Hi folks! I recently finished my first trip to Brazil. As is my custom, here are my thoughts and observations from the trip, along with some pictures.

I was invited to keynote the Startup Summit in Florianopolis, but since it’s a very long trip to Brazil, I added a few days in Sao Paulo for some more meetings and events.

I was very lucky to travel the whole way with my friend and business partner Jeff Abbott; while I had never visited Brazil before, he had actually visited the country many times in the early 2000s, and fortunately retained a working knowledge of Portuguese.

There aren’t any direct flights from San Francisco to Sao Paulo (the westernmost US city that has a direct connection to Sao Paulo is Dallas) so our itinerary had us fly Aeromexico and stop over in Mexico City.

The trip did not get off to an auspicious start when we discovered that Aeromexico had an absurdly low 10kg carry-on luggage limit. I’ve spent years convincing Jeff to avoid checking bags on our trips, and we were both forced to check bags to Sao Paulo. As we checked in, each set of passengers behind us found out about the policy and expressed their outrage as well. We asked the Aeromexico ticketing worker how often this happened, and she replied, “All day, every day.” Seems like something the airline should do something about!

The most frustrating part was when we went to the gate, it quickly became apparent that Aeromexico only enforced the limit in Business Class; many of the economy passengers had multiple bags that clearly violated the limit!

Perhaps because of the lack of sleep or the carry-on fiasco, I was pretty grumpy during the flight to Mexico. It didn’t help that the 737 we flew wasn’t particularly comfortable.

My mood soon worsened when we were forced to go through Mexican customs for a simple layover. The whole process was confusing, even for people who speak Spanish fluently (Jeff) or passably (me). We tried to get in line, and were told we needed to fill out a customs form (which included a space for where you’re staying in Mexico) even though we were only connecting. The customs form has one set of fields in English, and the identical fields in Spanish. So naturally, you’re required to fill out both! We filled out the English fields, and then were sent back to fill out the Spanish ones as well. Meanwhile, hundreds of other travelers were dealing with the same thing.

After making our way through the customs maze, we made our way to the Aeromexico lounge which was underwhelming. The food options were sparse, and the entire lounge was kept at a temperature of nearly 80 degrees. The beverages were good, however, with plentiful coconut water.

Our (unintentional) strategy for the Aeromexico lounge ended up working out pretty well: Sit close to the place where they brought out the food. Most of the food was disappointing, but once they had cheese empanadas and once they had beef empanadas, both of which were very good, especially with chimichurri sauce. Each time, the empanadas were gone within a minute or two, which meant that our placement in the lounge was key.

I ended up drinking three coconut waters and about six sparking waters to rehydrate. I wanted to take a photo of the urinal for the upcoming Savvy Urinator’s Guide book, but it was always too busy. I did manage to get through my backlog of seven urinal submissions I’d received, plus a photo I’d taken of my local Costco’s urinals.

Jeff also got a massage and shower at half the price of what it would have been in the US, so at least one of us had an enjoyable layover.

The second leg, to Sao Paulo was on a 787-9, which meant that it was a new plane (the first 787-9 was only delivered in 2014, and Aeromexico’s 787-9s were introduced at the end of 2019). The plane was great, and the food was good as well, including a delightful poached shrimp with quinoa “caviar” with an aioli sauce. I managed to sleep on my lie-flat seat for 4-5 hours between meal services (the eyeshade provided was one of the better ones I’ve ever been given on a plane) and was only awakened when the flight attendants were taking breakfast orders (I had smoked salmon and a very tasty pastry of some kind).

On the approach to Sao Paulo, I was struck by how lush the landscape was—nothing but green as far as the eye can see, a far cry from California these days.

When I’m on planes, I often listen to “concert” podcasts so that I have my own source of music in airplane mode. This time, “Walking On Sunshine” was playing in my ears as we landed. I took it for an auspicious sign.

The trip from the airport to Sao Paulo is about half an hour, unless there’s bad traffic. As we rode our Uber in, our friendly driver told us about the various neighborhoods, and warned us about some of the more dangerous ones, like the seemingly appropriately nicknamed “Crackland”. He noted that the most dangerous areas were the ones where there were only rich and poor, and the best places to go were where the middle class congregated. There’s some kind of lesson in that, I’m pretty certain!
Jeff and I checked into the excellent Canopy by Hilton in the Jardins. Canopy is a new brand from Hilton that offers upscale urban boutique hotels (think of my friend Chip Conley’s old company, Joie de Vivre). It’s a beautiful facility, with helpful staff, well-designed (if not overly large) rooms, and a great breakfast buffet included. I was in Room 903, and Jeff was in Room 803. More on this later.

During the trip down, my old Blackberry phone started to come apart. I’d previously repaired it with epoxy a couple of times, but the back of the phone kept trying to pull away from the bottom. Fortunately, the front desk at the Canopy lent me a roll of packing tape and a pair of scissors, and I was able to tape my phone back together. Even more amazingly, my hurried tape job held up the rest of the trip. I’ve been using Blackberry Android phones ever since they became available, mainly because I prefer using phones with physical keyboards. My first smartphone was the original Google G1; I’ve also used a Motorola Droid, an HTC Touch, and at least one other phone I can’t remember. What they all have in common, besides the physical keyboard, is the fact that they were all commercial failures, because very few people want a physical keyboard. The keyboards make the phones heavier, they often reduce the size of the screen, and because nobody designs software for keyboard phones, apps are often buggy and unreliable. People ask why I used keyboard phones. It wasn’t for speed; a software keyboard is generally just as fast for individual keystrokes. My issue with software keyboards is that it’s hard to properly capitalize and punctuate when you type. To access punctuation marks, you often have to shift to one or more secondary keyboards. Most people don’t care, because they are content to send messages with improper capitalization and punctuation (not to mention spelling and grammatical errors), like the savages they are. I insist on writing correct and complete sentences, even when responding to text messages (though I will occasionally settle for “OK” or even the “thumbs up” emoji to save time). Alas, it looks like I’ve reached the end of the line. There are no more Blackberries, and the crowdfunded keyboard phone that I bought last year makes too many compromises (it is too thick, too heavy, and its screen is too small for daily use). With sadness and regret, I bought a new Google Pixel that will be waiting for me when I get home from the trip.

During our time in Sao Paulo, Jeff and I had schedule that was packed with breakfasts, lunches, dinners, and even some meetings that didn’t involve food. While the subjects and participants in these meetings shall remain anonymous for now, a few patterns emerged. First, as was the case when I visited South Korea, people kept taking us to restaurants that served non-Brazilian cuisine. Three meals in a row, we ate at (very nice) Italian restaurants, while on another occasion we ate at a fantastic Japanese restaurant, Huto Kohi. Fortunately, one friend heard my plea for Brazilian food, and took us to a fantastic churrascaria, Figueira Rubaiyat, for one of the best meals of my life. I’m not sure I’ve ever been so stuffed, a fact which I blame on my friend for insisting that after we had already eaten a huge amount of meat, including ribs and fried pork belly, that we had to share a steak as well. The restaurant itself was beautiful, principally because it was literally built around a huge banyan tree, whose branches poked out through the windows.

Something that is public is that we partnered with our old friends at Astella (a top Brazilian VC) and our new friends at Scale_X and LabOf to hold an event at LabOf’s offices. This was one of the coolest venues you’ll ever see. LabOf is a creative agency that happens to run an amazing space…or perhaps it’s the opposite. They even had an artist-in-residence, an internationally famous street artist name Cusco, who was painting at the event. We had a fantastic time, as the photos below will attest.

Overall, I found Sao Paulo to be delightful. We stuck to our hotel and our scheduled meetings, and never felt unsafe (though we did pass through a favela on one of our visits, and it was pretty shocking…and I’ve seen the slums of India). That being said, we did travel by armored car twice, and we were told that most luxury cars in Sao Paulo are bulletproofed for safety. The people we met, even those we hadn’t met before, were warm and welcoming, but just as important, energetic and ambitious. More than almost any other ecosystem I’ve visited, there was a Silicon Valley-like energy, but with Latin flair. I could hardly ask for a better experience—I was treated like a VIP, and since Jeff speaks Portuguese (the result of spending the better part of a year in Brazil while working for GE in the early 2000s), we didn’t have any problems getting around. I was told that Sao Paulo was Uber’s single largest city market, and it worked well for us, though apparently driver cancellations are an issue, and we dealt with several cancellations each day.

At the halfway point of the trip, Jeff and I flew to Florianopolis so that I could speak at the Startup Summit, and at Exact Network (the quarterly meeting of our friends at Exact Sales). Many people had told me that Florianopolis was beautiful, and they were certainly correct. Florianopolis is split between the mainland and Santa Catarina Island, with two bridges connecting the two halves of the city. At one point, I was told that if Sao Paulo was like New York (the biggest city, focused on business) and Rio was like Los Angeles (glamorous, but juxtaposing glitzy neighborhoods with wrenching poverty), then Florianopolis was more like the Bay Area: relaxed and tech-focused, with the nickname “Silicon Island.”

The city made a great first impression as soon as we landed. The Florianopolis airport is just a few years old, and was built and is operated by a Swiss corporation that brought a very Swiss sense of order and understated aesthetic appeal. It was nicer than any airport I’ve visited other than the mega airports in the Middle East (Doha and Dubai) where money is no object.

The Startup Summit folks put us up in the Intercity Florianopolis. While not quite as nice as the Canopy, the hotel provided everything we needed, and right around the corner was the Almazen Rita Maria, an old factory or warehouse that had been converted into an upscale space for restaurants and retail, that included a Starbucks and gourmet market as well. Jeff and I spent a lot of time over there, since my one complaint about the Intercity was that its WiFi network tended to be to slow to work effectively.

The Startup Summit took place at the convention center, which was probably about a kilometer away from the hotel as the crow flies, but required a longer drive to reach. The first order of business was a book signing, hosted by ACIF. I thoroughly enjoyed this—I rarely get to do large book signings, and it feels good to have a hundred people waiting in line to get your autograph and take a photo.

After the signing, it was time for me to deliver a keynote on Blitzscaling in Bear Markets to a packed audience of about 3,000 people. I think it narrowly became the largest in-person crowd for one of my keynotes, displacing INBOUND 2018 in Boston. The energy at the summit was palpable, with talks going on simultaneously all across the building. From there, I was whisked away to the Iate Clube (Yacht Club) for a cocktail party, before I turned in for bed. I needed the rest!

The next day, I split the time between the Startup Summit and Exact Network, the quarterly meeting for our friends at Exact Sales. We had been introduced to Exact Sales by Astella, who led their most recent round of funding. Exact’s founders, Theo and Felipe, had greeted me warmly at the Yacht Club the previous night. Now they were on their turf. The event was held at their office up the coast of the island, another nearly-new space with a common area where the event took place, and your choice of top restaurants on the grounds. My lunch was at—what else—a chic Italian restaurant! Once again, I spoke about Blitzscaling in a Bear Market, then we held a 30-minute Q&A. The Q&A was actually easier than the talk; since we were using simultaneous translation, I had to wait a few extra moments whenever I interacted with the audience; this was easier to manage during a structured Q&A. From there, it was time for a happy hour in Exact Sales’ actual offices, and back to the hotel for some more rest.

The following day was Saturday, and to thank us for coming to Brazil, Theo and Felipe picked us up at the hotel and drove us on a quick tour of the most important startup locations on the island, including the top incubation space (the equivalent of the famous Google/PayPal office on University Avenue). Then it was on to the home of their first investor Adonay, who was our gracious host for an incredible lunch with an even more incredible view, as you can see from the pictures below.

When it was finally time for dinner, we had trouble finding a place to sit at the now-packed Almazen Rita Maria (seriously, it must have been a major hot spot), but fortunately the guys from SaaSholic Ventures recognized me from the conference, and let us sit with them. After a fun evening, Jeff even exchanged logo jackets, kind of like professional athletes exchanging jerseys!

Sunday was a day of rest. We slept, worked, and slept some more, closing the week with, what else, a great Italian dinner at Almazen Rita Maria. We turned in early so that it was a little less painful to get up and take an Uber to the airport at 5:30 am for the long journey home. This time, we voluntarily checked in Jeff’s bag since he was transporting two bottles of wine from Adonay’s award-winning family winery, yet another generous gift from a welcoming people. I was pleased that I didn’t have to check any bags, even in Mexico City. It was a long 24 hour trip home, but we were bouyed by the memories of our awesome trip.