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Career Hackers Classic: How Jack Dorsey used Free Work to Start His Career

I got into their system, and I found their email address list, for the entire corporation. I got the email for the CEO, I got the email for the Chairman, and I sent them an email.

Joel Bein
Joel Bein


A Career Hackers Classic, the full post originally appeared on the blog of Charlie Hoehn, legend of free work. (Snag his book here.) Photo Credit: Fast Company

Our takeaway:

  • You don't need a freaking resume. Just say, "hey I made this for you."
  • Send personal emails to human beings

This excerpt (Jack Dorsey speaking) says it all:

And then one day, I realized at 16, that there is a whole industry around this called “dispatch.” So I should find the biggest dispatch firm in the world, and I should go work there, because then I can see the entire city. I found one, it was called Dispatch Management Services in New York City. They had just gone public, and I could not figure out how to contact them.

By this time I was pretty good with computers, a very curious kid, and I figured out that they had a hole in their system. I got into their system, and I found their email address list, for the entire corporation. I got the email for the CEO, I got the email for the Chairman, and I sent them an email and said:

“I’m Jack. You have a hole in your system. Here’s how to fix it. And by the way, I write dispatch software.”

And a week later, I was hired. And that was my resume.


Read the full post here.

Charlie Hoehn is an author, speaker, coach, and Head of Multimedia for Scribe. He has been preaching the “free work” strategy for years… In Recession Proof Graduate, his Land a Job You Love course, and his TEDx talk. Charlie was also formerly Tim Ferriss’ “Director of Special Projects.”

CH ClassicsBurn Your Resume

Joel Bein

Joel Bein is Head of Growth at Career Hackers and passionate about personal growth and self-driven learning. As a classically trained musician, he is Founder of the New Orleans Chamber Players.