1. They’re drop-outs.
Interestingly, Anna’s badass quotient here exceeds Steve by far, having dropped out of secondary school at 16. She briefly returned to school to take some classes in fashion, but soon dropped out with the declaration that “You either know fashion or you don’t.” Meanwhile, Steve waited until he’d completed a semester at Reed College to leave it behind, as he wanted to honor his adoptive parents’ request that he give higher education a fair shot. Anna went back to working at the renowned boutique Biba, and Steve worked at Atari to make money for his spiritual retreat to India.

2. They’re both big fans of “spiritual retreats.”
Maybe we’re exaggerating in Anna’s case, but most would say that disappearing with Bob Marley for a week definitely counts. It may not be the same as Steve’s trip to India where he experimented with psychedelics, shaved his head and became a Buddhist, but the unknown parts of Anna’s adventure were likely just as fascinating.

3. 21 was a good age for them.
At 21, Anna got her first job in fashion journalism and first let it be known that she wanted to be editor of Vogue. Having been hitting up the social scene since her teens, by the time she entered her 20s anything seemed more interesting than a vodka tonic. Meanwhile, Steve founded Apple Computer with his friend Steve Wozniak. It bears comparison that when Steve Wozniak was 21, he was just meeting Steve Jobs – and Jobs was 16, already convincing Wozniak to invent the personal computer that would become the foundation of their company.

4. They don’t date quietly.
Whether it’s denying paternity or dating Joan Baez to get closer to the spirit of Bob Dylan, Steve’s known for pushing the limits of dating. Although Anna doesn’t go for denying parenthood or dating folk singers, she started dating older men at age 15 (in that case, a man 9 years her senior) and kept up the habit for years. It’s safe to say that both avoided dating experiences (and accidental children) that could hold them back, and kept striving to move upwards in the social stratosphere. Despite their obvious adventurousness and love of fleeting power, both have been married and Jobs still is (and has taken back that paternity denial of yore).

5. They’ve clashed with authorities…a lot.
It takes a lot to get fired from a position you created in a company that you created. For anyone who’s watched Pirates of Silicon Valley, it’s evident that Jobs earned his disgrace at the hands of John Sculley. Also, Jobs didn’t limit himself to antagonizing other authorities within Apple – his opinion that IBM (a more powerful competitor, at the time) was the enemy was a driving force behind his work on the Macintosh. Of course, Anna’s no innocent here, either. Fired from her junior fashion editor position at Harper’s Bazaar in nine months for putting the desires of her editor behind her own innovations, Wintour is known for stepping on the toes of many gatekeepers of the industry. Even when she first interviewed to work at Vogue with editor-at-the-time Grace Mirabella, Anna declared that the job she was after was Mirabella’s, and the interview ended shortly thereafter.

6. They clash with subordinates…a lot.
Known as “Nuclear Wintour” as soon as she began working at British Vogue, Anna is legendary for tearing apart the workforces and creative approaches of the publications she’s worked with. Acting as a strict curator, Wintour’s alienated many of the creatives beneath her by demanding new directions despite intense time pressures. Similarly, Jobs is renowned for his tantrums and rages when facing work he doesn’t like. Not limiting his tantrums to verbal bashings, when he first returned to Apple in 1996 he terrorized the campus with impulsive and brutal firings.

7. They define their industries.
I know this was said in the introduction, but it bears repeating – Steve Jobs spearheads innovation and trends in technology as Anna Wintour spearheads innovation and trends in design. The impact they’ve had on their respective industries has shaped the work of their contemporaries and their competitors for years, and will continue to for as long as they are active members. Surely, there’s something to be learned from their common examples of playing with fire, taking the consequences like a baller, and leveraging power with confidence. Just as surely, hanging out with a Marley…it can’t hurt.

Google does have an ever-growing suite of applications, and talented engineers creating and unifying them further. While Apple is a recognized innovator in the consumer product space, Google is the same for the space of internet services and applications. And there is definitely room for more innovation in the space of mobile services, and particularly VoIP technologies. While “regular” VoIP isn’t really a threat to AT&T, the reason is that the user experience of VoIP is sub-par, even in those that have a wide set of services – they are usually not very well integrated with each other, or with the phone. With the advent of push technologies and Google’s gifted manpower, they are the company most likely to provide and support a service powerful enough to supplant native calling and texting. From that perspective, allowing Google Voice applications to remain in the store would be to leave a gaping hole in AT&T’s defenses, which are already quite worn. But now that the FCC is involving itself, it’s not going to get easier for the cellular behemoth.

As far as the FCC goes, it’s interesting to see them stumble into the mobile space. Apple has been rejecting applications ever since the store was conceived of, and AT&T has had a death grip on their iPhone exclusivity deal (which is also coming under fire). Furthermore, the mobile space has always been messy and frustrating – mobile service providers occupy the same circle of Hell as insurance agents and tax attorneys as far as consumers are concerned. As Sascha Segan points out, there are bigger issues in the mobile space that really need to be tended to first:

The FCC’s time could be much better spent on actual industry-wide, anti-consumer collusions like overcharging for individual text messages, locking people into contracts well beyond the point when they’ve paid off their phone subsidies, or making exclusivity deals that prevent rural users from getting access to particular phones.

After all, such fundamental changes would allow consumers to easily switch to a phone they could install GV on, and this debacle would be irrelevant. FCC’s James Schlichting points out “pending FCC proceedings regarding wireless open access (RM-11361) and handset exclusivity (RM-11497)” exist, and it’s great to know that there are proceedings taking place. However, I’m surprised they aren’t focusing on those directly instead of sending letters to a company that is not on the decision-making end of wireless open access or handset exclusivity. I wouldn’t go so far as Segan to suggest that Eric Schmidt’s shoulder-nudge and wink-wink relationship with President Obama has played a role in the Apple smackdown, but since most FCC investigations go nowhere, I wouldn’t rule it out as a passive aggressive way to get on Apple’s case.

Google’s increasing move into Apple’s space, and Apple’s increasing desire to control every inch of that space have not been good bedfellows. It’s hard to imagine that Apple could maintain a completely healthy relationship with a direct competitor in both the phone and OS space for very long…
- Engadget

Isn’t a “completely healthy relationship” one where neither company has any undue sway over or actionable insight into the motivations and plans of the other? This paints Apple as a monopolist punishing Schmidt for Google’s entry into the mobile and OS space, and I find that unrealistic. As far as I can tell, it would be completely unhealthy to maintain a position where your direct competitor has more insight into the moves you’re planning to make than most of your employees do. Competition aside, it still doesn’t make sense for Schmidt to be on the board; having him step out of any discussion where he may have a conflict of interest is an efficiency killer. Also, Google has been making daring moves into several new spaces, and the areas in which Google may come to compete are completely unforeseen. Apple’s task isn’t to appeal to fair-weather fans, it’s to protect the company’s interests, as is true of any corporation. I have difficulty seeing an alternative that doesn’t consist of Apple making a poor business decision that impedes the efficiency, equity and security of the Board of Directors. Or as Fake Steve Jobs puts it:

You sat in our meetings and learned all of our secrets. You listened to our product development plans. Then you went off and copied our products and now you’re trying to fuck me in the ear with my own ideas. …”Don’t be evil?” Is there anyone left in the entire world who still believes that?

If Steve Jobs were on Google’s Board of Directors and the same thing went down, I highly doubt Google would be perceived as a tyrant, but as a company making an appropriate decision based on the way the cards were falling. But as Gizmodo says, “Pick your sides; this should be fun.”