Can CEOs Win Without Being Jerks? RunKeeper’s Jason Jacobs at XSITE

Unless they’re insanely lucky, pretty much every worker bee out there has a horrifying tale of a despicable boss.

They rule through threats, intimidation, and political gamesmanship. They’re unpredictable. And when they’re on the rampage, nobody’s job is safe.

If you don’t like it, tough—that’s the price of greatness, right?

Jason Jacobs would like to squash that idea. Jacobs is the founder and CEO of RunKeeper, a top fitness app for smartphones and other connected devices.

As one of the startup leaders building a new generation of tech companies in the Boston area, Jacobs says he’s trying to nurture a corporate culture that rejects the hard-bitten, scorched-earth template of some legendary CEOs of the past.

“It feels like, of late, conventional wisdom has almost been that in order to build the next Apple, you need to have Steve Jobs’s leadership style,” Jacobs says. “I’m of the school of thought that there is no one way to get there, and you need to find what feels best for you and surround yourself with others who ascribe to that same school of thought. And that you don’t have to be a ruthless jerk to get there.”


It’s certainly an idea that, deep down, you’d like to see succeed. And we’ve discussed this before with CEOs around Boston who are trying to do things differently.

But a nagging part of me wonders if it’s wishful thinking when you’re talking about companies of a truly grand scale. It could be that the great-culture CEOs will just get chewed up and spit out by Wall Street and more sharklike competitors.

This is one of the big ideas we’re diving into next week at XSITE, our annual all-day Xconomy Summit on Innovation, Technology, and Entrepreneurship at Babson College. Sign up here to get tickets—I’ll be moderating a talk with Jacobs and three other super-smart entrepreneurs about the lessons they’ve learned building their companies.

A Generational Change?

For his part, Jacobs thinks there doesn’t have to be a tradeoff between lasting company success and being a decent human. And, he says, a positive company culture actually is becoming an imperative for growing companies that want to hold onto younger workers who crave more autonomy and creative freedom.

“This new, emerging crop of workers is very different in terms of what is fulfilling to them, what their expectations are, what they’ll tolerate,” Jacobs says. “I think the whole concept that you’re going to follow instructions and bring something to life and leave the creativity to someone else—it’s just not going to fly.”

He says that cultural shift, particularly among valuable knowledge workers, is an outgrowth of the technological advances of the past 15 or so years, which have made side projects and even full-blown companies easier, cheaper, and faster to get off the ground.

“You don’t need to go raise $30 million in capital and have a huge team of people to get a product to market. You can do it with a handful of people in a coffee shop and 10 grand,” Jacobs says. With that as the backdrop, “everyone wants to be an entrepreneur in some way, shape, or form. And everyone wants to be an owner.”

Nice, But Not Soft

There doesn’t have to be a tradeoff between being a good-guy CEO and having high standards, Jacobs says.

“I’m a big believer, for example, in bringing in really strong personalities who can work independently, don’t want to be micro-managed, and really empower them to spread their wings and take ownership. So in that regard, I don’t believe in dictatorship at all,” he says.

Maintaining that culture, on the other hand, is worth getting ruthless about.

“If you want to achieve greatness, you need to be very clear about what your company stands for, what your culture is, and what your values are. And where there are elements of the company that don’t ascribe to those values, then you need to be ruthless about them getting the fuck out,” he says with a laugh.

Peers and Role Models

I’ve wondered about this leadership phenomenon myself, particularly how the news media builds up the mythology around smart, ruthless, insufferable success stories in business—Steve Jobs, Larry Ellison, Michael Eisner, Jeff Bezos, and more are celebrated as part of this phenomenon. (Meanwhile, Bill Gates has turned his early techno-brat image around through years of enormously generous personal philanthropy.)

You can find counterpoints if you look close enough. My favorite is probably Jim Sinegal, the co-founder and longtime CEO of Costco, who recently stepped down after grooming his successor for years from within the company.

Sinegal famously wore the discount business-casual clothes sold on pallets in Costco warehouses, visited nearly every store with a standard nametag that just read “Jim,” paid his employees very well (even when Wall Street wanted more profit), and didn’t have a public relations department, insisting that he and other top executives just answer their own phones.

The company’s employees tend to be highly enthusiastic about Costco as a career—almost as rabid as Costco’s dues-paying members get about shopping for enormous cartloads of merchandise.

There are some up-and-coming examples of this kind of leadership, too. San Francisco-based Dropcam has a “no assholes” hiring policy, sends its employees home at 6 pm to eat with their families, and has never lost a worker in one of the most competitive hiring environments in the country.

But stories like those seem to be spread a little more thin compared with the tales of domineering, intimidating captains of industry.

Jacobs says that, in his career, he’s had a hard time finding role models who have put the anti-Steve Jobs pattern into practice. “In fact, I wish I had more clear role models so I could bring them on as an independent director,” Jacobs says.

But what he has found are peers who want to change the way companies are run. In fact, I thought of this interview topic after seeing Jacobs tweet that he’d been discussing the “ruthless jerk” conundrum with Kinvey CEO Sravish Sridhar.

“It’s tricky, because it feels like we’re building a different kind of company than a lot of the companies that have been built around here before,” Jacobs says. “I don’t know if that’s because I’m a weirdo, or the landscape’s changed a lot, and it requires a different recipe for success.”

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