Why I’m Leaving Google After Only 9 Months

Last week was my last at Google. I spent the past weekend reflecting on my time there with good friends at a small music festival in Mendocino, a gorgeous town in Northern California. The truth is, when I joined Google in october of 2013, I didn’t plan to stay more than 6 months. Google was a stepping stone for me — something I needed to see in my life in order to get where I wanted to go.

When I was in middle school, my mom would take me to Walmart each week to buy candy. I’d put 50 airheads and a slip of paper in a gallon ziplock bag and I’d walk to the bus stop to catch the school bus like all the other kids. But once I got on the bus I’d have a line of kids waiting for me, and I’d take out the bag of airheads and sell them for $.25c each. I’d do the same on the ride home. When I got home, I’d sit on the floor in my room and count my quarters — usually 4 or 5 times. This was my favorite part. Oh, the slip of paper was for IOU’s. I’d then go buy more candy with the money I had and put the rest away to save. I’d continue to find ways to provide people with value in exchange for money throughout the rest of my years in school and well beyond. Remember when selling burned CD’s was a thing? Yeah.

I’d enter college as a biology major with the ambition of becoming a doctor. But ‘being a doctor’ in my head went something like this: I‘d graduate med school, hire a bunch of other doctors and build what I envisioned to be a large, elaborate hospitable system. We’d create a ton of jobs, help a lot of people and make a lot of money doing it. That’s the short of it. About 6 months into my freshman year I learned of the word ‘entrepreneurship’ and everything changed.


Here I’d have one of the biggest revelations of my life to date: I had no interest in being a doctor. I wanted to build businesses. I was born to build businesses. Of course, building a successful, meaningful business is another story entirely. I’m working on that. 

I’d complete college with a Degree in Marketing, a minor in Computer Science and a certificate in Entrepreneurship. I’d start 3 different companies while in college, all utter financial failures but epic successes on every other level. The latest company of the three, Wordio, would take a toll on me. I’d experience the challenges of building a team, relying on investors’ money to survive, firing friends and divorcing a cofounder. I’d wholeheartedly question whether I was born to build businesses or if I was mistaken. But I knew I’d fail again in the future when even more was at stake. I knew I could make the world a better place. I wanted to create. I wanted to build the future. Once you find your purpose, failing 10 more times doesn’t seem to bother you. If that’s what it takes to succeed, then on with the show.

At this point I was knee-deep in the software/technology space and I wasn’t going anywhere. I was obsessed. But I began to question whether there was a smarter, more efficient way to learn than building and failing, building and failing. And although it was hard to swallow, I decided I needed to insert myself into someone else’s system, someone else’s business — one which was succeeding — to intimately understand how it worked.

I’d eventually join Josh Greenberg, Co-founder and CTO of Grooveshark and one of our advisors to Wordio, to lead talent acquisition and growth for Grooveshark.com. I’ll forever be indebted to Josh for giving me the opportunity. I’d end up seeing Grooveshark grow beyond 120 employees, become profitable, hire, fire, manage, lead and get sued for $17,000,000,000. Seventeen. Billion. Dollars. It was exhilarating and so fast paced that I was able to stomach 2 years of building someone else’s vision instead of mine. I knew this would make me a better entrepreneur in the long run.

I joined Google for this exact reason. I wanted to become a better entrepreneur. How can you build a world-changing company if you’ve never seen what one looks like from the inside? How it behaves… how it operates… how it thinks?

I joined Google to understand these things — to develop a perspective that ranged from a 0-10 person team at Wordio to over 100 at Grooveshark to 40,000 at Google. I wanted the full cross-section. I knew fitting in at Google would be a challenge but I needed to see it. I needed to understand it. And it was an enlightening experience. After just 9 months, I now think a little differently. And that will last me a lifetime.

Here are some things I came to Google to see — my ‘checklist’ of sorts. Once I felt I had these down, any more time spent would have diminishing returns. Besides, serendipity struck right about the time I crossed the very last item off the list:

1) Data

No decision is made at Google based on opinion or gut feeling. This holds true all the way up the food chain. Anyone, regardless of seniority, can get sign-off on a project if there’s data to support it. This eliminates a lot of bureaucracy found in comparatively large companies. I now have some of Google’s data-driven DNA and I’m thankful for that. However, when building a company from ground zero there are countless instances where you have to rely on your instinct. Finding the balance is key.

2) Leadership and management

Once a company gets to a certain size (measured by employee count), the leadership influence you get exposed to is directly correlated with the leadership abilities of those you report to. Being closer to the bottom of the org chart than the top, I didn’t see great leadership up close but I did see it from afar. The line between leadership and management becomes blurred in large companies. Also, I now understand why middle-level management gets such a bad rap. Seeing it from the trenches will help me avoid it in the future.

3) The science of hiring

With a background in technical recruiting and hiring, I was very anxious to learn the science behind Google’s hiring process. Once the curtain was lifted though, I was surprised to learn there simply wasn’t much of it. Google has many of the same problems hiring as many other companies, the problems just happen to be larger since Google hires at enormous scale. This was enlightening to me as I’m very interested in attacking some of the problems in the hiring/recruiting space in the future.

4) Process and structure

When building a startup from ground up, process and structure can be toxic — even deadly. But once there’s a certain number of moving parts, a bit of process and structure becomes integral. I hadn’t seen or understood what this looks like. Grooveshark was the biggest company I had ever worked for and at best we were an organized mess. All startups are. Seeing how a company like Google keeps things in order was fascinating. I now know what process and structure looks like and how to determine when it’s needed.

5) Communication and negotiation

The only time problems ever arise is when there is a lack of communication. There’s truly no such thing as over communicating. Communicating within a large organization is especially tough because (usually) the more people you know and work with, the less you know each one. This means making the extra effort to make sure you’re on the same page with the people you’re communicating with. As part of Google’s negotiation training, I was introduced to one of my late favorite books, Getting More. It may seem obvious, but life is one continuous negotiation. Whether you’re trying to get a lunch meeting with someone you can learn from or trying to get your kids to clean their room, you’re always negotiating. It’s the way you communicate that determines the outcomes of these negotiations.

6) Network

I jokingly told many of my friends the reason I was joining Google was to become an ex-Googler. That was partly true. One of the reasons for this is pedigree. And along with the pedigree you gain access to ~40,000 incredibly smart people. People with whom you build relationships that will last much longer than your tenure at the company. This was my main goal when I joined the company - I went banging down plenty of doors. I made sure to build relationships that will carry with me into the future as I begin my next entrepreneurial journey. 

I gained a lot in my time at Google and I’m incredibly grateful for the opportunity to spend time with each and every person I met along the way. A couple months ago the stars began to align for me and I knew it was time for my next journey. The truth is though, that it’s scary for me. It’s been 3 years since I’ve worked full time on my own company and the unknown brings fear. Google was a place my friends and family were proud I was at, where there was no risk and plenty of financial security. There were many types of pressure, social definitely being one of them. But the only thing that will guarantee myself failure is to not try.

Because of this, I believe that it was more risky not to leave and try to build my dreams. So that’s where I’m heading — to build my dreams.

5 Lessons Learned at 25

1. Life is a marathon, not a sprint

Growing up, it was so easy to get lost doing the things I knew other people would approve of. This is human nature. I’ve realized that the hardest things to do in life are the ones that are best for you in the long run rather than the ones that are easily accepted in the short run. It’s too easy to get caught up in doing what society wants from you — it’s a lot harder to overcome this and accomplish what you want for you. If you can truly accept this and put it fully into practice, you can accomplish anything.

2. Success = sacrifice

There are so many things I want to do in life — but there’s such a short amount of time to do them. This is sad and beautiful at the same time because it makes me prioritize the things in life that really matter to me. If you really want to accomplish something big, you have to sacrifice a lot of the things you want just a little. This is a reality of life. The quicker we’re able to accept the realities of life, the quicker we’re able to navigate them and begin to use them to our advantage. It’s not easy to put aside things like entertainment, sports, leisure. I work hard to sacrifice these things because I know they won’t help me achieve my goals. Sometimes the smallest sacrifices have the biggest impact.

3. Never chase the money

I’ve learned over the last few years that chasing the money always leads me away from happiness. I always thought that money would make me happy because that’s what society led me to believe. As you get closer to having the money you want, you realize that you’re often farther away from accomplishing your real goals (which for me is impacting a lot of people). Accomplishing our real goals is what leads us to true happiness. The most financially successful people I know have one consistent thing in common — none of them ever chased the money. They chased what they loved and the money they earned was the side effect of being really great at that one thing. I think everyone begins to understand this more as they age. I’m working to understand this the best I can now so I have more time to be happy and enjoy my life.

4. You are who you hang out with

I heard this quote years ago and it stuck:

“If you’re the smartest one in the room, you’re in the wrong room.”

I never thought I was the smartest one in the room but this made me realize I need to make an effort to surround myself with people who are much smarter than me. I slowly started gravitating towards the people and situations I knew I can learn from. It was really hard to accept that I was mostly powerless in these situations, acting as a sponge rather than a firehose. But slowly I realized how much this helped me grow. To this day I strive to surround myself with only the people I can learn from — even if it’s one little thing. This is the only way I know how to grow.

5. Focus less on accomplishments, focus more on you

After lots of resistance and hesitation I had a revelation. The only common denominator across all of life’s situations is me — myself. I am the one thing that every event in my life will have in common. Therefore, I need to work on bettering myself in order to better the outcome of future events. I’ve always been goal oriented and accomplishments focused, but the realization here is that by working on myself and making myself a better person each day, I will accomplish much more in the end.

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I just didn’t know

At 22 I joined a startup to get as much exposure to different functions as possible. The idea was to work along side many different teams - and by along side I mean literally next to - so I can hear the conversations, understand the day to day, and really learn what it was that I had an affinity towards. This allowed me to rule out 90% of what I thought I might be interested in and focus on moving toward the 10% that I actually was interested in. If you have no idea what you want to do then I highly recommend optimizing your strategy for exposure: the goal should be to expose yourself to as many people with different backgrounds and focus areas as you can. I was able to realize the things I was both good at and interested in, and ultimately find the functions of business that allowed me to express both.