How I Think

🚀 i'm a chief revenue officer... imposter syndrome

Published 9 months ago • 2 min read

hey strangers. It's been a minute since I crawled into your inbox. But I'm writing to you my lovely reader about imposter syndrome.


I recently became the Chief Revenue Officer at Meow.

This forced me to rethink how I need to evolve to take our business to the next level.

Also... it forced me to face the fact that imposter syndrome never goes away. (for the uninitiated, imposter syndrome means you don't feel quite ready or deserving of your position)

Know why?

No one ever knows how to do something until they've done it.

Even Jeff Bezos was an imposter.

  • He had no idea how to run a billion dollar company until he did it
  • He had no idea how to run a trillion dollar company until he did it

So let's keep this little secret between us:

I have no idea how to be a Chief Revenue Officer for a $100M+ startup until I've done it.

Let me tell you a quick story...

August 23, 2021 was a big day.

It was my first day on the desk as an investment banking analyst at Goldman Sachs. It also happened to be my birthday.

I woke up that day, wrestled a shirt, suit & tie and fought the hustle and bustle of new york city down to the Goldman compound on 200 West Street.

This a place you can't approach without feeling a tiny bit intimidated. It looks like a place where Zeus and the Olympians hold court. We're talking 100 foot ceilings. Marble overload. It's straight out of a finance movie from the 1990s.

And summer 2021 just so happened to be the hottest time in the financial markets. So I show up that first day and immediately get tossed into the deep end.

My first 12 hours went by in the blink of an eye.

I'm in the trenches battling it out like any good investment banking analyst does.

My weapons?

  • 2005 Microsoft Outlook
  • 2007 Microsoft Powerpoint
  • 2009 Microsoft Excel

And a Skype messenger app that felt older than my grandma.

But we hit 7 pm and I'm hit with an assignment from my associate:

"Hey Chris, mind updating this cap table and putting this + these 2 other things on a few powerpoint slides?"

At first glance, this seems simple enough. So I dive straight in.

*1 hour later* Still trying to figure out where to pull the company's financials from. I'm horribly lost in our array of Goldman folders. I ping my associate with a question... she gets back immediately.

*2 hours later* My "work product" is a terribly formatted and 99% wrong capitalization table. It's currently taking me an excruciatingly long time to figure out the Goldman color palette.

*2 hours later* It's midnight and I'm way past the reasonable amount of time this assignment should have taken me.

Do I give up by 1 am? Do I call my associate for help? Do I reveal to her I have no clue how to do this? Do I reveal I barely know what EBITDA is?

...this hopeless pattern continues for days with different assignments.

At one point it's late at night and I stare myself down in the mirror and say...

"Am I cut out for this sh*t?"

I felt like the biggest imposter on the planet posing as an investment banking analyst with my cheap suit & tie sitting next to the most brilliant financial minds in the world.

For a solid 30 seconds, I considered giving up. But pride prevails.

Fast forward 6 months later and I was one of the top analysts and part of the team to execute a $5.4 billion Clearlake Capital buyout of Quest Software.

The lesson to all this madness?

If you want to do anything incredible in this world, you will feel imposter syndrome.

To take it a step further...

If you don't feel imposter syndrome, you are not pushing yourself and your career hard enough.

Talk soon,

Chris Hladczuk

How I Think

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