forests and anything else you can imagine. The culture is incredibly diverse and nearly unmatched anywhere in the world. And there is always a delicious local dish to eat within arms reach.

The startup scene is great. This means plenty of coworking space, with great wifi, as well as many very interesting people to talk to. The startup communities, combined with that South American flair, makes for really vibrant communities that without fail inspire us to do better.

Connectivity was a big consideration. We can’t go too long without either wifi or a cellular connections. South America has a plethora of hotspots and SIM cards with really inexpensive data plans.

South America is also not a typical nomad spot. And that is part of the challenge. Nomadism should be possible anywhere in theory, and that was important to test as part of our trials. And changing the perception of South America was a big part of this. Having lived in Santiago previously, I already had a sneak peek into the potential of working out of South America.

And perhaps it’s my counter-culture attitude, but I tremendously enjoy the underdog stories and in emerging markets, well almost everyone is an underdog. The fact that the Land Rover was in Argentina also played a key role in this voyage.

Which locations have been your favorite so far? Feel free to expand and list things that have been particularly awesome about each location (food, culture, museums, etc).

So much here, but I’ll list a few:

  • Lima has been my favourite city with the very bohemian Barrio Barranco sticking out in my mind as one of my favorite places to be.
  • In general, the food was most amazing in Peru. Not only was it exceptionally cheap, but the ingredients were incredibly fresh and varied, including but nowhere near limited to fish, ceviches, llama, fruit straight from trees, and more.
  • Patagonian Chile cannot be beat for landscapes with lakes, volcanos, peaks and waterfalls that are invariably surreal.
  • The coolest co-working space we found was Sinergia in Montevideo, not only for its great design and layout, but for one of the most varied and incredible concentration of ideas under one roof (think drones, 3D printers, SaaS stratups and the rest).
  • Crossing the desert from Chile to Peru was a great adventure. We got stuck in the sand, and slept in the car for several nights. There’s more sand out there than you would ever want to see.
  • Baños in Ecuador was great for activities like zip lining, jungle tours and waterfalls.

What are the biggest challenges you’ve come across in your travels, whether it’s changing team dynamics, tech related issues, or something else?

We thought connectivity would be a bigger issue than it was. There was a time in the Argentine Patagonia that we needed to race 15 miles to find cell phone reception for a call with a Fortune 500 client. Or another where the wifi cut out while in the last minute of a call that could’ve been tragic. Or the time where we closed a deal in an internet cafe surrounded by kids playing World of Warcraft (without headphones on). But overall, when we needed it, we managed to connect.

The biggest challenge we faced was figuring out to take what was a “9-5 job” (8 hours a day) back in Berlin and turning it into 2 hours. Travelling takes a lot of time. As does managing Startup Diaries. And limited connectivity at times (and slower connections). This taught us so much about using available tools to be much more efficient.

On a lighter note, we’ve had car troubles that borderline on the ridiculous. I could fill up pages with those stories alone. But lets just say our radiator was eating too many dragonflies and was getting quite sick. After half a dozen visits to garages, it seems to be in order.

Which services, tools and resources do you use to make sure that work runs smoothly even when you’re on the road?

When we are traveling, besides our trusty Apple devices (oh yes, we have quite a few in La Oficina), we would be lost without the cloud. Dropbox is so important. Basecamp, Skype, remote servers, Calendly (great for scheduling meetings across time zones), Evernote (we couldn’t live without it!), ReviewStudio (life saver when it comes to video production and collaboration with remote teams) and everything Google (Docs, Sparrow and Gmail).

Local SIM cards are very important to us for ensuring we can maintain our customer service that our clients know us for (besides new business calls of course).


This is often what work looks like

You’ve said that in your travels, you hope to meet other people who use technology to work independently and live the life of their dreams. Tell us about some of the most inspiring people or organizations you’ve come across so far.

It’s so hard to single out specific individuals. Everyone is working on projects that are inspiring for so many different reasons.

For example, Alejandro used to walk 1 hour to school every day in Puerto Montt, and noticed the farmers struggled with their production and making ends meet. So he worked at shifting their production to a more gourmet variety of garlic improving revenues and profits. Now, at the age of 20(!) he’s managed to secure government funding to setup a coworking office in Puerto Montt – perhaps the southernmost one in the world.

Valeria Figallo, from Lima, Peru decided to drop out of school at the age of 12, but not because she was lazy. She didn’t like school, if wasn’t fulfilling her ambition. So after presenting a rock solid case to her parents, they allowed her to take one year to prove she could learn and grow on her own. She landed her first website contract at the age of 14 with a model from the USA and now at the age of 24 runs her own agency.

Another fascinating example of the marriage of technology and the changing work environment is Mirna. As a well established Psychologist in Montevideo, deciding to relocate to Mallorca, left many of her clients not knowing where to turn. They convinced her to continue therapy over Skype. She now not only has a succesful in person practice, but incorporates Skype calls with her in person sessions.

I could continue, but there are too many.

How do you feel this project and traveling has changed you and your team? Were there some immediate benefits (or drawbacks) realized by making this decision?

As said previously, working more efficiently has drastically changed our habits. It will be fascinating to see how we will apply the same work ethic when and if we return to the non-nomad world. We previously wasted so much time in our offices, taking 8 hours to do the work that needed 2-3 hours. What will we do with that time when we aren’t traveling through a new country? We will need to see.

While I’m still planning on taking the company back on the road after a brief stint back in Berlin to refuel, participate in some conferences, catch up with friends and family, for others on the team, the nomadism wasn’t as appreciated. Dom is considering returning to Medellin (a nomad hotspot) to settle for a while and have some stability. So, at the very least, falling in love with South America is a huge benefit!

What do you think the future has in store for Startup Diaries?

We’re planning to continue the adventures only with a ramped up production crew and finding the people needed to take it to the next level. We also hope to find a few sponsors for the next season, to allow us to invest in all the necessary areas to get there. This has been an incredible learning experience. The difference between our first and last episodes is quite marked.

We’re planning to travel across Europe for the next season, and then hopefully onto Asia. The Land Rover is coming with us of course. I very proud of the work we’ve done. It’s quite an accomplishment to produce the content we have – it’s a very time consuming process

This process has also instilled in me a passion for empowering others to pursue nomadism and a more open mindset when it comes to work. Personally, the Startup Diaries project, partially due to extensive media coverage and a TedX Talk, has pushed me to share my experiences. I look forward to coaching others to be able to design their own path, whether in their careers or life-plans.

How did you find out about Teleport? If you’re familiar with it, then what do you think about the general idea behind what Teleport is trying to achieve?

The future of the global connected economy will require tools to facilitate mobility. We have been practicing what you are preaching – the world is your oyster. I heard a quote, I think credited to St Augustine “The world is a book and those who don’t travel read only one page”. In a sense you are helping to sell that book. The book is too thick in reality for anyone to really read. So, metaphorically speaking you guys are helping people discover a book of their own – and that is incredibly valuable.

You can follow the Startup Diaries adventures on our website, and by liking us on Facebook. If you’d like to contact Fabian personally about nomad coaching, efficiency training or any other inquiries, you can contact him through his personal website.

There’s also a series of webisodes you can catch up with!