FREE GUIDE
FREE GUIDE
Ready to lose the Golden Handcuffs?
Check out our Guide to Managing Concentrated Stock
FREE GUIDE
Ready to lose the Golden Handcuffs?
Check out our Guide to Managing Concentrated Stock
What We Do
Concentrated Stock Planning for North Carolina Executives
Holding $1 million or more in company stock creates decisions that ordinary investment management doesn’t solve. Reach Strategic Wealth helps North Carolina executives coordinate diversification, taxes, charitable giving, equity compensation, and an eventual corporate exit.
What We Do
Concentrated Stock Planning for North Carolina Executives
Holding $1 million or more in company stock creates decisions that ordinary investment management doesn’t solve. Reach Strategic Wealth helps North Carolina executives coordinate diversification, taxes, charitable giving, equity compensation, and an eventual corporate exit.
What We Do
Concentrated Stock Planning for North Carolina Executives
Holding $1 million or more in company stock creates decisions that ordinary investment management doesn’t solve. Reach Strategic Wealth helps North Carolina executives coordinate diversification, taxes, charitable giving, equity compensation, and an eventual corporate exit.
When One Stock Holds Too Much of Your Future
You've done something most people never do. You held the stock. You stayed through the volatility. You believed in the company, and now a single position represents the bulk of your net worth.
That kind of concentration is what built the wealth. It's also what now puts it at risk.
Selling triggers a tax bill that can feel impossible to swallow. Holding leaves you exposed to one company's headlines, one earnings miss, one bad quarter. And the longer the decision sits, the more it starts to weigh on everything else: retirement timing, family conversations, the life you're trying to build next.
You don't need someone to tell you to diversify. You need a plan that respects what got you here and gets you out without trading one problem for another.
When One Stock Holds Too Much of Your Future
You've done something most people never do. You held the stock. You stayed through the volatility. You believed in the company, and now a single position represents the bulk of your net worth.
That kind of concentration is what built the wealth. It's also what now puts it at risk.
Selling triggers a tax bill that can feel impossible to swallow. Holding leaves you exposed to one company's headlines, one earnings miss, one bad quarter. And the longer the decision sits, the more it starts to weigh on everything else: retirement timing, family conversations, the life you're trying to build next.
You don't need someone to tell you to diversify. You need a plan that respects what got you here and gets you out without trading one problem for another.
When One Stock Holds Too Much of Your Future
You've done something most people never do. You held the stock. You stayed through the volatility. You believed in the company, and now a single position represents the bulk of your net worth.
That kind of concentration is what built the wealth. It's also what now puts it at risk.
Selling triggers a tax bill that can feel impossible to swallow. Holding leaves you exposed to one company's headlines, one earnings miss, one bad quarter. And the longer the decision sits, the more it starts to weigh on everything else: retirement timing, family conversations, the life you're trying to build next.
You don't need someone to tell you to diversify. You need a plan that respects what got you here and gets you out without trading one problem for another.
COMPANY STOCK + CORPORATE EXIT
When Your Stock Decision Is Also an Exit Decision
Concentrated stock planning for executives
For executives approaching retirement or another transition out of corporate life, a concentrated stock position cannot be planned in isolation. The timing of your departure may affect your income, equity compensation, tax brackets, charitable opportunities, and how much risk your family can comfortably carry.
The real question
The right question usually isn’t simply, “Should I sell the stock?” It’s: how should I coordinate my company stock with the rest of my financial life before and after I leave?
Equity compensation and exit timing
Before setting a departure date, identify what remains unvested, which awards may be forfeited, when stock options expire, and whether deferred compensation or benefits are tied to continued employment.
Diversification and taxes
Selling everything immediately may create an unnecessary tax burden. Holding everything may leave your future dependent on one company. Model staged sales, tax-bracket opportunities, 10b5-1 plans, exchange funds, and direct indexing around your timeline.
Charitable and family goals
If charitable giving matters to you, appreciated shares may be more useful as a planning tool than as stock sold for cash. Donor-advised funds, charitable trusts, and family gifting can reduce concentration while advancing goals you already intend to fund.
Life after the company
The diversified portfolio needs a purpose. Connect the stock strategy to retirement income, future spending, healthcare, real estate, family support, and the work—or freedom—you want after leaving corporate life.
An investment manager may manage the portfolio after the stock is sold. Concentrated-stock and corporate-exit planning coordinates the decisions that determine when, how, and whether those shares should be sold in the first place. For North Carolina executives with significant wealth tied to one company, the goal is one coordinated plan: for the stock, the transition, and everything that comes next.
COMPANY STOCK + CORPORATE EXIT
When Your Stock Decision Is Also an Exit Decision
Concentrated stock planning for executives
For executives approaching retirement or another transition out of corporate life, a concentrated stock position cannot be planned in isolation. The timing of your departure may affect your income, equity compensation, tax brackets, charitable opportunities, and how much risk your family can comfortably carry.
The real question
The right question usually isn’t simply, “Should I sell the stock?” It’s: how should I coordinate my company stock with the rest of my financial life before and after I leave?
Equity compensation and exit timing
Before setting a departure date, identify what remains unvested, which awards may be forfeited, when stock options expire, and whether deferred compensation or benefits are tied to continued employment.
Diversification and taxes
Selling everything immediately may create an unnecessary tax burden. Holding everything may leave your future dependent on one company. Model staged sales, tax-bracket opportunities, 10b5-1 plans, exchange funds, and direct indexing around your timeline.
Charitable and family goals
If charitable giving matters to you, appreciated shares may be more useful as a planning tool than as stock sold for cash. Donor-advised funds, charitable trusts, and family gifting can reduce concentration while advancing goals you already intend to fund.
Life after the company
The diversified portfolio needs a purpose. Connect the stock strategy to retirement income, future spending, healthcare, real estate, family support, and the work—or freedom—you want after leaving corporate life.
An investment manager may manage the portfolio after the stock is sold. Concentrated-stock and corporate-exit planning coordinates the decisions that determine when, how, and whether those shares should be sold in the first place. For North Carolina executives with significant wealth tied to one company, the goal is one coordinated plan: for the stock, the transition, and everything that comes next.
COMPANY STOCK + CORPORATE EXIT
When Your Stock Decision Is Also an Exit Decision
Concentrated stock planning for executives
For executives approaching retirement or another transition out of corporate life, a concentrated stock position cannot be planned in isolation. The timing of your departure may affect your income, equity compensation, tax brackets, charitable opportunities, and how much risk your family can comfortably carry.
The real question
The right question usually isn’t simply, “Should I sell the stock?” It’s: how should I coordinate my company stock with the rest of my financial life before and after I leave?
Equity compensation and exit timing
Before setting a departure date, identify what remains unvested, which awards may be forfeited, when stock options expire, and whether deferred compensation or benefits are tied to continued employment.
Diversification and taxes
Selling everything immediately may create an unnecessary tax burden. Holding everything may leave your future dependent on one company. Model staged sales, tax-bracket opportunities, 10b5-1 plans, exchange funds, and direct indexing around your timeline.
Charitable and family goals
If charitable giving matters to you, appreciated shares may be more useful as a planning tool than as stock sold for cash. Donor-advised funds, charitable trusts, and family gifting can reduce concentration while advancing goals you already intend to fund.
Life after the company
The diversified portfolio needs a purpose. Connect the stock strategy to retirement income, future spending, healthcare, real estate, family support, and the work—or freedom—you want after leaving corporate life.
An investment manager may manage the portfolio after the stock is sold. Concentrated-stock and corporate-exit planning coordinates the decisions that determine when, how, and whether those shares should be sold in the first place. For North Carolina executives with significant wealth tied to one company, the goal is one coordinated plan: for the stock, the transition, and everything that comes next.
What to Expect
A Clear Path From Concentrated to Diversified
We know you're ready to move. Here's what progress looks like at every stage of unwinding a concentrated position.
30 Days
Getting Clear
We complete your discovery process and pull together everything that matters: cost basis, holding periods, restrictions, vesting schedules, and the full picture of your financial life around the position. You'll leave the first month with a clear map of where you stand and which moves are available.
90 Days
Strategic Planning
We model the tradeoffs. Sell now versus stage it. Exchange fund versus direct indexing. Charitable strategies versus straight liquidation. You'll see the after-tax outcome of each path side by side so the decision belongs to you, backed by numbers instead of a gut call.
6 Months +
Execute
Your plan is in motion. Diversification is happening on a timeline that fits your tax picture, your income needs, and your family's goals. We coordinate the moving parts: trades, tax withholdings, charitable transfers, so the strategy actually gets executed instead of sitting in a binder.
What to Expect
A Clear Path From Concentrated to Diversified
We know you're ready to move. Here's what progress looks like at every stage of unwinding a concentrated position.
30 Days
Getting Clear
We complete your discovery process and pull together everything that matters: cost basis, holding periods, restrictions, vesting schedules, and the full picture of your financial life around the position. You'll leave the first month with a clear map of where you stand and which moves are available.
90 Days
Strategic Planning
We model the tradeoffs. Sell now versus stage it. Exchange fund versus direct indexing. Charitable strategies versus straight liquidation. You'll see the after-tax outcome of each path side by side so the decision belongs to you, backed by numbers instead of a gut call.
6 Months +
Execute
Your plan is in motion. Diversification is happening on a timeline that fits your tax picture, your income needs, and your family's goals. We coordinate the moving parts: trades, tax withholdings, charitable transfers, so the strategy actually gets executed instead of sitting in a binder.
What to Expect
A Clear Path From Concentrated to Diversified
We know you're ready to move. Here's what progress looks like at every stage of unwinding a concentrated position.
30 Days
Getting Clear
We complete your discovery process and pull together everything that matters: cost basis, holding periods, restrictions, vesting schedules, and the full picture of your financial life around the position. You'll leave the first month with a clear map of where you stand and which moves are available.
90 Days
Strategic Planning
We model the tradeoffs. Sell now versus stage it. Exchange fund versus direct indexing. Charitable strategies versus straight liquidation. You'll see the after-tax outcome of each path side by side so the decision belongs to you, backed by numbers instead of a gut call.
6 Months +
Execute
Your plan is in motion. Diversification is happening on a timeline that fits your tax picture, your income needs, and your family's goals. We coordinate the moving parts: trades, tax withholdings, charitable transfers, so the strategy actually gets executed instead of sitting in a binder.
Inside the Engagement
What's Included in Your Concentrated Stock Plan
01
Tax Analysis
A full review of your tax returns, cost basis lots, holding periods, and AMT exposure to find the openings others miss. We look at QSBS eligibility, charitable strategies, and bracket management so the tax piece drives the plan.
02
Diversification Strategy
A recommendation on how to move from concentrated to diversified using the right mix of tools: exchange funds, direct indexing, staged selling, or a combination. You see the tradeoffs of each option modeled against your actual position.
03
10b5-1 Trading Plan Design
If you're an executive or insider, we help structure a Rule 10b5-1 plan that sells on a defined schedule, protects you legally during blackout windows, and removes the emotional weight of timing trades yourself.
04
Charitable & Estate Planning
A look at how donor-advised funds, charitable remainder trusts, and gifting strategies can lower the tax bill on appreciated shares while supporting causes and family goals you already care about.
05
Investment Plan
A diversified portfolio built for what comes after the position is unwound. Allocation, risk, income needs, and how the new portfolio integrates with retirement accounts, real estate, and other holdings.
06
Ongoing Coordination
We stay involved as the plan executes. Quarterly check-ins, trade coordination, tax estimate updates, and adjustments when life or markets shift. The plan is a living document, not a one-time deliverable.
Inside the Engagement
What's Included in Your Concentrated Stock Plan
01
Tax Analysis
A full review of your tax returns, cost basis lots, holding periods, and AMT exposure to find the openings others miss. We look at QSBS eligibility, charitable strategies, and bracket management so the tax piece drives the plan.
02
Diversification Strategy
A recommendation on how to move from concentrated to diversified using the right mix of tools: exchange funds, direct indexing, staged selling, or a combination. You see the tradeoffs of each option modeled against your actual position.
03
10b5-1 Trading Plan Design
If you're an executive or insider, we help structure a Rule 10b5-1 plan that sells on a defined schedule, protects you legally during blackout windows, and removes the emotional weight of timing trades yourself.
04
Charitable & Estate Planning
A look at how donor-advised funds, charitable remainder trusts, and gifting strategies can lower the tax bill on appreciated shares while supporting causes and family goals you already care about.
05
Investment Plan
A diversified portfolio built for what comes after the position is unwound. Allocation, risk, income needs, and how the new portfolio integrates with retirement accounts, real estate, and other holdings.
06
Ongoing Coordination
We stay involved as the plan executes. Quarterly check-ins, trade coordination, tax estimate updates, and adjustments when life or markets shift. The plan is a living document, not a one-time deliverable.
Inside the Engagement
What's Included in Your Concentrated Stock Plan
01
Tax Analysis
A full review of your tax returns, cost basis lots, holding periods, and AMT exposure to find the openings others miss. We look at QSBS eligibility, charitable strategies, and bracket management so the tax piece drives the plan.
02
Diversification Strategy
A recommendation on how to move from concentrated to diversified using the right mix of tools: exchange funds, direct indexing, staged selling, or a combination. You see the tradeoffs of each option modeled against your actual position.
03
10b5-1 Trading Plan Design
If you're an executive or insider, we help structure a Rule 10b5-1 plan that sells on a defined schedule, protects you legally during blackout windows, and removes the emotional weight of timing trades yourself.
04
Charitable & Estate Planning
A look at how donor-advised funds, charitable remainder trusts, and gifting strategies can lower the tax bill on appreciated shares while supporting causes and family goals you already care about.
05
Investment Plan
A diversified portfolio built for what comes after the position is unwound. Allocation, risk, income needs, and how the new portfolio integrates with retirement accounts, real estate, and other holdings.
06
Ongoing Coordination
We stay involved as the plan executes. Quarterly check-ins, trade coordination, tax estimate updates, and adjustments when life or markets shift. The plan is a living document, not a one-time deliverable.
Who We Help
Built for People With a Lot Riding on One Stock
We work with people who have built meaningful wealth in a single stock position, usually company equity, founder shares, or a long-held investment that grew past the point of comfort, and want a plan that's tax-smart, paced to their life, and built around what comes next.
Reach Strategic Wealth is based in North Carolina and works with executives and senior professionals throughout the state, including Charlotte, the Triangle, the Triad, Wilmington, and surrounding communities. We also work virtually with clients nationwide.
If that sounds like your situation, let's talk.
Articles to Read Before You Sell a Share
How to Manage a Concentrated Stock Position
Senior professionals and executives often have to manage large amounts of company stock as they plan to leave their corporate roles. Here is a framework to help.
Zachary Ashburn, CFP®, EA, AFC®
Financial Planning Strategies for High Earning Senior Professionals
Senior Professionals can use specific planning strategies to plan for financial independence and efficient exits from the corporate world
Zachary Ashburn, CFP®, EA, AFC®
Planning Lessons From Microsoft's Early Retirement Offer
Planning lessons for people who are considering a corporate exit like Microsoft's 2026 severance package (VRP)
Zachary Ashburn, CFP®, EA, AFC®
What Clients Ask Before They Get Started
What Clients Ask Before They Get Started
What counts as a concentrated stock position?
Do I have to sell everything at once?
What's an exchange fund, and is it right for me?
Can charitable giving really lower my tax bill on appreciated stock?
I'm an executive with restricted stock. Can you still help?
Do you only work with local clients?
Your Next Move
Turn One Stock Into a Plan for the Rest of Your Life
A concentrated position got you here. A plan gets you to what's next, with less tax, less risk, and a clearer line to the life you actually want.
Your Next Move
Turn One Stock Into a Plan for the Rest of Your Life
A concentrated position got you here. A plan gets you to what's next, with less tax, less risk, and a clearer line to the life you actually want.
Your Next Move
Turn One Stock Into a Plan for the Rest of Your Life
A concentrated position got you here. A plan gets you to what's next, with less tax, less risk, and a clearer line to the life you actually want.