

The Woolf Group at Morgan Stanley

Our Mission Statement
Our Story and Services
When we pose that question to new clients who have worked hard to build long careers, they are often unsure. After our combined 50 years in the industry, we’ve found that the most likely obstacle standing between you and your retirement goals is not a lack of wealth, but an incomplete understanding of what your wealth really means.
We want you to work if you WANT to work. Not because you think you NEED to work. Transitioning to retirement is a thoughtful process that we take ownership in being there every step along the way.
• When should you begin to claim social security?
• How should you manage your pension and Required Minimum Distributions?
• Should you utilize a ROTH IRA to bridge your retirement income?
Taking your money from the right pockets of your wealth can have major tax advantages. That’s why we map out a thoughtful, tax-efficient plan to fit your distinct needs and can work closely with your insurance, legal and tax advisors to orchestrate a plan for your continued prosperity. It helps ensure your wealth is working as hard as possible for you in a manner in which you are comfortable.
Whatever your specific life goals are is what will what dictate the financial approach we take for you. At the same time, we know that people change. What matters to you at age 50 might seem less important to you at age 70. So we don’t make financial decisions you can’t change.
For a complimentary second opinion on your current investments, or to discuss your goals, please email us at thewoolfgrp@morganstanley.com and we will get back to you the same day.
Our services include:
• Retirement Transitions
• Tax Reduction Strategies
• Helping clients decide when and how to precisely take Social Security
• 401k Rollovers
• Portfolio Management
• Banking and Lending Strategies
• Cash Flow Planning
• Financial Planning
• Cash Reserves Strategies
Typically, a retirement plan participant leaving an employer's plan has the following four options (and may be able to use a combination of these options depending on their employment status, age and the availability of the particular option):
1. Cash out the account value and take a lump sum distribution from the current plan subject to mandatory 20% federal income tax withholding, as well as potential income taxes and 10% early withdrawal penalty tax, or continue tax deferred growth potential by doing one of the following:
2. Leave the assets in the former employer’s plan (if permitted)
3. Roll over the retirement assets into the new employer’s qualified plan, if one is available and rollovers are permitted, or
4. Roll over the retirement savings into an IRA
Other factors to consider when making a rollover decision include (among other things) the differences in: (1) investment options, (2) fees and expenses, (3) services, (4) penalty-free withdrawals, (5) creditor protection in bankruptcy and from legal judgments, (6) required minimum distributions or “RMDs,” (7) the Tax Treatment of Employer Stock, and (8) the availability of plan loans (e.g., loans are not permitted from IRAs, and the availability from an employer’s qualified retirement plan will depend on the terms of the plan.)
A Roth Conversion may not be right for everyone. There are a number of factors taxpayers should consider before converting, including (but not limited to) whether or not the cost of paying taxes today outweighs the benefit of income tax-free Qualified Distributions in the future. Before converting, taxpayers should consult their tax and legal advisors based on their specific facts and circumstances
When Morgan Stanley Smith Barney LLC, its affiliates and Morgan Stanley Financial Advisors and Private Wealth Advisors (collectively, “Morgan Stanley”) provide “investment advice” regarding a retirement or welfare benefit plan account, an individual retirement account or a Coverdell education savings account (“Retirement Account”), Morgan Stanley is a “fiduciary” as those terms are defined under the Employee Retirement Income Security Act of 1974, as amended (“ERISA”), and/or the Internal Revenue Code of 1986 (the “Code”), as applicable. When Morgan Stanley provides investment education, takes orders on an unsolicited basis or otherwise does not provide “investment advice”, Morgan Stanley will not be considered a “fiduciary” under ERISA and/or the Code. For more information regarding Morgan Stanley’s role with respect to a Retirement Account, please visit www.morganstanley.com/disclosures/dol. Tax laws are complex and subject to change. Morgan Stanley does not provide tax or legal advice. Individuals are encouraged to consult their tax and legal advisors (a) before establishing a Retirement Account, and (b) regarding any potential tax, ERISA and related consequences of any investments or other transactions made with respect to a Retirement Account.
Woolf Group Principles
1. WE AVOID COMPLICATED INVESTMENTS
Our rule of thumb is: If we can't readily explain what it is, we don't invest your money in it. That means no risky alternative investments. No illiquid investments. We value transparency and integrity. While always accounting for your specific risk tolerance, we ensure you know exactly how your wealth is allocated and working for you.
2. CASH FLOW (NOT WEALTH) IS QUALITY OF LIFE
Retirement is a much happier time when you have a positive cash flow versus a high net-worth. When it comes to managing your assets, we have one main priority: we want to give you a raise every year. Because retirement is all about quality of life and having the freedom to finally live out the vision you previously could only imagine.
3. TAX EFFICIENCY IS PARAMOUNT TO GROWING YOUR WEALTH
Many of our clients are in a high tax bracket. Managing tax exposure and properly utilizing all available tax minimization strategies throughout the year is paramount to growing your wealth. We routinely review our clients' portfolios for opportunities to lower their taxes for the current and future tax years. (i.e. Roth Conversions, Tax Loss Harvesting, etc.)
4. LONG-TERM PERSPECTIVE
In the beginning years of retirement, people tend to spend. They buy the things they've been dreaming about during their working years. But they also tend to fill their newly found free time reading every economic headline that comes out. With this combo of spending and worrying, it's not unusual for recent retirees to make bad investment decisions. We know this; that's why we help you lead a prudent and confident financial life, ensuring emotion does not derail your plans.
5. REGULAR CLIENT CONTACT IN HUMAN TERMS
We enjoy working very closely with clients and connecting with them on a frequent, proactive basis. Throughout the year, we suggest four review calls and two tax planning calls at a minimum. We are mindful of clients' busy schedules and are here to help organize their wealth planning. We take ownership in providing ideas and financial tools to help simplify their lives. We value our deep client relationships and consider many of our clients family. Our approach isn't based on a textbook. Instead of talking abstractly about market trends and economic indicators, we're going to make numbers real for you and explain how they relate to your personal situation.
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Meet The Woolf Group
About Bob Woolf
A graduate of Skidmore College, Bob first entered the wealth management industry as a Financial Advisor with Merrill Lynch in 1989. In 2008, he joined UBS Financial Services as a Senior Vice President, Wealth Management. Then in 2014, he joined J.P. Morgan –– where he held the title of Managing Director and Wealth Advisor –– before coming on board with Morgan Stanley in 2022.
Though Bob likes to say that he fell into this business accidentally, the truth is that his roots in the industry started at a young age out of necessity. When he was 22 years old, his father unexpectedly passed, and suddenly he found himself with a family to take of: a mother who needed help running a family business; two brothers with disabilities; and a sister applying to college. Wealth management, therefore, was something he learned in real life terms, and with a deeply personal motivation.
Today, as the leader of The Woolf Group, Bob brings that same passion and commitment to his clients’ financial lives. With a focus on long-term financial health, he helps them enjoy the kind of secure, stable retirements they deserve after a long, successful career. From tax minimization and cash flow analysis to portfolio management and estate planning –– he strives to be a comprehensive and accessible resource whenever his clients are in need of trusted financial guidance.
Outside the office, Bob lives in Norwell, MA with his wife and their three sons. In his free time, Bob enjoys golf and tennis.
About Henry Perazzelli
A graduate of the University of San Diego with a B.B.A. in Business Economics –– Henry first entered the financial industry in 2012 as an Investment Associate at J.P. Morgan. For ten years with the Firm, he focused exclusively on the unique wealth management needs of high-net-worth and ultra-high-net-worth clients. In 2017, he earned the rigorous CERTIFIED FINANCIAL PLANNER™ designation in order to further enhance his offering for his clients. It was for that same reason that he joined Morgan Stanley –– a partnership that allows him to equip his clients with the technology, resources, and research from one of the most well-respected wealth management firms in the world.
With The Woolf Group, Henry primarily focuses on retirement planning and portfolio management. Working with executives, professionals, and families, he helps clients craft and execute financial strategies to help maintain quality of life long after their careers come to an end. One constant in his customized strategies is risk management, and the portfolios he designs purposefully avoid “trendy” investments in favor of those focused on dividend growth and long-term appreciation.
Integrity. Service. Trust. Those values are the pillars of his practice, the bedrock of his every client relationship. He prides himself on going above and beyond for his clients, helping them in big and small ways.
Outside the office, Henry lives in Newburyport, MA with his wife and their two sons. He currently sits on the Board of Directors for the Firehouse Center for the Arts. A former NCAA Division 1 rower, he enjoys staying active with cycling, surfing, and golf.

Contact Bob Woolf
The Power of Partnerships
About Stacey Herring
Private Bankers partner with Financial Advisors to develop a specialized approach for managing clients’ cash flow, liquidity and financing needs, leveraging our comprehensive suite of cash management and lending solutions.
Stacey began her career in financial services in 1994, and joined Morgan Stanley in 2014. Prior to joining the firm, she was a Mortgage Sales Manager at SunTrust Bank and a Senior Mortgage Loan Officer for over 17 years at Fifth Third Bank. Stacey is a graduate of Florida State University, where she received a Bachelor of Science in Business Marketing and a Minor in Communications.
Stacey currently serves on the Women’s Foundation of Collier County Board of Directors, as well as Junior Achievement of SWFL’s Advisory Board. In addition, Stacey has chaired many community endeavors, serving Naples Community Hospital, PACE Center for Girls of Collier County, and Youth Haven. She is a graduate of the Naples Chamber of Commerce’s Leadership Collier program, awarded Gulfshore Business Magazine’s “40 Under 40 Award”, and in 2013 was awarded the Glass Slipper Award by The Education Foundation, Champions for Learning. In 2014, Stacey was named a Woman of Initiative by the Community Foundation of Collier County for her philanthropy, dedication, and commitment to children’s causes.
Retirement
- 401(k) Rollovers
- IRA Plans
- Retirement income strategies
- Retirement plan participants
- Annuities
Investing
- Asset Management
- Wealth Planning
- Traditional Investments
- Alternative Investments
- Impact Investing
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