Rob counsels high-net-worth individuals and families on estate planning, estate and trust administration, and business succession strategies—often serving as a trusted advisor to multiple generations.
Known for his precision, creativity, and judgment, Rob focuses on long-term legacy planning and tax-efficient wealth transfer techniques that help clients preserve family assets and ensure continuity for closely held businesses.
A significant part of Rob’s practice involves designing complex estate plans that reflect a family’s values and goals across generations. He regularly advises founders and entrepreneurs on structuring the transition of family-owned businesses, often through limited partnerships, grantor trusts, and dynasty trusts that are tailored to minimize gift, estate, and generation-skipping transfer taxes. Clients value his ability to navigate sensitive family dynamics with discretion and care, making him a frequent confidant and strategic guide through life’s most personal legal decisions.
- Limited partnerships and limited liability companies for asset protection, investment, and wealth preservation purposes
- Strategic use of grantor-retained annuity trusts (GRATs).
- Installment sale of appreciating assets to intentionally defective grantor trusts (IDGTs)
- Creation of Dynasty Trusts that avoid the rule against perpetuities and exempt trust assets from the generation-skipping transfer tax and estate tax in the estates of future generations of beneficiaries
- Sales of closely-held business interests in consideration for self-canceling installment notes (SCINs) or private annuities
- Life insurance planning, including employer and private split-dollar arrangements, irrevocable life insurance trusts (ILITs), and funding techniques that avoid gift taxes
- Charitable planning using retained interest trusts (charitable remainder unitrust and annuity trusts), charitable lead annuity trusts (CLATs), and private foundations
Education
- LLM, Estate Planning, University of Miami School of Law
- JD, cum laude, University of Miami School of Law
- BA, University of Rochester
Bar Admissions
- Massachusetts
- Florida
Experience recognized
- Best Lawyers in America, Tax Law, 2008-2026; Trusts & Estates, 2008-2026
- Boston Magazine’s Top Lawyers, Trusts & Estates, 2022-2025
- Chambers High Net Worth (HNW) guide, Private Wealth Law: Massachusetts, 2019-2022
- Massachusetts Super Lawyers, 2005-2020
- Worth Magazine – Top 100 Attorneys in the US, 2005-2007
- 22nd Annual Estate Planning Conference, Massachusetts Continuing Legal Education (April 2021, Faculty Member)
- Rubin Rudman, Executive Committee Member
- Foundation for MetroWest Foundation’s inaugural 2022 “Distinguished Advisor Society Inductee” for Rob’s strong commitment to community and inspirational charitable giving while also working to advance philanthropy in MetroWest, Honored
- Boston Estate Planning Council, Member, Former Trustee
- American Bar Association
- Florida Bar Association
- Massachusetts Bar Association
- Foundation for Metrowest, Member, Former Board of Trustees
- Bentley College, Adjunct Professor, Law, Taxation and Financial Planning Department (2005–2007)
- Temple Isaiah, Lexington, Massachusetts, Former Member, Board of Trustees and Chair, Development Committee