Stephen J. Pessagno, CFP®

We begin with an in-depth conversation to understand your personal, professional and financial picture, including the decisions and opportunities most important to you.

• Personal & professional priorities
• Assets, liabilities & cash flow
• Equity, business & ownership interests
• Near-term decisions & financial needs
• Existing professional advisors

We evaluate how the different pieces of your financial life interact and develop a coordinated strategy around your priorities, risks and long-term objectives.

• Investment strategy & asset allocation
• Tax-aware planning
• Liquidity & concentration
• Insurance & risk management
• Estate & legacy considerations

Once the strategy is established, we coordinate implementation across your investments and broader financial plan, drawing on Morgan Stanley's resources and collaborating with your other professional advisors when appropriate.

• Portfolio implementation
• Lending & financing strategies
• Tax-aware investment management
• CPA, attorney & professional advisor coordination

As markets, careers, businesses and personal circumstances evolve, we revisit the strategy and make adjustments to keep your financial plan aligned with your priorities.

• Ongoing financial planning
• Portfolio & risk monitoring
• Tax considerations
• Career, business & family changes
• New opportunities & priorities

Incentive Stock Options (ISOs) and Nonqualified Stock Options (NQSOs) can create significant opportunity while introducing decisions around exercise timing, taxes, liquidity, and concentration. The appropriate strategy depends on the type of option, company circumstances and how the position fits within your broader financial plan.

Questions Worth Asking

• When should I exercise my stock options?
• How could an ISO exercise affect Alternative Minimum Tax (AMT)?
• What should I consider before exercising private-company options?

Restricted Stock Units (RSUs) and Performance Stock Units (PSUs) can become a meaningful source of wealth as awards vest. Planning should consider taxes and withholding, vesting schedules, performance conditions, trading restrictions and whether to hold or diversify the company stock you receive.

Questions Worth Asking

• Should I hold or sell shares as my RSUs vest?
• How should taxes, withholding and concentration affect that decision?

Private-company equity can create difficult decisions when potential value exists without readily available liquidity. Stock option exercises, AMT exposure, option expiration, tender offers, secondary transactions and pre-IPO planning should be evaluated against liquidity needs, taxes and the uncertainty of a future exit.

Questions Worth Asking

• Should I exercise my options before there is a liquidity event?
• How should I evaluate a tender offer or secondary transaction?
• What should I plan for if an IPO may be on the horizon?

When both your income and investment wealth depend heavily on one company, a concentrated stock position can create risks that extend beyond the portfolio itself. The appropriate level of company stock depends on taxes, career exposure, liquidity needs, time horizon and personal priorities.

Questions Worth Asking

• How much company stock is appropriate for my situation?
• How can I reduce concentration without losing sight of taxes and liquidity?

Diversifying highly appreciated company stock is not always as simple as selling. Depending on your circumstances, staged sales, exchange funds, direct indexing, tax-loss harvesting and other tax-aware strategies may help reduce concentration while considering the potential capital-gains impact.

Questions Worth Asking

• How can I diversify a low-basis stock position thoughtfully?
• Which diversification strategies may fit my tax and liquidity needs?

Company stock may be valuable without being freely or conveniently available for spending. Trading restrictions, scheduled sales and liquidity needs may call for coordinated planning that can include 10b5-1 trading plans, securities-based lending or advanced hedging and monetization strategies where appropriate.

Questions Worth Asking

• How can I create liquidity without selling all of my company stock?
• How should trading restrictions affect the timing of stock sales?

Equity compensation can create tax consequences at vesting, exercise and sale, while diversification may generate significant capital gains. Tax-aware planning can coordinate transaction timing, withholding, tax-loss harvesting and portfolio decisions with your CPA or tax advisor and your broader financial plan.

Questions Worth Asking

• How might an equity decision affect my overall tax picture?
• Can investment losses help offset gains from selling company stock?

Equity decisions rarely occur in isolation. Vesting, option exercises, taxes, liquidity, diversification, portfolio construction and long-term goals can affect one another. Coordinating these decisions within your broader financial plan can provide a clearer framework for deciding what needs attention now and what can wait.

Questions Worth Asking

• How should my equity compensation affect the rest of my investment portfolio?
• Which equity decisions should I prioritize now, and which can wait?

For many entrepreneurs, the business becomes both a source of income and the largest asset on the personal balance sheet. Understanding how business value, cash flow, personal assets and long-term goals interact creates the foundation for more coordinated financial decisions.

Questions Worth Asking

• How should my financial strategy evolve as the business grows?
• How much of my wealth depends on the business?

Ownership decisions can have long-term implications for control, liquidity and personal wealth. Founder shares, private-company equity, fundraising and dilution should be considered alongside personal liquidity needs, potential tax considerations and the value of maintaining ownership as the business grows.

Questions Worth Asking

• How should I think about ownership, dilution and control?
• When should I consider taking some value off the table?

Understanding the value of a business can inform decisions well before a sale is contemplated. A thoughtful valuation can provide important context for personal net worth, concentration, estate and succession planning, potential transactions and the amount of wealth that may ultimately exist outside the business.

Questions Worth Asking

• What is my business worth today?
• How could valuation affect my financial or succession plan?

Reinvesting in the business can support continued growth, but it can also leave personal wealth increasingly concentrated and illiquid. Distributions, secondary liquidity, borrowing and other sources of liquidity may create greater financial flexibility without requiring a full exit from the business.

Questions Worth Asking

• How much wealth should remain tied to the business?
• What options could create liquidity before a full exit?

A business transition does not have to follow one predetermined path. Strategic sales, private equity transactions, recapitalizations, internal or family succession, employee ownership and public offerings can have different financial implications, making it valuable to evaluate potential paths before a transition becomes imminent.

Questions Worth Asking

• What are my options for eventually stepping away?
• Which transition path fits my business and family priorities?
• How early should succession or exit planning begin?

Some planning decisions may need to be evaluated well before a transaction is underway. Depending on the circumstances, considerations may include Qualified Small Business Stock (QSBS) eligibility, gifting business interests, trust and estate strategies, charitable planning and coordination with legal and tax advisors.

Questions Worth Asking

• What should I consider before a transaction?
• Could my shares qualify as Qualified Small Business Stock (QSBS)?
• Which decisions may become harder once a transaction is underway?

A sale, recapitalization, secondary transaction, merger or public offering can fundamentally reshape the personal balance sheet. Planning should consider transaction structure, potential tax implications, liquidity needs and the timing of proceeds while coordinating the personal financial strategy with the broader legal, tax and transaction team.

Questions Worth Asking

• How will a transaction change my financial picture?
• How should the transaction team and my personal advisors coordinate?

A liquidity event can shift the challenge from creating wealth to managing it. Newly liquid assets may require a coordinated approach to cash management, diversification, portfolio construction, taxes, estate planning, philanthropy and capital for future businesses, investments and personal goals.

Questions Worth Asking

• How should I invest and manage new liquidity?
• What do I want my wealth to make possible after the business?

Contracts, salaries, signing bonuses, performance compensation and project-based earnings can create significant financial opportunities over potentially uneven career timelines. Financial planning can provide context around payment timing, liquidity and long-term commitments as compensation and career circumstances evolve.

Questions Worth Asking

• How should a new contract or major payout change my financial plan?
• What should I prioritize during my highest-earning years?
• How much flexibility should I maintain between contracts, seasons or projects?

Income can extend well beyond salary or primary career compensation. Endorsements, sponsorships, royalties, residuals, licensing, appearances, content and platform revenue can create additional income streams that should be considered alongside taxes, liquidity, investments and long-term financial goals.

Questions Worth Asking

• How should endorsement, royalty or licensing income fit into my broader financial plan?
• What should I consider before monetizing intellectual property or future income?

Income in the industry can be significant without being predictable. A coordinated cash-flow strategy can help establish appropriate reserves, separate near-term spending from long-term capital and create a disciplined framework for saving and investing through higher and lower-income periods.

Questions Worth Asking

• How much of a large payment should I keep liquid?
• How much can I sustainably spend when income changes from year to year?
• How should I plan when future income is uncertain?

Multiple income sources, uneven earnings, business interests, and work across different jurisdictions can create important tax considerations. I incorporate tax awareness into financial and investment decisions while coordinating with clients' CPAs and tax advisors on issues requiring specialized tax guidance.

Questions Worth Asking

• How should I prepare for taxes when income comes from multiple sources?
• How might working or earning income in multiple states affect my planning?

Career success and audience can create opportunities beyond earned income, including equity-for-endorsement arrangements, private-company ownership, creator-led businesses and other ventures. These opportunities should be evaluated as investments, considering valuation, liquidity, concentration, risk and their role withing your broader financial strategy.

Questions Worth Asking

• Should I accept equity in a company I promote or partner with?
• How should I balance reinvesting in my business or brand with building wealth outside of it?
• How should business ownership fit alongside my other investments?

Career earnings, business interests and future opportunities can create competing demands for capital. Investment planning should balance near-term liquidity with diversification, long-term growth and financial independence while preserving appropriate flexibility for future spending, investments and business opportunities.

Questions Worth Asking

• How much should remain liquid vs. invested for the long-term?
• How should I invest during my highest-earning years?
• How much capital can I reasonably commit to private or business opportunities?

Financial decisions in these careers often intersect with contracts, taxes, legal structures, business interests and career opportunities. I work collaboratively with clients' existing agents, business managers, attorneys, CPAs and other trusted professionals so related financial decisions can be considered in context.

Questions Worth Asking

• How should my financial advisor work with my agent, business manager, attorney and CPA?
• Are my financial, tax, legal and career decisions being considered together?

Career earnings may be significant without being permanent. Long-term planning should consider how today's income, investments and business interests can support financial independence, future career transitions, family priorities, estate and legacy considerations, philanthropy and opportunities beyond your primary career.

Questions Worth Asking

• How do I turn my highest-earning years into durable long-term wealth?
• What should change financially as my career and income evolve?
• What do I want my wealth to make possible beyond my current career?