Seven Questions with Jack Dorsey

Jack Dorsey is co-founder and CEO of Block (fka Square) and co-founder of Twitter. To both learn and become more self-aware, he actively seeks out new opportunities that make him uncomfortable.

What advice should first-time founders heed?

Focus your attention on the things that will help you learn. That might mean asking better questions, thinking more critically or developing your problem-solving skills. I think anything that helps you learn better or faster will improve your outcomes overall.

For me, learning has been about continuing to ask “Why?” and eventually getting to “I don’t know.” That’s where the process begins. Square is a good example, because we jumped in knowing nothing at all about the credit card industry. We started by reading all 800 pages of Visa’s operating principles, which was the driest material in the world, just to get an understanding. The biggest “I don’t know” we eventually encountered was why someone had to go through a credit check to accept credit card payments. The industry put up that blockade in part because it didn’t understand its potential customers, and only about 30% of people were getting through. By starting from a place of trust and using new technology to verify that trust, we were able to get to over 90% and enable a lot more people to participate in the economy.

What question are you asked more than any other?

When I talk with other entrepreneurs, a lot of their questions are about how we think about culture and what it really means. I think culture is ultimately about alignment around a common purpose—the reason we wake up and work on this particular problem when we could be doing something else. Your company values will evolve over time, and you’ll have multiple missions. But the purpose is the thing that endures.

I think it’s also important to focus on team dynamics rather than hiring individual superstars, because those dynamics can make or break a company. It can also be difficult to see before people start working together, though, so one thing that’s been helpful for us at Square is doing more contract-to-hire recruiting. Candidates get to test us out before they have to go all-in, and we can assess how they contribute to the dynamic—and whether we’re aligned on purpose. Usually, someone either falls in love with the problem we’re solving or they don’t. Both sides can very quickly determine if it’s a relationship we want to continue.

What experience shaped who you are?

I grew up with a bit of a speech impediment, and that made me very, very shy. I was always worried about mispronouncing something or saying the wrong thing. Eventually, in fifth or sixth grade, I realized I had to do something to break out of that trap—so I signed up for the speech and debate team, even though it was super scary to me, and eventually built some confidence. It’s been an ongoing journey, even as an adult. Getting up in front of 25 employees is much different than speaking to 5,000. But I’m able to operate at a level I couldn’t have imagined when I was a kid.

And that goes beyond public speaking, because facing that fear led me to seek out other opportunities to do things that make me uncomfortable—in business, but also in my personal life, in everything. Those are the experiences that have benefitted and propelled me the most.

What’s the best interview question in your toolbox?

The first question I ask is “Why us?” People can take it anywhere, but the answer usually gives me an understanding of who they are and what they want out of their career. I’m looking for alignment of purpose, but also a willingness to think about problems and solve them in creative ways. Sometimes I’ll hear, “Well, it looks like this company is going to be successful,” and that’s the wrong answer to me. But other times, I’ll hear, “My mom has a coffee shop and couldn’t accept credit cards. I think what you’re doing would help her.” And if they go on to say, “But here’s what I think you’re doing wrong,” that’s even better. Some of the best answers go on for 10 minutes, because the person is so excited about the problem we’re solving.

Ultimately, I’m more focused on how someone thinks than on their skills. If you’re smart and creative, you can apply that to lots of different problem sets where a specific experience doesn’t add much value. None of the first 50 or so people at Square had backgrounds in financial services or banking, and that was actually really beneficial. They had completely fresh eyes and questioned a lot of what the industry took for granted.

What book should every company-builder read?

The Score Takes Care of Itself, by Bill Walsh, the former head coach of the 49ers. The writing itself is very simple and straightforward, but I got a lot out of the way he thinks about building organizations. When he came in, the team was the worst in the league, and it would have been easy to focus on winning games. No one can argue with that goal. But instead, he focused on very small details, down to taking care of the locker room and players tucking in their shirts. It gave the team a sense of pride and ownership, and within a few years, they won the Super Bowl.

In a company, I think a lot of the little details are about how we communicate, but it can also be something as simple as pushing in your chair when you leave a meeting room. That shows you’re respecting the people who come in after you and the shared space where we all create. If you’re paying attention to a detail like that, it helps you pay attention to details in the service or software as well. And with that daily practice, as we get better and better at those little things, they ultimately become the big things.

What’s a lesson you learned the hard way?

In the early days of Twitter, we had an amazing engineer who was a master of all the code—they kept the servers running and the service up. Unfortunately, though, they were also super negative, and that toxicity was bringing the whole team down. I knew that was the case, but so much knowledge lived in this person’s head that I was worried if they left, we’d never be able to keep the service running or scale it.

After about six months, I decided I had no choice but to cut ties—and the service did go down, but three people rose to the occasion and brought it back up. By finally removing that toxic presence, we also allowed new people to level up and advance, and eliminated the single point of failure that had been getting scarier every day.The lesson for me was to act more quickly—assuming I have what I need to make an informed decision—but also that I really need to pay attention to how a team works together, rather than just the individual and their skills.

What invention do you hope to see in your lifetime?

I’d like to see an internet-native currency that actually works globally. Bitcoin has already been invented, of course, and it’s come a long way—but there’s still a lot of work to do in terms of accessibility, security and speed before it’s something my mom can use to buy coffee. So it’s less an invention and more a constant iteration to get the adoption we need.

Having a sound global currency will enable so much more innovation and collaboration. Currency and communication are the foundation of everything we do; if we want inventions like better AI or flying cars, we need a better sense of traded value. And when something is global, with more people participating, that means more diversity of opinion. That’s how you start to see all the edge cases and solve problems that aren’t specific to just one culture or nation or group.