Mysteries of a Gen-Y Confidant Rotating Header Image


Woman Holding her hand in a stop motion

Keepers of information, walls to progress, impassable chasms of detriment!

Whichever metaphor you chose each of us has encountered a “Gatekeeper,” these people hold us back, with paperwork, egos, scheduling, anything you can imagine. A lot of problems stem from the inability to get passed these obstacles and achieve our ultimate goals. I wonder how many people have been discouraged to the point of giving up. We need to stay motivated, persevere, and move past these obstacles for our companies to survive.

Consider these responses to the following question:

What is the worst experience you’ve had with a “gatekeeper” and how did you accomplish your goal?

Matt Wilson founder of Under30 CEO

I absolutely hate the gate keepers in large bureaucracies.  This is the entire reason I’m an entrepreneur–I want to control my own initiatives.  In the field of collegiate entrepreneurship it is often frustrating working with big institutions scheduling speaking engagements and programs working with students.  I’d love to put on more seminars but it takes forever to get past the gatekeepers.

My advice would be get to know the gatekeepers–the secretaries who hold the keys to the important people’s schedules, filter emails and setup their phone calls.  Get on their bad side and you are blacklisted forever.

Patrick Sargent founder of Work Your Way Up Productions

Patrick SargentWhen making “Work Your Way Up” I reached out to several very well known entrepreneurs such as “Life is Good” founders Bert and John Jacobs. Obviously the better-known people you have in your film, the more likely people are going to want to watch and hear about those people’s stories. Unfortunately several very prominent entrepreneurs turned me down. In filmmaking people themselves, whether actors in narratives or key interview subjects in documentaries have a huge impact on your film. Having Denzel vs. a no name first time actor can make or break your film. When I became aware that several of the people I was counting on for my documentary were not going to participate I had to search for more entrepreneurs who had intriguing stories as well. I learned that although you may not be able to get the exact people you initially desired, there are always tremendous people out there and many times they would love to participate in your project. The key is finding them and showing them that you have a worthwhile project for them to get involved with.

Mike Thoene founder of Fixit Repair

Mike ThoeneThere are very few gatekeepers in my life, but one that stands out the most would have to be the fact that a paper certificate means so much in this world that it will completely towers over straight experience. For instance, I worked for four years for a single company as the Head IT Technician, without any sort of certificates or anything such as that, sadly that company had to close its doors. I have applied to several other positions that took the exact same skill base, but because of a few required certificates that I did not hold, I did not receive those jobs. I had to move on and create my own company and show all of those folks that I have the knowledge to get the job done efficiently and correctly. But, even still, I find customers calling me up and one of the first questions they ask “Are you Microsoft certified?” Sadly, I am not. I am only A+ Certified and it hurts me that clients don’t know what that means. Because of this paper gatekeeper that seems to be a mile wide, I am working to achieve a Microsoft Certification. Hopefully I will have it within a month. This type of gatekeeper is definitely getting in my way, and I will persevere and overcome!

Rob Ianelli founder of

Rob IanelliI can’t really say I’ve had “the worst experience” with a gatekeeper, but more importantly, I have these moments all of the time. Pretty much everyday you’re going to encounter a gatekeeper and it’s going to try and push you down through the floor. It’s something that any entrepreneur has to be able to acknowledge and for the purposes of this response, overcome.

One that vibrantly comes to mind is back when I was launching and I had been reached by one of the local island newspaper reporters about putting together a story. As you can imagine, I was ecstatic and my small team and I were jumping around with the prospect of getting press coverage weeks upon our launch of the business. What was a joy filled moment soon became business reality when the lead editor of the newspaper caught wind of what my company was planning to do (We’re a New Media Company) and squashed the entire article. You can imagine, that I was pretty upset with how we were treated. I needed that press, or at least I “thought” I did.

This editor which feared the shift in media that is already taking place, made sure of it that throughout the entire Summer we had zero press about us, even when other companies we were working with were featured when they put on the events that we co-sponsored. So, I did what I believe is the power of the entrepreneur. I went after every single person in our market, guerrilla style. I found another way to get noticed.

We didn’t advertise, we didn’t make up a ton of stickers and pamphlets, but instead, made up a business card and busted our ___ to get the recognition we needed. What could have really put me in a funk turned out to light a fire inside that has not, and will not ever go away.  We ended up rocking out the initial season and built a ton of traffic and brand recognition without a single piece of traditional advertising.

Bottom line. We didn’t need an article about us.

So, when you’re thinking that there’s just one more person after the other trying to put you in your place, remember it’s going to be like that for a long time. What’s most important is “never staying on the ropes” and keep swinging back. Then, and only then will you be able to take down any gatekeeper and build your business to where it’s meant to be.

Keep swinging.

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  1. MattWilsontv says:

    Hey Brian, good stuff my man. Keep collaborating and putting out good content!

  2. MattWilsontv says:

    Hey Brian, good stuff my man. Keep collaborating and putting out good content!

  3. Brian Cox says:

    Thanks a lot Matt, I appreciate the encouragement!

  4. Rob says:

    Brian, thanks for the shot at this! Guys, great job above. Enjoyed reading your responses.


  5. Brian Cox says:

    Absolutely Rob, I'm glad you shared with us, let me know if you would like to contribute again!

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