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 direc-
tor in the office of the CEO at Apple
Inc., spent most of his career report-
ing 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 fa-
mously leery of digital media, having
moved aggressively against Napster and publicly threaten-
ing (and following through on those threats) to sue individ-
ual illegal downloaders. Like a cluster of besieged fiefdoms,
they were lashing out defensively, desperately clinging to
their crumbling domains, and appearing bereft of a long-
term 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 game-
changing 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

36 lifestyles magazine New Year 2013


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 develop-
ment 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 report-
ers about this, either, so I’m a little bit reluctant.” (Walter
Isaacson’s well-received biography on Jobs was developed
Profile
James Higa
with Jobs’s cooperation and was re-
leased 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.”
New Year 2013 lifestyles magazine 37
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 par-
ticipating 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 survi-
vors of an American attack on their
village during the brutal Battle of Oki-
nawa in World War II, and were saved
by happenstance when, having been
sent to run an errand in a neighbor-
ing village, they narrowly escaped the
carnage. At the war’s end, the United
38 lifestyles magazine New Year 2013
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 will-
ing 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 broth-
ers at elementary school and my dad saying to repeat af-
ter 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

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 photo-
graphs, 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 im-
portant. A Renaissance perspective on the world. Because
it was always about the intersection of technology and lib-
eral arts.”
Given your reticence to discuss all things Apple, what
“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 tim-
ing 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
Profile
James Higa
on dispensing with cumbersome ap-
plication procedures that can pose
significant, often insurmountable
hurdles to worthy grant recipients.
Philanthropy and the tech sector
share the same need for speed, he ar-
gues. “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 operat-
ing 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 sexi-
ness 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 dur-
ing my time with Steve. He had an
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 ben-
efit. PVF was able to facilitate a joint
venture between the county and Code
New Year 2013 lifestyles magazine 41
Profile
James Higa
for America, a rather ingenious non-
profit, which, in its own words, “con-
nects 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, “I see Philanthropic Ventures Foundation
civic leaders.” Engineers, as the intersection of grassroots
programmers, and software
designers from prominent
philanthropy and technology. “
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 pro-
gram.
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.
42 lifestyles magazine New Year 2013
We understood and respected the creative process. We de-
veloped many of the tools that the artists and labels used
to create music after all. We had permission to try. Inno-
vate or die was in our DNA.
“We were trying to make a dent in the universe at Ap-
ple. I see philanthropy as no different. It’s going to places
where people often say, ‘No, that can’t be done.’ It’s about
insanely creative ideas. It’s about not us vs. them but how
do we come together on the same page. It’s about connect-
ing good ideas and good people, like our newest Code for
America-San Mateo County project that brings a founda-
tion, 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 technol-
ogy. 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 activi-
ties.
“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 po-
ems in.”

He and Kimi met when he was with Jobs at NeXT Com-
puter, 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 ar-
ranged 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 com-
plex 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 writ-
ing 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 sea-
sonal 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
Profile
James Higa
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 hap-
piness. 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 look-
ing to compose, but with his head in-
stead of his lens.
Another e-mail arrives, this time
with a couple of his haikus. They’re in
Japanese, in beautiful Japanese char-
acters, accompanied by an English
translation.
One of them, he says, is “about
Steve’s passing.”
A nova
flickers out
autumn’s end
New Year 2013 lifestyles magazine 43