For the 1st part of my 30th birthday, I went to the F1 races, then Noah threw me a surprise party that night.

For the 2nd part of my 30th bday, I went to Cuba (actually Noah planned this whole trip too…..that was damn nice of him eh!)

Cuba was appealing because it’s this weird “time capsule” of a place.  The United States has an embargo against Cuba, so Cuba has very little importing options….not to mention it’s a communist country (well….I guess technically it’s “socialist”).  This means the government can strictly control the imports, exports, the currency….and thus, the people.

For example, for the locals of Cuba:

  • …they are not allowed to leave Cuba.
  • …they are not allowed to use the internet.
  • …they are not supposed to get close with any tourists.
  • …they are not allowed to openly talk bad about the government.
  • …all sorts of other stuff.

There’s also not a lot of industry going on in Cuba….this means most of the local population is quite poor, many of them making something like $13 to $18 U.S. dollars A MONTH.  That’s right, A MONTH.

A doctor in Cuba, even a surgeon, gets paid only $40 A FREAKIN’ MONTH.

Almost hard to believe.

The way they survive on this small sum of money is because Cuba has two currencies (both of which outside of Cuba are worth nothing).

FIRST CURRENCY is called the Cuban Convertible Peso, and is roughly 1-to-1 with American dollars.  Tourists use this currency, and prices everywhere are pretty decent with this currency.  We could eat a nice lunch, complete with beers, for 6 people, for about $30 to $45.  Not bad.  Unless you’re eating at the really nice tourist-y places, you probably won’t spend a crazy amount on food.

SECOND CURRENCY is the Cuban Peso, and is for locals only.  Tourists aren’t supposed to use it, and the locals aren’t “supposed to” accept it from tourists (notice the “supposed to” in quotes).  This currency is 250 per 1 American dollar.  My friend heard that you could buy things RIDIIIICCCULOUSLY cheap in local areas if you somehow get a hold of this currency.

He found a place that would let him get some, and he decided to change just $20 U.S. Dollars. The lady at the front asked him, “Ummm….are you SURE?”  He agreed, and got a HUGE STACK OF $5,000 IN LOCAL BILLS.  It was like a giant strip-club stack of $20 bills!
Whenever we went to local places that accepted this currency, this is what we spent:

  • 4 bowls of ice cream at a sit-down ice cream parlor (4 scoops per bowl) = $0.20 USD total
  • Bottle of rum + mixers = $2.90 USD
  • Personal pizza =  $0.15 USD

After paying with local currency at every place possible (sometimes convincing is needed), my friend still had $10 USD in local currency left over!

However almost everyone we spoke with about Cuba told us the local currency was useless for tourists.  It worked well for us because 3 of us were brown, and my friend using the currency spoke very fluent Spanish.

However this local currency only worked in certain places, definitely not everywhere.  I still ended up spending about $2,000 in six days (about 20% was skimmed off each money exchange, and much of it was to pay for the big penthouse condo we rented).

One of the greatest parts about living in a society that’s “slightly less than 1st world” is bribing (well…presuming you’re rich in that country….otherwise it sucks for you)!

Anytime there’s a long line at the airport, it “can be solved” with some monetary lubrication.
Anytime you need a table at a restaurant with a huge wait… problem.

In a perfect society, I’d think doctors, teachers, and businessmen should make the most money…..HOWEVER, in Cuba, we found out one of the best jobs to ever have is a bartender in a touristy spot!

The bartenders sling drinks all day, and get tipped in Cuba Convertible Pesos (about 1-to-1 with American dollars).  This means they can rake in $150+ a day.  And when you consider the average Cuban peasant makes something like $13 to $18 a MONTH, that’s a helluvalot of money.

The next best job is a taxi driver.  The government “owns” the taxis, but the drivers get to keep much of their tips.  Someone shuttling around tourists all day can make decent tips, and support an entire family pretty well on that job.

It was interesting yet kinda sad how a bartender or taxi driver make literally 100x what a doctor makes.

The country actually felt VERY safe.  I have a reasonably good “Spidey Sense” of what situations will get me into “fake” trouble (ex: security guard telling you to stop doing something), and what will get me into “real” trouble (ex: going to jail in a communist country).

….and I gotta say, Cuba was pretty safe.  Since their criminal justice system is so harsh on crime, there is very little of it.  I heard pickpocketing and petty crimes are reasonably common, but serious crimes are not.

Actually in Mexico and China I’ve felt MUCH stronger security presences than Cuba.  I really expected to see armed guards everywhere around Cuba, but alas hardly saw a single one.  Even the police officers seemed chill and nice, and about 80% didn’t even carry guns.

Pretty much everywhere we went, the vibe of the country was “super chill”.  It was very safe.

Pretty much any other country in the world can openly travel to Cuba with no issue.  However Americans can’t legally go “just like that” because of the embargo we have against Cuba since 1962.  But there are many options to go:

American Citizens can go to Cuba legally if they have family members there, going for diplomatic reasons, going for foreign aid reasons……and the most common is “cultural” reasons.  This is for students and tourists.  There are many tour companies that will charge you money and get you a “legal” visa to Cuba…..but I’m almost certain some of these are scams, read the next way of entering the country:

U.S. citizens can “try” this little stunt if so chosen:
Get a flight to some country such as Mexico, Belize, Guatemala …wherever.  Then fly to Havana, Cuba from there.  Your passport will get stamped on the way out of the country, however, Cuba stamps only the Cuban visas (which any person can buy at the airport for $25 each).  This visa is just a piece of paper that’s NOT affixed to your passport.

This means for Americans, they stamp the paper on the way into the country, and the way out of the country.  So your passport is untouched.

For example, one could “just hypothetically” do this:

  • Go to Cancun, Mexico.
  • Buy a flight to Cuba.
  • At the airport, find a place to get Cuban visas.  They’re $25 each.
  • Fly to Cuba, have a good time.
  • Fly back to Cancun.
  • Fly back to the U.S.

From what I understand through research and talking to many people who’ve done something similar, the U.S. no longer takes the Cuban embargo ultra-seriously.



One of the main reasons I wanted to visit Cuba right now, is the “time-capsule” effect the American embargo has on the country.  Essentially they have a bunch of old cars from the 50’s rolling around, no internet and very limited cell phone use.

I can go to a rural farm in India, and the farmer will be text messaging his kids.  However in Cuba I hardly saw ANY locals with a phone.  The only phones I saw being used were carried by hustlers, tourists, or students.

It was also almost wholly “brand-less” when driving around.  No billboards, no overt advertisements except inside the actual establishments.



You’ll definitely need to know some Spanish if you visit.  However you can make it around the tourist-y areas ok without it. All 6 of us on the trip spoke and understood at least A LITTLE Spanish.  Two people with us spoke damn-near fluent, so that helped a ton for using local currency, getting information, and exploring areas where tourists don’t go.



Initially I thought we’d see propaganda everywhere, kind of like I’ve seen in China….but to my surprise it was shockingly little.  Instead the people are left relatively ignorant of the outside world through not being able to leave the country, no internet, and mainly: Very little access to outside information.

Their bookstores only sold American literature if it was something like an old classic novel (Charles Dickens, Ernest Hemingway etc).  There were a lot of books about Fidel Castro and Che Guevara.  But completely absent were any new releases.

Almost no Cubans have ever left the country.  Almost no information about the outside world is easily seen.


After researching Cuba, it turns out things were pretty safe.  So here’s how I rationalized it:

  • 98% chance things would all work out completely fine and we’d all get home safe.
  • 1% chance of us getting stopped for questioning….perhaps get a small fine.
  • 1% chance that I somehow end up in a Cuban jail with no way out.

In the REALLY OFF CHANCE that I (or someone in the group) were to end up in some really deep-shit trouble whilst in Cuba, I made a small document called “The Contingency Plan.”  

I sent the document to two close friends who I trust, and also know my family & friends well enough to get things in motion.

The document contained certain contact information, and also instructions on where to find a small envelope which contained some bank account information. This bank account had immediately access to $200k in cash… if by some REMOTE CHANCE I didn’t arrive back home from Cuba…..the contingency plan would kick into gear and be well funded.

After going on the trip and seeing how safe the country actually was, I probably wouldn’t deem a Contingency Plan necessary for the next trip……but it was nice to know I had backups coming for us in case something happened.




















Here’s some video highlights of the trip (me and my brother bought a $60 guitar in Cuba and made VERY good use of it)!

Blog posted on: December 27, 2012

51 comments on “Cuba

  1. Alex

    I have been to Cuba. As a Canadian it was no effort getting in. Loved the people loved the country, but limited Internet made me go crazy. Would go back again.

    1. Neville Post author

      Yup, it was 6 full days of total communications blackout for us. Longest of my life!

      However it wasn’t so bad since I expected it.

    1. Neville Post author

      Glad I got it accurate!

      Do you know why people had the Apple logo everywhere? It seemed like having an Apple logo was almost a status symbol over there.

  2. Shirley Hayes

    Awesome! Your pics remind me of my first trip to Brazil. I loved the post I couldn’t stop reading it! I will have to put Cuba on my list!

    Gracias y … Feliz Cumpleano Neville!

    1. Neville Post author

      Thanks Shirley!

      I think the combination of text, pictures, and videos really give you an idea of the vibe of our trip (and the cool people we had) :-)

  3. John B

    Great trip Nev! I’ve been once to Varraderro and did a few trips around when there. Great people – is it me Or Has that adversity made the people the coolest and most amazingly honest people to hang out with :-)

    1. Neville Post author

      They are very cool and open to Americans.

      My friend put it well:
      “Since the locals get limited info about the outside world, they see tourists like Americans and almost think of them a bit deity-like. They seem well dressed, educated, rich, and FREE.”

  4. Jeremy

    love the detailed post and after reading you make Cuba quite enticing (go figure that your copywriting will drive lots to go there) . also the video of a guy getting pick pocketed…classic.

    1. Neville Post author

      HAHAHAH…..I couldn’t believe how bold those tranny’s were! If you watch carefully them essentially swarm the guy and he has no clue who took what.

      1. Kuno

        You got the pickpocket in action. When the tranny is dancing hard with the guy, it’s friend literally creeps around to the back, and yoinks the guy’s wallet from his fanny-pack. Then she struts around proud about how easy it was. It’s very clear in the video who took that guys wallet.

        A warning to future travelers.

  5. Vincent Vittorio

    Great post and pictures! Having lived in Miami as a boy I have always been interested in one day visiting Cuba… Through this post you might have bumped up Cuba on my places to travel que…

    1. Neville Post author

      I actually had a fantastic time there, and would recommend it before the embargo is lifted (I’m guessing 5-10 years).

      Also if you speak Spanish, try to get the local currency. It will go a looonnnnggg way on your trip!

  6. Valerie

    Interesting read. Happy belated birthday. You’re too f*cking young to be so successful. I need you to be a role model to my 22 year old. Oy vey.

    Interesting read about the currency. That explains the entire segment of Michael Moore’s “Sicko” movie and why medical care was so cheap there. Makes me wonder what kind of education their doctors actually have.

    1. Neville Post author

      THANKS Valerie!

      From what I understand, the doctors are actually really good……because anyone willing to live a shitty life on $40/month does it because they LOVE IT (a good doctor generally doesn’t care about the pay).

      However I’m not fully sure if they have full access to all the equipment and medicine a normal country will have.

      Also I think the diet in Cuba is “reasonable” (not totally healthy, but not bad either)…..and everyone walks a lot. So you don’t see a lot of fatties roaming around like more developed countries.

  7. Brian Kwong

    Don’t know nothing about Cuba until this post and it is very interesting to see the development and how people live in a country being cut off from the outside world, the TIME-CAPSULE EFFECT.

    I wonder if people are more happy there. I know you say people are chill over in general, what is the first thing you think of the people and culture in Cuba?

    1. Neville Post author

      I think ignorance breeds complacency.

      So if you have a reasonable quality of life, and aren’t exposed to much outside your own little world…..your brain wouldn’t be that ambitious.

      HOWEVER… of the common things about a lot of Cuban people we talked to, was for them to leave Cuba.

      1. Brian Kwong

        Interesting, this is the same no matter if they are first world or third world country, example like Austria, where I live now.

        Many of the locals here tells me their dream is to go to America or its “cool” to live in America and when I ask why, they can’t really tell me why.

        I think “reasonable quality of life” breeds complacency no matter what people and what country they are in.

        Which is why I love reading your blog, seeing an awesome entrepreneur testing things, being in action and surrounding yourself with good people.

        And I am Looking forward to see more awesome stuff from you in 2013!


  8. Melinda

    BRILLIANT!! Happy birthday Neville!

    Cuba’s amazing, and yes its a digital detox, but its good, cause it rewires us to go do/explore something else.

    1. Neville Post author

      I could really notice the impact whenever we were having breakfast/lunch/dinner…..that no one sat around playing on their phones. Instead we talked and enjoyed each others company.

    1. Neville Post author

      Thanks Eduardo! I still haven’t made it to Carnaval. It’s not like a huge goal of mine or anything, but at some point I may swing by to checkout the craziness!

  9. Chi

    Thanks Nev and Happy belated birthday.

    Totally not what I expected from your email but a fascinating read. Cheers

  10. Chris

    Hi Nev. Happy birthday and I’m glad you had a great birthday. What really struck me about it was what a great friendship that you and Noah have. Of course it’s evident in the AppSumo vids, etc. but it’s really cool to see that it’s true on your chill time as well.

    As for Cuba, I’d caution against romanticizing it this much. A cage, however gilded, is still a cage. I’m most familiar with the Christian Liberation Movement. But the incredible oppression of free speech and ideas there ought to give someone who makes his living with words pause. Imprisoning almost as many journalists as China(!) with decades long sentences, torture and ‘reeducation’ please think more carefully on the price paid for the smiles you saw.

    “My nostrils dilate while savoring the acrid odor of gunpowder and blood.”

    Che Guevara

    Anyone wanna’ see a Cuba you can’t write about but might just blow your mind? Find someone in the underground church movement. Only for adrenaline junkies though.

    Sincerely Neville, it was great to get a visitors perspective on how everyday folks are coping in Cuba. Happy birthday again and many more.

  11. Ronnie

    I’ve heard that Cuba is a paradise for sex tourism. So tell us Nev, were there alot of pushy young prostitutes? Did anyone in your group sleep with one of these hookers?

  12. FIDEL CASTRO SUPERFAN #1 !!!!!!!!!!

    Anyone see the irony that the guy with all the monetary success chooses to vacation in a socialist country?

    I wish Nev would go back to the blogging style that made him famous. You know, with some TRANSPARENCY. Nev, we want to hear about finances. This is supposed to be a financial blog, after all.

    1. Chris

      In my opinion, this post is exactly spot on with what Nev is about. It couldn’t be more transparent. And he discussed, extensively, how different the two economies were between the nearly free market ‘tourist’ economy and the local socialist economy.

      Assuming your being sarcastic with your name, I didn’t read anywhere that he was a fan of Castro. In fact, I think the trip puts the lie to the communist pipe dream better than any political argument can. They found happy people there, under one of the most repressive governments in the world.

      What I understood from the post was proof of Frankl’s ‘meaning of life’ thesis.

  13. FIDEL CASTRO SUPERFAN #1 !!!!!!!!!!

    Nev rarely talks about the financial aspects of his business. After he had some success, he stopped giving numbers actual dollar amounts. This is what I meant by “transparency.”

    He used to be transparent about his finances. Now he just posts product ads and vacation pics.

  14. Justin

    Looks like a great time with a down to earth bunch of guys. A great trip to realize just what a wonderful thing capitalism is in the states. Nev, I have a couple wantrepreneur questions, if you could email me back.

  15. Chris Altamirano

    Haha that was such an awesome video Nev. Your homie with the guitar was getting down! And Noah pouring beer on that chick was hilarious.

    I’m sure a lot of us have always wanted to hit up Cuba but just never had the right information. Being a bit of a wuss to go has probably been on our minds too..focusing more on the consequences than the actual adventures ahead.

    Thanks for the share bra, I feel like I’ve been to Cuba now!


    – Chris

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  17. Joel

    Seems like you guys saw many images of Che and you guys wore some too. Here in Miami if you go to Little Havana you will not see one single image of Che, nor will you ever in this city see one single Cuban immigrant wearing a Che T-shirt. That is because the many people here who lost direct family members to Che and to the Castro brothers. Family members who were aspiring, creative and hard working like you. He went to people like you that had access to bank accounts with 200k and then he said, “You, are already going to die, if you want your kid to live then give me everything in that bank account, before I kill you, otherwise I kill them too.” How’s that for a contingency plan? I once smiled at a Cuban here when they told me they were from Cuba, I said, “CUBA LIBRE!” I was talking about a Rum and coke with lime. To them it meant something else and they said “Ojala Que!”

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  22. Albert


    First time on your blog, love what you are doing. I heard an interview with you and Steve from MWQHJ and just had to check you out here!

    Anyways – keep up the good work. Would love to buy you a drink if you’re ever in San Francisco.


    -I also *ahem* went to Cuba *ahem* recently, and blogged about my experience. If you’re bored – take a glance at my specially curated shortlink just for you here ->

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