Page 17 - Alumni Horae: Vol. 94, No. 3 Spring 2014

open palm, while his iPhone is on silent and face down
on the counter. He listens to Kevin, entirely focused on
the conversation they’re having here and now, refusing
to interrupt their dialogue by checking his messages or
taking a call.
Once again, Tim is simplifying the process by reducing
the friction points. He has eliminated the distractions,
separated the various aspects of his life in motion right
now, and committed himself to being completely engaged
in the present activity. He asks questions and waits to
absorb the answers before moving onto the next. The
reduced potential for distraction enables him to be entirely
curious and present.
Kevin and Tim are assessing the marketplace that
Shyp hopes to disrupt and ultimately dominate. As an
indication that the tech boom has come full circle, Tim
observes that we’re seeing a “return to localization”
with the new products and services that startups are
bringing online. More and more companies compete to
dominate a local market first before expanding into
other markets.
San Francisco and the rest of Silicon Valley have been
the optimal laboratory in which to conduct these exper-
iments. The tech-savvy and discerning user base is
primed to test the new products and services and judge
which of these will emerge in this particular marketplace.
“Profitability can be the most critical business priority,”
Tim observes. “But in Silicon Valley, where many of the
markets are winner-take-all, it’s critical to grow as
quickly as possible to a dominant scale, where you force
competitors to be reactive.”
Tim’s route to St. Paul’s School was in some ways an
accident. Born and raised on Long Island, he attended
East Hampton High School for a year before reconnect-
ing one vacation break with a childhood friend, David
Starr-Tambor ’93, who had recently enrolled at St. Paul’s.
A “gut feeling” after his visit told Tim that St. Paul’s
was the right match. According to his Fourth Form
adviser Richard Greenleaf, Tim quickly established
himself at St. Paul’s as a high-achieving “front-row
student” and a writer with “a literary touch of elegance,”
distinguishing himself outside the classroom in Coit
North, and as an athlete in both football and wrestling.
Tim began taking Spanish to fulfill his language re-
quirement, but he soon realized he was already too far
behind and switched to a Japanese class led by Masa
Shimano. Mr. Shimano remembers Tim as “a talented,
courteous, and self-disciplined young man, fascinated with
Japanese culture.” From the Spring Term of his Fourth
Form year through the Winter Term of his Fifth, Tim studied
in Tokyo at the Seikei School as part of the now more
than 60-year-old St. Paul’s-Seikei exchange program.
Tim’s year in Japan was transformative. “What he
accomplished there was truly amazing to me, consider-
ing the fact that he went to Seikei with only one year
of Japanese under his belt,” Mr. Shimano says. “When
he returned to SPS, he was fluent in Japanese, and his
Japanese sounded as if it came from someone thoroughly
familiar with the Japanese mindset.”
Today, Tim remains in touch with his host family and
classmates from his year at Seikei. He even has a copy of
A Generous Idea: St. Paul’s School and Seikei Gakuen by
David T. Dana ’55 on a bookshelf in his living room, as
well as framed prints he won as prizes for judo tourna-
ments in which he competed while at Seikei.
When it came time to apply to colleges, Tim specifically
sought out East Asian studies programs, deciding on
Princeton after an early-action acceptance. After earning
his degree in 2000, Tim moved to California. “That was
the time, I’d imagine a lot like these days, when startups
were hot, fortunes were being minted,” he says. “And I
was very eager to get away from the gray dreariness of
East Coast winters, so I moved to the Bay Area.”
The 4-Hour Workweek was born from Tim’s experience
running BrainQUICKEN, a sports nutrition company he
founded in 2001 and later sold in 2010. The consuming
nature of his role with the company pushed Tim to
reexamine his relationship to his work, which led to the
foundation for the book.
Tim is a natural experimenter, the evidence of which
crops up in nearly every crevice of his life. With the
access he gained from the success of Workweek, Tim
Tim’s advice for
aspiring entrepreneurs
1. Learn before you aim to earn.
2. Work for a startup of 15-30 people and
ensure you can report directly to master
dealmakers and observe them in action.
The industry is not as important.
3. You are the average of the five people
you associate with most.
4. Learn to write very, very effectively, and
be concise. Superfluous words will get
your e-mails deleted.
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