As they pursue alpha, private equity (PE) sponsors constantly look to new and niche markets for unexploited investment opportunities. In recent years, the cannabis industry has been an alluring area for investment despite limited traction caused by a tangled web of state and federal regulations. Just as PE sponsors have seemingly navigated these obstacles from a legal and compliance perspective, they have faced valuation issues and limited financing from banks. A recent program presented by Sadis & Goldberg (Sadis) provided a comprehensive overview of the current state of cannabis regulation and legalization in the U.S., along with the resulting business and legal risks associated with investments in cannabis-related companies. Sadis partner Paul Marino moderated the discussion, which featured Eliott Frank and Robert Cromwell, partner and counsel, respectively, at Sadis; and Michael Feinsod and Hunter Garth, CEO and vice president, respectively, at General Cannabis Corp. This article summarizes their insights. For further commentary from Sadis attorneys, see “The SEC’s Proposed Form CRS: Does It Accomplish Its Goals? (Part Two of Two)” (Jun. 7, 2018); and “How Investment Managers Can Advertise Sub-Adviser Performance Without Violating SEC Rules” (Dec. 1, 2016).