1983 — Nearly failed kindergarten after refusing to learn the alphabet when the teacher offered no explanation beyond “I’m the teacher—that’s why.” Permission to draw sharks was preferred.
1991 — First job as a minimum-wage cleaner at an ice cream parlor exposed duplicated effort by management. Cleaning finished in one hour instead of eight, leaving time for kung-fu magazines and karate kicks outside.
1993 — Volunteered for a one-year exchange in Japan, observing extreme work culture (karooshi) and cultural quirks about religious identity over a lifetime.
1996 — Admitted to Princeton despite SAT scores far below average and advice to be more “realistic.” Began in neuroscience, then switched to East Asian studies to avoid putting printer jacks on cat heads
1997 — Invested summer-job earnings to produce 500 copies of an audiobook titled How I Beat the Ivy League, sold exactly zero, and allowed the tapes to be discarded only nine years later—an exercise in baseless overconfidence
1998 — After a campus incident involving four shot-putters, quit the highest-paying on-campus job and launched a speed-reading seminar plastered across campus with neon flyers proclaiming “TRIPLE YOUR READING SPEED IN 3 HOURS!” Students annotated them with “bullsh*t.” Sold 32 spots at $50 each, realized the value of finding a market before designing a product, then closed the operation two months later out of boredom—services weren’t a fit, needed a shippable product
Spring 1999 — In three months, accepted and quit roles as a Berlitz curriculum designer and an analyst at a small political asylum research firm. Attempted to launch a gym chain in Taiwan but was shut down by Triads.
Fall 2000 — Returned to Princeton with confidence restored and thesis still undone. A peer sold a company for $450 million, prompting a move west to California with billion-dollar ambitions.
Spring 2001 — At TrueSAN Networks, growth from 15 to 150 employees accompanied managerial directives like “start with A” and dial for dollars. Questioning the tactic was met with “Because I say so”
2002–2003 — BrainQUICKEN LLC scaled to more than $40K per month instead of per year, but the workload ballooned to 12+ hour days seven days a week, creating intense misery.
A one-week family “vacation” to Florence turned into 10 hours a day in an Internet café freaking out—sh*t balls. Began teaching Princeton students how to build profitable companies
Steps were taken to simplify and become expendable; both deals ultimately collapsed, and attempts by others to replicate the product led to multimillion-dollar losses
June 2004 — To avoid spiraling into reclusive obsession, everything was upended and the first one-way ticket out of JFK to Europe was purchased. Landing in London with plans for Spain, the first morning brought a nervous breakdown
July 2004–2005 — Four weeks abroad stretched into eight, then into an indefinite experiment in automation and experimental living with email limited to one hour each Monday.
1977 — Born six weeks premature with a 10% chance of survival. Survival followed by rapid weight gain that made rolling onto the stomach impossible.
An eye-muscle imbalance caused the eyes to point in opposite directions, prompting an affectionate maternal nickname of “tuna fish.” So far so good
1983 — Nearly failed kindergarten after refusing to learn the alphabet when the teacher offered no explanation beyond “I’m the teacher—that’s why.” Permission to draw sharks was preferred.
Sent to the “bad table” and forced to eat a bar of soap, planting a lasting disdain for authority
1991 — First job as a minimum-wage cleaner at an ice cream parlor exposed duplicated effort by management. Cleaning finished in one hour instead of eight, leaving time for kung-fu magazines and karate kicks outside.
Terminated in a record three days with the parting line, “Maybe someday you’ll understand the value of hard work”
1993 — Volunteered for a one-year exchange in Japan, observing extreme work culture (karooshi) and cultural quirks about religious identity over a lifetime.
A language slip turned a request to be awakened (okosu) into an accidental request to be violently raped (okasu), leaving the host mother baffled
1996 — Admitted to Princeton despite SAT scores far below average and advice to be more “realistic.” Began in neuroscience, then switched to East Asian studies to avoid putting printer jacks on cat heads
1997 — Invested summer-job earnings to produce 500 copies of an audiobook titled How I Beat the Ivy League, sold exactly zero, and allowed the tapes to be discarded only nine years later—an exercise in baseless overconfidence
1998 — After a campus incident involving four shot-putters, quit the highest-paying on-campus job and launched a speed-reading seminar plastered across campus with neon flyers proclaiming “TRIPLE YOUR READING SPEED IN 3 HOURS!” Students annotated them with “bullsh*t.” Sold 32 spots at $50 each, realized the value of finding a market before designing a product, then closed the operation two months later out of boredom—services weren’t a fit, needed a shippable product
Fall 1998 — A major thesis dispute and fear of becoming an investment banker prompted an academic withdrawal notification to the registrar.
Family reactions ranged from convinced the departure was permanent to “no need to be a drama queen,” while the student assumed life was over
Spring 1999 — In three months, accepted and quit roles as a Berlitz curriculum designer and an analyst at a small political asylum research firm. Attempted to launch a gym chain in Taiwan but was shut down by Triads.
Returned defeated, learned kickboxing, and won the national championship four weeks later with an unorthodox style
Fall 2000 — Returned to Princeton with confidence restored and thesis still undone. A peer sold a company for $450 million, prompting a move west to California with billion-dollar ambitions.
Despite a hot job market, remained jobless until persistence—32 consecutive emails to one start-up CEO—resulted in a sales role
Spring 2001 — At TrueSAN Networks, growth from 15 to 150 employees accompanied managerial directives like “start with A” and dial for dollars. Questioning the tactic was met with “Because I say so”
Fall 2001 — After a year of 12-hour days, discovered being the second-lowest-paid person at the company.
Time was spent aggressively surfing the web until researching a sports nutrition business revealed that manufacturing and design could be outsourced.
Two weeks and $5,000 in credit-card debt later, the first batch was in production and a website was live—fired one week after that
2002–2003 — BrainQUICKEN LLC scaled to more than $40K per month instead of per year, but the workload ballooned to 12+ hour days seven days a week, creating intense misery.
A one-week family “vacation” to Florence turned into 10 hours a day in an Internet café freaking out—sh*t balls. Began teaching Princeton students how to build profitable companies
Winter 2004 — Approached by an infomercial production company and a conglomerate interested in acquiring BrainQUICKEN.
Steps were taken to simplify and become expendable; both deals ultimately collapsed, and attempts by others to replicate the product led to multimillion-dollar losses
June 2004 — To avoid spiraling into reclusive obsession, everything was upended and the first one-way ticket out of JFK to Europe was purchased. Landing in London with plans for Spain, the first morning brought a nervous breakdown
July 2004–2005 — Four weeks abroad stretched into eight, then into an indefinite experiment in automation and experimental living with email limited to one hour each Monday.
Removing the bottleneck increased profits by 40% and triggered existential terror about what to do with freed-up time
September 2006 — Returned to the U.S. in an oddly Zen-like state after systematically dismantling assumptions about what’s possible