Things learned about success from a random narcissist in Silicon Valley

June 11, 2019

Things learned about success from a random narcissist in Silicon Valley

I recently had the pleasure of working with a narcissist. I’ll call him Michael (after everyone’s favorite narcissist Michael Scott, of The Office). While we ultimately had to part ways in the interest of preserving mental health, I learned a lot from him.


Michael never revealed to me that he was a narcissist — but identifying that became easy once I started actively paying attention to his behaviors, whims, promises, etc.

When asked about his life story, Michael had a crazy story to tell. He dropped out of college due to the stress of his parents not believe in his abilities. This led to him getting addicted to video games. Through hard work and will, he managed to claw his way to graduating from a 4 year college. He was surprised when he got offered a job at a top tech company. At some point, his manager told him he wasn’t doing a great job. He disagreed. He told his manager that he wanted to pursue his own startup. His manager told him he wasn’t ready. He hated it when people made assumptions about him and didn’t believe in him.

Michael showed up to the office early and left late. He loved being the first person in the office and the last one out. It was the perfect way to show his dedication to the company that he loved. He loved bringing up that one amazing week that he woke up extra early every day. He was incredibly productive. Everyone should try it sometime, he urged.

Michael loved the idea of having a shared apartment/office for the whole team. He was convinced that it was the key to a great startup experience. When asked about what concrete benefits it would have for our specific business, he had difficulty articulating how amazing it would be. When questioned about respecting work/life boundaries, he had difficulty understanding why people had trouble committing to the company in this way.

Michael always had an opinion and feedback to give. He had so many opinions on so many different things, that he hardly had time to work on his own deliverables. But that was okay, because his feedback was important and valuable and could potentially be a game changer. It’d be a shame if he never got a chance to give it. Michael would always say that one of his best traits was his ability to give feedback and criticism. He was so good at it, in fact, that he was surprised when some people didn’t appreciate what he had to say. That confused him sometimes.

Sometimes, Michael’s voracious appetite for giving feedback left him with little time to spend on his own work. He was unreliable on his deliverables, but Michael always had a good reason for that. He was focused on helping his teammates succeed — after all, he aimed to do the best thing for the company and if he could prevent someone from making a mistake, he wanted to do that.

Other times, someone would call Michael out for the low quality of his work. Michael believed, however, that if everyone reciprocated his willingness to sacrifice his own time to give his teammates feedback and to “collaborate”, his work would have been better. Things seemed so unfair. His teammates weren’t great team players.

Michael loved being the center of attention. In every celebration of a team achievement, he wanted to make sure everybody knew of his contributions. After all, without Michael, the team wouldn’t have struck goal.

The best way to ensure this was to first to make sure no one else was going to recognize him first. Then, if there was a lull in the celebration it was Michael’s time to shine.

"Hey everyone, I'm so glad I was browsing the web that one time and landed upon that one piece of content. After reading it, I knew we should pursue talking to the author. Because of that our sales team reached out to that one talent agency that led to multiple meetings over the course of a month that landed that contract. I should browse the web more, right?"

Michael made big bets — because making big bets was exciting. Exciting ideas got other people excited, and that was a great feeling. How would we make the big bet worth it? It doesn’t matter — he’d find someone who could figure it out later. He just needed to be the idea guy.

When people on the team expressed their concerns about Michael’s actions (usually some sort of disappointment) with Michael he mostly just nodded. It was a quick way to end the conversation without offending anyone and gave off the impression that he was really accepting and appreciative of advice. When things didn’t approve, and the conversations became fueled by frustration and anger, Michael showed his true colors. He wrangled with his rationalization on why he wasn’t the problem. “I don’t lowball people, I’m just focused on saving money. I know he showed me the math behind what he thought was a fair salary. I definitely didn’t short change him. If he’s surprised with the low amount showing up on his paychecks, then it’s his fault for misunderstanding me.”


Michael crafted and recrafted his backstory until it was something that other people could believe and admire. The more other people responded well to it, the more it replaced his actual reality. His story last year was that he picked himself up and forced himself towards success, all on his own. People doubted him every step of the way and he proved them wrong. I later found out that his parents covered 4 years of room and board at a private university and even found a family friend to put in a referral for the job. He was incredibly unappreciative of that, stating quite simply that he got to where was on his own despite the folks who didn’t believe in him. He even blamed his parents for his dropping out the first time he attempted college. Acknowledging the help he had from his privilege would shatter his understanding of his identity and his successes.

He never got an official diagnosis for Narcissistic Personality Disorder but after 8 months of working with him, it became entirely believable to me that he was one.

The American Psychiatric Association uses the DSM-V (Diagnostic and Statistical Manual of Mental Disorders) to diagnose and classify mental disorders. While it’s use is controversial in some circles, its contents stands on top of decades of research dating back over over half a century.

Here is the diagnostic criteria for Narcissistic Personality Disorder:

  • A pervasive pattern of grandiosity (in fantasy or behavior), need for admiration, and lack of empathy, beginning by early adulthood and present in a variety of contexts, as indicated by five (or more) of the following.

    • Has a grandiose sense of self-importance(e.g. exaggerates achievements and talents, expects to be recognized as superior without commensurate achievements)
    • Is preoccupied with fantasies of unlimited succeed, power, brilliance, beauty, or ideal love.
    • Believes that he or she is “special” and unique and can only be understood by, or should associate with, other special or high-status people (or institutions).
    • Requires excessive admiration
    • Has a sense of entitlement (i.e., unreasonable expectations of especially favorable treatment or automatic compliance with his or her expectations).
    • Is interpersonally exploitative (i.e., takes advantage of others to achieve his or her own ends)
    • Lacks empathy: is unwilling to recognize or identify with the feelings and needs of others
    • Is often envious of others or believes that others are envious of him or her
    • Shows arrogant, haughty behaviors or adttitudes

Yes, Michael fits into this diagnosis easily no question. Someone else who had worked with him who saw these words for the first time said that if this was a checklist, he checked all the boxes.

Closing Thoughts

I had no idea that I’d be signing up to work with a narcissist when I first met Michael. I got to hang out with him briefly in casual settings like a restaurant, cafe, and bar and he was extremely charming and confident. He told his story with an underlying humbleness that drew people in. His vision for the company he wanted to build was grand. Experience A for Market X was going to be vastly improved. People were going to love it, and this needed to exist soon. This was potentially a trillion dollar opportunity. It was practically there.

After a couple of months of chatting with him and seeing how many other people seemed to get charmed by him, I was enamored by him. He was so different from me, and it seemed like a ton of people liked him. I was convinced that starting a company with him was a good idea.

It turns out that this is something that is common amongst narcissists. First impressions are always positive — they seem incredibly charming and radiant. I hypothesize that this is the result of constantly requiring positive attention to feel at peace.

Later on however, as we got into the weeds, it became clear that Michael wasn’t a team player. He’d make promises, and then back out of them. He’d claim responsibility for things that went well, and deny accountability for things that didn’t. He’d use my words against me, often times repeating the same words and phrases that I’d use to support his case. He’d begrudgingly tell me that my strategic analysis made sense, and that he couldn’t poke holes in it, but for some reason he couldn’t explain, he didn’t like it. He went along with it, and when it started working, he did two things:

  1. Wanted to claim credit for the things that were working. “I put this team together! Of course this would work! I’m a 4 million dollar man!”
  2. Sat back and relaxed while the rest of us made sacrifices and worked diligently to capture the momentum of our success

Today Michael has a girlfriend, and is trying to build another team around him. On one hand, I want to warn them of Michael’s destructive path, but on the other hand, maybe Michael is entitled to having just that.

I learned from Michael that it was possible to sell people on a grand vision that he didn’t even have any idea on how to achieve. From a certain perspective, I learned a very hard lesson about finding the right person to work with — but from another, I learned that being somewhat grandiose, charming, and purposefully oblivious to reality can be an effective way to start a team around an idea. You don’t need to have everything else figured out to get started.

Written by Lewis Chung. Founder @ ShopWith. Previously: Coursera, Amazon. Writes about technology, products, and life.