This is a story about company stages, skill sets and workplace environment. While at Oracle I even answered this question on a
Quora / Forbes forum as it’s a thematic curiosity most have about career choices.
Startup vs. Corporate
One thing that became clear to me and my closest conspirators while we spent nearly three years at Oracle after the
Dyn acquisition was that as much as some of us tried to fit in, we didn’t. Looking back, I certainly, was a fish out of water or a fish simply in the wrong body of water.
In many situations over my three-year tenure, I was an obvious outcast living in a distant world of modus operandi between entrepreneur and large company executive. It felt many days like The Seinfeld episode
‘Bizarro World’ where myself and my teams were in business situations, but simply skewed from the environments we had grown accustomed to. I often had out of body experiences where I’d be talking and wondering what the audience thought of me in the context they saw me in. How did I view myself? It was unnatural, but like entrepreneurs do, we persevere to learn, expand our horizons, network, do our jobs, and make a dent.
In actuality, this reality was the precise point and exactly as intended for both willing parties. I was a pawn — or cruise missile or samurai warrior as my bosses Thomas Kurian and Don Johnson would say — in the corporate game for Oracle to become and look more modern, younger, more innovative, more disruptive, more startup, cloud, developer and entrepreneur friendly. That is why M&A’s become “strategic” M&A’s. I wasn’t alone by any means in this effort. It’s a multi-front, multi-year, existential crusade for $ORCL.
This is also just what happens to executives from acquired assets. They are on borrowed time and will be leveraged. That’s a two way street. You need wide open eyes to this reality when you sell your business. I also took full advantage of the unique opportunity to learn, network, grow and mature. While employed by Big Red, I was on every stage and in every media or analyst interview I could find. I evolved, matured myself, and represented change. Change is a good thing for individuals and companies. I relished it and went all in and while it was great while it lasted for both, it was clearly a short lived experiment in the long game of both my career and obviously of an institution like Oracle. For some acquired talent it works, for most in leadership it simply does not and can not. People like me come and go.
Every meeting room I walked into, every stage I spoke on, every interview I did, it was quite clear I was “different” and was that fish out of water. It actually became a part of my schtick. If I acknowledged it upfront, then it was out of the way and we could proceed as normal. I embraced it wholeheartedly, but it was palpably obvious on each interface. I’d sit on panels and folks would talk about their tenure there, 35 years, 32 years…
3 years and I was acquired. Being acquired has a stigma (not good or bad, just a stigma) in established juggernauts like Oracle. The same was true in internal meetings. “Who does this guy think he is? It’s our product or company he’s referring to!” You’re just not the same as a new hire (chosen by said staples) from like company or a lifer. Especially in executive settings as it’s clear to those in the acquiring badge, you made some meaningful money out of their coffers. They wonder “why are you here?”
The Suit
Beyond tenure, DNA, pride and bank account envy, it was also the suits. Literally and figuratively. When I would get dressed for an event or a trip to Redwood Shores, I would grow annoyed on my journey to the rarely used parts of my closet. Nothing was ever ironed, dry cleaned and my Himalayan and Siamese cats are the arch enemy of suits. My peers, this was their daily attire. Their uniform. The degrees, the MBAs, the certifications, the big company logos on their resumes. I lacked them all and their eyes reminded me of that. They wouldn’t be so foolish to own fancy cats or shedding pets. That’s a naive entrepreneur move.
Entrepreneurs are known for hoodies, afterall.
I don’t write this to knock one career track or person or culture in favor of another — although I’ve seen both sides and have
my pick. For some, the large company is for them. I write this to ensure that you understand your role in the environment you’re in, even if just for a time, and embrace it to the max. Never be inauthentic or lose your genuineness. When you’re plugged in a situation or a meeting or a company and it’s different, don’t contrive, evolve and be unique. That’s your competitive edge and also your challenge to overcome and thrive within!
I promise, if you embrace every day, you will always find your way back home… true north is true you. Find it. As I always say, play the long game and be loyal… oh, and know what and where and which environment is built for you! Startup vs. Corporate. I’m at home with York IE.
Kyle York
