Working in Silicon Valley

Today was my last day at Skyscanner, and that ends a long and pivotal chapter of my life that started nine years ago. And this is the short story of how it played out.

It was raining when we landed on SFO; the date was March 21, 2011. My brother came to the airport to pick us up. He also had just moved to the US to work for Google the month before. So my wife and I slept the first night on his couch.

We arrived on a Saturday. On Sunday, we drove to Menlo Park to map the area where Gogobot’s office was. The contrast was so weird; we came from sunny and hot in Brazil to rainy and cold early spring in California. It felt strange. We parked the car and went for a stroll on Santa Cruz Ave downtown Menlo Park.

The air was eerie. The streets were empty. We checked the office and explored the area a bit and went back to our temp place in Santa Clara.

I remember going up the carpeted stairs on my first day—heart pounding. I got to the office, and Sharon (head of product) and Travis (CEO) greeted me. They asked about my flight and some other random stuff, and I did my best to answer in my broken English, but I got by.

Ori (CTO) introduced me to the rest of the team, and I got off to work setting up my dev environment, I was excited, scared, and overwhelmed, all at the same time. I was now working for a startup in Silicon Valley!

I could barely sleep the first night, my task for the day was to set up my laptop to run the stack which was Ruby on Rails and MySQL. I was getting all sorts of errors that I couldn’t figure out, so there I was on my first day already working after hours trying to impress my peers with no success.

The beginning was tough. Long days, pressure mounting, Ori breeding on my neck to deliver features while I was still battling with my English and doing my best to learn Ruby on Rails on the go as fast as I could. I had never worked so hard in my life up to that point. Every day I would get back home, have dinner and crash, the pace was insane, it was, heads down, day in day out.

Gogobot was founded in late 2010 by Travis Katz, a former MySpace exec and Ori Zaltzman, chief architect at Yahoo, serial entrepreneur, and adrenaline junkie. Travis, a travel fanatic, founded Gogobot to build a social travel app for like-minded travelers and to disrupt the travel industry and dinosaurs like TripAdvisor.

When I joined, Gogobot had already raised $4M in a Series A round, and in total, it raised over 40M dollars from top VC companies in the Valley in three rounds.

Also, in 2010 back in Brazil, I was toying with some ideas, and my girlfriend - now wife - teased me saying I should do something travel-related since we were getting ready to go on a two-month surf trip to California. On a random day while I was running, I had an idea for a travel app, something that was utterly different from what was out there back then. I knew I was into something and that I had to build it.

Mentaway was a travel journal powered by location tracking on third party services. Mentaway connected Foursquare and Facebook check-ins (it was huge back in the day), plus Instagram, Twitter, and Posterous (Medium predecessor) and combined everything into a neat Google maps with pins where you could document your trips and share with friends. It was revolutionary! (At least in my point of view).

Our little pet project got some traction, so we applied to Y Combinator but got rejected (although they end up funding a few startups with very similar ideas in the future). Still, luckily, Techcrunch took an interest in our project and wrote an article on it, and that was a game-changer!

After the article came out, we got VC’s pitching in, a few doors opened, and that’s how I got my foot in Silicon Valley.

The early days working for Gogobot were tough, the team was strong with engineers from Google, MySpace, Stanford. Everyone was friendly but also competitive; the pressure was on all the time. I was learning and giving my best, plus juggling with a new life in a new country and trying to figure everything out as I went.

When we moved to our first apartment, a one-bedroom in San Bruno, we didn’t have a single piece of furniture except for two plates, some utensils, and an air mattress for over a month, talk about being frugal!

Everything was different and exciting, we didn’t know shit, we had no credit and my only worry, to be honest, was not to get fired and go back home like a failure.

I’ve made all the mistakes in the book, like deploying on a Friday evening right before taking the train home to get a call from Ori half an hour later saying the site was down or from Travis that was testing something in the middle of the weekend. I still get chills just remembering seeing the words P0 in an email, every time that happened. It meant to drop everything you’re doing and fix whatever bug, ahh the good old days. It was intense, just like the cliche “move fast and break things.”

One time around 2012, I worked for 24h hours straight. Yes, that’s right, nonstop working fueled by Redbull to finish a feature that we would present at the F8 Facebook developers conference, it was wild, and I don’t recommend that to anyone for your health sake.

The days became months, and months became years. Things started to settle. We built a ton of cool stuff and had good momentum. The team grew. We raised a couple more rounds, moved to a bigger office, got featured numerous times in the media, and also by Google and Apple app stores, and I kept getting more and more responsibilities.

Around April 2013, our Green Card application got approved, we learned fast how the system works and applied precisely one year in our H1B, but things were far from easy and straightforward. I cold-called an immigration lawyer (recommended by someone from Google) several times until they finally put me through, and she agreed to take on our case. We had to work hard on it for months alongside her while managing my day job and Gogobot paying all the expenses.

Work continued to be fast-paced. The product grew to almost 5M users, with hundreds of thousands of reviews, millions of photos an award-winning iOS and Android apps. The team bonded; the culture was great. We had lots of fun in company events like kayak water polo, paintball, Halloween parties, karaoke, I would go snowboarding with Ori in Squaw and Mammoth. Still, there were signs that things were slowing down, the market was consolidating, and the wave of new travel startups was fading.

That’s when Travis, a savvy businessman, managed to pull off one of the most incredible deals I’ve ever seen, by somehow convincing Orbitz to transfer the coveted domain trip.com to us. It helps that Orbitz was owned by Expedia, which happened to be one of our investors, but everything started with a simple whois domain search. Talent is not enough. You gotta, hustle. That was around October 2015.

The moment we got trip.com, I knew our future was set. We wouldn’t go under not with that splashy domain name. It also helped that as soon we rebranded from gogobot.com to trip.com, we launched the product internationally in more than 13 languages. And just a little under two years after our rebranding, we were acquired by Skyscanner, a flight search engine leader in Europe and their parent company Ctrip from China, a giant with more than 20k employees.

Having an exit by being acquired or going IPO is the goal of any startup. It was my dream when I joined, and the reason why I refused so many other opportunities over the years. I wanted to experience the whole thing. To make it or break it. I wanted to live through the ups and downs.

The deal with Skyscanner was that we all had to stay one full year, aka golden handcuffs, to get our retention bonuses. They offered us another bonus for another 12 months for a total of two years so we could finish integrating our product into Skyscanner.

It wasn’t life-changing money. Still, it was generous enough to set me on the path of a possible early retirement if I don’t blow it. By the end of the second year around mid-2019, they announced they were going to close the office in Palo Alto, and they offered me another six months to keep helping them in the transition. I was the last man standing.

What a journey it has been. From moving to America, to working my butt off, having a daughter, buying a house, becoming a US citizen, and living the startup life in Silicon Valley, I couldn’t have imagined an outcome like this in a million years.

Of course, none of this would have happened without the immense support of my wife Gisele, my family, all the guys and gals from Gogobot (you know who you are). And especially Travis and Ori, for giving me this fantastic opportunity that I would be forever thankful.

So what’s next for me? First, I’ll take a month off to reset, and then I’ll be taking my chances in another early-stage startup and do this all over again. 🙌