Jonathan Sposato ’89 said he learned everything he knows about business by owning a bar. After producing PC and console games for Nintendo and selling a photo-editing site to Google, the self-described serial entrepreneur now chairs GeekWire, a cheeky website that covers the world of technology.

By Edward Weinman

Jonathan Sposato

He is a geek hipster who refuses to wear socks and once met President Obama.

“It was during his reelection campaign. I was involved with contributing to his campaign and helping to rally the troops.”

What about those socks?

“I wear a lot of loafers and I think they just look wrong with socks,” said Sposato, who as a Whitman student studied politics and dramatic art, played lacrosse and was a member of Tau Kappa Epsilon.

“I haven’t worn socks in years.”

Sitting in Reid Campus Center the day after delivering the 2013 William M. Allen-Boeing Lecture, Sposato is in fact sockless, his bare feet protected by black loafers. But peculiar footwear is not this entrepreneur’s only quirky characteristic.

Despite his business success, the startup guru derives as much pleasure waxing about the sci-fi film series “Star Wars” as he does stock options, margin calls and raising capital.

“‘Star Wars’ changed my life,’” he said.

“First there’s this concept that all these different alien creatures can co-exist. That’s a powerful place to build a universe of ideas from. Then there’s the sense of the purity and heroism of the Jedi. The first two concepts merge beautifully with Yoda, where he’s the most powerful Jedi but cannot be judged simply on his diminutive and strange looks.”

While his love of science fiction can be described as geeky, it’s not a non sequitur, because he is chairman of GeekWire, an irreverent website that covers the world of technology and is read by captains of industry like Bill Gates and Paul Allen. Therefore, it’s Sposato’s job to mull over technology futures and high-tech gadgets dreamt up in sci-fi films, gadgets that have now hit the marketplace, like Google Glass.

“The area of embedded, wearable computing, something right over your eyes” is where technology is currently headed, he said.

Embedded computing sounds chilling, as if Google Glass might be the first step to the implantation of microchips into our brains, or barcodes tattooed on our wrists enabling doctors to scan us for our medical histories. If living online, all the time, is our future, will all this connectivity impact us positively or negatively?

Sposato is mixed. He worries that spending too much time connected, perpetually trawling social media sites, can cause behavioral changes. He points to recent studies indicating that our brains are more fractured, and that our devices and gadgets are changing the way we think.

However, he believes technology actually tightens social bonds. To prove his point, he mentions that he can post a photo of his son on Facebook, enabling his relatives to stay updated on his family life regardless of whether they live with him in Edmonds, Wash., in San Francisco or halfway around the world.

Jonathan Sposato ’89 details a few of his successes he “blames” on Whitman during his lecture in Kimball Theatre.

“It’s a net positive. There is all this verbiage that our technology disconnects us. It’s counterintuitive. In the final analysis, these things make us more connected than disconnected.”

Oh, but what about the teachings of Obi-Wan Kenobi? The seminal moment in “Star Wars” is when Obi-Wan implores Luke Skywalker to turn away from technology and rely on the mystical Force to help him destroy the Death Star, the technologically advanced home of Darth Vader, who is the personification of evil, a character with technology embedded within him – an advanced form of Google Glass, per say.

Surely the movie that Sposato said changed his life presents an acute warning about the dangers of a society too enamored with technology.

“I think the message is clear; staying connected via technology should not come at the expense of human intuition, spirituality (however you may choose to define it) and a certain code of ethics as embodied, in this case, by the Jedi,” Sposato said.

Sposato is a geek savant who, at times, sounds like a philosopher. The secret to his success, though, is this very ability to blend philosophy and business with pop culture in order to make judgments that help him construct strategies that lead to the next cutting-edge startup. In fact, his Boeing lecture was titled “Everything I Learned in Business I Learned Owning a Bar.”

“Bartenders need to be good-looking, social and not overpour their drinks,” Sposato said, explaining how this translates to technology startups, by adding, “In other words, in business, don’t overthink who needs to do what. Find the best person you can to do a particular job. You don’t always have to look for someone with a super broad range of skills.”

Sposato’s 9 tips for business success
+ 1 fashion tip

  1. Be tolerant of things being imperfect and scary.
  2. Manage your fear.
  3. Be okay with the “fog of war.”
  4. Be resilient to marketplace chaos.
  5. Be okay with failure.
  6. Be able to screw up fast.
  7. Don’t over think who needs to do what.
  8. Build a business that women will like. And men will follow.
  9. Believe that the customer is right.
  10. And don’t wear socks.

Other nuggets of wisdom that Sposato gleaned by owning a bar: “When building a business, whether it’s a bricks-and-mortar bar, or a photo-editing website, design it so it’s appealing to women. If you build a place for guys, only guys will show up. Women are not so interested. But build a place that is attractive to women, friendly, puts them at ease and resonates with them emotionally, amazingly, both men and women will show up.”

While owning a bar might have taught this “Star Wars” fan everything he needed to know about business, it was at Whitman where Sposato built the foundation for his entrepreneurial success.

“Everything that happens in business is a conversation between two people. Whether it’s a big company buying your start up, or a partnership agreement, or you’re trying to hire someone, or you’re on a stage trying to market your product.

“This comes down to core communications skills: powers of persuasion, critical thinking, putting together a well-constructed argument. Those are things you get in spades at a liberal arts school like Whitman College,” Sposato said.