All Articles Finance Jack Dorsey on childhood, Twitter and what's next for Square

Jack Dorsey on childhood, Twitter and what’s next for Square

At SIFMA's annual meeting, Twitter and Square CEO Jack Dorsey shares how both companies look to connect people and give them agency.

4 min read


Square Stand


Not many people have had such a view into a changing technological landscape as has Jack Dorsey during his multiple stints as Twitter CEO. Fewer have done the same in two industries, but Dorsey has as co-founder and CEO of Square, which is part of a sea change in transactions.

Put the two together, and you have someone whose companies have altered culture and, in perhaps a smaller way, the economy, making Dorsey the perfect guest to discuss both at the opening of the SIFMA Annual Meeting in Washington, D.C., with questions from R. Martin Chavez, Goldman Sachs chief information officer.

Dorsey’s theme, whether talking about his upbringing, his discovery of computers and code, his charitable work or the impact of Twitter and Square, kept coming back to connecting people. In Twitter’s case (and his advocacy for voting), that means giving people an easy means of expressing their voice.

For Square, that means helping formerly cash-only businesses remove a barrier to a sale. As Square’s technology accelerates, improving speed and security while minimizing fees and other transactional costs, Dorsey noted the desire to “give time back to people.”

Dorsey (Credit: Twitter)

Now, not all is rosy. Twitter is struggling no matter how you measure it and is rumored to be up for sale. Square has never turned a profit. On the other hand, Twitter’s problems are much bigger than one man, and there’s a strong case to be made for Square’s fundamentals, particularly its businesses besides transaction fees.

So, what remains? Well, Jack Dorsey has founded multiple companies, each in a different industry and with a lasting impact (even the software for his failed dispatch-routing service outlasted the company). He has helped two companies to go public, each with a new form of revenue stream (Twitter with its version of online advertising, Square with its reach into small businesses).

And what is the influence, the driving factor behind these accomplishments? As Dorsey told it, a lifelong habit of becoming intrigued, then obsessed with something, and then doing everything he could to learn about it. He got a computer, wanted to learn how it worked. He loved maps, wanted to see how a map could be inputted into a computer. He loved trains, wanted to route them better. He became interested in messaging, and Twitter was born (he got laughs by noting that “Twitter was not solving anyone’s problem.”)

And his interest in making transactions easier, faster and more secure comes from a number of influences, not least his parents’ lives as small-business owners. Much as with maps or transportation, Dorsey didn’t initially know much about hardware, the credit card system or the financial industry, but he knew there was a problem to be solved, and he and his co-founders went to work on it.

What’s next for Square?

Among other things, Dorsey discussed the continuing effort toward safer and faster transactions.

In terms of security, he cited numerous industry and company-specific advances and touched on the important potential of the cloud and blockchain, especially given the shortcomings of traditional magnetic stripe technology. At the same time, Square is being accommodating, with its latest Square Reader offering NFC, EMV and good ol’ magnetic stripe capabilities.

To become faster necessitates moving toward a software environment, and that also matters for security. “We can update software instantly” and be proactive rather than reacting to someone finding a flaw, he said. A hardware mistake is a six-month setback, he said. Conversely, if something fails in the blockchain or the cloud, that doesn’t take the whole system down.

Ultimately, being D.C., the talk closed with politics, as the Q&A with Dorsey was held only a few hours before the first presidential debate. Here, he noted the longtime effect politics and Twitter have had on each other.  Following the debate on Twitter means “you’ll see some fact-checking, you’ll see some snark” and much more, Dorsey predicted.


James daSilva is the longtime editor of SmartBrief’s leadership newsletter and original content, as well as newsletters for entrepreneursHR executives and various other industries. Find him at @SBLeaders or email him.