How To Get Past Fake “Gatekeepers”

by / ⠀Entrepreneurship / January 14, 2014

The following scenario surprised, enraged and inspired me — so originally, I wrote this on my Facebook wall.

I got some many comments from friends that I just had to turn it into a post.

I’m super curious: What would you have done in my shoes?

Leave a comment when you’re done reading and let me know.


So I’m at Starbucks (I’ve been here for a few hours), and I’m in Atlanta…which is a music hub…so there are lots of singers and songwriters lurking around.

And there’s this young singer…maybe 20-21…with another guy who I suppose is his manager.

The manager wants the kid to sing in the middle of the cafe to get some feedback. So he goes around to the different tables to say, “Hey, we’re going to sing in a minute, just wanted to let you know.” Then he goes to the counter and he asks the Starbucks staff if it’s “OK”.

He doesn’t even as a manager, mind you… just a regular barista. And of course she says, “No, you can’t sing in here.”

Why? Is it because she doesn’t like music? Probably not.

It’s because she doesn’t want to get in trouble, do anything out of protocol or do anything that might possibly draw attention to herself. It’s not even about the kid singing. It’s about her.

And I’m thinking to myself two things:

First, the manager shouldn’t have asked for permission the kid to sing.

He should have just had the kid do it. People would have most likely broken into applause (we love surprises, flash mobs, etc) – then if the baristas or managers were still mad…he could have just asked for forgiveness later.

Ask for forgiveness…but never ask for permission to demonstrate your worth or power. 99% of the time people will say “no” to you, or reject you, because they are scared.

ask for forgiveness not permission

Second, this is a perfect example of how gatekeepers are often unqualified to evaluate us.

The people who reject book deals, venture funding and movie scripts are usually never the real decision makers. They are usually the interns and low-level employees just filtering through the crap for the boss. Even the bosses are just gatekeepers to the public. These people all have agendas of their own. It’s all about them. It’s never about you. Yet we let rejection from these people make us think that the world is rejecting us.

The world isn’t rejecting you. How can the world reject us if it hasn’t even SEEN us?

If we just skip the gatekeepers entirely and find our way to the decision makers, we have much better shots at getting what we want.

So fuck the gatekeepers. How can we figure out ways to get around them and go directly to the source?

Daniel DiPiazza is the founder of Rich20Something, where he teaches young people how to stop doing jobs that they hate and break free of 9 to 5 boredom by starting their own businesses. Click here to join his tribe of hungry young entrepreneurs and get inside strategies to launching your first digital business.

About The Author

Matt Wilson

Matt Wilson is Co-Founder of Under30Experiences, a travel company for young people ages 21-35. He is the original Co-founder of Under30CEO (Acquired 2016). Matt is the Host of the Live Different Podcast and has 50+ Five Star iTunes Ratings on Health, Fitness, Business and Travel. He brings a unique, uncensored approach to his interviews and writing. His work is published on, Forbes, Inc. Magazine, Huffington Post, Reuters, and many others. Matt hosts yoga and fitness retreats in his free time and buys all his food from an organic farm in the jungle of Costa Rica where he lives. He is a shareholder of the Green Bay Packers.