2 min read

How Jack Dorsey used Free Work to Start His Career

"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.""
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