After graduating from
Columbia University, Underwood worked briefly for an investment bank in
New York City.[3][4][5] After one month, he quit and backpacked across Central and South America.[6] Upon returning to New York, he founded a
hostel in Brooklyn.[7][8] In December 2014 Underwood founded HK Austin, a hostel in Austin, Texas, with investors including
Matthew Kepnes, after staying in 150 hostels across 30 countries.[3][9][10][11] For 2015, HK Austin was the highest rated hostel in the United States.[3][6][12] Underwood later became a partner in the marketing firm Brass Check.[4][13][14]
In February 2016, Underwood published a photo of his foot on
Amazon as a book titled Putting My Foot Down.[15][16][17][18][19] The resulting article in the New York Observer received attention from a variety of media outlets and from authors including
Neil Gaiman and
Nick Bilton.[13][20][21] Underwood was then offered a publishing contract from
Thought Catalog to turn Putting My Foot Down into an expanded paperback version.[18] The paperback version received attention from a variety of news outlets.[16][17][18][22][23][24][25]
Cerro Gordo
In July 2018, Underwood purchased the former mining town of
Cerro Gordo alongside the
Cerro Gordo Mines for $1.4 million with a group of investors.[26][27] The purchase included over 360 acres and 22 structures.[28] Underwood stated plans to develop the town into an artist destination for tourists and group events, while maintaining the historic nature of the property.[29][30]
Since March 2020, Underwood has been living at Cerro Gordo full-time[31] and has regular visitors.[32] Visitors have included
Jeff Goldblum,
Cole Sprouse,
G-Eazy, and others.[33] The town's hotel burned down on June 20, 2020, in a fire of undetermined origin but possibly electrical wiring failure, during a heat wave. Underwood has plans to rebuild it.[34] He was isolated there for ten weeks in 2020, unable to leave due to the
COVID-19 pandemic and a heavy snowstorm.[35] As of February 2024, Underwood still resided in Cerro Gordo.[36]