Following his graduation from UCLA in 1987, Galloway worked as a fixed income analyst at Morgan Stanley.

In 1992, he founded Prophet, a brand and marketing consultancy firm. In 1997, he founded RedEnvelope, an e-commerce site specializing in unique and personalized gifts. In 2010, Galloway founded the digital intelligence firm L2 Inc, which was acquired in March 2017 by Gartner for $155 million, and the now defunct Firebrand Partners, founded in 2005, an activist hedge fund that invested over $1 billion in U.S. consumer and media companies. In 2019, Galloway founded the online education startup Section4. He raised $30 million in the Series A round in 2021 for a total funding of $37 million.

He was elected to the 1999 class of the World Economic Forum's "Global Leaders of Tomorrow", which recognizes 100 individuals under the age of 40 whose accomplishments have had impact on a global level.

He has served on the board of directors of Eddie Bauer, The New York Times Company, Gateway Computer, Urban Outfitters, and Berkeley's Haas School of Business. Galloway is also known for his public presentations and TED-style talks, called Winners & Losers, in which he presented L2's Digital IQ Index results, ranking over 2,500 global brands across numerous dimensions including e-commerce, social media, and digital marketing.

Galloway teaches brand management and digital marketing to second-year MBA students. Much of his research focuses on the Big Four tech companies, Alphabet, Amazon, Meta, and Apple, which he refers to as "The Four" or "the Four Horsemen". His first book, The Four: The Hidden DNA of Amazon, Apple, Facebook, and Google, was published in 2017. It analyzes the Big Four's peculiar strengths and strategies, their novel economic models, their inherent rapacity, their ambition, and the drastic consequences of their rise that people face in both social and individual terms.

In May 2017, Galloway anticipated Amazon's acquisition of Whole Foods Market, a transaction that became reality the following month. He denied any insider knowledge and said he was "just lucky" on that call. In early 2018, Galloway predicted the planned Amazon HQ2 would be located in either the New York metropolitan area or the Washington metropolitan area; with the decision to create two locations, Galloway ended up predicting both correctly.

In September 2018, Recode and the Vox Media Podcast Network launched Pivot, a weekly news commentary podcast co-hosted by Kara Swisher and Galloway. In February 2020, Galloway launched The Prof G Show, a weekly podcast answering listener questions on business, money, and tech.

In August 2019, Galloway published a highly critical analysis of WeWork's initial public offering filing, criticizing the company's unprofitability as well as its culture, corporate structure, nepotism, and the evidence of self-dealing on the part of founder Adam Neumann, while also castigating JPMorgan Chase and Goldman Sachs, the investment banks underwriting the launch, saying that they "stand to register $122 million in fees flinging feces at retail investors.  On September 28, 2021, CNN announced that Galloway would be a host on its CNN+ streaming platform, though the platform went off the air shortly after launching.

In 2022, Galloway's weekly newsletter No Mercy/No Malice won the Webby Award and Webby's People's Voice Award for best Business, News & Technology Websites and Mobile Sites.

WeWork: or The Making and Breaking of a $47 Billion Unicorn

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