tl;dr:

Andreessen makes bets on technology x people. The tech has to be provocative and world-changing, but more importantly, the people behind the tech have to be thoughtful, bold and unique in their worldview.

Interesting points:

- A16z makes bets on consumer tech in later rounds (more risk earlier, increased cost later worth the more sure bet) - i.e. Oculus

- Invests in enterprise tech earlier (less risk of a fickle consumer / competition)

- What's better than telling investors (or at least a16z) what they want to hear is providing them with insight as to why their assumptions might be wrong and you have better answers (phrased here as "It’s a delight when they look at you with contempt—You idiot—and then walk you through the idea maze and explain why your idea won’t work.")

Read the article, you won't regret it.

Some of my favorite excerpts:

[1]
In 1996, when Horowitz was a Netscape product manager, he wrote a note to Andreessen, accusing him of prematurely revealing the company’s new strategy to a reporter. Andreessen wrote back to say that it would be Horowitz’s fault if the company failed: “Next time do the fucking interview yourself. Fuck you.” Ordinarily, relationship over. “When he feels disrespected, Marc can cut you out of his life like a cancer,” one of Andreessen’s close friends said. “But Ben and Marc fight like cats and dogs, then forget about it.”

[2]
A16z led Airbnb’s B round. Soon afterward, the company was battered by headlines about renters who trashed a San Francisco home. It wasn’t axe murders, but, Chesky said, “It was a P.R. nightmare. We had just expanded from being ten people living in a three-bedroom apartment and we had no idea how to be a billion-dollar company. Marc came to our office at midnight and read the letter I’d written to our community about the Airbnb Guarantee, and the two changes he made changed the company forever. I’d said we guarantee five thousand dollars for property damage, and he added a zero, which seemed crazy.” Andreessen also added the proviso that claimants would have to file a police report, which he correctly believed would discourage scam artists. “And he told me to add my personal e-mail address. He gave us permission to be bold.”

[3]
A favorite Andreessen response to underlings’ confusion was “There are no stupid questions, only stupid people.” Jim Barksdale, the company’s C.E.O., said, “I’d tell Marc after meetings, ‘You don’t have to tell a dumb sumbitch he’s a dumb sumbitch.’ ” Andreessen told me, “I needed Netscape to work, it had to work—it was my one-way door—so I was absolutely intolerant of anything that got in the way”—meaning, he clarified, “people.” He could never relax: “I am very paranoid. And the down cycle hurt a lot more than the up cycle felt good.”

[4]
[...] Peter Thiel suggests, is that Andreessen may not be as suited to making early, counterintuitive investments as he is—a point that Andreessen concedes: “Peter is just smarter than I am, and in a lateral way.” But, Thiel says, Andreessen is well positioned, because of his broad knowledge and flexible mind-set, to respond to incremental changes in an array of fields. And that, he argues, is what the times reward: “While Twitter is a lesser innovation than flying cars, it’s a much more valuable business. We live in a financial age, not a technological age.”

[5]
One challenge for Andreessen is whether venture itself has a skills problem. If software is truly eating the world, wouldn’t venture capital be on the menu? The AngelList platform now allows investors to fund startups online. Its co-founder Naval Ravikant said that “future companies will require more two-hundred-thousand-dollar checks and way fewer guys on Sand Hill Road.” Jeff Fagnan, of Atlas Venture, which is the largest investor in AngelList, said, “Software is already squeezing out other intermediaries—travel agents, financial advisers—and, at the end of the day, V.C.s are intermediaries. We’re all just selling cash.”

Andreessen sometimes wonders if Ravikant is onto something. He’s asked Horowitz, “What if we’re the most evolved dinosaur, and Naval is a bird?” Already, more than half the tech companies that reached a billion-dollar valuation in the past decade were based outside Silicon Valley. And as Andreessen himself wrote in 2007, before he became a V.C., “Odds are, nothing your V.C. does, no matter how helpful or well-intentioned, is going to tip the balance between success and failure.”

[6]
He acknowledged, though, that his optimism dims once human beings—with their illogic, hidden agendas, and sheer bugginess—enter the equation. “We’re imperfect people pursuing perfect ideas, and there’s tremendous frustration in the gap,” he said. “Writing code, one or two people, that’s the Platonic ideal. But when you want to impact the world you need one hundred people, then one thousand, then ten thousand—and people have all these people issues.” He examined the problem in silence. “A world of just computers wouldn’t work,” he concluded wistfully. “But a world of just people could certainly be improved.”