How Jack Dorsey used Free Work to Start His Career

Photo Credit: Fast Company

From this talk by Jack Dorsey (co-founder of Twitter, founder and CEO of Square).

“Twitter started because I had this fascination with cities.

I had this obsession with what was happening around the street corners in St. Louis, Missouri, that I wasn’t present at. I had this obsession because my parents had always lived in a city. They had a police scanner. I could hear the police cars and the fire trucks and the ambulances roam around my city. My parents bought a Macintosh in 1984 when I was 8 years old and I was blown away by that.

I decided that if I really wanted to see what was happening in the city, I needed to make these maps that I was obsessed with that move around, and I could do that with a computer. So therefore, I had to learn how to program. I never wanted to be a programmer, I never wanted to be an engineer.

I just had to do it to see this idea work out.

At 14 years old, I actually learned how to do enough where I could draw the map on the screen and then I could draw some dots, and I could move the dots around, and figured out how to constrain it within the streets, which was a great day for me. And then I would listen to these ambulances and they would be on 5th and Broadway. “I’m going to St. John’s Mercy, I have a patient in cardiac arrest.” I would type that into my program. I could see the dot move, and that would be an ambulance move in my city of St. Louis, Missouri.

So, suddenly I had this picture of what the city was doing. And I had added more and more data sources. I figured out how to get into some databases that I could actually see some of these things myself. And then I could put it in my program.

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.”

(HT Travis Descoteaux)

Sound familiar?

This “free work” strategy is what I’ve been preaching for six years… In Recession Proof Graduate, my Land a Job You Love course, and my TEDx talk. Thousands of people — including some of the most accomplished and wealthy members of our society — have used it to land jobs, including Ryan Graves (the billionaire head of global ops for Uber).

Segment 12:10 – 14:28

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Charlie Hoehn is the author of Play It Away, Play for a Living and Recession Proof Graduate. His work has been featured on NPR's TED Radio Hour, Forbes, Fast Company, and Harvard Business Review. Previously, he was the Director of Special Projects for Tim Ferriss. Currently, he is the Head of Video at Book In A Box. He lives with his wife and daughter in Austin, Texas.

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