Dobkin worked as an IT consultant when he co-founded the blog
Gothamist in 2003 with his Columbia classmate, Jen Chung.[8][9] He left his job to work for the blog full-time in 2005. In 2007 and 2008, he and Chung were named one of "New York's coolest tech people" by
Business Insider.[10]
He once criticized The New York Times prior to a panel with media critic
David Carr, calling the paper's “old-fashioned reporting” out-of-touch with a younger generation of readers.[11]New York magazine and
Gawker claimed that his comments sabotaged the company's supposedly successful acquisition by
James L. Dolan's media company
Cablevision.[12][13][14][15]
In 2017, Gothamist was purchased by
DNAinfo, founded by conservative billionaire
Joe Ricketts, and Dobkin was kept to run the blog.[16][17] Ricketts shut down the site in November 2017 after writers voted to unionize.[18]WNYC announced in 2018 that it has pooled the resources to buy the blog and hired Dobkin and Chung.[19]
In 2013, he started a column called Ask a Native New Yorker, and adapted his columns into a book of the same name that was published in 2019.[20] He is also a photographer of street art and urban landscapes.[21][22]