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Sometimes you just need to take a leap of faith

The story of how I went from Microsoft to Amazon in 2009

A few days ago, I had been contemplating life choices from my lovely private corner office at Microsoft, in impeccable, upscale Redmond, Washington. Like every day for the last 11 years, I had driven my Mercedes S-500 with heated seats gently massaging my back, listening to classical music and sipping on a perfect latte. This morning though, I was meandering around homeless tents and garbage on the street, trying not to step on heroin syringes. Jackson and 5th was definitely a rough part of downtown Seattle. I had taken the 358 bus line, a grimy milk-run that stopped every other block on Aurora, filled with prostitutes, drug addicts and people getting in fist (and knife) fights. I finally made it to Amazon. The building inside was dingy, claustrophobic, with flickering fluorescent lights. Depressing rows and rows of desks right next to each other. It felt like that office scene from Joe vs. the Volcano. I took a sharp breath. Don’t judge a book by its cover, I said to myself, look beyond this. I had deliberately chosen this path, although on that particular day, I very much had second thoughts.

It was April 6, 2009. To understand how I got there, I’ll take you back to December 31st, 2008. Every New Year’s eve I do some soul searching and reflect on where I’ve been and where I’m going. I had been progressively unhappier at Microsoft for a number of reasons. I decided I needed a change. I polished off my resume and sent it to Google and Amazon. Within a week, I had lined up interviews with both. Interviews with both Google and Amazon went well, so I ended up sitting on offers from both. I had a choice to make.

Google was definitely my top choice. In 2009, it was anybody’s top choice. It consistently ranked as the best company to work for. My experience interviewing in their Kirkland office had been awesome. Everybody I spoke with was nice and crazy smart. The benefits were amazing. The office was beautiful, with perks everywhere, bright colors and big spaces. The company was going places. There was so much to like.

My experience with Amazon couldn’t have been more different. The office was dingy. The bus to get to the office was dingy. The perks were non-existent. It was, from beginning to end, a lackluster experience. Even my friend, who had worked at Amazon for 3 years, told me point blank I was going to hate it.

So, I went with Amazon.

This is the point where you pause and do a double-take, thinking is this guy an idiot?

Maybe… it certainly was the unexpected choice. But I carefully thought about this for weeks before I made up my mind, and I knew, for me, it was the right choice at the time.

There was a personal reason for my choice.

I was coming from a long stasis at Microsoft. I had gotten comfortable and lazy and complacent and my career had stalled. Google was so awesome, so comfortable, I could see myself falling in the same behavioral patterns that I was trying to shake off. It wasn’t going to be Google’s fault, it was mine. On the other hand, Amazon seemed to not be a place I was going to fall in love with. I figured I’ll work here for a few years, focus hands-down on learning, delivery and proving myself again, then I’ll go to Google. It will be easy to leave Amazon, because, well, because I’m going to hate working there!

I couldn’t have been more wrong. I ended up falling in love with Amazon and spending 11 years, 3 months there. The only thing I got right was: I did end up going to Google, but in 2020.

There were also other reasons for my choice.

In 2009, I could see the Cloud was going to be a Thing. Microsoft didn’t, and it was about to miss the boat (it has taken years for Azure to catch up). Google too (GCP is still catching up). But Amazon saw it. AWS was essentially a tiny little Amazon startup in 2009, but I knew it was going to change the world. If I didn’t join when I joined, I was going to regret it. I had to be a part of it. This sort of opportunity doesn’t come often in a lifetime. Their future inspired me. The sheer determination and purpose with which people worked made an impression on me.

But it was a huge leap of faith… Amazon was a very different company in 2009 from what it is in 2021. Today, Amazon is everywhere, with retail, cloud, devices. It’s flirting with a 2 trillion dollar market cap. It has over 50,000 engineers. It is innovative and it has changed the world in so many ways. Benefits are actually competitive. But in 2009…Amazon was one of many retail websites that sold books and a few more things, with a relatively small team focused on Cloud. It only had 3000 engineers, which was a huge step down from working in a 100,000 engineer behemoth like Microsoft. It had a market cap of 20 billion dollars, not bad, but it had barely survived the dot com bust and didn’t have a particularly great track record of profits. Analysts consistently predicted it to go under, time and time again. Yet Jeff Bezos ignored them and kept chugging along on his vision, patiently and stubbornly. I was intrigued.

So, I joined AWS in early 2009. My first team was a 2-pizza team that eventually grew to become AWS Cloudwatch, AWS Elastic Load Balancer and AWS Auto Scaling. Today, each one of these products is supported by hundreds and hundreds of engineers and makes millions. But back then it was just a few guys in a conference room. My second job there was another 2-pizza team that released the very first version of Amazon Relational Databases Services (RDS). I remember vividly discussing the API that RDS was going to have! That org alone today is thousands of engineers and also makes millions. I’m proud I was there at their birth.

The growth of AWS (and Amazon) I got to be a part of between 2009 and 2020 was vertiginous.

But there were, oh-so-many-times, particularly in 2009, that I wondered what the hell have I done?

I had many adventures on the 358 bus (today’s E-line) that got me downtown every morning. It certainly was not glamorous. One day two guys right next to me started a fist fight over a drug deal, and eventually one pulled a knife and sank it into the other’s abdomen. The bus driver stopped the bus and screamed at both of them to get off his bus, one guy, literally half dead. They continued their fight on the sidewalk as our bus pulled away. Annoyed with the pool of blood on the seat, the driver grabbed some paper towels and wiped it off. Just another day on the 358. I very quickly learned to not make eye contact with anybody on that bus. I would just sit down, open up my laptop and focus on work for my 45-minute ride. It certainly was a step down from the comfort of my S-class Mercedes and the butt-massages from its warm leather seat. Daily, I had offers for cocaine, or fellatio. But driving to downtown during rush hour was painful and parking downtown was expensive, plus I took some amount of pride in being carbon-friendly and riding public transport instead of driving my gas guzzler, so I rode that bus for 11 years.

Surviving the bus was the first of many challenges. Amazon’s buildings (named US1 and US2) were located in a seedy part of town, surrounded by homeless. There was often people defecating right outside the building. The smell of (human?) urine on the façade welcomed me to the building every morning. I made it a point to leave before dark.

I cannot understate what a shock it all was for me, coming from over a decade working at Microsoft in an upscale suburb. It opened my eyes though. I had been living in a bubble of upper-middle class America, my only friends being other microsofties comfortably in six-figures. Downtown Seattle was a melting pot of cultures with a vast range of income and life conditions. I had been so naive in my little bubble. This was real, raw life.

US2 was right next to Chinatown, so I had 30 great Chinese restaurants to choose from for lunch within a 4 block radius. Around that time, some Amazon guys started a blog to rate all the restaurants in the district, called msg150 — it was our culinary guide to exploring Chinatown every lunch break.

This is where my Amazon adventure started

Occasionally, the retail site had surplus they needed to get rid of asap, so they would dump a bunch of unwanted crap right in the lobby and you could just help yourself. I ended up with a ton of obscure CDs of music I had never heard before.

A year later, I moved offices from US2 to PacMed, about a mile south, in Beacon Hill. PacMed was a 1932 Art Deco monstrosity that had been a hospital for a long time before Amazon chose it as its headquarters for some odd reason. It certainly had character.

PacMed! Amazon’s headquarters in the old days

PacMed was quirky and also not particularly glamorous. My tiny office (that I shared with one more guy) had been a VA hospital room for fifty years, and it still felt and looked that way. Many patients had died in that building over the decades, and the building was rumored to be haunted by the ghosts of some of them… nobody wanted to work there late at night. I occasionally felt the hairs in the back of my neck stand up for an unexplained reason.

It was quirky in other ways too. The very first thing that you saw when you entered the building was a prehistoric Ice Age cave bear skeleton purchased by Jeff Bezos from Amazon Auctions. It was Jeff’s peculiar way to remind us that it’s okay to experiment and fail for the sake of innovation: although Auctions resulted in a failed venture, it later led to the success of Amazon Marketplace. The skeleton now lives in the Van Vorst building in the Amazon SLU campus.

Jeff Bezos’ prehistoric Ice Age cave bear skeleton greeted us every morning!

Amazon was so miserably cheap back then. It didn’t pretend not to be, which I appreciated: they were frugal and they embraced it and were very upfront and proud. The benefits were bare bones. Perks were non-existent. When I got back from my first business trip, there was a huge taxi line at Seatac International Airport and I had been flying for 17 hours on Economy back from Eastern Europe, so I decided to take a towncar back, which was $70 instead of a $50 taxi. My manager rejected my expense report — “you should have taken the bus for $3” was his comment. You got one, and only one, 19" monitor. This was a six-figure job, and they were nickel-and-diming us over a $200 second monitor that could increase our productivity significantly. But we quickly learned how to game the system: you hosted an intern during the summer, and then, you could keep the intern’s monitor as your second monitor! Attrition also meant you had to quickly snatch up that monitor the minute your co-worker left the building, before helpdesk could come and get it back. We even developed a waitlist among team members for who got the monitors we could scrounge up. It became a game.

Amazon is an entirely different company today, miles away from those humble beginnings. The SLU campus is actually very nice. The benefits today are surprisingly good, including, yes, perks such as multiple large monitors. I don’t think I would have ever, remotely imagined, in 2009, as I walked past the crack addicts pooping outside the rundown offices, that someday Amazon would build a mini rainforest in futuristic spheres in a billion-dollar campus.

Amazon 2020… a different world!

Yet, when I think about those early days, I always smile. Amazon was certainly not a clear choice for employer in 2009. It was ridiculously frugal, the offices were awful, the location was awful and the benefits were awful. If I was just judging my future based on appearances, or short-term benefit to me, I would have ran away from Amazon in a second. But there was always something under the surface, pulling me strongly to stay. I’m glad I did. Amazon super-charged my career. I wanted to build something meaningful, that impacted society at large, and I was willing to take a leap of faith to be a part of it. The determination and passion of other amazonians around me inspired me. The environment was intense, but that energized me.

Before you feel too sorry for me and my bare-bones benefits, I did just fine, with the stock the company gave me growing ~100x from $40 to $3700 in a decade, and several promotions all the way to Principal Engineer. I’m 45 and I could retire if I wanted to. I built some things I’m very proud of. And I left a mark in the company.

Work Hard, Have Fun, Make History.

And, don’t judge a book by its cover.

Amazon yellow-border badge at 5 years, red-border badge at 10 years



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Carlos Arguelles

Carlos Arguelles

Hi! I'm a Senior Staff Engineer at Google. Prior to Google, I spent 11+ years at Amazon. And prior to Amazon, I spent 11+ years at Microsoft.