The mobile payment company was founded in 2010, processes more than $15 billion in transactions annually and employs 1,000 in San Francisco, New York City, Atlanta, Tokyo and . . . downtown Kitchener.
From the ninth floor offices at
305 King St. West in Kitchener,
Dorsey talked for 30 minutes about why he located his Canadian operations in Kitchener, big trends in
technology and how he stays grounded after becoming a billionaire technology
entrepreneur in his early 30s.
Dorsey is worth an estimated $1.3 billion. He walks to work, or takes a bus. He was wearing a black t-shirt, blue jeans and slip-on running shoes. He has an athletic build, a full head of hair and a beard. There is a tattoo on his left forearm, a large f-hole. The f-hole is found in the sound boards of violins, violas, cellos, double basses and some guitars. It is homage to his violin-playing days, and his university studies in math because the f-hole looks a lot like the integral symbol in calculus.
Nobody has an office at Square. Information is shared with all employees. That levels the company and reinforces this visionary entrepreneur’s belief in the power of the commons.
Your first trip to Kitchener-Waterloo was last September to speak with
entrepreneurship. What were your first impressions of this area, and what are
your impressions today? University of Waterloo
“We have the good fortune of having some pretty amazing engineers who hale from Waterloo-Kitchener, have made livelihoods here, families here, want to stay here. I was introduced to the area by them first and foremost. When I actually saw the college and university, and the community that is being built around it, I felt there are a lot of parallels to what we see in
San Francisco and Silicon
Valley. By that I mean there is a sense of real community, and
support and mentorship, and these are definitely things that have made the area
where we have started the company and built a company important to us, because
you can very quickly learn from others’ failures, others’ successes, and there
is a support network to help you as you progress through that. You can literally walk up to anyone and ask
them as question about what has worked for them, what has not worked for them,
from building actual code to building teams, to managing people and policy, and
people are very apt and likely to share it. Just in conversation with a number
of students and the professors, it felt like there is something similar here,
and then digging deeper and getting a better sense of the area from our
engineers and our people, I think that’s proven to be the case. We are
attracted because of that, because there seems to be a lot of parallels, and
the support network and community, but also just the massive amount of talent
coming out of the and the
area. It has been a focal point for
building pretty innovative technologies, something nobody can really ignore,
and something we want to invest heavily in.” University
All the tech entrepreneurs I speak with say talent attraction and retention is probably there number one challenge. What has been your experience as you build Square?
“It is really a function of what people are working on. Our Waterloo office right now is focused on building an app we call Cash, which is a peer-to-peer money transfer product, which allows people to quickly split the bill at a restaurant or request money from their friends, or send money to their friends, all for free. And we have some really amazing engineers who have reached out through their networks and attracted like-minded engineers because the purpose of the service is compelling to them and something they want to take on as a challenge. I think the attraction and hiring and retention is all about the challenges you put in front of people. If they align with that purpose it is easy to keep them interested. If they don’t then it’s probably best for both parties for them to go elsewhere. I think these things naturally work themselves out, as long as you have alignment of purpose and you have something that is really challenging people and people really wake up excited about every day.”
The CEO of OpenText, Mark Barrenechea, calls the Kitchener-Waterloo/Toronto corridor
Valley North. What are you big-picture thoughts on that?
“I think from a big picture, I hear a lot, I have travelled, a lot of cities are trying to recreate
and what happened there. I think that’s a wrong direction, absolutely. I think it minimizes the natural character
found within each locale. I think that
local character is extremely important.
We see it in our own sellers and merchants, something we want to see
surface more is that character. So the
comparisons, the parallels and the drive to be, or to replicate what happened
there over here, I think is always something, takes the energy away from what
is really magical about this place that has its own unique blend of people and
perspectives, companies and university and teachers and that is what we should
focus on, as something unique unto itself, rather than try to replicate
something over here. So that is the
broader topic. I do agree that this
corridor is rich with amazing talent and the theme, if I were to peg one theme
around what it is, it seems like it is more mobile focused. It seems like it’s the intersection of mobile and really big applications, and maybe
that is due in part to RIM, maybe it’s because of the ,
maybe it is a number of other things. If
I had to pick one thread it seems like there is a lot of attention on mobile
and a lot of expertise around that. And
maybe we should be talking about that instead of how we look more like University of Waterloo Silicon Valley. I
think New York
has a similar thing. We spend a lot of
time in New York, we have an office in New York, it is growing in the same that way we are
growing Waterloo, and New York has applied the term Silicon Alley
to itself. And they also have a very
unique perspective on technology because of the density of the city. It is not just a horizontal consideration; it
is a vertical consideration too, which not a lot of cities in the world
have. So there is something very unique
about that, that I think other cities, including Silicon
Valley, can learn from. So
I would ask the question more: How does Silicon Valley and the area where we
are based learn more from Waterloo and Kitchener and learn more from New York.”
I know it has been only 24 hours since Apple’s event in Cupertino yesterday, but what are your thoughts on ApplePay and what if any impact will it have on Square?
“We are really excited about it. We’ve always held the philosophy of, we are going to accept every form of payment that comes across the counter. And if you look at our history, five years ago we started the company because merchants were losing sales because they couldn’t accept a credit card. They could accept cash, no problem. Accept cheques, slight bit of problem because they had to wait for the deposit and sometimes the cheque would bounce, but they couldn’t accept a card, a pre-paid card, debit card, credit card. The problem is buyers want to use them everywhere because they are really convenient. So when we made the reader we just enabled them to never miss a sale. From that developed this philosophy that we need to make sure every form of payment that reaches mass, mainstream adoption, they are empowered to accept. We have a very, very small start with Bitcoin for instance. A buyer can pay with Bitcoin on Square Market. EMV is a huge movement in the world, not so much in the
but it will be next year. We are
building an EMV reader. We will be ready
for that transition in the United
States and also around the world
probably. We have always held this
philosophy and Apple is really exciting because yes, there will be a transition
of paying more and more with this device.
The fortunate thing is it is backed by that same credit card. To us, what it looks like is the swipe of a
card, but it is another interesting feature, which is a tap and pay. We hope to see a lot of activity. It is really, really compelling and we will
build what we need to build to make sure our sellers are empowered to accept
that, and they don’t have to think about it.”
The tech community in
Waterloo Region has made it a priority to have regular,
all-day, fast train service between Kitchener
and . What are you thoughts on that? Toronto
“We think it is amazing. One of the great things about this office is that it is going to be close to that end point. I think any time you make things easier for people to transfer great distances, things get better. We see this with the Cal-Train in the Bay Area. We have a lot of people coming up from
There are a lot of companies in the South Bay South
Bay and a lot of people live in San Francisco. People get on those trains, there is Wi-Fi,
they can work on the trains. They get to
live their lifestyle they way they want to, and it also might save some
time. They are not stuck in traffic,
they get their very quickly, and they have all their attention on whatever they
want it to be instead of honking their own and waiting for traffic to clear, so
I think it is a fantastic move.”
What are your thoughts about what John Chen is doing to turn around BlackBerry?
“I like John a lot. I am on the Disney board and he’s also a Disney Board member, so we talk every now and then. I think RIM/BlackBerry has something that people love and it’s about doubling down on what that love is. What I hear is around BlackBerry messenger, and what I hear is around the keyboard. There is still something there that people love and drive for. I still have a lot of friends who use their BlackBerry and won’t give them up. And I think choice is a good option and we want to make sure competition is always thriving, so I think he has some good ideas, he’s got to really see them through.”
Where do you see this office and your company five years from now?
“We have about 10 people today and we have enough space in this particular office for about 30, and we are hiring. And we want to hire the best people we find in the area, bring hem here, work on all sorts of projects, including Square Cash. Five years is always that question you get asked. We really have to see where the market goes, we have opinions on where it should go, we have opinions and strong points of view on what we want to build and what we want to see, but ultimately it is all around making commerce easy for both sides of the counter. So someone who is starting a business, or running a business, or intends to grow their business, can instantly download our software for free, and get insights about how to make decisions and how to grow their business, have tools necessary to accept every form of payment, have things like Square Capital, which allows them to capitalize their business, and invest more into it. And then on the buyer side, giving them more super powers around more interesting experiences such as delivery, or such as pickup, and cash. The very intent of communicating: ‘I am going to send you five dollars,’ actually sends five dollars. We think there is a lot there. It is a big part of what we are pushing in.”
Some of the big trends in tech today, the Internet of Things and Big Data. What in your opinion is the next big thing and where does Square fit in?
“I think we get lost in these terms. We talk about Big Data, and we talk about technology, we talk about the Internet of Things, they are just turns of phrases. They don’t really mean anything. They are very abstract. When you have something that abstract it is very hard to approach and see and feel and do. So I always appreciate when we can bring it back to common ground, and what are we actually building. It’s not about Big Data, it’s about giving people information and insights they can use to make better decisions, whether it be about their health, whether it be about running their business, whether it be about how they communicate externally and internally. These are all things that data feeds into, but is not something unto itself. Our own position on that is, our job is to take all this data around a business, and everything that is happening around say a coffee store’s industry, and distill it down to an insight they can actually take action on. So it is a lot of work. We want to get really good at it so we can do it instantly. We have countless examples of people using our data, such as my mom’s favourite coffee store in
Louis was looking at their Square Dashboard and they
saw that they would get all these sales at 3:50 p.m., and they closed at 4
p.m., and they decided for the next two weeks we are going to close at 5 p.m.
We are going to stay open one hour later, and they had a 20 per cent increase
in their revenue. It seems obvious, but
it is not that obvious until you really see it in front of you. So now our job is to make sure that we are
telling people that before they even have to ask the question. And that’s not easy to do. As you said, there is a lot going on and it
can be somewhat overwhelming. And then
in terms of all the other venues, it is just really about how can people get
instant value from whatever they are using? They are the only one who can
determine if it is valuable or not. So I
caution us about using these big terms, like technology or Big Data, or
Internet of Things, because at the end of the day they are just tools. And it it’s useful, it’s useful and people
use it. If it’s extremely useful, and
it’s a great tool, not only is it useful and bring back value but it saves
people time. We want to build a tool
that saves our sellers time, so they can focus on their customers. And saves buyers’
time so they can focus on their kids, their friends or what they are about to
enjoy. What they are about to partake
Do you have any thoughts or observations Jack about what all levels of government in
the municipal, the provincial and federal could or maybe should do to help
nurture the tech sector in southern ? Ontario
“I don’t have a lot of context for this particular government and the surrounding area. I think generally and broadly, any time governments speak up about wanting to support this energy, it is a good thing. At Square we faced a lot of regulation in the early days from the United States government, indirectly through the banks and our banking partners, so being open to questioning old rules that don’t really scale any more to this time, to the future, and stating that we are open to that, and that we are working as quickly as possible to look at them, is a huge step forward. I believe the government’s role, any government’s role, is a balancer. It balances the concerns of the common with the concerns of the corporate and the concerns of the overall governance. And it has to be that governor in between everything to make sure that everything is in constant balance. Sometimes things go way out of whack and to extremes and its job is to make sure that either everything is rising to that level or that is pushed back down. In some cases there are regulations by governments that are resistant to change, and resistant to movements that people naturally want. And the common good actually benefits from. So it is just stating: We are supportive of this and we are going to look at this and we are going to move fast.”
Forgive me if this sounds too personal, but how do you handle and stay grounded and stay real when you have had such tremendous success at such a young age?
“I don’t consider myself that young (laughs). I don’t know, I guess I just don’t think about the, I don’t think about my age, about my place and success. I feel fundamentally that if we sit back and say: ‘Wow, we have succeeded.’ Then that is kind of overwhelming and it feels like: ‘Well, we’re done. We are finished. There is nothing else to do.’ Like, I don’t feel like we are finished at all. I feel that Twitter is at one per cent of its potential. I feel that Square is at one per cent of its potential. I mean, we have road maps five years out, we have ideas 10 years out, we have a sense of where we are going, we are excited about things, we are little bit impatient about getting those things out. So I worry about feeling successful actually. I would rather feel, and I do, that we are not doing enough, we are not moving fast enough. And there is a point where you are like, slow down a bit. But it is just a push, pull back in terms of what’s right for us, what’s right for the market. Sometimes I think we are ahead of our time, sometimes I think we are behind where we should be, but we want to be precisely on time. And the struggle goes back to that balancing factor, so I stay grounded by being on the ground. I walk to work every day, I take the bus, try to talk to every single person in my company, don’t have an office, don’t have an assigned desk, we have a lot of practices within the company that stay very open. No one here has an office, it is rare that these rooms are used or if the door is closed physically or on any information in the company. And that really levels it, the company. I am just a huge, huge believer in the commons and what that means. It’s always what I want to try for personally and also everything I do.”
I read an article that said you are the next Steve Jobs. How do your react to that?
“I appreciate it, but I do not like the comparison. I mean, I think every person has to be their own person. I think the press has put a lot of this upon not just me, but other people. so it is just this canon of well Jack is the next Steve Jobs, or Elon Musk is the next Steve Jobs, or this person is the next Steve Jobs. Bill Gates is not the next Steve Jobs. All these things just become noise ultimately. And it’s distracting. So I try not to pay attention to it. That said, we have a lot of gratitude and appreciation for everything he did, everything Apple has done, and we owe that to them and I am deeply grateful for that. I never met him, but far away, by just watching everything they are doing, there are a lot of successes and whole lot of failures and learn from each one of them. We go through the same things, but in different ways, because if we are not going through them in different ways we are not actually learning anything at all, we are just repeating the old mistakes again and again. I wish we would stop as a society, trying to make all these comparisons, I mean we are back to Silicon Valley versus the Waterloo concept, and make all these comparisons, and just let people be who they are and let the local character shine. It’s really hard to do in our society, because we are always looking for: ‘That’s what I have to be, that person exactly, that’s cool, that’s not cool. I have to be exactly that.’ It takes away all diversity.”
Finish this sentence for me, Jack Dorsey is a man who . . .?
“(Laughs) That’s a great question. Jack Dorsey is a man who (pauses for a second or two) is curious. I will just leave it at that, both active and passive.”
What do you like to do when you are not working?
“I have the great fortune of living in an area that has just outstanding nature, and really diverse nature. I love
as a city that has diversity of people, you walk a block and you see the world
and it keeps changing. I love San Francisco because you
drive for an hour and you see a completely different eco-system. You can drive an hour and you can be in 104
degree weather, or you can be in 64 degree weather or you can be on the beach,
or you can be in the mountains. The
diversity and the intersection of all this is stunning and it’s really a
question of where you get your inspiration more from. I tend to do a bit of both. I love the people but I also love the nature,
so when I am in San Francisco,
I walk, I hike, I sail, just be outdoors as much as possible. And in New York, it is dinner with people, drinks, conversation,
music, that’s what New York
is to me.”