For as long as I can remember, I wanted to work at Google. I remember applying for Google’s APMM program as a graduating senior and getting rejected. It sucked, but I got over it. After graduation, I took a gig at Abercrombie corporate as a merchant, which in retail, is essentially nagger in chief. My job was to ensure everything for my product line (Hollister shorts, pants, swim) made it to stores in time for the seasonal launch (i.e. B2S aka Back-to-School).

Abercrombie & Fitch Campus

Abercrombie & Fitch Campus

In my 2.5 years there, I learned some not so useful things like the difference between
egg white vs. off white or how fabrics can emote feelings like happy and moody. I also learned a bunch of cool stuff like managing vendors in Asia and the Middle East, as well as weathering the 2008 recession through cost-cutting and pricing strategy (a term here which means bumping retail prices and then marking it down X%). Oh and I also met some really awesome people, many of whom I still keep in touch with today. And yes, working at Abercrombie corporate was a bit cultish (more to come about that in a future post).

But Ohio and retail were never long-term in my mind, so I left in 2010. Despite knowing almost no-one in California, I decided to take the leap and move out there because 1. that’s where all the tech was happening, 2. I imagined everyone there looked like the cast of the O.C. and 3. I had dreams of surfing every morning before work (also influenced by the O.C.)

Only 1 out of the 3 was true.

California, Expectation vs. Reality

California, Expectation vs. Reality

Turns out California is not just one big episode of the O.C. At least not San Francisco. If Silicon Valley had been on TV at that time, my expectations might have been a bit more in line with reality.

I joined eBay’s IM (Internet Marketing) team. I learned how to do marketing (liberal arts major in college) and got to work on some kick-ass projects in places like Buenos Aires, Barcelona, London and Zurich. I was part of one of the highest performing teams (to-this-day) which taught me no matter the project or company, surrounding yourself with passionate, brilliant people will always result in something great.

But after 1.5 years, the itch was still there from college. And it was growing. The itch to work for the company down the street (OK, technically a few neighborhoods over, but you get it).

I joined Google in the fall of 2011 and was there for about 4 years. It was fantastic and I learned so much. How to build a great product. Focusing on the user. Always thinking about 10X’ing something (Google term for thinking REALLY BIG impact). [Read about Google’s 9 principles of innovation].

I helped grow Google Engage for Agencies (now Google Partners) into one of the biggest revenue programs in North + South America. I launched Google Fiber for Small Businesses across a buncha cities in the U.S to help SMB owners pay less, get more, and work faster. I traveled to London, Dublin, Tokyo, New York, Paris, Mexico City, Toronto, and even Disney World and worked with + learned from some of the most brilliant minds along the way. But after about 4 years of Google and living in the Silicon Valley bubble, another itch had emerged. The startup itch.

Startup vs Corporate

Startup vs Corporate

As a wise mentor once told me, you join an
established company like Google, Facebook, Apple so they can invest in your development. You join a startup when you’re ready to invest in the company. There was still so much I didn’t know, but I felt as ready as I’d ever be to leave the comfort and safety net of Google.

In 2015, I scratched that itch and left Google. [I also moved across the country to NYC]. My friends were like wtf. My parents were like WTFFFF. For the right reasons of course. From the outside, Google seems like the paradise of workplaces. Sure, there’s a ton of amazing free food, and you get to work on revolutionary things like virtual reality and self-driving cars. But at the end of the day, it’s still a 60,000+ employee company that’s spent years building its brand. Because of that, they needed a buncha processes and complex approval chains, which after 4 years, became a bit suffocating. I was ready to move fast and break things.

Facebook Mantras

Facebook Mantras

On Monday, June 15, 2015, I joined DoorDash, a food delivery startup looking to take on giants like Seamless / GrubHub and I remember that day because it was the day we launched DoorDash in Manhattan. It was also the day we got a C&D (cease & desist) from Chipotle. I was out in Palo Alto at the time for on-boarding and was cc’d into an email chain about the NYC local team launching a $5 Chipotle burrito promotion, without permission from the brand. The order volume was
amazing that day, but it also set the scene for a hilarious, dysfunctional sales process with them in the ensuing months. But this was the kind of stuff I wanted – move fast and break things. Ask for forgiveness, not permission.

Over the next 14 months, I learned so much about building a business from the ground up. [I also aged about 14 years]. At Google, I learned how to build a great product, but not a great business. Google’s bankroll on incubating businesses meant lots of resources to make a product great. But it also meant a lack of opportunity cost and trade-offs of profitability vs. viability.  Suffice it to say, my time at DoorDash was the year where I grew the most professionally – 1 year there felt like 4 years at Google, on steroids.

But launching and growing a business in a competitive market took it’s toll. After over a year, I was completely burnt out, and needed a break. It was one of the hardest decisions I’ve ever made – leaving behind a business and team I’d spent the past year building. I reckon building a business is a bit similar to raising a kid. After my last day at work, I went home and slept for 16 hours. I woke up, ate, and slept for another 16 hours. It’s funny how your body keeps a running tab on you.

I went to Hawaii, my happy place. I surfed a bunch. I came back. I decided I wasn’t ready to start working again, so I packed my bags again and left for Europe. It was my first solo backpacking experience. I packed everything into a 40L backpack and hit up 20 cities along Europe’s southern coast and the Middle East. Top 3: Tel Aviv, Cinque Terre, and Ibiza. In that order.

There’s a nice quote from Timothy Bertrand on why we travel:

In front of me are copies of Herman Melville’s Moby Dick, Tolkien’s The Hobbit, and Homer’s epic poem The Odyssey (the wonderfully condensed Samuel Butler translation, if you’re wondering). All three are hailed as landmark pieces of literature, and all three share a common theme: travel. The hero’s journey, known in literary circles as the monomyth, is a narrative technique ubiquitous across storytelling traditions. A hero must leave behind all that is familiar, all that is safe, wherever or whatever they call home, and venture into the unfamiliar.

It’s easy to see why this theme has been so successful in fiction. When Bilbo sets off with the company of dwarves, he sheds the daily monotony of the Shire—and how many of us fantasize about doing just that? It resonates with something inside us, a gut feeling that we are the heroes of our own stories. We crave danger as much as we fear it, if only to look back on a life well-lived. But adventures are few and far between in the real world. There are relatively few of us who do it for a living, and even then—adventuring full time is a slightly more nuanced exercise than we’d find in the pages of Melville, Tolkien, or Homer.

And that’s where travel comes in. It’s the one element of the monomyth we can successfully replicate. There may be no gold-hoarding dragons, or obsessive ship captains, or wine-loving cyclopes—but they aren’t needed. In the real world, travel alone suffices. To leave behind that which is familiar is to challenge oneself, and meeting that challenge is all the adventure we’re likely to need.”

I had an amazing 6 weeks abroad and I was ready to come home. And that brings me to the present. A few weeks after returning, I accepted an offer to work at a startup in the HR software space called Justworks. They’re a pretty cool company trying to make HR easier and simpler for SMB’s so they can focus their time on more important things, like their business and their team. The people are stellar – like genuinely amazing human beings. The first 3 months have flown by and I’m excited for what’s to come.