These five characters now mean a lot more than the co-founder of Twitter and Square had ever anticipated.

On Thursday, Jack Dorsey inspired the audience at the University of Waterloo’s Humanities Theatre, which was filled with students, young entrepreneurs and members of the tech community.

On the same day, Dorsey announced that his latest venture, Square, plans to set up a permanent office in Waterloo Region, employing 30 people. He also had lunch with local tech entrepreneurs and toured the Communitech Hub, which clearly left an impression.

“I thought the space was awesome; it feels like a very free, open collaborative space,” Dorsey told Communitech. “You could walk in and be your most creative self. Space is as important as ideas because it can really take away and distract from the idea or support it. I think investing in a space like this is fundamental to success.”

In his speech at UW, Dorsey told the engaging story of his life, starting at birth – or as he put it, his “founding” – and took the audience on a journey through the many left turns that have brought him to this point.

“I have always had a curiosity about the way the world works, what’s out there, and I want to see every aspect of it,” Dorsey said.

This curiosity and drive to figure out how things worked led him down different career paths – tour guide, denim designer, massage therapist – and often concurrently.

From wanting to be a sailor to a train engineer as a boy, Dorsey pursued knowledge and adventure from the start.

“The other thing that always inspired me and really helped me see the world in a different way were artists,” he said. “I was always fascinated by surrealists. These folks always had crazy ideas and some really beautiful things that just gave me pause.”

As a teen, Dorsey took a left turn into punk rock, which led him to the other thriving scene in St. Louis at that time: hacking.

He described hacking as “a culture that was similar to punk rock, which is open source; people who want something out there immediately and learn while they are doing it, and learn from others who were critiquing their code.”

It was the inspiration to find out how New York City functioned that led him to discover that messenger bikes were crucial to things getting done. When he hacked his way into the top dispatch company’s systems, showed the company the holes and how to fill them, they gave him a job.

“I didn’t grow up wanting to be a programmer at all; I grew up wanting to figure out how to visualize a city,” Dorsey said.

When text messaging took hold in the U.S. in 2006, Dorsey was reminded of his previous work in messenger-bike dispatching, updating people in real time.

Dorsey and a team from Odeo, where he was then working, built Twitter in two weeks – most of what we still see today.

“One of the things I’m most proud of is that the company has really learned from the people using it,” he said.

The “@” symbol and retweet function were developed from observing user behaviour, which led to improvements that made Twitter easier to use.

“It worked out because it resonated with people; people wanted to use it, people wanted to work on it, and we had passion for wanting to use it the world.”

Twitter’s simplicity and ease of use reflects Dorsey’s need to understand how something works and provide a simplified way of doing it, which is also how his latest venture, Square, came about.

Dorsey looks to the Golden Gate Bridge and how it was built as a point of inspiration for Square.

“Under budget, ahead of time, and not only did they have the audacity to build it across this span, but they also had the audacity to make it beautiful,” he said.

“It has one job in the world and that’s to get people from point A to point B, not to fall down,” Dorsey said. “We have to build a company that builds a bridge like this that stays up 100 percent of the time.”

Just like the bridge, Dorsey’s companies provide valuable connections for people, and simplify processes so they can spend more time on meaningful things.

“An entrepreneur doesn’t mean that you start companies,” Dorsey said. “It means that you take significant risk in order to do something and see something different in the world.”


With files from Kayleigh Platz