Discussions about technology are often factual, sometimes forward-looking, but rarely philosophical. But Salesforce Chairman and CEO Marc Benioff and Uber Co-founder and CEO Travis Kalanick are not typical technology leaders. In a fireside chat during Dreamforce last week, Benioff revealed that he’s a frequent Uber user, and engaged Kalanick in a conversation that went beyond Uber’s features, even going so far to say that “Life is like an Uber journey. You get on and you get off.”

Here are other philosophical moments from their discussion.

The evolution of the narrative

Kalanick, fresh off an interview with The Late Show with Stephen Colbert told Benioff that he is just starting to get comfortable with telling the Uber story.

“As an engineer you make stuff and let the work speak for itself,” Kalanick said. Since the phenomenal growth of Uber, he’s realized that actions don’t always speak louder than words and that he’s had to learn how to tell the Uber narrative, otherwise other people will almost certainly decide to fill in the blanks themselves. “I’m just learning to get out in front of it.”

When Benioff asked him why he started Uber in the first place, Kalanick responded that his inspiration was the challenge faced by taxi cab drivers to make a decent living without working around the clock.

“Taxi drivers are good people being treated badly,” he said.

When Benioff challenged him on this inspiration, intimating that this narrative must have changed over time, Kalanick conceded that it had, quipping “You’ve gotten better at telling your story, too.”

Finding a company’s heart

During their discussion, Benioff asked Kalanick how he knew Uber has a heart. After putting his hand on his chest and joking that he could feel it beating, Kalanick shared his perspective on the topic.

“You know it when you see it,” Kalanick said. “You ask that question every day because you want to go to work and feel it.”

Kalanick then shared some of the company’s philanthropic efforts including Uber’s Military program, which encourages unemployed or underemployed military veterans to sign up and drive for the platform. Additionally, he mentioned a program delivering gifts to kids during the holiday season and transporting “goods, food and water” to displaced migrants fleeing Syria.

The difficulty in showing heart, Kalanick suggested, is that much of what is done happens at a very local level.

“Every day…we’re doing three or four of these things. This is how we show heart,” he said. 

Benioff, recently referred to as the “tech world’s moral conscience” in Vanity Fair, encouraged Kalanick by citing Salesforce’s own 1-1-1 model and recognizing that there’s always more to do.

“I think that it’s really about getting back to what is the culture and what are you trying to create. There are a lot of different ways to create success. There’s a wide spectrum of leaders and there’s a wide spectrum of success and so you can be intentional on where you’re trying to go,” Benioff said. “I look at what we’re able to do with our 1-1-1 model – we’ve done a million hours of community service, or we run 25,000 non-profits, or have given away $100 million. But when I look at the spectrum of what other organizations do for the world, it’s just a speck of sand on the beach.”

Developing a philosophy of work

Both Salesforce and Uber have strong, proud cultures – and it’s not accidental. According to Kalanick many companies don’t dig as deeply as they should when it comes to corporate culture.

“We’re in the process of creating what I call a philosophy of work. You spend half of your day working, and it should matter,” Kalanick said. “It should be more than work; it should be something you believe in. And the principles and how you approach your work should matter too.”

For Kalanick culture is integral to a company’s success.

“The most important thing...is creating a culture at your company of people who want to invent, want to create, want to make a difference and who you love working with – super smart people who work really hard, who are creative problem solvers and are super optimistic,” he said. “Because if you have that, and you don’t know the destination in your journey…your journey’s going to be amazing.”

Taking the metaphor a step further, Kalanick stated that "We're on the road, we're driving, it's a little bit foggy, and we don't know where it's going, but we're really psyched to be on this journey."

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