Bio

Matthew Portnoff has a broad-based corporate, tax, and general business transactions practice focusing on mergers and acquisitions (M&A) and the investing activities of high-net-worth individuals and family offices. Matthew frequently counsels on and provides structuring advice for choice of entity considerations and negotiating complex M&A. He also helps clients navigate a multitude of transactional matters, including tax-deferred investments and exchanges under Internal Revenue Code Sections 1031, 1033, and 1400Z; employment tax issues; tax ruling requests; and tax controversies. Matthew has significant experience with advising technology start-ups and emerging growth companies and represents fintech companies that are venture backed. Matthew also counsels the emerging commercial cannabis and industrial hemp industries, having represented public and private companies, including Canadian public companies, lenders, property owners, and investors across multiple states and countries, with a particular focus on the state of California. He is viewed as a seasoned advisor to cannabis businesses who frequently navigates complex tax structures implicating Internal Revenue Code Section 280E, negotiates and documents numerous cannabis-related celebrity and influencer licensing transactions, and regularly advises on a myriad of issues related to media, advertising, state and local regulatory compliance, Food and Drug Administration (FDA) compliance, and protection of intellectual property (IP) rights. During his legal career, Matthew has advised on numerous matters associated with taxable and tax-free M&A transactions, spin-offs, restructurings, joint ventures, debt and equity financings, partnership transactions, start-up and venture capital investments, and special entities, including tax exempts and S corporations. He has counseled clients on the tax consequences of transactions totaling in the billions of dollars and regularly advises on entity formation, capitalization, reorganization, and dissolution. In another area of focus, Matthew designs and implements tax-efficient, multi-entity acquisition, holding, and operating structures. His clients include family offices, high-net-worth individuals, financial partners, private and public businesses, private foundations and public charities, multistate businesses, liability-remote and bankruptcy-remote vehicles, IP holding companies, and special-purpose entities for complex business transactions. In his tax controversy practice, Matthew negotiates administrative appeals and pre-litigation dispute resolution involving the Internal Revenue Service (IRS), the California Franchise Tax Board (FTB), the California Board of Equalization, the California Department of Taxes and Fee Administration (CDTFA), the California Department of Cannabis Control, the City of Los Angeles Office of Finance, the City of Los Angeles Department of Cannabis Regulation, the California Office of Tax Appeals (OTA), and tax assessors and collectors throughout the state of California, its cities, and other local government agencies.