Advisor’s Guide to Mastering Stock Options and Equity Compensation

The Bucket Plan® On-Demand Podcast

Advisor's Guide to Mastering Stock Options and Equity Compensation

In This Episode

About the Episode:

Stock options and equity compensation represent significant wealth-building opportunities for clients, but they also present complex planning challenges that many advisors aren’t equipped to handle. In this insightful discussion, host Dave Alison, President and Founding Partner at C2P, welcomes Greg Dillon, CFA, CFP ®, CLTC®, NSSA®, Principal at OneTeam Financial and C2P Partner, to share strategic approaches for helping clients maximize their equity compensation.

Greg brings his extensive experience working with pre-retirees in the pharmaceutical industry, while Dave offers insights from his work with tech executives and Silicon Valley professionals. Together, they break down the critical differences between various equity compensation vehicles, including Restricted Stock Units (RSUs), Incentive Stock Options (ISOs), Non-Qualified Stock Options (NSOs), and Employee Stock Purchase Plans (ESPPs).

Key Topics Discussed:

  • Stock Option Types and Mechanics: An overview of the different equity compensation vehicles and their fundamental characteristics.
  • Tax Optimization Strategies: Effective approaches to minimize tax implications when exercising options and selling equity compensation.
  • Concentration Risk Management: Methods for transitioning clients from concentrated equity positions to properly diversified portfolios.
  • Liquidity and Cash Flow Planning: How to help clients manage the cash requirements associated with exercising options and paying resulting taxes.
  • Stock Option Document Analysis: The critical importance of reviewing plan documents to understand specific rules that impact planning decisions.
  • 10b5-1 Trading Plans: The benefits of implementing automated selling programs for executives with significant equity positions.
  • Charitable and Estate Planning: How to integrate equity compensation into broader wealth transfer and philanthropic strategies.
Advisor's Guide to Mastering Stock Options and Equity Compensation

About the Host:

Dave Alison, CFP®, EA, BPC, is a seasoned financial planner and entrepreneur committed to elevating advisors’ businesses and planning capabilities. As the President and Founding Partner of C2P Enterprises, Dave drives a shared vision of simplifying financial planning for a global audience of one billion people. He leads the company’s growth strategies, shapes its corporate direction, and guides the executive team, demonstrating a remarkable ability to transform vision into reality.

Beyond C2P, Dave contributes his expertise to various leadership roles, including Prosperity Capital Advisors, and Clarity 2 Prosperity, enhancing the financial landscape. Dave’s proficiency in integrating complex financial, tax, investment, insurance, and estate planning into comprehensive strategies led to the creation of Alison Wealth Management, which serves clients nationwide. A member of the Financial Planning Association®, Dave has consistently demonstrated his dedication and expertise, earning accolades such as the 2023 40 Under 40 recognition and won a ThinkAdvisor’s LUMINARIES award for Thought Leadership and Education at C2P.

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About the Guest:

Greg Dillon, CFA, CFP ®, CLTC®, NSSA®, is the Managing Partner and Head of Wealth Management and Retirement Income Planning at OneTeam Financial. He leads the firm’s wealth management division, collaborating with specialists in Social Security, Medicare, and long-term care to design tailored, holistic retirement plans. Greg’s approach prioritizes financial flexibility and risk management to achieve clients’ unique goals and objectives. His journey in finance began at Fairfield University’s Honors Program, where he earned a Bachelor of Science in Finance and Accounting, followed by a successful seven-year stint trading fixed income and options at UBS Financial Services.

Beyond his work at OneTeam, Greg is a respected speaker at conferences, president of the Red Bank Chapter of the American Financial Education Alliance (AFEA), and an advisory board member for Best Buddies New Jersey, where he helps support individuals with intellectual and developmental disabilities.

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