Capshaw's career in the music industry began in 1991 when he was the owner of Trax, a venue where he gave Dave Matthews Band their first weekly gig.[6] Seeing the success of the band locally, Capshaw began managing the band out of Trax and helped grow them from playing in nightclubs to amphitheaters and stadiums.[7]
In 2000, Capshaw founded e-commerce company Musictoday to generate direct-to-fan e-commerce tools for the artists he managed to sell their merchandise, tickets, and other fan-related products directly to their audiences, bypassing traditional retail channels. By 2005 the company's roster had more than 500 clients and gross sales exceeding $100 million.[10]
In 2006 Live Nation Entertainment acquired a minority stake in the company and eventually purchased the company outright.[11]
In 2014, after making Musictoday’s ticket-sales operation, Ticketstoday, a division of its Ticketmaster division, Live Nation sold the remainder of the company to Delivery Agent, an interactive-commerce company that specialized in digital transaction platforms for TV networks and sports partners. Delivery Agent filed for Chapter 11 bankruptcy in September 2016.[12]
In 2017, Capshaw reacquired Musictoday. As of 2017 the company employed approximately 140 people.[13]
Ascend Amphitheater is an open-air amphitheater in Nashville, TN located inside the Metro Riverfront Park with a capacity of 6,800. Capshaw developed the amphitheater in partnership with Live Nation Entertainment.[19]
Ting Pavilion is a covered amphitheater located on Charlottesville's Downtown Mall. The venue was built in 2005, as a joint endeavor between the City of Charlottesville and Capshaw.[22]
Capshaw owns The Jefferson Theater, a historic theater-turned concert venue on Charlottesville's Downtown Mall. The venue reopened on November 27, 2009, after a comprehensive restoration. Since re-opening, the venue has hosted performances from hundreds of artists including FUN., A$AP Rocky, Luke Bryan and St. Vincent.[24][25]
The theater was built in 1912 and originally played host to silent movies, vaudeville acts and live performers, including Harry Houdini and The Three Stooges.[26]
Capshaw has won the Pollstar Magazine's "Manager of the Year" award five times in 1998, 2003, 2010, 2018 and 2019.[29] He has been nominated for the award more than twenty times.[30]
In 2011, Capshaw became the first artist manager to receive Billboard's Humanitarian Award in recognition of his commitment to local, national, and international community efforts and philanthropy.[31]
In 2017, Capshaw was the recipient of the City of HopeSpirit of Life Award and helped to raise $4.8 million for cancer research.[32]
In 2018, Capshaw along with Dave Matthews Band announced a $5 million donation toward the renovation and/or replacement of all of the city’s public housing and the construction of additional affordable housing on underutilized land.[33] The Charlottesville Redevelopment and Housing Authority (CRHA) and the Public Housing Association of Residents (PHAR) are partnering with Red Light Management, the Bama Works Fund of Dave Matthews Band, Riverbend Development, Castle Development Partners and the Virginia Community Development Corporation to rebuild affordable homes in Charlottesville.
The group has raised a total of $25M towards a goal of $30M. This private philanthropy helps leverage federal, state and local funding to help build what will ultimately be approximately $200M worth of new, affordable housing.[34]