I help my clients to develop and implement tax-efficient investments, transactions and structures.
Christopher (“Kip”) Cawley is a partner and chair of the firm’s tax practice with more than 20 years of experience advising sponsors, investors, and operating companies on the tax aspects of private investments, complex transactions, and business structures. He works closely with clients to design and implement creative, practical, and tax‑efficient solutions that align with business objectives and risk tolerance.
Kip represents private investment fund managers on the tax aspects of fund formation and operations, including tax structuring for private equity, venture, hedge, and credit funds; portfolio acquisitions and exits; co-investments; investor negotiations; management company and general partner economics; and ongoing compliance and information reporting. He regularly advises institutional investors, family offices, and sovereign and pension investors on tax considerations for private investments, including treaty eligibility, withholding, and reporting, and structuring tax‑efficient investments for non‑U.S. and U.S. tax‑exempt investors.
Kip has extensive experience counseling partnerships, LLCs, C corporations, S corporations, and individuals in domestic and cross‑border mergers and acquisitions, joint ventures, restructurings, recapitalizations, minority and growth investments, and financings. He frequently addresses issues involving choice-of-entity, partnership allocations and distributions, blocker and feeder structures, co‑investment and carried interest arrangements, and information reporting and withholding.
Kip also maintains a robust tax controversy practice. He represents clients in federal and state audits, examinations, collections proceedings, mediations, and administrative and judicial appeals, including matters before the U.S. Tax Court. He prepares and negotiates voluntary disclosure submissions and closing agreements, seeks private letter rulings and other administrative guidance, and manages technical issue resolution before tax authorities to achieve efficient, business-oriented outcomes.
In the cannabis sector, Kip advises operators, investors, and ancillary service providers on federal and state tax considerations related to mergers and acquisitions, joint ventures, business structuring and operations, and compliance. He regularly counsels clients on the impact of Internal Revenue Code Section 280E, and works with clients to develop inventory costing, structuring, and reporting strategies designed to address 280E exposure and other tax issues that are unique to the industry.
