Talk to us 
Wealth Planning
Bay Area Tech Professionals: You’ve Built Real Wealth. What Comes Next?
Turning tech wealth into long-term clarity and confidence
| Let’s explore the emotional and financial inflection point many tech professionals reach after building substantial wealth—and how thoughtful planning, especially around concentrated equity and tax-aware diversification, can unlock flexibility and long-term peace of mind. |
Now that we’ve entered 2026, many high-earning tech professionals are revisiting the financial milestones and hard choices that defined the past year. One theme kept surfacing in Bay Area conversations: tech professionals who spent two decades building real wealth now asking a quiet, honest question—what’s next for all of this? Success looked one way on paper but felt very different in real life.
This is where many people we meet find themselves—accomplished but unsure what comes next.
That’s not a failure. It’s a turning point.
For many, wealth didn’t arrive all at once. It built gradually through long hours, late-night launches and the quiet accumulation of equity at companies that reshaped entire industries.
Today, many of the new families joining the Aspiriant community are at a similar inflection point. They’re often in their early to mid-40s, deeply embedded in the tech ecosystem and earning significant income—frequently seven figures between salary, bonus and equity compensation.
Some are preparing for the next phase, thinking intentionally about marriage, children or a growing family. Others are already raising young kids, balancing demanding careers while beginning to feel the weight of financial decisions that now extend well beyond themselves.
“Many did a lot of things right—selling some stock, maxing out retirement accounts and steadily buying low-cost index funds.”
As income climbed, so did complexity. Many did a lot of things right—selling some stock, maxing out retirement accounts and steadily buying low-cost index funds. When equity compensation pushed them into higher tax brackets, they incorporated donor-advised funds (DAFs) to convert appreciated shares into meaningful charitable impact while managing capital gains along the way.
And yet, despite doing so many things right, a new challenge often emerges at this stage.
How much of our wealth is tied to one company?
Many high earners believe they’ve diversified their portfolio. But when we look closer, it often tells a different story. Maybe you’ve had the same thought.
The illusion of diversification
Much of their wealth is still traced back to a single company or sector—often 70% to 80% of their investable assets, even after years of “diversifying.”
Hidden risks in familiar holdings
What once felt like concentrated upside now carries a different emotional weight. The stakes are higher, and the margin for error feels smaller.
This is the point where diversification stops being an abstract investment concept and becomes intensely personal.
If you’re in a similar position, you may feel the same tension: knowing you’re concentrated but hesitating to act because trimming means a visible tax bill today. From your perspective, selling can feel like writing a large check to the Internal Revenue Service—especially when your company stock keeps reaching new highs and the same mega-cap tech names appear throughout your index funds.
|
“It’s hard to sell when your stock keeps rising and it’s everywhere in your portfolio.”
— Nayan Lapsiwala CFP®, CAIA, CPA® |
How can we diversify without triggering an unnecessary tax hit?
For many individuals and families we meet, this is the most pressing question. The tax impact of selling company stock can feel like a penalty for doing the right thing.
But it’s just one part of the bigger picture. Keep in mind that every person’s financial situation is unique, and there’s no one-size-fits-all solution. That said, we’ve worked with families and individuals who’ve found value in strategies like pacing sales across tax years, donating appreciated shares, harvesting losses or choosing to sell shares with smaller built-in gains all with the goal of managing the tax impact more thoughtfully.
These approaches don’t eliminate taxes entirely. But with the right guidance, they may help reduce the burden over time and support a more intentional, less disruptive path toward diversification.
Still, knowing there are strategies doesn’t always make it easier to act, especially when it feels like the cost of selling is both financial and emotional.
The tax hit is real but so is the risk of waiting
What starts as a tax question often reflects something deeper: a desire to protect your family, avoid mistakes and make smart choices at a pivotal moment. That’s why meaningful planning doesn’t start with numbers. It starts with listening.
If you’re facing a similar decision, this may be the right time to talk with a financial planner or wealth advisor. Someone who can help you weigh the trade-offs, not just the taxes.
How much risk are we really taking by doing nothing?
We often meet founders, employees and senior executives who’ve done many things right—selling some stock, maxing out retirement accounts, steadily investing over time. And still, they hesitate to act.
The real price of doing nothing
The first step is recognizing that “doing nothing” is still a decision. And it comes with consequences.
At this stage, many portfolios behave like an amplified bet on a single growth-heavy tech stock, layered with additional exposure to similar giants embedded in index funds. A sharp drop in that single stock, or the broader sector, could undo years of progress. It may limit choices around private school, college funding, housing or the ability to slow down at work.
“The true cost of inaction doesn’t show up as a line item on a tax return. It tends to appear as lost flexibility, postponed milestones and decisions made under pressure instead of by choice.”
This can be a key turning point in tech executive wealth planning. It’s where equity compensation strategy intersects with life planning. And where talking with a financial advisor who understands the stakes may bring clarity.
What does a tax-aware diversification plan look like?
There’s no one-size-fits-all answer but there are strategies that can help reduce risk and manage tax exposure more intentionally.
Set a glide path, not a deadline
Instead of defaulting to “just sell it,” the strategy often shifts toward pacing and purpose. Exposure to a single stock may be capped at a defined percentage of net worth, with a gradual transition to that target over three to five years.
If you’re in the middle of a vesting schedule or bonus cycle, a pre-planned sale framework can offer clarity and remove the pressure to react to headlines or earnings reports.
Explore how to manage capital gains from concentrated stock positions.
Use tax tools to offset gains
Across the rest of the portfolio, tax-loss harvesting, careful lot selection and strategic donations of appreciated shares to DAFs may help soften the impact of realizing gains. These strategies not only support diversification, but also create DAF benefits that support both personal and philanthropic goals.
“The objective isn’t a perfectly efficient tax outcome every year.
It’s about steadily moving toward a more resilient balance sheet.
One that reduces concentration risk and preserves flexibility as your life evolves.”
It’s about steadily moving toward a more resilient balance sheet.
One that reduces concentration risk and preserves flexibility as your life evolves.”
Will hiring a financial advisor leave you better off?
It’s a fair question, especially if you’ve been managing things on your own for years. For many tech professionals, the hesitation isn’t just about giving up control. It’s about cost.
Will a wealth management advisory fee actually improve your outcome or is it just another layer of expense?
We’ve worked with many do-it-yourselfers who weren’t looking to hand over the reins. They simply wanted to make smarter decisions as their financial lives became more complex. When the stakes get higher—kids, equity, taxes, timelines—having a clear-eyed partner can bring confidence, not constraint.
Two paths. One big difference.
To address the wealth management fee question in a real-world context, we often compare two common paths:
| Scenario A | Scenario B |
|
Stay concentrated, self-manage the portfolio and hold low-cost funds around the edges. |
Follow a diversification roadmap, pay an advisory fee and layer in tax-aware strategies, charitable planning and a more intentional investment mix. |
Explore when to exercise stock options and how to plan for taxes.
What the numbers tend to show
We model each approach based on your actual situation—company stock, timing, goals and potential tax exposure. The analysis is framed not in theory, but in trade-offs:
- What happens if your company stock drops 20% or 30%?
- How might that affect your timeline to slow down, retire or fund your children’s education?
- How confident would you feel navigating that change alone?
In many market environments, Scenario B tends to show a narrower range of outcomes—potentially less downside, steadier progress toward key milestones and greater flexibility to make life choices on your terms.
Over time, thoughtful realization of gains—with a plan to offset taxes—may result in lower lifetime tax drag than a large, reactive sale down the line.
What kind of relationship do you want with your financial advisor?
Let’s be clear: Financial advice isn’t just about outperforming a benchmark. It’s about helping you make confident decisions in complex moments.
A decision partner, not a portfolio manager
The advisory fee shouldn’t be viewed in a vacuum. It reflects a broader approach—one that may include managing concentration risk, thoughtful after-tax planning and staying disciplined through both strong and volatile markets.
You may find yourself ready for that shift—from managing your wealth reactively to stewarding it more deliberately. Not because you can’t do it yourself, but because the stakes have grown, and the cost of missteps can be harder to recover from.
Read more about planning through sudden wealth events in tech.
Over time, the core question often evolves from “Is the fee worth it?” to something more intuitive: “This is the first call we make before any big decision around stock, taxes or cash flow.”
For many high-earning Bay Area professionals, the real choice may not be “advisor or no advisor” but whether staying concentrated in a low-basis position truly feels as safe as it looks on the screen.
Meet the Aspiriant team behind the strategy
| Behind every Aspiriant plan is a team of credentialed, experienced professionals. People who care deeply about helping you navigate the complexities of wealth with clarity and confidence. From equity compensation strategies to multi-generational planning, our advisors work closely with you to support decisions that align with your life.
See what financial advisor designations mean and meet the team who shows up every day to help you turn complexity into possibility.
|
Planning from a position of strength
The real goal isn’t to maximize returns at all costs. it’s to create options that feel right, even during uncertain times.
Flexibility is a powerful form of wealth
A thoughtful, after-tax, after-fee plan may reveal that measured diversification doesn’t just reduce risk, it can expand the range of possibilities. It gives you more freedom to make decisions about work, housing and lifestyle from a position of strength.
And with the right financial and tax planning partners, you don’t have to figure it out alone.
More options, fewer regrets
Once the trade-offs become visible, the conversation often shifts to the question that really matters: “Given everything we can now see, how much risk do we actually want to carry for our family?”
Or more simply: “What kind of life do we want this wealth to support?”
When the answers become clear, so do the next steps.
Let’s talk about that.
If you’re wondering whether it’s time to diversify, reduce your exposure or simply get organized around your next big financial decision, we’re here to help. Let’s talk about your goals and create a thoughtful, tax-aware plan that brings more confidence to what comes next.
