Rejected By Silicon Valley — What It Means

Tim Denning spent nine months trying to land a dream job in Silicon Valley and got nowhere. Maybe its just as well. Here’s what he learned along the way.

by Tim Denning in The Start-up on March 12, 2019

Prior to wanting to work for one of these tech companies, I’d worked with many of them over a three year period. I visited their offices in San Fran, went to their events, met with their people and became immersed in why the valley has become what it is today.

Last year, I spent a chunk of my career chasing positions at Silicon Valley companies. I’m not the only one. Many of you have tried to work for these same tech giants and never quite made it.

You might be angry because of the rejection. Silicon Vally Tech might still elude you and you might even fantasize at night about one day getting into this illustrious club where the worlds toughest problems are solved and you can have a kickass time in the process.

I want to share with you how I was rejected by Silicon Valley and the lessons that happened after the whole process.


During the summer of 2018, I started on a path to work for a Silicon Valley tech company — it’s worth noting that I didn’t have my eyes on solely one company, there were many. One afternoon I sat at my desk (it wasn’t a stand up in case you were wondering) and began sending messages to people I knew who already worked in these shiny Ferrari’s of tech.

Once I’d contacted as many of the people I already knew, I went to LinkedIn to search for actual jobs that were available right now. I thought this two-pronged approach would fast track my dream and get me where I wanted to go in record time (I was even dumb enough to tell people it would take weeks). The job ads were full of bright colors, huge promises, stock options, gym memberships, health insurance — you name it.

I’d use my multiple open Chrome tabs to simultaneously look at the company’s website. Everyone in the office photos looked like they were having so much fun. It kind of reminded me of when I was visiting the Lyft office in Silicon Valley back in 2016 and was taken back to when there was music pumping, people cheering and enough alcohol to get an elephant drunk.

Image Credit: Matt Johnstone

By the end of that week, during a long hot Australian summer, I’d submitted more than a dozen applications to the tech gods. Many of the people I knew personally had also replied to my messages. It seemed as though the stars were aligning all for me, and rejection in Silicon Valley would be impossible. The first sign that something was up was when I only received a couple of real interviews. Many of the applications I sent were lost in cyberspace and doomed to be never read by an earthling. Still, I told myself “They’re probably busy; they’ll get to it.”

The marathon of coffee catch ups began. I started meeting with each of the contacts I had in these Silicon Valley tech companies. The meetings seemed to go well and I got introductions straight through the front door without having to do an online application. It felt as if the years I’d spent helping people on LinkedIn could have been finally paying off. The future appeared bright almost in the same way that the Casino was appealing when I was eighteen with all of its bright lights, live sport, places to drink, food and of course the odd bet or two.

I did the two interviews I got from doing online applications. Nothing.

Then I did a few phone interviews thanks to the kind people who referred me in the front door. Again, nothing.

The short-term disappointment quickly dissolved and I put it all down to “Maybe it’s harder than I thought. That’s okay.” I kept applying for more jobs and using a bit of what I call ‘networking finesse’ to drum up more chances to interview. At no stage did I think any role was a guarantee, but I definitely believed that it was a numbers game and the more interviews I did, the sooner I’d reach my goal. As my inner circle dissolved and I resorted to contacting people in the valley that I didn’t know, it became much harder. Some people brushed me off, ignored my messages, told me I was dreaming or gave me a few harsh truths.

Now maybe I’m stupid, but I still kept applying and interviewing. The process had become my circle of life or my daily ritual (if you can call it that). It went on and on and on. I was relentless in my approach even though I didn’t appear to be making any visible progress. What started out as a few weeks, turned into nine months of blood, sweat, tears and one too many red wines on occasion.

Towards the end of my nine-month battle, there was light at the end of the tunnel. A friend of mine finally managed to get me a meeting with someone in HR at what I thought was a dream company. She was new to the role and full of energy — I’d later learn she was new to the Silicon Valley way of working and perhaps naive to my lack of ‘fitting in’ with the whole scene. The phone interview happened and I felt as if I’d hit it out of the ballpark. Sure enough, the day after she invited me in for a face to face coffee with the hiring manager. That coffee went well and we were instantly in rapport. We liked the same books, had similar mutual contacts, laughed at the same stuff — it was similar to my experience the year before doing lots of first dates.

While this opportunity was moving along nicely, it still seemed weird that it was the only real thing I had on the go. Still, my ego had taken over now and I thought I was on the home stretch (my ignorance is hilarious now that I look back on 2018). The day after my slam dunk coffee interview, the HR person rang me back and told me I had made it to the second round of interviews with what would be my bosses boss (if I got hired). The interview was during the week, at their office in the city. I put on my finest business casual outfit, shined my favorite brown sneakers, shaved my beard, threw on a bit of the old Calvin Klein Number One, and took the train to the interview.

I arrived at their office. It was stunning and had views of the entire city. As I looked around the office, everyone seemed so calm and happy. I wanted to be calm and happy too. On the coffee table of the reception, there was a beautiful looking book with sharp colors, bold mission statements and more photos of people that looked like everything they touched turned to one hundred dollar bills. I read through the book to look as though I was prepared and knew what on earth they were all about. I imagined myself working for this tech giant and recited their values in my head in the hope no one could see how stupid I looked.

The door to the promise land opened. A bright light shone through the doorway (turns out it was the sun changing angle and purely a coincidence). I was ushered into a meeting room with a huge TV screen on the wall. The coffee man who I’d had a successful meeting with prior, sat me down. His boss and the HR person were on the VC. It all came down to this moment. The interview was in-depth and I was asked to talk about my experience and how I solved problems.

Then there was a weird point where we went through my mutual connections on LinkedIn with the big, big boss. We had over a hundred mutual connections and I thought this would be my secret weapon in the fight to join the tech race. The questions kept coming and the look on their faces suggested I was somewhere in the pocket of where I needed to be.

Humility screw up

Most of the interview was a success until the HR person asked me about a time when I demonstrated humility. In that moment, I began answering the question as best as I could.

By the end of my explanation, I realized I’d completely stuffed up and explained empathy instead of humility. For someone who was supposed to be a self-improvement blogger after hours, this was a pretty stupid mistake to make on my part.

Image Credit: Shutterstock

It was too late to go back, but I don’t think it would have entirely messed up the opportunity. The next part was weird: more radio silence. I waited a week and heard nothing. Then two weeks passed and still nothing. I emailed the HR person and asked politely what was happening. Her response was strange:

“We are still interested in you but we have other priorities right now and the hiring managers attention has shifted. So, I guess what we’re saying is you haven’t got the job, but you haven’t not got the job either.”

The following day I contacted one of the people who referred me. I asked them if they could look into it and maybe work out what had happened. It turns out that the hiring manager contacted someone I knew on Linkedin (without me knowing) and they’d secretly given me a horrible reference. The frustration lasted a day and then I realized it was something that was out of my control.

What I’ve just described is my experience with being rejected by Silicon Valley. There are quite a few other stories during my search to work in tech that I won’t go through in this post.

The part I want to focus on is what I learned from all of this about Silicon Valley.

It might stop you from thinking what I thought or even making the mistake of thinking Silicon Valley is something that is better than everywhere else in the world.


Lesson #1 — Transparency

These tech companies that can be idolized by those looking to work for them are not necessarily transparent.

This doesn’t mean you shouldn’t trust them; it just means you have to understand that what you see from the outside is different from the inside. The transparency is hard to deal with because you can get sucked into the idea that these companies will be at the pinnacle of your career only to realize like I did, that the company has nothing to do with your happiness or how successful you’ll be.

My experience taught me that not everything is as it seems, and you really need to do your research and find a way to look under the hood — so to speak — before you dedicate a part of your career to the Unicorns of Tech.


Lesson #2 — It’s hard to see in

The people that work in these companies are often hard to reach which makes getting an inside look difficult for most people.

It takes a lot to get in, and once people are in, they don’t always want to assist others in following their footsteps.

The tests, many rounds of interviews, the need to know people and your prior high performance, screens out so many normal people who — if given a chance — could probably do just as well if not better than those who are the ‘chosen ones.’


Lesson #3 — Some snobbery does exist

I may cop a lot of flack for saying that, but based on my experience, it’s certainly true.

There is definitely an element of elitism that exists in the valley and attempts to separate those who are smart from those who are normal.

The people that are forced into the normal category are often excluded in a way that mimics the A/B testing philosophy that Silicon Valley runs off.

It’s in some ways a form of digital racism where human beings are separated based on intelligence and their obsession for lines of code.

Unfortunately, the meaning of your life will probably never be found hidden in a single line of code.


Lesson #4 — There’s nothing special

What makes a company special is not whether it started in Silicon Valley; what makes a company special is its people and the culture which acts like a heartbeat drumming through the building and uniting people to do their best work to solve a problem.

There are plenty of companies who are just as good and weren’t born in the tech hub of San Fran.

Placing any location or company on a pedestal is a dangerous habit.

This habit prevents you from seeing all the good company’s in the world who may have never built an app. The truth is every company is a tech company and that’s not going to change.


Lesson #5 — Overworking is the norm

From the beginning of 2018 to now, I’ve been interviewing and talking to people that work for these Silicon Valley giants. At first, I didn’t want to believe it. The truth is I can’t ignore what I discovered: all of these tech companies encourage people to overwork.

Image Credit: Peter Berkowitz

The idea of work-life balance is non-existent. The addiction that exists to exceed targets and expectations forces people to make their work, their life.

Often, in the middle of all this is partners or children who have accepted that this way of life is the way it is. The families associated with the workers of Silicon Valley have got used to the idea. It’s not bad; it’s just normal for them.

Through my journey last year, I heard stories of people working into the night to be on call for other timezones, people sleeping in the office, holidays not being taken (or even cashed in with a cult-like dedication to work) instead of playing or exploring one’s creativity.

The overworking culture I witnessed was probably the most challenging thing I discovered.


Lesson #6 — Hidden Bias

Technology from Silicon Valley is often spoken about as democratizing industries or making things fair for the average person. The hiring process taught me that there are hidden biases.

The biases are not race but skill level, your network, the way you talk or your knowledge of the technology stack.

The bias in the hiring process rules out so many candidates because maybe they had a gap in their career, haven’t worked in tech, became parents or didn’t have enough EQ.

These same people have gone through some of the toughest adversities that stop them from being pretentious, entitled, arrogant or ungrateful. Many of these award-winning traits are being ignored — I’d argue the people needed for the next wave of technology are these exact people.

These toxic traits that can be produced from a biased hiring process, lead to bigger problems later on such as greed, selfishness and dishonesty.


The value of rejection

The reason I wanted to share this experience with you and some of my thoughts is because there’s always value in rejection.

When you get rejected — whether from Silicon Valley or not — you can take a birds-eye view of your life and work out what you really want. I decided at the end of the process to still work in tech but not for a Silicon Valley company.

Rejection teaches us more about who we are and what we don’t want.

The challenges of the Silicon Valley tech companies were too big for me at the time to ignore. I’m obsessed with how people are treated and whether I’m contributing to something fundamentally good, or perhaps a flawed view of the world that one day soon may get disrupted.

As we evolve more with the technology that has taken over our lives, I believe we will question some of what I experienced while trying to get a job last year at a few of these tech unicorns.


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