Attorney Profile

Diana Espanola Esq.


Diana assists executives and enterprises in implementing business formation, growth and exit strategies, with a special focus on planning for the related tax implications of such activities.

With over 20 years of experience, Diana works with business and individual clients in both the for-profit and non-profit arenas. Diana provides a broad range of counsel for tax and tax sensitive transactions, including, for example, choosing a form of and setting up entities, implementing governance and policies, financing with debt and equity, negotiating joint ventures, funding investment vehicles, compensating service providers, designing reorganizations, and structuring mergers and acquisitions.

Diana also represents individuals and entities before taxing authorities and other government agencies in connection with private letter rulings, determination letters (including obtaining tax-exempt status), Streamline Offshore Procedures for international account and asset reporting compliance, and dissolution of charities with and without assets.

Prior to starting her own firm, Diana was a Member at Morse, Barnes-Brown & Pendleton, P.C., in Waltham, MA, an Associate at Bowditch & Dewey in Worcester, MA and an Associate at Hill & Barlow in Boston. Before becoming an attorney, Diana worked as a consultant at both Andersen Consulting and Coopers & Lybrand (now PwC).

  • Boston University School of Law, LLM in Taxation
  • Boston College Law School, Juris Doctor, magna cum laude
  • Georgetown University, Master of Science in Foreign Service with Concentrations in International Trade and Finance and International Business Diplomacy
  • Amherst College, Bachelor of Arts
  • Massachusetts
  • United States Tax Court
  • American Bar Association
  • Boston Bar Association
  • Panelist, LLCs Demystified, presented half-day programs to lawyers on limited liability companies, MCLE
  • Panelist, Fundamentals of Business Tax Law Dissected, providing overview of the most common business taxes, MCLE
  • Presenter, Managing Legal Matters in an Organization focusing on the benefits of being a 501(c)(3) organization, the basic legal and compliance requirements, and the duties and responsibilities of its officers and directors, 4th Leadership Management Seminar for Filipino American Community
  • Panelist, Advanced Tax Issues of Entity Selection, CLE / CPE Webinar
  • Presenter, Basic Tax Issues for Solo and Small Firms, invited to give solo and small firm lawyers a primer on choice of entity and tax considerations in running a law practice, Boston Bar Association
  • Equity-Based Compensation Grants for Limited Liability Companies
  • Quoted: Valuing Employee Stock Options: The Rules, NASDAQ Private Market™, The Wall Street Journal
  • Basic Tax Issues in Choosing a Business Entity
  • IC-DISCs: Tax Savings for Exporters
  • Common Stock Valuation and Option Pricing by Private Companies: Ten Years of Section 409A
  • Tax FAQ for U.S. Inbound Transactions
  • Life Cycle of an IRS Audit