“The essence of investment management is the management of risks, not the management of returns.” — Benjamin Graham
Strategic Today. Diversified for the Long Haul.
When a single stock dominates your portfolio, it can feel like both a blessing and a burden. Whether your shares came from years of company service, an IPO, or a successful startup exit, the challenge is often the same: how do you reduce your risk without setting off a massive tax bill?
At Suttle Crossland, we specialize in helping clients thoughtfully transition from concentrated positions to more diversified, tax-efficient portfolios. This isn’t about selling everything overnight. It’s about developing a personalized strategy that considers your goals, your tax exposure, and your broader financial plan.
From pooled strategies and charitable giving to corporate structures and options overlays, we help you navigate the complexity and take action with clarity.
Purposeful Moves for Complex Wealth
We help you use advanced planning tools the right way.
There isn’t a one-size-fits-all solution for concentrated stock. The right approach depends on your specific needs, not on a product someone’s trying to sell.
We evaluate and coordinate a range of tax-aware, institutionally vetted strategies — combining traditional financial planning with access to tools typically reserved for larger investors
Exchange Funds
Contribute your stock into a diversified pool without triggering capital gains.
Section 1202 & 351 Exchanges
For qualifying C-corp stock, eliminate or defer gains under the right structure.
Options Overlay Strategies
Use covered calls, protective puts, or collars to manage risk without selling.
Donor-Advised Funds
Gift appreciated shares for an immediate deduction and long-term charitable flexibility.
Direct Indexing
Rebuild market exposure while harvesting losses and controlling when you realize gains.
Securities-Based Lending
Access liquidity while keeping your shares in place.
The Hidden Risk of Standing Still
Waiting often feels safe — but it isn’t.
When most of your wealth is tied up in a single company, it can feel familiar, even comforting. You know the brand, the leadership, the market — maybe you even helped build it. But that familiarity can create a false sense of security. Overexposure to a single stock introduces a unique kind of risk: the slow, quiet kind that builds over time and often goes unnoticed until it’s too late to act without consequences.
Market downturns, regulatory changes, internal scandals, or simply shifting investor sentiment can all derail even the strongest company narratives. And unlike a diversified portfolio, a concentrated position doesn’t have other assets to absorb the shock. What seems like smart loyalty today can turn into painful regret tomorrow — especially if your financial goals depend on that one stock performing indefinitely.
We help clients step back from the emotion and evaluate their positions with objectivity. Through risk modeling, scenario analysis, and a broader review of your total financial picture, we bring clarity to the question most investors avoid: what happens if this stock stumbles? This isn’t about abandoning what’s worked. It’s about building a strategy that protects what you’ve earned and allows you to move forward with confidence.
More Than Just a Tax Problem
This is about flexibility, not just capital gains.
Capital gains taxes often become the focal point when thinking about selling a concentrated position — and yes, the potential bill can be meaningful. But focusing only on taxes can distract from the bigger issue: when most of your wealth is tied up in one stock, your hands are often tied too.
Delaying action may feel prudent, but it often leads to missed opportunities — like diversifying before a downturn, funding a giving strategy, or unlocking liquidity when you need it most. The true cost of inaction isn’t always visible until it’s too late.
Our approach is to help you move with intention, using thoughtful planning to expand your options — not just reduce taxes. That could mean gifting strategies, partial sales over time, or combining diversification with other long-term goals. The key is to gain flexibility now so you’re not stuck later.
Designed to Work With the Rest of Your Plan
No strategy exists in a vacuum.
Managing a concentrated position isn’t just about investment risk — it touches everything from your tax return to your estate plan, from charitable giving to retirement income. That’s why we integrate these strategies into your full financial picture, rather than treating them as standalone solutions.
We begin by understanding what matters most to you: your goals, values, timeline, and obligations. Then we assess how your concentrated holding affects other areas of your plan — and where coordination can unlock better outcomes. It’s not just about reducing risk; it’s about aligning your resources with your bigger vision.
We also work closely with your other professionals — CPAs, attorneys, philanthropic partners — to make sure nothing slips through the cracks. That way, the plan we design isn’t just smart on paper — it actually works in practice.
Frequently Asked Questions
Most financial professionals agree that holding more than 10% of your investment portfolio in a single stock introduces significant concentration risk. This means that if something unexpected happens to that company — like a regulatory issue, leadership change, or poor earnings report — your overall financial health could be disproportionately affected.
As a general guideline, exposure above 5% is worth monitoring closely. When a position grows beyond 10%, many consider it a threshold where serious planning should begin. Once exposure reaches 20% or more, the portfolio is typically viewed as highly concentrated and at elevated risk from company-specific events. While these thresholds aren’t strict rules, they offer a helpful framework for identifying when a position may require closer attention.
That doesn’t mean immediate action is always necessary — but it does suggest the need to evaluate your position within the context of your broader financial goals. We help clients assess these risks, explore planning options, and make informed decisions that preserve flexibility without disrupting what they’ve worked hard to build..
In some cases, yes — depending on your situation and goals. Certain strategies may allow you to defer realizing gains while gradually shifting away from a concentrated position. These might include pooling your shares into a diversified investment structure, gifting appreciated shares to a charitable account, or reinvesting gains through a qualified opportunity strategy.
Each approach has trade-offs and eligibility requirements, and they don’t work in every situation. We help clients evaluate these tools objectively and design a plan that aligns with their broader goals — not just the tax outcome.
A diversification strategy (such as an exchange-based approach) typically allows you to contribute your stock to a structure that provides broader market exposure without triggering immediate capital gains. These strategies are designed to reduce risk while maintaining portfolio value and can offer long-term flexibility — though they often include holding periods or other constraints.
A charitable strategy — like donating appreciated shares — is focused on maximizing the impact of your giving while potentially reducing your tax burden. By donating stock directly rather than selling it first, you may be able to avoid capital gains and receive a charitable deduction.
One is built for diversification. The other is designed for giving. In some cases, both can be part of the same plan.
Yes — there are strategies that allow you to maintain your position while managing downside exposure or improving liquidity. These may include options-based strategies (like protective puts or collars) or using your holdings as collateral for a line of credit. These tools can offer flexibility without triggering a sale — but they also involve costs, complexity, and risks of their own.
We help you weigh the pros and cons of each approach and determine whether maintaining the position is truly the best way forward — or if more meaningful diversification would better serve your goals.
Some advanced strategies do have high entry points or accreditation requirements, but many practical, effective tools are accessible to a broad range of investors. It’s less about how much you have, and more about whether a given solution fits your specific goals, tax situation, and risk tolerance.
We’ve worked with clients who hold concentrated stock across a variety of account sizes and financial stages. The key is building a plan that reflects your unique circumstances — not just chasing the most complex option available.
If you’re actively earning restricted stock units (RSUs), options, or other forms of equity compensation, it’s especially important to plan ahead. The tax treatment of these awards can vary significantly depending on your elections, vesting schedule, and holding period. Planning early — even before shares vest — can increase your ability to manage future gains more efficiently.
While we do not provide tax or legal advice, we frequently collaborate with clients’ CPAs and attorneys to help ensure that your compensation plan, investment strategy, and financial goals are aligned. The sooner we start, the more options are typically available.
We typically offer concentrated stock planning as part of a broader wealth management relationship. That’s because managing a large position effectively often involves coordination across investments, taxes, estate planning, charitable giving, and cash flow — not just one isolated decision.
That said, we’re always happy to begin with a conversation. If you’re unsure where to start or whether your current strategy is serving you well, we’re here to help you explore your options — without pressure or obligation.
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