

Robert DiCicco, CIMA®

My Mission Statement
About Me
Many of his clients have been working with Robert for as long as he has been in the securities industry, and he sees it as a privilege to now be guiding many of their children and grandchildren. By keeping his practice limited to a select group of clients, Robert can deliver an extraordinary level of attention and service, including the myriad white-glove services he believes his clients deserve, while leveraging the global resources of Morgan Stanley.
Robert, a Certified Investment Management Analyst® (CIMA®), is also a strong believer that a knowledgeable investor is a comfortable investor. Therefore, he takes the time to educate his clients in easy-to-understand language about the many opportunities available to them and how to best capitalize on those opportunities to achieve their life goals.
Born in Philadelphia and raised in Dallas, Robert has made his home in Texas for more than two decades. When he’s not working, he loves spending time with his wife and two daughters, as well as their bird dogs. He also loves to cook.
Experience
With nearly two decades of experience as a wealth management professional, I have dedicated my career to helping clients navigate their financial lives with clarity and confidence. A former analyst, I have a deep understanding of portfolio strategy, municipal bond management and asset allocation, and I have an eye for tax efficiency. Add to that my experience with estate, trust, family governance and philanthropic planning and I am able to deliver a customized, comprehensive wealth management experience with an extraordinary level of service.
In 2025, Robert's team, The Cypress Grove Group, was recognized as a Best-In-State Wealth Management Teams by Forbes.
Source: Forbes (Awarded Jan 2025). Data compiled by SHOOK Research LLC based for the period 3/31/23–3/31/24. https://www.morganstanley.com/what-we-do/wealth-management/forbes-top-wealth-advisors-lists-2025
The individuals mentioned as the Portfolio Management Team are Financial Advisors with Morgan Stanley participating in the Morgan Stanley Portfolio Management program. The Portfolio Management program is an investment advisory program in which the client’s Financial Advisor invests the client’s assets on a discretionary basis in a range of securities. The Portfolio Management program is described in the applicable Morgan Stanley ADV Part 2, available at www.morganstanley.com/ADV or from your Financial Advisor.
NMLS#: 1622256
Custom Process & Planning
The Cypress Grove Group provides our clients with a distinctive process and an exhaustive planning approach, both tailored to the character and needs of executives and entrepreneurs.
We follow a high-touch process of accountability and frequent reporting that closely mirrors corporate and business operational methods. We supplement the customary four step process—discovery, analysis and recommendation, implementation, and governance—with defined periodic interactions that allow for frequent status and result reviews.
Our planning goes beyond the traditional approach, taking into account the unique needs of our clients. We add executive and business owner planning elements to the traditional package of financial, investment, retirement, wealth and asset protection planning.
Executive Planning
Benefits and Incentive Compensation Analysis
- Types and provisions
- Income tax implications
Stock Options
- Vesting Analysis
- Optional exercise strategies
Concentrated Position Analysis
- Risk analysis
- Diversification strategies
Executive Stock Monetization
- Sales of restricted shares under Rule 144
- Rule 10b5-1 trading plans
- Loans and hedging strategies
Business Owner Planning
Business Needs
- Ownership
- Control and liquidity
- Key opportunities
- Key challenges
Cash Management and Capital Needs Review
- Deposit/ Treasury services
- Lines of credit
- Growth capital
- Key challenges
Retirement and Benefits Assessment
- 401(k), profit sharing an defined benefit plans
- Non-qualified deterred compensation
Risk Management
- Continuity planning
- Buy sell agreements
- Key employee life
- Split-dollar life
Succession or Exit Planning
- Strategic Client Group / Investment Bank (private sale)
- IPO
- Valuation maximization
- Strategic sale
- Financial recapitalization
- Employee stock ownership (ESOP)
The Challenge of Concentrated Stock Positions
There are many reasons you've had a successful career. You're among the best at what you do. You're an innovator. But perhaps most important of all, you're an enterprise leader with the dedication and vision to value the organization's interests as much, if not more than, those of your own unit or department. That's why you've been rewarded with sizable equity compensation in the form of stock grants or options.
While you have additional assets in your retirement plan, other investment accounts, insurance, and real estate, this concentrated stock position in your company represents a significant part of your total wealth. This also represents significant challenges, such as tax implications, liquidity limitations, and potential volatility. You need the help of someone who understands the complex regulations as well as the potential political ramifications surrounding equity compensation.
How We Can Help
The Cypress Grove Group at Morgan Stanley specializes in helping executives manage equity compensation issues and craft bespoke, all-inclusive wealth plans. Drawing on our team's experience and expertise, as well as Morgan Stanley's resources, we help corporate insiders navigate insider trading regulations and reporting requirements.
We can suggest tax-efficient approaches to diversification and strategies to address cash flow needs before stock liquidity is available.
- Exchange Funds: Provide diversification without triggering taxable gains through IRS-approved tax-deferred investment vehicles
- Opportunity Zone Investments
- Donor Advised Funds: Gifting appreciated long-term gain stock to offset income tax in a year when there is a liquidity event
- Portfolio Line of Credit: Borrowing against stock in a portfolio line as needed for immediate cash flow requirements
- 10b5-1 Plans: Preset diversification plans to sell through open and closed windows, approved by legal counsel and executed by third parties
- QSBS Exclusion: Gain from the sale or exchange of qualified small business stock (QSBS) may be 100% excluded from income
THE CHALLENGE OF MONETIZING BUSINESS VALUE
You've devoted yourself to building your own business. It was never really about the money; that was just a way to keep score. It was actually about pursuing your passion, being your own boss, challenging the status quo, and creating something lasting. Through your ingenuity, determination and grit, you've achieved success.
Now you're ready for another challenge, you'd like to spend more time with your family, or both. But you have substantial net worth that's difficult to access. You know your success in business doesn't automatically qualify you to steer your family through this very complex transition. You need advice and guidance from a team with the expertise and experience to help you manage what could be the transaction of a lifetime.
How We Can Help
The Cypress Grove Group at Morgan Stanley specializes in working with entrepreneurs just like you. We help you leverage personal wealth for business growth or liquidity as well as examine potential exit strategies in light of family as well as financial needs.
Drawing on our in-house expertise and the resources of Morgan Stanley we can help you through every stage in the life of a successful entrepreneur:
- Strategic Client Group / Investment Bank (private sale)
- IPO
- Generation: gain access to liquidity for business and personal use through approaches best suited to your needs and circumstances
- Monetization: model alternative strategies to monetize the value of your enterprise and consider how the proceeds hold be structured and invested
- Retirement: calculate cash flow needs, determine post career priorities and implement succession plans for continued family ownership
- Transfer: prepare younger generations with the education and support needed to assume control of family business and philanthropic legacies
Location
The Power of Partnerships
About Randy Payne
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.
Randy began his career in financial services in 1993, and joined Morgan Stanley in 2014 as a Private Banker. Prior to joining the firm, he was a Divisional Sales Director at Wells Fargo Advisors.
Randy is a graduate of Rensselaer Polytechnic Institute, where he received a Bachelor of Science in Management. He lives in Northlake, Texas with his family. Outside of the office, Randy enjoys spending time in Oxford, MS with his family cheering on Ole Miss football and baseball teams.
About Kaitlin Martin
Kaitlin began her career in financial services in 2015 and joined Morgan Stanley in 2022. Prior to her current position, she worked at Raymond James, BBVA Private Banking and a boutique financial firm in Birmingham, AL.
Kaitlin graduated from The University of Alabama and holds CERTIFIED FINANCIAL PLANNER™ designation. Kaitlin lives in Plano, Texas with her husband Daniel and their giant schnauzer Leo, who helps keep them active. They enjoy most outdoor activities like hiking, scuba diving, golfing, and, of course, Alabama football.
Portfolio Insights
Investing
- Asset Management
- Wealth Planning
- Traditional Investments
- Alternative Investments
- Impact Investing
Family
- Estate Planning Strategies
- 529 Plans / Education Savings Planning
- Long Term Care Insurance
- Special Needs Planning
- Trust Services
Financial Wellness
- Reduce employee stress,
- Improve retention and engagement, and
- Set themselves apart by offering comprehensive financial wellness benefits.
For more information, please see the Morgan Stanley Smith Barney LLC Client Relationship Summary.
2Alternative Investments are speculative and include a high degree of risk. An investor could lose all or a substantial amount of his/her investment. Alternative investments are appropriate only for qualified, long-term investors who are willing to forgo liquidity and put capital at risk for an indefinite period of time.
3Morgan Stanley Smith Barney LLC (“Morgan Stanley”), its affiliates and Morgan Stanley Financial Advisors and Private Wealth Advisors do not provide tax or legal advice. Clients should consult their tax advisor for matters involving taxation and tax planning and their attorney for matters involving trust and estate planning, charitable giving, philanthropic planning and other legal matters.
4Morgan Stanley Smith Barney LLC (“Morgan Stanley”), its affiliates and Morgan Stanley Financial Advisors and Private Wealth Advisors do not provide tax or legal advice. Clients should consult their tax advisor for matters involving taxation and tax planning and their attorney for matters involving trust and estate planning and other legal matters.
5Morgan Stanley Smith Barney LLC (“Morgan Stanley”), its affiliates and Morgan Stanley Financial Advisors or Private Wealth Advisors do not provide tax or legal advice. Clients should consult their tax advisor for matters involving taxation and tax planning and their attorney for legal matters.
6Morgan Stanley offers a wide array of brokerage and advisory services to its clients, each of which may create a different type of relationship with different obligations to you. Please consult with your Financial Advisor to understand these differences or review our Understanding Your Brokerage and Investment Advisory Relationships brochure available at www.morganstanley.com/wealth-relationshipwithms/pdfs/understandingyourrelationship.pdf.
7Morgan Stanley’s investment advisory programs may require a minimum asset level and, depending on your specific investment objectives and financial position, may not be appropriate for you. Please see the Morgan Stanley Smith Barney LLC program disclosure brochure (the “Morgan Stanley ADV”) for more information in the investment advisory programs available. The Morgan Stanley ADV is available at www.morganstanley.com/ADV.
8The returns on a portfolio consisting primarily of Environmental, Social and Governance (“ESG”) aware investments may be lower or higher than a portfolio that is more diversified or where decisions are based solely on investment considerations. Because ESG criteria exclude some investments, investors may not be able to take advantage of the same opportunities or market trends as investors that do not use such criteria. Diversification does not guarantee a profit or protect against loss in a declining financial market.
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