iJames

If you expect to sit across from James Higa and extract memories about his long relationship with Steve Jobs,
you’ll leave with an empty notebook. But if you ask him to write a poem on the subject, you’ll get every answer you were hoping for. By Darren Gluckman Photography by Jessica Lifland

“I

don’t know” was his first English phrase. Now he knows a lot, but still speaks with great circumspection. James Higa, former senior director in the office of the CEO at Apple Inc., spent most of his career reporting to Steve Jobs, Apple’s legendary co-founder, who passed away in 2011. Among the signature achievements Higa cites in his public CV (at least the one trumpeted by Philanthropic Ventures Foundation, where he has recently landed as executive director) is his involvement in negotiating the licensing agreements with the major record labels that were a necessary precondition to launching iTunes in 2001. Back then, the major labels were famously leery of digital media, having

moved aggressively against Napster and publicly threatening (and following through on those threats) to sue individual illegal downloaders. Like a cluster of besieged fiefdoms, they were lashing out defensively, desperately clinging to their crumbling domains, and appearing bereft of a longterm survival strategy. The last thing they seemed capable of was rallying around a model for the digital distribution of their product—getting them to sign on to Apple’s gamechanging platform was, to put it mildly, a pretty big deal. So, James: What was that like, how did it come about, and what was your role in getting them on board? There’s a long pause where one wonders if perhaps the phone connection has been lost. Then, at last: “I’m a little uncomfortable in this territory because it’s something that Apple doesn’t talk about much, and I’m a bit sensitive to people taking advantage of Steve’s death

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Profile James Higa

and their closeness to him. So I’m trying to figure out how to talk about this in a general way.” So let’s not take advantage of Steve’s death. Let’s do talk about this in a general way. What was the argument that was put to the record companies at that time? How were they persuaded to come along? Long pause. “I’m trying to figure out how to talk about this without going into all the dirt.” Okay, let’s do this dirt-free (although a little dirt wouldn’t hurt, would it?). After all, this was a fairly historic development in the media landscape, and you’re surely entitled to discuss your involvement in it, especially on terms that you’re comfortable with, no? “I’ve not talked to Walter Isaacson or any other reporters about this, either, so I’m a little bit reluctant.” (Walter Isaacson’s well-received biography on Jobs was developed

with Jobs’s cooperation and was released shortly after his death; Higa admits to starting but not finishing it “or any of the other books for that matter, as none of them capture the true essence of those times.”) Well, James, what’s the issue for you here? “The issue for me is in many ways more about my journey with Steve. I feel like I’ve really been blessed to have had that, and so a lot of it is sacred, if you will, to me, and I am where I am because I was able to be completely trusted and discreet in all these things.”
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Profile James Higa

Okay, what if we don’t talk shop, what if we just discuss Steve’s impact on your life? “I need to find my own way and time to do that.” Another item on Higa’s PVF bio touts the “vision and energy” he brought to the creation of iTunes University, the online, downloadable learning platform with over 800 participating schools and over 500,000 free lectures, videos, books, and other resources. Can we talk about your involvement there, or do we face the same issues? “We face the same issues.” Oy.

Higa’s motHer and Her
younger brother were the sole survivors of an American attack on their village during the brutal Battle of Okinawa in World War II, and were saved by happenstance when, having been sent to run an errand in a neighboring village, they narrowly escaped the carnage. At the war’s end, the United
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States offered so-called “goodwill” scholarships to the Japanese. The prevailing propaganda at the time was that anyone foolish enough to take the Americans up on this offer would, in effect, be surrendering and could be subject to rape, torture, and murder. Consequently, few were willing to “jump into the heart of the enemy,” as Higa puts it. But his mother and father, Fumi and Yoshimitsu (both still living in Okinawa), decided their children (yet to be born) would benefit by being Americans. James first saw the light of day in Indiana, but when he was 2, the family returned to Japan. Yoshimitsu was a Protestant minister, and church staffing vacancies dictated the ocean-hopping itinerary of the young family. They returned to Indiana when James was about 7, and then went to Oregon (with Yoshimitsu working as an assistant pastor in both places). “I can still remember being dropped off with my brothers at elementary school and my dad saying to repeat after him: ‘I don’t know.’ We walked into school and it was, ‘What’s your name?’ ‘I don’t know.’ ‘What do you want?’ ‘I don’t know.’ We were in tears by the time the end of the school day rolled around.” After a couple of mostly tear-free years, Fumi secured a teaching position at the American high school on the U.S. military base on Okinawa, and the family returned again to Japan. After high school, Higa pond-hopped once more, securing an undergraduate spot at Stanford University (despite the discouragement he received from high school

Profile James Higa

counselors when he talked about wanting to apply—“No one from here gets in,” he was told), where he majored in political science and supported himself doing freelance photography, mostly covering sports for the local paper. “I loved photography. Our father had taught us; he had an enlarger that took over the laundry room. Our mother hated it. There were chemicals everywhere; she couldn’t get the wash done.” After graduating, he continued doing freelance work for several years. “I hated going to parties because all my friends, who were in consulting and investment banking, would give me the guilt trip from hell about how I was wasting my Stanford education.” Little did they know... “I got an assignment at Apple, and in the course of that assignment I met Steve Jobs. Instead of taking photographs, I ended up speaking to him for a couple of hours. This was right about when the Mac was getting introduced, in 1984, and he made me an offer to join the Mac Group.” Higa became part of the international marketing team. It’s not hard to see what a 26-year-old freelancer might see in Apple, but what did Steve see in you? “Two things. One was an ability to be frank, honest, and able to go toe-to-toe with him on any question. The other was wide peripheral vision. He’s always wanted that in the people around him. The ability to connect dots is really important. A Renaissance perspective on the world. Because it was always about the intersection of technology and liberal arts.” Given your reticence to discuss all things Apple, what

on dispensing with cumbersome application procedures that can pose significant, often insurmountable hurdles to worthy grant recipients. Philanthropy and the tech sector share the same need for speed, he argues. “You can’t sit around and think about things and do white papers and focus groups and stare at your navel for six months as the competition whizzes by. You need to have a bias for action.” The second thing he mentions is what he calls the fundamental operating principle of Bill Somerville, PVF’s founder. “Bill’s tenet has always been: Find good people and fund them. For me, in technology, it’s been the same thing. It’s really not about the sexiness of a technology or the polish of a business plan. If I’m going to work with you, I want to meet you, I want to look you in the eye, I’m gonna fly out, I want to see how the receptionist is being treated. So I think it all comes down to people. And it’s people that you really need to bet on. And that’s one of the huge lessons I learned during my time with Steve. He had an

“If I’m going to work with you, I want to meet you,
I want to look you in the eye, I’m gonna fly out, I want to see how the receptionist is being treated.”
attracted you to PVF? “Two things about PVF that really resonated with me were: one, rapid response.” He cites, as an example, teacher resource grants for up to $500 (for a field trip, art supplies, etc.) that can be dispensed within 48 hours. “The right timing is as important as the dollar amount.” Especially for small grants, the application process should be simple, and PVF, which operates mostly in the San Francisco Bay Area (“We want to be very grassroots,” Higa explains, “and stay within our circle of competence, which is all the great people doing great work in our backyard”), prides itself

uncanny ability to bring together the most amazing talent.” He describes one of PVF’s recent successes. CalFresh is the Food Stamps program for San Mateo County. But many people who are eligible for the program face difficulties registering for it, and administrators have issues reaching out to those who could benefit. PVF was able to facilitate a joint venture between the county and Code
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Profile James Higa

for America, a rather ingenious nonprofit, which, in its own words, “connects forward-thinking cities with the talent from the Web industry to develop reusable civic technology. Partnering cities will not only solve a critical problem using technology, but also help cultivate the next generation of tech-savvy, civic leaders.” Engineers, programmers, and software designers from prominent tech companies like Google, Apple, and Facebook apply for a one-year fellowship with CfA. Hundreds apply, with only a few dozen selected, who are then sourced out to needy urban administrators. PVF connected CfA with San Mateo County to improve the efficiency of the CalFresh program.

We understood and respected the creative process. We developed many of the tools that the artists and labels used to create music after all. We had permission to try. Innovate or die was in our DNA. “We were trying to make a dent in the universe at Apple. I see philanthropy as no different. It’s going to places where people often say, ‘No, that can’t be done.’ It’s about

“I see Philanthropic Ventures Foundation as the intersection of grassroots philanthropy and technology. “
insanely creative ideas. It’s about not us vs. them but how do we come together on the same page. It’s about connecting good ideas and good people, like our newest Code for America-San Mateo County project that brings a foundation, government, and a tech nonprofit together to create together. Apple is the intersection of technology and the liberal arts. I see Philanthropic Ventures Foundation as the intersection of grassroots philanthropy and technology. To me, it’s the same mission.” For Higa, weekends are spent schlepping the kids to soccer and ballet. Jasper is 17, Olivia almost 13. Dad has swapped photography for videotaping Jasper’s soccer games, which he posts online for family members. But schlepping isn’t the full extent of his extracurricular activities. “My wife and I have been doing haiku poetry for about 15 years. And I’m struggling today because our deadline for next month is coming up and I have to get my five poems in.”

several days after tHe
conversation, Higa, having had time to reflect, sends an e-mail to me with his thoughts on iTunes. “Everyone thought a service like iTunes couldn’t be negotiated or pulled off. We succeeded because it was a triumph of new audacious ideas. Because it wasn’t tech vs. them.
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Profile James Higa

He and Kimi met when he was with Jobs at NeXT Computer, during Jobs’s exile from the company he would later return to and triumphantly resurrect. Higa was in Tokyo, and was due to attend a music festival with a large group in Fuji, but a typhoon dashed the plans. The organizer arranged for everyone to meet instead at a local bar. James and Kimi were the only two who showed up. When they lived in Japan, they studied haiku with a teacher. Each month, five poems were due. Two required the use of a particular word, and two required a reference to the current season. The fifth and final assignment was posted on the door on the way into class, and had to be turned in by the end of the session. In Japan, Higa explains, haiku occupies a rather prominent and formal place in society. In terms of language, the homogeneous culture allows for a richer set of shared signifiers, and the complex graphology of the letters allows for the multilayered compression of meaning in a way that English doesn’t. The couple still have the same teacher, still adhere to the same deadlines. Only now they fax in their assignments. What do you get out of writing haikus? “Two things. One is I find it amazingly similar to writing great software. Because it’s about having a piece of code do the most in the least amount of space, with the least amount of characters. And being severely tied to constraints and parameters and rules. Haikus have to be a five-seven-five [set of syllables]. In Japan, haikus are even more restrained because they have to incorporate a seasonal word that’s defined in a seasonal haiku dictionary, so by the time you pick one of those words, you may have six or seven syllables already spoken for. For me it has the

same aesthetic as good software, in that it’s highly efficient, compresses a lot of meaning, and does a lot in a small space under tremendously constrained rules. So that part of it appeals to me aesthetically. And the second thing is it forces you to be aware of the world around you more profoundly. Because you can’t talk about large issues like peace or happiness. You want to come at it from being able to observe something very small, like a dewdrop on a flower. So you’re constantly looking around for subjects. My wife and I, if we’re on a trip, we’re constantly like, ‘I saw that first!’” Haikus, he says, put him in a photographic state, where he’s looking to compose, but with his head instead of his lens. Another e-mail arrives, this time with a couple of his haikus. They’re in Japanese, in beautiful Japanese characters, accompanied by an English translation. One of them, he says, is “about Steve’s passing.”
A nova flickers out autumn’s end

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