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Jack Dorsey on Breaking the Law


We all know ambitious people, but do you know anyone that’s actually broken the law to get the job they want? Jack Dorsey did, but we prefer to think of his little misdemeanor as ‘creating an opportunity.’

Jack Dorsey, the serial entrepreneur best known for Twitter and more recently as the founder of the successful Square, didn’t always have as high of aspirations.

At one point, Dorsey, who was in college at the Missouri University of Science and Technology, just wanted to work in the dispatching industry. He had his eye set on the world’s largest dispatch company, Dispatch Management Services Corp (DMSC). Instead of applying for a job with a resume like a normal person, Dorsey decided he would prove his skills in his “application.”

He realized there was no contact information on DMSC’s website, so he took matters into his own hands. As Greg Kidd, the founder of DMSC remembers it, Dorsey “hacked into DMSC’s computers and crafted an email from Mr. Kidd’s email account explaining that there was a security hole in the company’s website that he could fix.” He was hired right away and flew to New York the next day.

Dorsey didn’t see it as a crime, as he states here in an interview on 60 Minutes, and neither do we.

Jack Dorsey: I found a way into the website. I found a hole. I found a security hole.
Lara Logan: Is that– are you– is that the same thing as hacking?
Dorsey: It’s– ha– yes. Hacking– hacking is– hacking is– is–
Logan: A crime.
Dorsey: Well, no. Criminal hacking is a crime. Hacking is actually a–
Logan: Hacking for a job application is not a crime?
Dorsey: No, no, no, no, no. No, not a crime at all. And I emailed them and I said, “You have a security hole. Here’s how to fix it. And I write dispatch software.” And
Logan: And they hired you.
Dorsey: And they hired me a week later. And it was a dream come true, which is a weird dream for a kid.

[See full 60 Minutes interview with Lara Logan here.]

Working at DMSC, Dorsey liked the way the dispatchers talked to each other in short bursts about where they were and what they were doing. He wanted to recreate this communication method on a social medium, which sparked the idea for Twitter.

He didn’t wait for opportunities to come to him — he created them. He showed DMSC they needed him before they even knew it themselves. He showed people they wanted a micro-blogging platform, again, before they knew they wanted it, but Dorsey was determined to make it happen and his bold brave moves paid off (in the billions).


While we don’t recommend you break the law to create your opportunity, we do recommend you apply the same tenacious attitude Dorsey did. Like him, maybe you see a void in your workplace that you have the skills to fill. Have the courage to make the case for why your company needs it and why you’re the person to do it.

Maybe creating your opportunity involves you leaving your company and taking your skill set to a place that would really value it. The point is, sometimes opportunity won’t ‘come knocking.’ Sometimes you need to find it so start banging down doors!

This article was originally published at Year One and appears here with the permission of the author.

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