American founder Alex Greenberg left a small town in Vermont for Shanghai in 2015 after a single job offer to teach skateboarding, a move that would shape a decade-long career in creative media.
Unexpected start in Shanghai
Greenberg arrived in the Chinese megacity speaking no Mandarin and with a one-year contract to coach skateboarding. The city’s burgeoning street-skate scene quickly became his social hub, and he spent evenings filming tricks and everyday moments, later posting them to an Instagram account called Shanghai Observed.
He described the early days as a “wild” experiment, questioning his path while “throwing everything at the wall.” In addition to skate lessons, he taught English to supplement his income, using spare time to document Shanghai’s streets without any formal business plan.
From hobby to professional media work
In 2016, Greenberg secured an internship at PUSH Media, a local agency that handled campaigns for brands such as Adidas, Vans and The North Face. He rose to project manager, overseeing events and digital content that blended his skate culture insights with brand storytelling.
Meanwhile, the Instagram project grew organically, amassing over 280,000 followers and generating millions of monthly views, mostly from audiences outside China curious about daily life in the city. Though never a primary revenue source, the account opened doors to collaborations and freelance gigs.
Greenberg’s ability to capture authentic moments gave him credibility with brands seeking a genuine voice in the Chinese market.
When the COVID-19 pandemic struck in early 2020, Greenberg flew home to New York for the holidays and found himself unable to return to Shanghai. He spent 15 months with his parents before relocating to Kauai, Hawaii, where he worked on a pineapple farm and converted a school bus into a tiny home.
During his two-year Hawaiian stint, he added skills as a drone pilot, surfed, played poker and baseball, and continued managing his Instagram presence from afar.
In 2023, Greenberg moved to San Diego for a remote brand-manager role, paying $2,400 a month for a one-bedroom apartment in Encinitas. The coastal lifestyle appealed to him, yet the high cost of living prompted a reevaluation of where his money could stretch further.
He realized that returning to China, specifically a less expensive city, would allow him to invest more in his growing media business while maintaining a comfortable lifestyle. This calculation led him to Chengdu, a southwestern metropolis known for its relaxed pace, tea houses and burgeoning creative community.
Greenberg now rents a furnished studio in Chengdu for 3,000 yuan—about $420 a month—on a month-to-month lease. A bowl of noodles costs roughly $2, and a coffee is $1.50, highlighting the city’s affordability compared with Shanghai’s competitive market.
Expanding the studio’s reach
Beyond commercial work, he continues to experiment on the personal Instagram feed, sharing daily snapshots that blend city life with spontaneous encounters. The account remains a testing ground for new visual techniques that later inform client deliverables.
Everyday life in Chengdu
Daily routines revolve around the city’s famed tea houses, where long conversations over steaming brews are a common backdrop for informal networking. Meals consist of simple noodle bowls and street-side snacks, keeping living costs well below those of coastal metropolises.
Leave a Reply