Charles McKenna Rial's first venture was Bitterroot Reforestation. Founded in 1975, the company planted trees for the U.S. Forest Service across the Intermountain West. In 1978, Charles started Abacon Business Resource which provided accounting, tax and business planning services for entrepreneurs in Western Montana. Charles was recruited to co-found Alaska Consulting Group (ACG") in late 1979. ACG, based in Seattle, provided economic development consulting services to Native Alaskan organizations and various tribes across the U.S., as well as foundations and local governments.

Charles moved to Chicago in 1983 to start Charles Rial & Associates ("CRA") which continued the consulting services provided by ACG. Shorebank Corporation of Chicago became a major client and ended up acquiring CRA in 1988 to form Shorebank Advisory Services ("SAS"). SAS became the expansion arm of this development bank. Charles entered the private equity business in 2000 and raised capital, initially for The Riverside Company and later(through Bass Creek Advisors) for a variety of private equity fund managers. Since 2000, Charles has helped raise over $2 billion for private equity fund managers.