What happens when two of the world's most innovative and well-known entrepreneurs find themselves in the same room? Well, for starters, a seriously wide-ranging conversation. Netscape founder Marc Andreessen spent an hour interviewing PayPal founder Peter Thiel for an October episode of the a16z podcast.

Don't have time to listen? Here are the seven biggest takeaways:

1. The eBay acquisition of PayPal was famously drawn-out and, in fact, took five separate negotiations to finally complete. After the fourth, it looked like there was “going to be this crazy eBay-PayPal war that was going to escalate,” but Thiel told the story of the fifth and final one: "In June 2002, there was this eBay convention in Anaheim. We managed to get a booth there even though they weren’t that friendly to us at the time, so we sent 30 people down to the convention. And we handed out all these PayPal T-shirts. They saw all their power sellers wearing PayPal T-shirts, and at that point, they decided to buy the company.”

2. The PayPal Mafia--a group of early PayPal employees--has spawned tremendous numbers of foundational businesses, including Elon Musk’s Tesla and SpaceX, Reid Hoffman’s LinkedIn, and YouTube and Yelp. “One of the lessons you learned at PayPal was that it was hard--but possible--to build a great company,” Thiel said. “Most of the time, people are either in companies that fail--and then the lesson you learn is that it’s impossible to build a great company, and so the next time around, you try to build something that’s less ambitious, and then you certainly will not build a great company. Or you are in a company where everything works just phenomenally from Day One, like Microsoft or Google, where you then learn the lesson that it’s easy to build a great company. There’s a way in which both the lesson that it’s easy and the lesson that it’s impossible are equally wrong, because both lessons tell you that there’s no point in working hard.”

3. Thiel and Andreessen also talked management strategies. “Conflict happens when different people want to do the same thing,” said Thiel. “The challenge you have as a boss is to try to have people do different things. If you’re a sociopathic boss, you tell two people to do the exact same job and you’ll generate a fight out of nothing … The challenge in a startup is that there’s a lot of fluidity in the roles, and so people end up doing a lot of different things in ways where these roles overlap.”

4. Is Silicon Valley in a tech bubble? Thiel thinks not: “I tend to think the bubbles always required the public to be involved in a very big way, and they were these psychosocial phenomena on some level, and the public is not really involved because companies are not going public until extremely late in the cycle.”

5. One lightning round question regarded monopolies like Google and their ability to remain innovative. “As long as the founders run the companies, there’s usually enough pressure to keep doing things,” Thiel said. “Once the founders are replaced with politicians who act like CEOs, you end up with much less incremental stuff happening.”

6. The trend toward tech companies remaining private hasn’t gone unnoticed by Thiel. “I think we have a permanent shift toward privately held tech companies,” he noted. “The interesting question would be: Could you build a great tech company in Silicon Valley that stays private forever?” Andreessen replied, “And do you believe the answer is yes?” Thiel’s answer: “I think the answer is yes.”

7. The two discussed artificial intelligence in what’s surely a nod to Elon Musk’s comments on the subject (the conversation also included the anecdote of how Musk crashed his uninsured million-dollar sportscar with Thiel in the passenger seat on the way to a venture capital meeting). “It always gets framed as this question: Will computers take our jobs? Will they replace us?” Thiel said. “And if you had general artificial intelligence, this would be as significant as aliens landing on this planet, and the first question would not be, ‘What does it mean for my job?’ It would be, ‘Are they friendly or are they unfriendly?' So I think the political question is far more important than the economic one--but I think that’s still one for the 22nd century.”

Published on: Oct 20, 2014