Bob O’Connor works primarily with privately held companies throughout the region, overseeing tax compliance and financial statement preparation and helping his clients build wealth, minimize taxes and obtain financing. With over 35 years of experience, Bob has particular expertise advising clients on how to obtain loans. He helps clients prepare a full disclosure statement and offer a persuasive and creative loan package for a lender’s loan committee — whether a bank, government guarantee program (such as the SBA or Massachusetts Development Authority) or a private lender.

Additionally, Bob has represented hundreds of clients in audits and disputes. He has years of proven experience before the Internal Revenue Service (IRS) and various departments of revenue in New England. With the belief that IRS and state tax authority audits ought to be resolved at the lowest possible government official level, Bob works to settle audits for clients as quickly as possible with the agent or the agent supervisor.


Master of Science in Taxation, Bentley University

Bachelor of Science, Boston College

Professional Affiliations

American Institute of Certified Public Accountants (AICPA)

Massachusetts Society of Certified Public Accountants (MSCPA)



Bob O’Connor had a well-established CPA practice when he merged with Edelstein & Company in 2012.He focuses on closely held businesses, primarily in the manufacturing, construction, retail and service industries.

Bob began his career at Ernst & Young, initially in the audit division, working with public and privately held clients. Hired by an Ernst & Young client, he served as the controller of a major New England plumbing and heating manufacturer with annual sales in excess of $60 million. After four years, he returned to public accounting and established his own practice.

Bob is committed to the co-operative education program for accounting students in the Greater Boston area, a program that he has enthusiastically supported for many years. Bob enjoys training and watching college students grow professionally and personally. Over the years, he has seen many of his co-op students go on to successful careers in the financial industry.



  • Develop strategies to minimize tax liability
  • Evaluate the tax consequences of business transactions
  • Provide effective tax planning and compliance for individuals and businesses
  • Help clients manage cash flow and minimize tax payments
  • Prepare and analyze financial statements
  • Help businesses obtain financing with excellent terms and low costs, through established banking relationships


  • Helped four franchise owners obtain financing through the Massachusetts Development Authority, financing a Massachusetts-sponsored Industrial Revenue Bond of $4.2 million with a 20-year fixed rate below the market lending rate to purchase the land, construct the building and acquire the equipment for a commissary delivering product to more than 135 franchisee retail operations.
  • While assisting a client with an estate plan, Bob found that four life insurance policies being funded by his client for the benefit of an ex-wife under a divorce decree were never transferred from the husband's ownership to the trust for the ex-wife. More than $380,000 was needlessly being included in the client's estate. By assisting his client's attorney and financial advisor, the policy ownership was transferred to the ex-wife, reducing his client's Massachusetts estate taxes by approximately $49,000.
  • Disputing the finding of an IRS Agent, Bob filed an appeal to the Boston Internal Revenue Service Appeals office on behalf of a client, successfully reducing the tax assessment by $84,000.