Moving Tech’s Moral Compass From The Inside Is Harder Than It Looks

Whether or not it actually lives up to its ideals, the tech industry has a long history of trying to hold itself to a higher standard in its rhetoric. (This literally goes back like 50 years or more.)

But as founding a company has become de-risked over the last 10 years and many growth-stage companies begin to veer into highly regulated areas like education and transportation, this messaging can miss the mark.

A classic example of this mismatch came up a few weeks ago when Asana co-founder Justin Rosenstein gave a speech at TechCrunch Disrupt in New York based off an essay he published two years ago called “Do Great Things.” In it, he urged other engineers, product managers and founders in the industry to devote their talents and limited time to meaningful work instead of products that quickly and solely produce revenue or exits.

On stage, he repeated the message he first set forth in the essay, saying, “Let’s do great things. Let’s do things that really, substantively work to help humanity thrive. Let’s solve the big problems. Let’s dedicate our energy to consciously moving the world in the direction of our dreams.”

The speech was polarizing. On the one hand, Rosenstein said he was inundated with positive e-mails from people who said they were inspired or were considering changing their career paths.

On the other hand, he was ridiculed both on ValleyWag and on Boy Genius Report for “the worst tech speech ever” that channeled “every obnoxious Silicon Valley delusion, all at once.”

So I’ve known Justin for years, and I do believe he’s coming from a genuine place. After establishing himself as an early engineer at Google and then Facebook, he set out to build Asana, a startup that builds software for teams to collaborate productively. He’s taking the Giving Pledge to contribute at least half of his wealth to charity, while his co-founder Dustin Moskovitz, who used to be the world’s youngest billionaire, plans to have pretty much nothing left by the time his life ends.

Yet messages like his can reek of the very sort of clueless entitlement that the tech industry is already under public barrage for.

“The guy behind me said he wanted to punch him in the face,” Disrupt attendee Tomas Puig, who currently heads marketing for WP Engine, told me.

After hearing some of the divided reactions over his talk, Rosenstein called me up and sounded a bit exasperated.

“There’s this frustrating catch-22 for those of us in the tech industry who’ve been arguing for social good,” he said. “Before you’ve achieved success, no one listens to you. And after you achieve success, you’re considered out of touch.”

He went on, “People protesting the “privileged techies” are saying that we’re being selfish, that we’re hoarding wealth without creating value. So here I am saying, ‘Hey, fellow privileged techies! Let’s care about the impact of our work, let’s be thoughtful about how leverage our privilege. Let’s give back.’”

Why did his message fall so flat for certain people?

For one, it’s hard to be told by anyone — even our parents — to do more meaningful work. It’s even more aggravating when it’s coming from a person who will never have to worry about feeding his or her kids or putting a roof over their head.

Rosenstein reiterated that his message wasn’t really for everyone. It was for people who have been lucky enough to have educational opportunities and connections to multiple career opportunities. He’s worried that the culture of the Valley has become increasingly oriented toward money over the last five to 10 years, and that conscious business isn’t even part of the conversation. It’s a concern echoed by other long-timers like Om Malik, who published a worrying essay about a culture of entitlement recently.

“My experience in talking to most, but certainly not all, hotshot engineers is that they really want to ensure they maximize what they get out of the opportunity like money and experience. But they don’t even bring up social good as on their list of considerations,” Rosenstein wrote me in an e-mail. “That’s not because they’re bad people, it’s because it’s not sufficiently part of the cultural zeitgeist or conversation. We need more cultural celebration of missionaries vs. mercenaries.”

Then, when TechCrunch writer Alex Wilhelm grilled Rosenstein afterward on stage, he pointed out that his message lacked specificity. Who gets to say what helps humanity thrive?

It’s fuzzy. Rosenstein was critical of social games like Candy Crush Saga. But even though Zynga, say, makes FarmVille, which has been a massive time suck for its targeted audience of middle-aged women, the company is considered one of the better ones in terms of its philanthropy and local civic engagement in San Francisco.

Likewise, online ad-based business models incentivize clickbait and content that splinters people’s attention. But it’s the boring ad-based businesses that mint cash for companies like Facebook and Google, so they can aim for more ambitious and outlandish pursuits like virtual reality and self-driving cars.

And while those ad-based businesses may seem boring today, putting the world’s wealth of knowledge at a person’s fingertips on their phones or connecting more than 1 billion people through social networking are still stunning achievements.

Rosenstein said he looks up to a specific cohort of companies that are both for-profit and aim for social good like Coursera, SolarCity,, Lending Club, Zipcar, Quora, ResearchGate and Tesla.

Check Your Privilege?

Lastly and most importantly, to be a great leader, you need be a great storyteller. You need to tell a convincing story about what a person or a community could become. And to be convincing, you have to know in a very human and empathic way what it is like to live another person’s life.

The problem with delivering this message from a standpoint of privilege is that people like Rosenstein may never know what it is like to feel powerless. We live in a country where so many people feel powerless, in their ability to pay for basic needs like food and housing, in their ability to provide a better future for their families, in their ability to stay in and keep contributing to their communities.

In his original speech, Rosenstein said, “Cynicism is just a symptom of disempowerment, and we are too powerful to be cynical.”

OK, fine, we might be more powerful than we realize. But if you never truly understand what it is like to be powerless, how effective will you ever be in convincing people that they can transcend their own circumstances?

There are tech leaders in the past who have done it well. Jobs’ 2005 commencement speech is pretty much the only thing that comes to mind. It was effective not just because of his achievements, but because his speech was about powerlessness in the face of death. That powerlessness before mortality is a universal human experience.

Missionaries turning into mercenaries

Anyway, I raise these questions about messaging because while it’s easy for outsiders to lob spitballs or point out hypocrisies in tech, there is a dialogue that needs to happen internally too.

Doing it is much harder than it looks. It’s like herding a bunch of cats.

There are the hoards of MBAs and ex-Wall Street types that have come in over the last few years, who arguably have a totally different set of values than the engineers who showed up here 10 years ago right after the first bust.

Then there the companies who have grown up and seem to behave in ways that have questionably little to do with their origins.

TechCrunch founder Michael Arrington posed that question to Y Combinator’s new head Sam Altman earlier this month, “Something I’ve been thinking a lot about lately is about the evilness of companies. And how companies that started off in this incredibly naive and great way saying, ‘We’ll never be evil,’ end up becoming Microsoft in some way.”

He went on, “The gist of it would be, Google’s motto was, ‘Don’t be evil.’ But what that means is they redefine what evil means to fit their behavior as opposed to changing their behavior to not be evil.”

Altman replied that different kinds of people are attracted to work for companies at different stages, and that changes their internal culture.

“You start with missionaries and end with mercenaries,” he replied, around the 20:00 minute mark in the video below.

Then there are billionaire tech luminaries who are trying to have impact through philanthropy with mixed results, like Zuckerberg’s $100 million gift to the Newark school system (which was brutally chronicled in the New Yorker last week).

Then there are, of course, San Francisco’s problems. Several tech leaders that have reached out in the last few weeks, asking for feedback on how they can better engage with the local community after we published this long story on housing.

A lot of people are worried. They don’t want to live in a monoculture. They don’t want to live in an exclusively wealthy city sanitized of all that’s interesting or special or historic about it. The gradual suburbanization of U.S. poverty where the less privileged are being shunted out to exurbs, far away from job opportunities and social services historically provided in the urban core, is disturbing.

Still talking past each other

I don’t really know the answers to these very complex problems. But I do know that the conversation has been fragmented for a very long time.

In the context of San Francisco, solving these issues means sitting down at the table and listening. There are lots of non-profits representing different interests from the Tenants Union to Mission Economic Development Agency to arts-focused groups like Gray Area that have been working on economic development, social mobility and housing for years.

These conversations are thankfully starting to happen, but sitting at the table will mean receiving a lot of anger, sadness and frustration. It means people may yell or scream at you. It might take hours. Realistically months or years. It may mean listening to things that sound untrue or unfair. It means sitting there and taking it. Because even that much is educational. Only then will you begin to understand the depth of the losses that are happening.

I was speaking with a longtime former Apple executive and Gray Area board member named Peter Hirshberg for another story. We were talking about the notion of civic hackathons, and he said the methodology needed to evolve.

“There’s this conceit that if you’re well-intentioned and you think you’re a good developer, you can show up at a very real problem that is systemic, not knowing anything about it, put 48 hours into it, help it and walk away,” he said.

He added, “It leads to something like a civic Tourette’s syndrome. It’s not that the tech industry doesn’t mean well. They’re just busy and naive and then they just show up in matters of community and into very real problems.”

Rosenstein’s speech wasn’t just about San Francisco. It was about many issues from health to education to clean energy. Even if his message isn’t new, it still needs to be said and repeated. There is a conversation that needs to happen inside the tech industry too.

So I turn the table to you, readers. What’s the way to have this conversation without seeming like a bunch of pricks?