How My Risky Cover Letter to Uber Paid Off

It’s Super Bowl Sunday and everyone has football, Beyonce, food, and beer on their mind. The other thing the majority of us are going to rely on tonight to get us to and from our Super Bowl parties is Uber. This morning I read an article called Why Uber Should go Public by Mark Suster and thought about the opportunity of owning stock in Uber. Not only do I love how Uber has changed the way we think about sharing transportation, but it is their strategy of continually challenging the status quo that draws me to the company.

Thinking of this, the morning made me think about the cover letter I once wrote to Uber explaining why I wanted to work there. It was a bit unconventional but it paid off!


As previously posted on BreakingBayStreet on December 8, 2015

Using conventional strategies gives you conventional results. If you want to stand out, or make something happen often you need to use an unconventional method. The one good thing about using a conventional approach is that the outcomes of that strategy are more certain. When you apply an unconventional strategy, you increase the risk of both more desirable and less desirable outcomes.

Recently, I found myself having a conversation about this topic with someone who wanted to break into investment banking. They told me they had taken all the standard approaches they were taught in school and couldn’t land an interview. I told him it was time to think outside of the box an employ a new strategy and I decided to share with him a story of my own.

Before I left BMO, I had always dreamed of working in the tech industry. I would search for jobs at the coolest start-ups and send my application in. I must have sent over 100 applications and never heard anything back.

But that all changed when I found a posting at Uber. The posting asked for a copy of my resume and a cover letter outlining why I wanted to work at Uber. After failing with a traditional cover letter at every other start-up, I took a risk and decided I would write a truthful letter about why I loved the company. When I sent my application off, I literally felt sick to my stomach and thought I had just made the biggest career limiting move of my life. About a week later, I got called for an interview. I was shocked.

I am not recommending you send a similar cover letter to an investment bank (because it will most likely not work). However, remember that when you are chasing after something that you really want, you sometimes need to change your mindset and adjust your strategy to in order to realize superior outcomes.

My Cover Letter to Uber

15 years ago, I stood in a crowd with 15,000 other sweat soaked fans, the majority of us under the age of 18, under the hot August sun awaiting the band Rancid to take the stage. A roar let out from the crowd as the lead singer, Tim Armstrong took the stage. In a distorted slurred voice, he shouted out, “F%$k you, Toronto.” Energy in the air was atomic. He screamed, “it’s time for a change, and that change starts here today. Who is tired of being ripped off by the major music labels? It’s time we destroy these corporations together … music is for the people!” Within seconds there were 30,000 middle fingers in the air chanting, “F%$k the major labels.”

I will never forget the next fortyfive minutes of my life. The crowd danced, partied, fought and screamed. As Bob Dylan once said “revolution was in the air.” From this moment, I knew the coming generation of kids was going to flip the status quo on it’s head. It was obvious the ways of yester year was not for these kids, and I NEEDED to be a part of this change.

Where this revolution began is unknown. The earliest I can remember was Napster. Sharing music became free. It was the greatest thing I had ever stumbled upon. Listening to music is my passion and now I had any song I ever wanted at my fingertips. Napster forever changed the way a generation of people viewed how they owned and shared information.

Now Uber has come along and thrown the way we view ownership of tangible assets on its head. It is not a company that is merely a replacement for the traditional taxi, but something far bigger than that. Uber provides people access to an asset without having to own it directly. It is expanding and defining a culture of sharing. It has flipped upside down the conventional system of our views of ownership and society is struggling to keep up with Uber.

This is WHY UBER! I want to be part of the revolution. I want to be part of the change that has already started.

Nothing is achieved without effort. But when you believe in something, it is no longer work, it is your passion. I am passionate about what Uber is doing and I want to use my passion to influence change.”

BreakingBayStreet BuzzLinks

How Google Passed Apple to Become the World’s Most Valuable Company (Vox)

The Bay Areas is Donating 25% of its Super Bowl Funds to Local Non-Profits (Quartz)

Don’t Drop Everything to Start a Business (CNBC)

The Secretive Hedge Fund Generating Huge Profits for Yale (Bloomberg)

Imagining Football’s Future Through Super Bowl 2016 (Wired)

Why Uber Should Go Public (Both Sides of the Table)

Why Bonds are So Confusing (A Wealth of Common Sense)

“Apocalypse,” Or How I Learned to Stop Worrying and Love AI (TC)

If there is a Recession in 2015, This is How it Will Happen (The Upshot)

The Tech Behind the Super Bowl (Mashable)


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