John Doerr on the great entrepreneurs of the last half-century

In his nearly 40 years in Silicon Valley, John Doerr has worked alongside many of the greatest entrepreneurs and leaders in history. The first: Former Intel CEO Andy Grove, with whom Doerr worked closely in roles ranging from intern to a leading sales person at the microchip company. Over the next four decades Doerr invested in, mentored, sat on boards of directors with, and otherwise observed Jeff Bezos, Larry Page (and Sergey Brin and Eric Schmidt), Reed Hastings, Steve Jobs and many other luminaries.

Speaking to a packed house at tonight’s PandoMonthly fireside chat in San Francisco, Doerr shared his impressions of each of these men, as well as a few personal bits of wisdom.

Andy Grove

Doerr’s first exposure to Andy Grove was when the CEO taught a course titled Organizational Philosophy of Economics at Intel University. Doerr’s job as a summer intern was to create benchmarks demonstrating the superiority of Intel’s latest generation chips over the models that came before them. After Doerr excelled at this, Grove invited him to travel to Europe with him for the summer as his personal assistant.

“Grove is tough – ruthlessly intellectually honest,” Doerr said, sharing that those who arrived after 8:05 am for morning meetings had to sit in the parking lot for an hour so that everyone would see them being reprimanded. “But he was the epitome of a great entrepreneur and a great leader – and those are two very different things. When they come together, extraordinary things happen.”

Doerr continually referred to Grove’s intensity and discipline, but he also described him as “humble and purposeful for the organization, putting the team before himself and willing every fiber of his being into the company.”

While Grove is famous for saying, “Only the paranoid survive,” Doerr believes that this was a motivational philosophy – even though he described paranoia as a “disease” state and a mercenary quality.

“You can build very valuable companies with both cultures [mercenary and missionary]. And I don’t believe that any company is all of one of these,” Doerr said. “But my advice to young people is that you need to understand the values of the place you’re going to join and make sure that you’re aligned with them.”

Grove was also “Level 5 Leader,” according to Doerr, in the Jim Collins sense of the phrase, meaning he embodied the mix of humility and strong will.

Jeff Bezos

John Doerr is an Amazon investor and board member and recalls a meeting of senior executives in the company’s early days that was attended by famed business consultant and author Jim Collins. Jeff Bezos, then a young and inexperienced CEO, confessed to Collins in front of his entire team to feeling “less than a Level 5 Leader,” Doerr recalls.

Asked for his advice, Collins told Bezos, “Go to work every day and make getting better your North Star. Aim at that every day,” Doerr recalls.

Apparently Bezos was a good student because he has since disrupted multiple industries and built one of the most enduring and valuable Web 1.0 companies. Doerr describes him as “Very aggressive – he’s that guy. He’s very technical, and takes a very long term view of everything.”

Very early in Amazon’s life, the CEO set the goal of getting big fast. He was never concerned with appeasing Wall Street investors, saying, “All the investors who want to find us, will,” according to Doerr.

They always had a very simple clear strategy, Doerr says, which was to be the world’s most customer-centric company, to offer the broadest selection, and to have the best prices. Amazon has a multitude of spiders crawling the web searching for competitors’ prices, and matches them whether it’s Walmart or a mom-and-pop dotcom site. This clarity of thinking – what he’s doing and also what he’s not doing – is a common trait Doerr sees among great entrepreneurs.

Another aspect of Bezos’ strategy was his insistence on always planting a lot of seeds, Doerr says, noting that this makes him a lot like Google’s Larry Page. The Amazon CEO is addicted to new ideas and always open to ideas from the outside. The key for both Amazon and Google has been the ability to shut things down when they’re not working, and to be disciplined about the ones that they choose to pursue.

Larry Page

“One of the great things about [Google co-founder] Larry Page as a CEO is that he’s so passionate about product,” says Doerr, an early investor and longtime Google board member. Leaders don’t need to be great creators, according to the Kleiner Perkins partner, but entrepreneurs need passion, drive, for product-first thinking.

Asked whether founders should always remain CEO of their company, Doerr said, “If they can grow with their business, yes.”

“When Google started it was my view that [Larry Page and Sergey Brin] weren’t ready – weren’t ready to run the company at Google scale,” Doerr says. “There wasn’t enough time for on the job training.”

But bringing in Eric Schmidt to assume the CEO role was one of the best things that ever happened to the founders and the company, according to Doerr, though it was alway seen as a short-term situation. “The plan always was that Larry would grow faster than the company,” he says. The three leaders always maintained a mutual respect for one another, Doerr says, with Schmidt often deferring publicly to the founders. And in the rare cases when they disagreed, they did so behind closed doors.

Doerr calls Page’s greatest strength his “incredible ambition and imagination.”

“He just reeks of ambition. I bring him an idea and he will 10X it.” He offered an example of this trait, recalling an exchange the two had when discussing the Google Fiber project. In response to Doerr’s suggestion that Google work to deliver its high speed fiber network to every community in the US, Page told him, “You’re not thinking big enough, John. We need to look beyond fiber.”

Reed Hastings

Despite his stellar track record as an investor, Doerr has missed out on his share of great companies. He named Microsoft and Cisco as his biggest omissions. But more recently, Netflix is one that he wishes he could have been a part of, largely due to his admiration for founder and CEO Reed Hastings. Instead, Doerr had to abstain due to a potential conflict with his existing investment in Amazon.

“Reed is one of the best entrepreneurs of our time,” Doerr says.

Without delving too deeply into his business, Doerr shared a story about Reed Hastings the man. Despite his enormous obligations as the CEO of rapidly-growing public company, Hastings found time to serve as the president of the California State Board of Education from 2000 to 2004.

“He was so passionate about improving the state of these poor public schools,” Doerr said.

Steve Jobs

Since his death in 2011, late Apple founder and CEO Steve Jobs has been mythologized by entrepreneurs. Given this, Sarah asked Doerr, “When people talk about Steve Jobs, does it sound like the man you knew?”

“It was really surprising to me when Steve passed away,” Doerr says, “just how many entrepreneurs for some reason came up to me and said, ‘You know John, I want to tell somebody what a difference Steve made to me and what an inspiration he was in building my company.”

Doerr doesn’t think that these entrepreneurs necessarily want to be like Jobs, referencing his infamous demanding and difficult style.

“For entrpreneurs to try to be like Steve Jobs,” Doerr says, “that’s a failing mission. He was unique. He was original. He was iconic.”

Michael Carney

Michael Carney has spent his career exploring the world of early stage technology as an investor and entrepreneur and has participated in building companies in multiple countries within North and South America and Asia. Ultimately, he is an enthusiast of all things shiny and electronic and is inspired by those who build businesses and regularly tackle difficult problems. You can follow Michael on Twitter @mcarney.