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.[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] His book "Ghost Town Living" was published in March 2024 [37]
Ghost Town Living (Book)
In 2024, Penguin Random House published Underwood’s book, Ghost Town Living: Mining for Purpose and Chasing Dreams at the Edge of Death Valley, about his time living at Cerro Gordo.[38] The audiobook version of the book was recorded 900 feet underground in Cerro Gordo’s Union Mine.[39]