- 1997: Marcus' Martini Heaven opens in Pioneer Square
- 1999: Bad Juju Lounge opens on Capitol Hill
- 2001: Takes over Capitol Hill Block Party with Dave Meinert (sells shares in 2012)
- 2001: Jack's Road House opens on Capitol Hill
- 2003: Neumos Crystal Ball Reading Room opens on Capitol Hill, with partner Jerry Everard[3]
- 2005: Spitfire opens in Belltown, with partners Jerry Everard and Jonathan Sposato
- 2005–2006: Sells all businesses except Capitol Hill Block Party
- 2008: Juju opens in Belltown
- 2008: The Crocodile is purchased and renovated in Belltown before reopening in 2009[4][5]
- 2011: Local 360 Cafe & Bar opens in Belltown
- 2013: Sells Juju space to cannabis dispensary
- 2014: Bell + Whete European Kitchen & Lounge opens in Belltown[6]
- 2016: Bell + Whete closes for renovations before reopening as Belltown Brewing in 2017
In 2013, Charles co-founded Juju Joints with Rick Stevens of Seattle. Juju Joints are disposable electronic joints (e-joints) pre-loaded with cannabis oil and THC and allow for discreet, odorless consumption of cannabis.[7] Juju Joints launched in Washington cannabis dispensaries in April 2014. Stevens, a 30-year tobacco industry veteran, developed the technology for the innovative e-joint, alongside Charles.[8][9][10]