CHAPTERS
- 0:00 – 1:15
Uncompromising weekend writing rituals while working a day job
Craig describes a period when he was working in Silicon Valley but protected his writing time by disappearing to a San Francisco hotel every weekend to write essays on digital books and publishing. He frames this as a hard-won refusal to compromise the “literary” part of himself, even while earning a very strong paycheck.
- •Booked a San Francisco hotel each weekend and wrote from Friday night through late Sunday checkout
- •Focused the essays on digital books and publishing
- •Describes having built “asceticism” in his 20s to stay uncompromising
- •Says he wrote “militantly” to avoid letting the job override his creative identity
- 1:15 – 3:24
Setting the stakes: adoption revelations and a travel/overtourism story
Tim asks what would make the conversation worthwhile, and Craig proposes two emotionally and culturally rich threads. He highlights meeting his birth mother as a major event he hasn’t discussed publicly in English, and also teases a story tied to cities, travel meaning, and tourism surges.
- •Craig identifies meeting his birth mother as the most affecting recent story
- •Says he hasn’t written or spoken about the adoption story in English publicly before
- •Flags a second thread involving cities, travel today, and overtourism
- •Mentions tourism surges and questions about mitigation and dispersal
- 3:24 – 5:59
How they first met: early encounters and the Japan walk connection
Tim and Craig reconstruct their first meetings, starting with a brief hello in San Francisco and a quick exchange at Foo Camp. They agree the first real conversation came later around Craig’s Japan walk project, which Tim recalls in printed book form.
- •Craig recalls saying hi to Tim in a San Francisco café while working with a Flipboard engineer
- •They also crossed paths at Foo Camp (including a bathroom exchange)
- •They identify the Japan walk as when they first truly talked
- •Tim mentions revisiting the printed book of the walk with photographs
- 5:59 – 8:03
Connecticut origins: books, video games, and the first lifelines to computers
Craig traces his childhood in a lower-middle-class, post-industrial Connecticut town and explains how early love of books, writing, and games pulled him toward technology and Japan. A neighbor’s generosity—access to a computer, a key to the house, and even a phone line—becomes a pivotal “sliding doors” moment.
- •Grew up in a post-industrial factory town in Connecticut with limited cultural archetypes around him
- •Loved books and writing, and also video games that came from Japan
- •A divorced neighbor let him use a computer constantly, gave him a house key, and bought him a phone line
- •Craig later tried to find the neighbor to thank him but learned he had passed away
- 8:03 – 10:27
Early internet communities to real-world opportunity: IRC, ANSI art, and a cross-country drive
Craig explains how IRC and the ANSI art scene became his entry point into design, programming, and online collaboration. Those teenage relationships later translated into a California internship, prompting him to drive cross-country and experience the intensity of early web opportunity firsthand.
- •Got onto IRC and joined the ANSI art scene, collaborating with older peers
- •Saw computing and design as tools for storytelling
- •Online connections later offered him a summer internship in California
- •Drove across America in a Honda Civic to take the internship and work on early web projects
- 10:27 – 16:06
Escape velocity: adoption, scarcity, and a mistrustful relationship to the American system
Craig describes adoption as part of an early sense of disconnection, paired with a strong urge to leave his hometown and build independence. He recounts opening an early online brokerage account, scanning for ways out, and then feeling a stark resource and confidence gap upon arriving at a strong university.
- •Says adoption contributed to feeling disconnected and driven to get far away
- •Joined a high school stock club and opened an early online brokerage account despite no family precedent
- •Describes college as an immediate shock: classmates seemed to have radically different resources and archetypes
- •Says this gap fueled a desire to live abroad to rebuild himself outside the U.S.
- 16:06 – 19:20
Moving to Japan at 19: Waseda, the bubble collapse, and the UPenn detour
Craig lays out a macro timeline: moving to Japan at 19 in 2000, studying for a year, and then changing course when the Silicon Valley bubble burst. He transfers to UPenn, returns to Japan for internships and language study, and ultimately bases his life there.
- •Moved to Japan at 19 (2000) and studied at Waseda
- •Initially planned Japan briefly, then Silicon Valley, but the bubble collapse altered the plan
- •Transferred to UPenn for a computer science and fine arts-oriented program
- •After graduation, returned to Japan for intensive language study and stayed long-term
- 19:20 – 23:33
How Craig learned Japanese: music, immersion, and peers ahead of him
Craig attributes rapid language progress to strong listening skills built through years of drumming and to deliberate immersion choices. He describes homestay with no English, joining a Japanese-only music circle, and learning alongside highly advanced international students.
- •Says language learning is easier with a musical background; he played drums obsessively in his teens
- •Did a homestay where the family spoke no English
- •Joined a Japanese-only music circle and spent constant time with Japanese people
- •Explains learning benefits of spending time with people slightly more advanced; cites very high-level students in the program
- 23:33 – 33:44
Homestay chaos and culture shock: cold houses, udon meals, and extreme awkwardness
Craig recounts a stressful and often absurd homestay situation in Tokyo: constant udon, a freezing house, cockroaches, and an 11-year-old’s inappropriate behavior that Craig didn’t have the language to address. Tim adds his own host family stories and notes the common reality of poorly insulated homes and flying cockroaches.
- •Host family ran an udon shop, so nearly every meal was udon
- •House was extremely cold; someone bought Craig a full-body snowsuit to sleep in
- •Craig describes repeated incidents involving the family’s 11-year-old and the difficulty of communicating boundaries
- •Tim and Craig discuss Tokyo cockroaches, including the tendency for cockroaches to fly, and Tim shares his own host-family conflict story
- 33:44 – 44:41
From UPenn into publishing and design: mentors, book obsession, and color blindness
Craig explains how a Tokyo magazine internship led to an offer to help start a publishing company and how UPenn’s Digital Media Design program shaped his design sensibility. He credits two professors for major influence and connects his color blindness to a long-running black/white/red aesthetic.
- •A Tokyo magazine editor-in-chief invited Craig to help start a publishing company as art director
- •At UPenn, studied a program combining fine arts and computer science
- •Describes formative teaching from Joshua Mosley and design professor Sharka Hyland, including harsh critique that sharpened his thinking
- •Reveals color blindness and says it contributed to a long-standing black/white/red design palette and early choices
- 44:41 – 51:59
Alcohol, lost love, and supernatural Tibet: the dream reader episode
Craig describes heavy drinking in his 20s, a sudden intense romance, and a 40-day trip through Tibet marked by eerie experiences. He recounts an episode in Lhasa involving speaking in Tibetan while asleep and a local referral to a dream reader who provided rituals and instructions without demanding payment.
- •Craig says drinking escalated in Japan and he could drink large amounts, often blacking out
- •Describes falling intensely in love and taking a 40-day Tibet trip soon after meeting
- •Recounts a night in Lhasa where his partner said he cradled an invisible object and spoke Tibetan while asleep
- •Hotel manager connected them to a dream reader who gave a blessing, seeds, prayers, and temple instructions; Craig emphasizes it didn’t feel like a scam
- 51:59 – 56:20
Rebuilding self-worth: running, pricing courage, and the Annapurna Base Camp milestone
After the relationship ended, Craig describes reaching emotional rock bottom and beginning to run as a way to change identity and reduce drinking over time. He then ties these incremental steps to a Nepal trek to Annapurna Base Camp, including a deep bond with a young guide and a powerful moment at altitude on his birthday.
- •After breakup, describes rock-bottom despair and starting with a late-night 5K run
- •Set a marathon goal as an anchor for quitting drinking and building a new identity
- •Began charging much more for consulting work and found clients accepted it, reinforcing self-worth
- •Went to Nepal, hired a guide last-minute, and reached Annapurna Base Camp on his 29th birthday under a full moon
- 56:20 – 1:07:53
Viral craft: the camera review that paid the rent and the iPad essay that changed his life
Craig explains how he turned the Nepal experience into a meticulously crafted long-form camera review that went viral and generated substantial affiliate revenue. He then describes publishing an iPad-era books essay that drew attention from The New York Times and rapidly expanded his visibility and opportunities.
- •Wrote a Panasonic GF1 field-style camera review blending long-form writing and web design
- •Says the review spread widely and affiliate links generated about $20,000 in a month, covering years of living costs in Tokyo
- •Describes how Tokyo’s low cost of living supported an uncompromising creative lifestyle
- •Published “The Books and the Age of the iPad,” woke up to New York Times coverage, and says it transformed his career trajectory
- 1:07:53 – 1:12:35
Why physical books endure: making artifacts that digital can’t replace
Craig states that books—especially physical books—have been his core focus since childhood, with other pursuits serving that mission. He argues that the iPad-era thesis was to make non-throwaway physical books, leaning into materials and formats that can’t be replicated digitally, and he reflects on why digital books didn’t evolve as imagined.
- •Says books have been the central focus since he was eight or nine years old
- •Emphasizes physical books as objects and advocates making them beautiful and materially distinctive
- •Mentions features like cloth binding, silkscreen, foil, special papers, and lay-flat spreads
- •Says digital books didn’t develop as expected, citing market dynamics and limited investment incentives
- 1:12:35 – 1:16:06
Belonging and outsiderhood: adoption, Japan’s social support, and the safety of never fully integrating
Craig connects a recurring sense of “flailing” to being adopted and not feeling like he belongs anywhere. He describes Japan as simultaneously supportive—society taking care of people across economic levels—and psychologically safe because, as a permanent outsider, he can’t be “thrown away” by the in-group.
- •Says adoption shaped a lifelong feeling of not belonging
- •Describes a personal narrative of being “thrown away” and growing up around violence and instability
- •Contrasts Japan’s social support with what he saw growing up, across socioeconomic strata
- •Frames outsider status in Japan as a paradoxical emotional safety: never fully part of the system, so never rejected by it
- 1:16:06 – 1:22:54
Silicon Valley and Flipboard: hugs, high pay, and protecting the writing life
Craig explains returning to the U.S. to work at a bigger scale, joining Flipboard early as part of the iPad-era digital publishing wave. He describes living simply while earning a large salary, being changed by the warmth of housemates, and using hotel-weekend isolation to keep writing from being eroded by paycheck psychology.
- •Moved to Silicon Valley to collaborate with bigger-thinking peers after outgrowing local collaborators in Tokyo
- •Joined Flipboard early and describes it as a beautifully designed social media “magazine” for the iPad era
- •Recalls emotional impact of living with affectionate roommates and realizing how few hugs he’d had previously
- •Says he earned very high monthly pay but forced himself to keep writing every weekend to stay uncompromising
- 1:22:54 – 1:40:33
MacDowell residency and the power of archetypes: serious art, lasting books, and creative discipline
Craig describes applying to MacDowell as a way to leave Flipboard and immerse in a community of highly accomplished artists. He highlights how residencies provide templates for serious creative life, then shifts into his beliefs about protecting attention—staying offline—and building a decades-long relationship with non-ephemeral work through rereading and marking up books.
- •Applied to MacDowell on a recommendation and used acceptance to exit Flipboard
- •Describes residency structure: silent workdays, communal dinners, and intense ping pong
- •Mentions meeting writer Lynn Tillman and repeatedly rereading Denis Johnson’s Train Dreams for its economy and poetry
- •Advocates strict attention protection (phone out of the bedroom; delaying phone use) and emphasizes rereading/annotating books over ephemeral media
- 1:40:33 – 1:51:18
‘Things Become Other Things’: a COVID walk on the Kii Peninsula and the friend he lost
Craig introduces his forthcoming book and explains it grew from a long COVID-era walk on Japan’s Kii Peninsula, during which he wrote daily and reflected deeply. He describes how memories of his childhood best friend Brian—who was later murdered—entered the narrative, turning the book into both a walk story and a meditation on systems, class, separation, and duty of remembrance.
- •The book centers on a 600-kilometer walk on the Kii Peninsula during COVID-era Japan
- •Craig says he wrote thousands of words daily and photographed throughout the month-long trip
- •Reflects on a childhood friendship with Brian, their paths diverging through opportunity gaps, and Brian’s later murder
- •Frames the book as celebrating the peninsula’s people and deep history while honoring Brian’s memory
- 1:51:18 – 2:00:43
Where to follow Craig: Modland, Special Projects, and a call to pursue residencies
Craig points listeners to his website and describes his Special Projects membership, including archives and recorded “board meetings” with Q&A. As they wrap, he and Tim preview a second episode and Craig encourages creatives to apply to artist residencies, accept rejection as part of the process, and support residency institutions through donations when possible.
- •Directs listeners to craigmod.com and explains the Special Projects membership program
- •Says membership enables more vulnerability and deeper conversation through a smaller, more intentional audience
- •Notes the program is free for students who email him
- •Encourages creatives to apply widely to residencies, learn from rejection, and donate to support residency institutions if able
