The Canadian entrepreneur spent his early childhood without electricity, taught himself to code, and studied philosophy at Cambridge before falling into a tech career that’s now pitting him against Microsoft and Google.

Butterfield’s biggest business success, Slack, is a corporate communications tool that arouses the kind of devotion that brings to mind Blackberry’s early days—and is aimed at reducing some of the 269 billion emails sent around the world each day. In person, Butterfield is soft-spoken and thoughtful, as one would expect from a guy who once contemplated a career as a philosophy prof. He joined us at RBCDisruptors earlier this week, where we had a chance to talk to him about effective communications, the merits of Silicon Valley and why corporate values are important. Here’s some of what we learned.

An Accidental Success Story

Stewart Butterfield didn’t start out to create either of his startups, Flickr and Slack. They were by-products of his efforts to create web-based, multiplayer games. The gaming ventures went nowhere. But in trying to build shared fantasy worlds, he came up with the photo-sharing software that became Flickr, and later the chat tool that morphed into Slack.

While he knew he was onto something with Slack, Butterfield didn’t initially think the tool would work for large organizations. Slack has 9 million users and counts IBM and Oracle among its biggest customers. While the path may not have been planned, building Slack into the company it is now—a challenger to the mighty Microsoft—was no accident, Butterfield says. “It’s a lot of work.”

An Antidote for Email

Butterfield’s luck with startups shouldn’t obscure his big ambitions. He wants to fundamentally change the way people collaborate, whether they work at IBM or as wedding planners. His solution is Slack, an alternative to the ubiquitous office email that Butterfield says is a “terrible choice” for intra-company communications. To illustrate, Butterfield describes a new hire signing onto corporate email and staring at an empty inbox. If that employee joins an organization using Slack, she or he has access to all the work that’s been done on a given project, right on Day One.

With the average 1,000-person company sending out an estimated 40,000 emails each day, it isn’t surprising that Slack has a community of evangelists.

Slack’s greatest advantage, Butterfield says, is that it provides a high degree of transparency across an organization, and quickly. That gives individuals and teams the clarity and alignment they need to perform their jobs.

The Valley Still Wins

Butterfield said more than once during the event that he’s a “patriotic Canadian,” and he believes Canada has all the talent it needs in terms of engineers, designers and marketers to staff Canadian startups.

So if given the choice, why would he start his next company in Silicon Valley? Butterfield’s answer was one we’ve heard before from entrepreneurs: It’s still the place with the deepest bench strength for recruiting specialized executive tech talent.

Corporate Values Matter. Like Playfulness

Butterfield took a page from Netflix’s playbook in assigning Slack some core values. But he wanted to make sure those values set Slack apart, reminding employees both how they should act and how Slack views them. He suggested any company should think carefully about its corporate values and ensure they tell employees and customers what makes it unique.

In case you’re wondering, Slack’s values include courtesy, playfulness and craftsmanship. Courtesy, for Butterfield, means empathizing with the client and always being open to understanding his or her needs. By emphasizing playfulness, he wants his employees to “look at the world sideways” in order to find creative solutions to problems. Craftsmanship is more than a call to avoid shoddy work—it’s Slack’s way of telling employees their individual work has meaning and value.

China’s Off Limits. Everywhere Else is Fair Game

When it comes to the massive and lucrative Chinese market, many tech companies want in. Slack isn’t one of them: Butterfield said the company isn’t prepared to give Beijing access to the company’s messaging data. But he is targeting the 600 million or so knowledge workers around the world that aren’t in China. He’s doing that by making Slack available in other languages and ensuring it supports specific industries and regulatory environments.

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Materially improving gender, ethnic and cultural diversity, particularly within executive teams correlates with a wide range of successes – specifically being able to recruit top talent and improve employee satisfaction and decision making.

Diversity can also help drive technological innovation and disruption. Consider Montreal-based Lightspeed, one of Canada’s most successful tech start-ups.

The software firm launched in 2005 by Dax Dasilva and a group of LGBT+ colleagues, and has grown in size to now include 600 employees in eight offices around the world.

A culture of inclusion was essential. So, too, was a recognition that innovation through diversity is as much evolution as revolution.

“Company culture is just as important as code,” Lightspeed’s CEO and founder Dax Dasilva told RBCDisruptors, our monthly event looking at innovation and how technology is changing the world around us.

Dasilva stressed that companies need to iterate in order to innovate.

As part of Pride Month, RBCDisruptors profiled Dasilva, a leading voice for the LGBT+ community in business and technology.

After Dasilva founded Lightspeed, he developed a mantra to ensure that everyone, regardless of gender or sexual orientation, had a seat at the table.

“That gave everybody the freedom to help us to grow the way that we wanted,” he said. “It allowed anyone at the company to be themselves and who they wanted to be.”

Lightspeed’s growth has soared since its start in a converted Montreal home and has become one of Canada’s most successful tech start-ups in recent years after its latest financing round in October that values the company around $1 billion. The company makes a cloud-based point-of-sale system that runs on tablets and computers aimed at for independent retailers and restaurants who annually process $15 billion worth of sales in over 100 countries.

Several recent studies that examine the business impact of LGBT-positive workplaces conclude that inclusiveness results in a more innovative and productive workplace. A study published in the journal Management Science in 2016 found that companies in U.S. states that are considered to be more gay-friendly are actually significantly more innovative, specifically producing higher rates of patents.

On average, companies based in U.S. states that passed laws that prohibit discrimination based on sexual preference or gender identity experienced an 8% increase in the number of patents and an 11% increase in the number of patent citations, compared to states that did not pass such a law.

And yet, LGBT+ people are among the most marginalized employees, according to a recent report by Diversio, a Toronto-based firm.

Diversio surveyed 2,100 people in 20 companies in Canada, the U.S. and Britain and found that LGBTQ2+ employees felt more at risk of workplace harassment, and were twice as likely to feel their opinions were not sought out or valued by their employers.

Dasilva shared an example in which he encouraged Lightspeed’s management to focus on diversifying the company’s data science team to gain additional perspectives.

“If we only build certain predictive models, it’s a self-fulfilling prophecy that creates a certain set of solutions. As great as the AI community is in Montreal, we have to have other viewpoints work on that data science and find new and different angles.”

Supporting LGBT+ inclusion also makes better business sense. A 2017 report by the Center for Talent Innovation concluded 71% of LGBT respondents and 82% of LGBT-supportive allies are more likely to purchase from LGBT-inclusive companies. Even more importantly, LGBT+ inclusiveness drives market innovation as teams with members whose sexual orientation matches the target consumer are much more likely to understand the market, the report found.

“We’re all looking for sources of innovation,” Dasilva said, stressing that one of his goals in technology is creativity. “All of the best of us is when we’re involved in something that’s creating good.”

After Dasilva launched Lightspeed, he discovered he had created a “monoculture” by hiring people from his own network of friends and acquaintances. It limited the company’s growth. “You have to own up to your mistakes and widen your circle,” he said. “You have to get out of your comfort zone of the people who are like you.”

In addition to managing Lightspeed ahead of a possible IPO next year, Dasilva also runs Never Apart, a Montreal-based non-profit organization that encourages social change through cultural programming. He understands that his role at both groups is to foster and build leadership, in the corporate world and within the LGBT+ community.

“The purpose of these two organizations is to build up leaders. You can’t make change in the world without having everyone see themselves as a leader.”

But with Bitcoin meeting gravity — falling from a high of $20,000 in December to $7,000 this month — is it also at risk of becoming the latest bubble to pop?

We put that question to three cryptocurrency experts at our most recent RBCDisruptors event:

Hilary Carter, Research Director at the Toronto-based Blockchain Research Institute;

Christian Lassonde, Founder and Managing Partner of Impression Ventures, who specializes in fintech investing;

and Matthew Spoke, the CEO of Nuco, a blockchain company that’s building a network to connect blockchains around the world.

Lassonde thinks crypto is more of a speculative asset than a medium of exchange, and fueled largely by greed and hype. Spoke disagreed, believing cryptocurrencies address a discontent with the centralized financial system. Either way, Carter thinks big companies and governments need to explore underlying blockchain technologies that can eliminate the frictions and costs of centralized book-keeping, whether for financial transactions or other methods of exchange.

<!– To hear our full discussion, listen to the RBCDisruptors podcast on Soundcloud or iTunes. –>

Here’s some of what was said:

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1. What’s the Problem?

For centuries, money has been centrally controlled and managed, for reasons of personal security and economic stability. But with universal access to electronic exchanges and cloud computing, those central ledgers may no longer be needed. Or so the cryptocurrency advocates would have you believe. They think every financial transaction can now be instantly recorded — and encrypted — on every computer in the world. Think of it as one of those card games that doesn’t require a dealer. But what if we like having a dealer, to keep track of the cards and score, and to keep an eye on the other players for us? Centralization is something most consumers seem happy with, whether it’s centralized social media platforms (Facebook), entertainment platforms (Netflix) or money (U.S. dollars). And we’ve already got a range of systems, including digital payments, that work fairly well. Even where there are areas of friction — cross-border payments, for instance — improvements are emerging through technology and competition. Carter still believes cryptocurrencies may be most useful in parts of the world where technology and competition are not widespread, or where trust in the banking system may be weak. She estimates there are 2.5 billion “unbanked” people in the world without access to traditional financial institutions. For them, cryptocurrencies offer an alternative — and may even be necessary for those wanting to protect their money from corrupt governments.

2. Isn’t That a Side Door to Money Laundering?

Crypto is sounding alarm bells with regulators because of its obvious appeal for those who want to go unnoticed. Even big investors may not want to be connected to it because of its links to the underground economy and illicit activities like smuggling, tax evasion and terror financing. As Lassonde put it, “the money that’s coming in doesn’t want to be known, doesn’t want to be traced.” He thinks cryptocurrencies are so useful to money launderers and sanction-busting governments that they won’t escape the long arm of global regulators for much longer. Can those concerns be addressed in time? Spoke, a crypto proponent, admits that’s unlikely, as the technology is out of the bag and “regulatory arbitrage” is already underway. But he feels the underlying technology can still be useful to identify patterns of abuse, and root out the wrong-doers, who will always be looking for alternative channels to move money. Throw out crypto, he said, and the evaders will find something else. “With every new technology, comes the good and bad and you just hope that over time, the good outweighs the bad, and this is a perfect example of that.”

3. What If Regulators Move to Shut It Down?

The Chinese government has cracked down on crypto activity, last year banning Initial Coin Offerings (ICOs) and this year announcing it will scrutinize crypto exchanges. Do crypto investors in Canada face similar risks of a regulatory crackdown? Lassonde thinks so, likening it to the peer-to-peer music sharing platforms that disappeared after regulations were imposed. “We may see a change in the laws here in the next five plus years, where the ownership of crypto has become illegal — there’s very effective tools from centralized states to crush this stuff,” he argued. Carter and Spoke see it differently, with an opportunity for Canada to lead. Recognizing cryptocurrencies as currencies would allow the federal government to license digital wallets, a move that would help Canadians keep their assets safe, they said. But Spoke worries public officials aren’t spending enough time on the issue. “If anybody understands this the least,” he said, “it’s governments and regulators around the world.”

4. With So Many Concerns, Will Crypto Ever Become Mainstream?

Crypto remains on the fringes, used largely by early tech adopters, speculators and thrill-seekers. Lassonde believes that taking that into the mainstream will require massive behavior change. And that usually requires a large organization investing heavily in the infrastructure needed to create platforms for entrepreneurs and developers. He likened it to what Apple did for smart phones — except with crypto, no major developer is stepping forward. Without that investment, he argued, massive growth will be hard. Spoke agreed, saying,“if we can’t get these systems to a point where they’re significantly more accessible and more efficient, I don’t think they will hit the mainstream.”

5. Could Crypto Find a Second Life in Other Areas?

If regulators crack down on crypto-currencies, the underlying technology may find a home in less regulated fields like voting and business registration. Carter says governments are interested in “non-payment applications” as a way to reduce inefficiencies, and they may be willing to launch test cases in fields that currently require a centralized ledger. Drivers licenses and vehicle registration, for instance. “If you’re the Blockbuster of today,” she asked, “what’s the Netflix of tomorrow?”

Fast forward to 2018, and another big American thinker, Dan Doctoroff, is aiming to join a new urban revolution in Toronto, this one fueled by data more than division.

Doctoroff would balk at any comparison to Jacobs, who made her name as a writer and rabble-rouser. He’s a corporate leader and builder. But he recognizes they both would see the power of sustainable neighbourhoods as a bedrock to any future city.

A former deputy mayor of New York, who help lead the city’s renaissance after 9/11, Doctoroff is CEO of Sidewalk Labs, a company he created with Google co-founder Larry Page to radically change the way design our cities.

Sidewalk Labs is now focused on Toronto, where they’ve won the right to build a 12-acre community called Quayside on the downtown waterfront — an urban lab, really, where up to 5,000 people will live, work and play. They’ll do that by harnessing technology to reduce the financial, environmental and emotional cost of city-dwelling.

“A set of technologies are converging that can fundamentally bend the curve on the quality of life,” Doctoroff says.

He calls it a “fourth urban revolution,” following the steam revolution that gave us trains and the connected city, the electric revolution that gave us the vertical city, and the car revolution that gave us the sprawling city.

Doctoroff spoke at the most recent session of RBCDisruptors, our regular series on innovation, disruption and how technology is changing the way we live. You can listen to the full conversation on our podcast on iTunes or SoundCloud.

Here are some of the highlights:

1. If It’s Technologists Versus Urbanists, We All Lose

Doctoroff and his Sidewalk Labs team studied 150 so-called smart cities around the world and found none had worked. Simple reason: they didn’t harness humanity. Too many tried to impose master plans (the stuff of urbanists) and master technologies (the stuff of techies) on residents, rather than letting them play with technology and see what might emerge. “Cities cannot be planned all the way down to the last detail. You want people’s creativity and imagination and ideas.”

2. We Need to See Cities As the New Smartphone

Quayside will be a platform for others to build on, with apps, systems and buildings that connect with each other through a kind of open-source neighbourhood. “What makes smartphones so revolutionary is that they enable through reasonably open APIs, for people all over the world to build on top of it, creating things that no one ever imagined were possible, and that’s what gives it the power that it has.”

3. Diversity Will Matter; Inclusion More So

Toronto is renowned for its diversity but its inclusiveness is what caught Doctoroff’s eye. People mix easily in the city, and the inflow of 100,000 people a year hasn’t led to any signs of social fray. This was critical to Sidewalk Labs’ decision to focus on Toronto rather than the other 51 cities it surveyed in North America. “People here (are) more open to new approaches and new ideas… If Amazon sees what we see here, it wouldn’t even be close.” Diversity will define Quayside, but its inclusions is what will make it relevant globally.

4. Avoiding a Digital Palace

Diversity is about more than people’s background. Quayside will need a vibrant mix of income groups and lifestyles if it’s to be useful as a lab. In other words, it can’t be a shiny palace on the hill for technologists. Doctoroff thinks a key to drawing middle-income families, including from the suburbs, will be its ability to meld community design and building to cut housing costs. He thinks Quayside’s living costs will be 15–20% cheaper than elsewhere in the city. “Imagine for that family that makes $80,000 a year, if you can save them 15%, or $12,000 a year, that’s a meaningful change in people’s lives.”

5. Building a Mobility Lab

Quayside’s first priority is mobility. Only autonomous-driving vehicles. A lot of vehicle and bike sharing. And experimentation in pathway design, from tighter corners (efficiency) to curved roads (aesthetics) to bigger sidewalks and laneways (open space). Doctoroff thinks Quayside’s design will reduce the footprint of roads and driveways, which take up 30–40% of North American cities. “If you can reclaim that, you can double the amount of public space, putting everyone within a very short walk of a park.”

6. An Environmental Moonshot

Doctorff is aiming for “the first climate positive community in the world.” That starts with buildings, which in Canada consume a lot of energy. The deep waters of Toronto’s harbour may act as a heating and cooling system. Trees along the waterfront can also help buffer residents from the lake’s winds as they walk or bike. And underground service corridors can feed electricity and fibre-optic cables to residents — along with goods to local shops and the removal of waste.

7. Privacy Remains a Paramount Challenge

Quayside has three guiding principles for privacy. First, protections will be built into all products. Second, all data collected will be used to improve quality of life, and not for commercial purposes. Third, the process used to develop these policies will be open and collaborative. Doctoroff says Toronto has the chance to create “a global standard” for privacy.

8. Toronto As a Global Hub

Doctoroff says Toronto has the chance to draw urban thinkers, and developers, from around the world, in a way Jacobs never envisioned. If Quayside works, cities from China to Nigeria will pay attention — and those who help build it will have a global market. He thinks the project may actually create a new kind of Silicon Valley, around city-building. “One of the great opportunities for Toronto is to set the global example for what urban living can actually be, and to become the hub of urban innovation.”