Obama and Sposato
President Obama with Jonathan Sposato '89 and his wife Heather Lowenthal

Jonathan Sposato ’89 is a self-described “serial entrepreneur” who says he learned everything he knows about business by owning a bar. But first he was a Whitman College student who studied politics and dramatic art, played lacrosse and was a member of Tau Kappa Epsilon.

Sposato is a startup guru who co-founded Manly Games, producing PC and console games for companies like Nintendo. His startup Picnik gave “everyday, real people photo-editing superpowers.” And the “Star Wars” fan now chairs GeekWire, an irreverent website that covers the world of technology. He is what’s known as a  “geek hipster,” and he has met President Obama.

Sposato recently spoke at Whitman as the 2013 William M. Allen-Boeing lecturer.  Whitman’s staff writer, Edward Weinman, visited with Sposato, who talked about entrepreneurship, a liberal arts education, Obama and “Star Wars”:


Edward Weinman: What were you doing hanging out with President Obama?

Jonathan Sposato: It was during his reelection campaign. It was an opportunity for him to meet with business leaders in the Seattle area. I was involved with contributing to his campaign and helping to rally the troops.

EW: Your thoughts on meeting him?

JS: There is a marked difference between the president you see in the media versus the person who is the president. On the human scale, President Obama was incredibly approachable, warm, sincere and candid. That’s who he is.

EW: You’re an über entrepreneur. What’s the secret to your success?

JS: My answer always changes, but number one, you must be tolerant of things being imperfect, things being chaotic and things being scary. You can’t be afraid of risk, or, you’re afraid of risk but you have to manage your fear. You must be okay with the “fog of war.”

EW: The “fog of war”? That sounds serious.

Jonathan Sposato: When running a startup things are not deterministic. The outcome that you want is not the outcome that you will necessarily get. You have to be resilient to market place chaos. You must be okay with failure. I always say, “You have to be able to screw up fast.”


EW: You’re a Whitman alumnus. How does a liberal arts education develop entrepreneurial skills?

JS: Being an entrepreneur means you’re wearing many hats. A liberal arts education helps with that. 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.

EW: How is GeekWire different from other news sites reporting on technology?

JS: The brand and editorial voice of GeekWire are edgier. I like to think of it as an indie rag, like “The Stranger.” GeekWire is “The Stranger” for the technology industry. The biggest compliment I’ve been paid is that the captains of industry, people like Bill Gates and Paul Allen, read it on a daily basis.

EW: What is your definition of a Geek?

JS: Someone who unabashedly goes crazy with his or her passion. If someone is really into “Star Wars” and so at their startup company they name every conference room after “Star Wars” characters, like the Jedi Knight Room or the Yoda Room, that’s a geek. They are not going to apologize for it. They reveal their passions in a way that is delightful and charming.

EW: So let me guess. You’re a fan of “Star Wars.”

JS: The movie changed my life.

EW: What draws you to the film series?

JS: 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.  

EW: In our universe that is not so far, far away, we have Facebook, Twitter, smart phones and tablets. What will tomorrow bring?

JS: It’s already here. There is the area of imbedded wearable computing, something right over your eyes. Like Google Glass. It gives you two things: an information consumption experience, which is that much closer to you, and the information creation experience, where you can walk around with these glasses and take pictures of things or record things. Maybe you will be wearing Google Glass to interview me one day.

EW: Today’s gadgets are fun to play with, but how are they altering our society?

JS: The debate around Google Glass, around privacy, is a classic debate. It’s the debate that happens every time there is an epoch-making change like imbedded computing. We will all be very uncomfortable for two years. And then the technology will become ubiquitous and we will accept it. And then something bad will happen. And that will catalyze a round of discussion but the technology will not go away.

EW: So is the trend towards constant connectivity positive or negative?

JS: I’d say 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. My relatives feel like every few days they are totally up to speed with what’s going on in my life. If my mom does something funny with my son, who is not yet four-years old, I post those photos and the rest of my family can see them immediately. I think social media and technology connect us. The downside is there are behavioral changes. I’m not an anthropologist, but I worry about how our bodies and brains might be remapping to fit our current technology. There is research that our brains are more fractured and that our devices are changing the way we think.

EW: Your lecture was titled “Everything I Learned in Business I learned Owning a Bar.” What did you learn in your bar?

JS: Many things, but I’ll share three with you now. Bartenders need to be good looking, social and not over-pour their drinks. In other words, in business, don’t over-think 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.

Second, whether you build a place that is a bricks-and-mortar bar or a website, if you build a place for guys only guys will show up. Women are not so interested. But if you build a place for women, amazingly, both men and women will show up. So make a place that is attractive to women, friendly, puts them at ease and resonates with them emotionally.

Finally, don’t judge your customers. People will do crazy things, certainly at a bar, but even, say, on a photo website. Have the fundamental belief that your customers are right and create the features that will make them happy with your product.