Meet the doppelgangers of the PayPal mafia

Google Ventures and Vator teamed up last night for the first of a newly-launched series of Startup Sessions, which features one keynote speaker who shares his or her startup stories. Startup Sessions sold out a couple days ago and had a waiting list of attendees who wanted to join us.

The event sold out two days prior, and there was a long waiting list of people eager to get in!

Kicking off our series was David Sacks, founder and CEO of Yammer, which was bought by Microsoft for $1.2 billion in cash this past June. Sacks spoked to a standing-room-only crowd. 

Vator CEO Bambi Francisco opened up the first Startup Session with a funny slideshow introducing the different members of the so-called PayPal Mafia, a group of “superhero entrepreneurs and angel investors,” as Bambi called them, who were founders or early employees of e-commerce service PayPal. All of them went on to found their own tech companies, as well as fuel the next-generation of startups.

So who are the members of the PayPal Mafia? And, who are their counterparts?

An “unconventional thinker” and the guy who you never know what he is going to say, Peter Thiel is the Socrates of the group.

Fittingly, Thiel, who was co-founder and CEO of PayPal, majored in philosophy in college. 

He is also the Founder and President of Clairum Capital Management and Managing Partner at The Founders Fund, but Thiel is most widely known as an early investor in Facebook, where his $500,000 investment in 2004 made him the first outside investor in the company. He recently sold over 20 million shares at between $19.69 and $20.70 a share, netting him roughly $406 million. Thiel now only owns 5.6 million shares of Facebook stock.

At Vator VentureShift last year, Thiel told the crowd, “The contrarian thing is not to be with the crowd, or fashionably against the crowd, but to think.”

As Sacks points out, Socrates was forced to drink poison for his heresy, but, as Bambi put it, “he will be controversial always.”

Elon Musk, who also co-founded PayPal, is Iron Man, simply because he “has no gene for risk aversion,” as Bambi pointed out. According to Sacks, Musk, whose favorite book is Gates of Fire, which is about the Battle of Thermopylae, depicted in the movie 300, is a “larger than life, heroic figure.” On a side note, when asked who Sacks would make a movie out of (if he had to choose from among his fellow PayPal colleagues), he said it would have to be Musk.

Musk is currently the CEO and Chief Designer of SpaceX, CEO and Product Architect of Tesla Motors and Chairman of SolarCity.

Due to his long, flowing locks, Chad Hurley has the “glam hair” rock-star look going, and is the Jon Bon Jovi of the group, to which Sacks would only say, “No comment.”

Hurley is the co-founder and former Chief Executive Officer of YouTube. Before that he designed the original PayPal logo.

YouTube was sold to Google for $1.65 billion in 2006.

Jeremy Stoppelman is the bachelor, said Bambi. So he gets to be George Clooney (pretty lucky, I’d say.) Sacks joked that Stoppelman was going to like his alter ego better than Hurley would.

Stoppelman is the co-founder and CEO of Yelp, which went public in May and immediately soared 63% in its debut. The stock is now trading at $24.85 a share.

Kevin Hartz, is the mastermind, much like Billy Beane, said Bambi. Beane is the man who brought the Oakland A’s to the top of th AL West this year, beating out the mighty Texas Rangers, with nothing but grit, gumption, and consistency.

He is Founder and CEO of Eventbrite, and was previously Founder and CEO of Xoom Corporation, an international money transfer company, servicing more than 40 countries worldwide. Xoom is backed by Sequoia Capital, NEA, Fidelity Ventures, Stanford University and, Hartz’s old PayPal buddy, Peter Thiel.

Hartz also co-founded ConnectGroup, a start-up providing high-speed Internet access to the hotel industry, which was acquired by Lodgenet. 

He is also an early stage investor and advisor to start-ups including PayPal, Geni, Friendster, TripIt, Flixster, Adnectar, Yammer, TokBox, iControl, Boku, Flexilis, Anonymizer, and Trulia, and currently serves on the Board of Directors of Xoom, Flexilis, and TokBox (observer).

Reid Hoffman, partner at Greylock and founder of LinkedIn, is Yoda. Much like the Star Wars character, he has this “force” about him when it comes to startup investing, and building companies. Hoffman is the Jedi Master of Silicon Valley. He’s calm, collected and everyone listens to him.

Max Levchin is a very smart dude. He’s Stephen Hawking, who’s considered one of the most brilliant minds of our generation. Hawking is a physicist and theoretical cosmologist, dedicated to understanding the nature of the universe.

Levchin was a co-founder of PayPal. In 2004, Levchin founded Slide, which was sold to Google in 2010 for $184 million Levchin was also an executive producer of Thank You For Smoking.

And finally, there is the man of the hour himself, David Sacks.

So out of everyone, who is Sacks?

He plays in the World Series of Poker. He likes to play chess. His Beverly Hill mansion was in Pulp Fiction. He was nominated for a Golden Globe for producing Thank You For Smoking, in which Katie Holmes had a steamy sex scene (Sacks was not in that scene, btw).

David Sacks, PayPal’s former Chief Operating Officer and founder of Geni and Yammer, which he sold to Microsoft earlier this year for $1.2 billion, is the Most Interesting Man in the World.

Be sure to catch our next Startup Sessions on Nov. 13. 

(Image sources: Wired, Silicon Angle, Knowyourmeme, Wikipedia, Wigsarethenewwags, charmingfame.com, abcnews.go, stars.wikia, blog.debate.org