20 Serial Entrepreneurs: An Analysis

Serial entrepreneurs want to change the world and “make meaning” but successful ones also make money, and lots of it.

Here is a list of 20 serial entrepreneurs and the companies they helped create:

1. Andy Bechtolsheim: Sun Microsystems, Granite Systems, Arista Networks
2. Biz Stone: Twitter, Xanga, Blogger
3. David Duffield: PeopleSoft, Workday
4. Dennis Crowley: Dodgeball, Foursquare
5. Elon Musk: PayPal, SpaceX, Tesla Motors
6. Evan Williams: Blogger, Twitter
7. Jack Dorsey: Twitter, Square
8. Jason Calacanis: Silicon Alley Reporter, Weblogs Inc., Mahalo, Launch, OAF/TWI
9. Jim Clark: Silicon Graphics, Netscape, Healtheon, MyCFO, Neoteris
10. Kevin Rose: Digg, Pownce
11. Marc Andreessen: Netscape, Opsware, Ning
12. Mark Cuban: MicroSolutions, Broadcast.com, 2929 Entertainment, HDNet, Magnolia Pictures, Landmark Theatres
13. Mark Pincus: Tribe.net, SupportSoft, Zynga
14. Max Levchin: PayPal, Slide, WePay
15. Nick Grouf: Firefly, PeoplePC, SpotRunner
16. Niklas Zennström and Janus Friis: Kazaa, Skype, Joost, Atomico, Rdio
17. Scott Jones: Boston Technology, ChaCha
18. Sean Parker: Plaxo, Napster, Facebook, Causes, Founders Fund
19. Steve Jobs: Apple, NeXT, Pixar
20. Wayne Huizenga: Blockbuster, Waste Management, Auto Nation

Birds of a feather flock together

Of the companies listed, you may have noticed some repeated names. When we sort the list by the companies with at least two serial entrepreneurs from our list, we get three companies:

1. Twitter: Biz Stone, Evan Williams, Jack Dorsey
2. PayPal: Elon Musk, Max Levchin
3. Blogger: Biz Stone, Evan Williams

Similar Industries

And of the companies listed, another trend emerges, which is the similarities in industries.  The companies can be narrowed down into a surprisingly small number of groups, which could be categorized as ‘Technology’ and ‘Other’, but broken we see a large amount of Web 2.0 and Entertainment companies as well as Transportation:

1. Software: Twitter, Blogger, Xanga, PeopleSoft, Workday, Dodgeball, Foursquare, Netscape, Ning, Plaxo, Napster, Facebook, Digg, Paypal, Slide, WePay
2. Hardware: Sun Microsystems, Arista Networks, Granite Systems, PeoplePC, Apple, NeXT
3. Entertainment: Pixar, 2929 Entertainment, HDNet, Blockbuster, Zynga, Magnolia Pictures, Landmark Theatres
4. Transportation: SpaceX, Tesla Motors, Auto Nation

This follows a pattern in economics called ‘barriers to entry’ of which software has the lowest barriers in terms of cost and transportation, the highest.  Hardware and entertainment, it seems, falls in the middle, which is what you would expect.  So in the future, we can probably expect more serial entrepreneurs in the software arena, probably culminating up through app makers, which has the lowest barrier of entry and the highest audience: a combination ripe for the next round of serial entrepreneurs.