About a month ago I wrote about Another Kind of Silicon Valley Exit and how I systematically arrived to Colombia as the next place I should live at. Here’s some of the stuff I have learned from my move so far.


Only two weeks short of my trip I realized I haven’t looked into vaccinations. It was pretty much the last time to get the required shots to be effective in time. Luckily I did not pass out on an early morning meetup with potential partners minutes after the shots, but timing the required shots better is obviously something software could help solve. Getting a few reminders well ahead of your move should do the trick.

My second trouble was figuring out health insurance for my destination. After browsing around a bit and pinging people on the #nomads chat, pretty much the only answer that came back was WorldNomad. Although happy about not having to deal with the stress of choice, I quickly learned that their offer is far from optimal for the real perpetual travelers. Although you can get insurance even after your trip has started, getting the optimal package just wasn’t possible. Their extreme sports covers paragliding only for US residents and it was impossible for me to apply as one (though I just lived in US for four years) as the country of residence determines the repatriation destination (which I needed to be in Estonia). It was also impossible to get coverage in the country you would want to be repatriated to (I haven’t lived in Estonia for years and hence don’t have coverage there as well and would just like to have coverage without defining a country of residence).

What nomads need is an insurance that covers whatever countries we choose as our destinations, with whatever levels of sports risk we’re planning to take and with whatever repatriation country we choose. At the beginning of the year we might just have zero knowledge of which countries residents we’re going to be for the year. That’s our whole plan to make countries compete for us! :)  You’d guess a company named “WorldNomad” would have this figured out, but it was not the case. Contacting their support also left the feeling of an old-school insurance company with prepackaged answers and no attempt to even understand my concerns. I think insurance for the new generation of mobile talent is definitely an area that would benefit from more innovation and competition. Anyone?

My next challenge was finding a place to stay. In Bogota I had a friend whose place I could crash at and it was immediately obvious that knowing people ahead is one of the best means of reducing friction of moving and anxiety of the unknown. The real challenge started with my move to Medellin where I knew no one. A few pings to friends and the name El Poblado kept repeating as the safest and hippest area. A quick look at Airbnb revealed surprisingly high prices and as I later learned there’s only like 5% of the properties available for short term rentals due to local laws. The reality is that you’ll have to cash out quite a bit for your first stays when you’re still scoping out the area to figure out the long term plans.

I ended up crashing at an awesome Airbnb penthouse apartment of a Vietnam veteran from US who had two other senior gringos staying with him. How many of you have lived together with three 60+ year old dudes in your life? :)  As funny as it sounds they were actually super laid back, fun and very helpful in explaining how things work around here. There’s also something cool about seeing what type of different folk travel through here – who’s here to fix their teeth, who’s here to enjoy paid girls while hiding the fact they’re in Colombia from their parents (even thought they look 35) etc.

A noteworthy downside of living a nomadic life is the huge overhead of trying to organize everything. I spent countless hours searching for Airbnb places, trying to contact hosts, going to see apartments and trying to find friends so I wouldn’t go crazy at the end of the day behind the computer. In essence you only deserve this freedom when you’re productive, but spending a long workday behind the computer leaves you with little energy and time to address all that overhead. Again i see this as an opportunity for entrepreneurs and startups like GoTrotter, CaravanseraiNomad HouseAttache Arrivals etc. to solve each of these pain points. Let us know if you’re building something that can help people on the move! There are just too many things broken for Teleport to fix. :)


The best way of meeting new friends so far has been giving talks at local startup accelerators. I gave one at HubBog in Bogota and one at Socialatom in Medellin and again was pleasantly surprised how effective your own diaspora (in interests, not homeland sense) is in helping you understand the locals. I even got out of a dodgy situation at night when some folks from the talk recognized me and helped me evaluate the situation I was in (with their local expertise). :)

Later, after getting fed up with hearing “quires canabis, cocaina, las chicas?” on the street every night, I resorted to Meetup.com and ended up at a local scotsman’s pizza place with a bunch of people interested in practicing English and Spanish. The meetups don't last long, but they are definitely fun and I would easily recommend the platform for finding things to do.

As a foreigner it is also reasonably easy to approach people on the street for a friendly chat. Just express your desire to learn Spanish and stay clear of the people who seek you out first (they usually have a business proposal ;) ). I ended up at a local high school class reunion this way and was happy to learn how locals spend time.


All and all my first month in Colombia has been fun and full of learning. Although frustrating at times (due to things software hasn’t fixed yet) it obviously beats sitting in a cubicle. Most startup and software people haven’t realized yet that they share something with digital nomads. It might not be the desire to experience the havoc of constant travelling or working from the road, but it surely is the freedom – the freedom to choose where to live.

I decided to move to Colombia and although there are a thousand things that need to be fixed when it comes to moving, in essence it was all just two flights, two Ubers and one Airbnb booking away.

See you out there!