Do you work at the University of Vermont? Get the resources you need and expert insights from financial professionals who specialize in helping University of Vermont faculty and staff make the most of their compensation package and benefits.

Whether you’re a new University of Vermont employee, faculty member, or you’ve moved into a senior administrative role over a multi-year career, it’s important to make smart money moves with your income and employee benefits. For example:

✅ Do you know the right moves to make to get the greatest value from the University of Vermont benefits available to you?

✅If you’re thinking about leaving the University of Vermont for another job or planning to retire from the school in a few years, are you taking the right steps today to ensure you will receive all of the compensation and benefits that you’ve earned?

Get the Most Value from Your University of Vermont Benefits and Compensation Package

Throughout the year, the University of Vermont provides its faculty and staff with updates about their benefits ranging from health insurance and health savings plans to retirement plans. While the university offers many useful resources and access to knowledgeable staff who can assist with questions, you’ll also find financial professionals not affiliated with the University of Vermont who specialize in helping UVM employees make the most of their income and benefits.

Whether you work at the University of Vermont main campus in Burlington, Vermont, another location around the state, or remotely from home, you may have questions about your compensation package and benefits better suited for a financial professional who can offer unbiased advice and guidance.

For example, sensitive topics like discussing the steps you should take before quitting your job at the University of Vermont to work elsewhere or deciding when you should plan to retire are all conversations that may be more comfortable with a trusted financial advisor.

Should you hire a University of Vermont specialist financial advisor or an advisor close to home?

You’ll likely find dozens of nearby financial advisors well-suited to help you reach your money goals with a personalized plan. But it may be more difficult to find a financial advisor who specializes in serving University of Vermont employees.

Fortunately, many financial advisors offer virtual services so you can meet online no matter where you (or they) live.

This means you can choose to hire a specialist financial advisor who lives hundreds of miles away if you decide their knowledge and experience working with University of Vermont employees is a better fit to help with your unique needs.

💡 In the Q&A below, you’ll gain insights from financial advisors who work with University of Vermont employees to help them make smart decisions to get the most value from their compensation and benefits, reduce their money stress, and prepare for a comfortable retirement.

🙋‍♀️ Do you have questions not yet answered? Use the form below to submit questions anonymously and watch this article for updates with answers to your questions. You can also reach out to the financial advisors below to set up an introductory call or contact them with your questions by email.


💸 Smart Money Insights for University of Vermont Faculty and Staff

This page is organized into sections to help you quickly find the information you need and get answers to your questions:

  1. Q&A: Financial Planning Tips for the University of Vermont Faculty and Staff
  2. Get Answers to Your Questions About Your University of Vermont Benefits and Career
  3. Browse Related Articles

Q&A: Financial Planning Tips for University of Vermont Faculty and Staff

Answers to UVM Employee Questions with Nev Kraguljevic, MBA, CSLP

Nev Kraguljevic is a financial advisor based in Shelburne, Vermont, who specializes in offering financial planning services to University of Vermont faculty and staff. Nev helps his clients get the most value from their UVM benefits and compensation package so they can enjoy life and feel confident about their financial future.

Q: As a financial advisor with experience helping University of Vermont faculty and staff save for their retirement, how do you help them make the most of their employee benefits?

Nev: First, I like to ensure that they are maximizing on the benefits provided by UVM, anywhere from their 403(b) and 457 retirement plans as well as the Retirement Health Savings Plan (RHSP) which helps with health costs during retirement as well as health benefits options while they are employed and looking to leverage the HSA and FSA opportunities. Next, I look for opportunities to ensure employees maximize on other insurances, such as disability and life and for clients who are seeking additional education or have college-bound children, I am a huge fan of the tuition reimbursement and employee discounts. Finally, I always ask my clients if they have student loans, as it impacts our plan and timeline for their PSLF (Public Service Loan Forgiveness).

Q: When you first speak with a University of Vermont employee, what questions do you like to ask to better understand their unique circumstances and determine how you can best help them achieve their goals?

Nev: I start every client relationship with “getting to know you” meeting. During this 90-minute interaction I like to understand not only their current and future goals, but also their life-time and family relationship with money, their upbringing, their values, the current circumstances, and behavior when it comes to any and all financial decisions. I believe in holistic planning and like to consider their aging parents or other family members, like siblings, children, or anyone else who may become financially dependent on the clients, as I believe all of that impacts how we approach their plan and our collaborative approach to building it.

Q: Is there a particular benefit available to UVM employees you feel isn’t as well utilized or understood by employees as it should be?

Nev: Yes! Three specific pieces come to mind: HSA v. FSA, Disability insurance, and retirement contributions. I find that employees often don’t understand the difference between HSA and FSA and the impact it can have, not only on their healthcare and retirement, but also taxes. I also find, especially with younger employees that they deeply discount disability insurance coverage as an event that they believe has a super-low probability of happening, meanwhile research tells us that the probability is rather high. Finally, the number of employees who don’t even meet the UVM contribution match is really high. I often have to remind folks that this is free money that is readily available to them.

Q: Beyond the University of Vermont employee benefits for retirement savings, are there other types of benefits offered by the school that you find valuable to discuss with your clients?

Nev: Absolutely! First, tuition reimbursement is huge. In the era where a college degree can cost as much as a home, having a benefit where even a portion of that cost can be reduced or even completely removed is tremendous. Second one that I really like is the PSLF track for folks who have student loans. And finally, ability to participate in multiple retirement savings vehicles can give folks a ton of flexibility.

Q: For University of Vermont employees thinking about leaving the school to accept a job elsewhere, what actions do you recommend they take before resigning and shortly thereafter?

Nev: Most of the UVM employees when they leave, they go into a different university or college. I have them evaluate not only the new salary, but also benefits that are offered and if they are moving out of state we consider the cost of living in the new area. If they are leaving education or non-profit as a whole, I like to account for the student loans and calculate the impact. And of course, just like any other job, I like to look at the retirement vesting to make sure we account for everything.

Q: For University of Vermont employees approaching retirement age, how do you recommend they prepare to make the transition from living off their salary to relying upon other sources of income?

Nev: This is often challenging, no matter what job or company you are leaving. For some individuals, in addition to income and expenses we talk about the social, purpose, and scheduling impact. For nearly all individuals I have conversations about mental-model change where we shift from accumulation phase to decumulation phase. I find that for many folks this is really hard concept to grasp, which makes perfect sense – you spent your whole life being taught to save and now you have to stop doing that and start taking funds out of it. It can be very weird, uncomfortable, and just plain scarry for many. So we plan and we talk about it and we strategize.

Q: For University of Vermont employees who have managed their finances on their own to this point, what would you suggest they consider to help them decide if they should begin working with a financial advisor at this stage in their lives?

Nev: I will be honest to say that I am a little biased here, as I truly believe that everyone can benefit from working with a financial planner. With that being said, here are a few questions to ask yourself:

  1. Do you enjoy dealing with finances, picking holdings and rebalancing your portfolio, keeping up with changes, and continuously learning about money and finance?
  2. Can you have an open and honest conversation with your spouse/partner and other family members about the finances and ensuring everyone is aligned and “rowing” in the same direction?
  3. Are you comfortable spending at least a little bit of time each week or month going through your finances?
  4. Do you know and understand your cash flow (how money comes in and from where and where does it go when it reaches you) and does it support your needs and goals?
  5. Are you maximizing all of the benefits, ensuring proper risk management and insurance coverage, and having a sufficient retirement savings rate?
  6. Have you gone through estate and legacy planning and do you review your documents on regular basis?
  7. Do you understand the financial industry lingo (like difference between stocks and bonds, ETFs and Mutual Funds, expense ratios, load fees, FSA v. HSA…)?

If you have answered yes to all these questions, chances are pretty good you are fine to continue on your own. I do believe (see my self-disclosed bias above) that having a neutral party build and regularly review your financial plan may be a really good idea and beneficial to you.

If, however, you answered most of these questions with no or maybe, I believe you’ll benefit greatly in working with a financial planner, who can not only help you with investment management, but also build other aspects of your financial plan and then work with you to ensure it’s either being followed or ammended, as your situation changes.

If you have answered yes to all questions except for number one (the “enjoy” one), I truly believe you’ll benefit from working with a financial planner well beyond the merely financial perspective.

Q: What are some of the unique financial planning challenges you commonly see among your clients who are University of Vermont employees and how do you help them overcome these obstacles?

Nev: Two main challenges come up with UVM employees: academic employment and union vs non-union, staff vs faculty vs executive. And then if we broach into the UVM Health world then we have a whole new set of challenges that play the part. This makes for individualized, unique, and specific planning challenges and opportunities, but all are doable with proper planning.

Q: What questions do you recommend University of Vermont employees ask financial advisors they’re considering hiring to help them decide if they’re a good fit?

Nev: I always tell folks to find individuals who will build their financial plan with them and help them manage and amend it regularly. Second, I remind folks that we all use the same handful of software and set of investments. I truly believe that the real difference is finding someone who gets you, someone who makes you feel seen, heard and safe, and someone that will have your best interest at heart always. Here are a few tips I can offer:

  • Trust your gut, even if you can’t put your finger on it.
  • Find someone who will proactively reach out to you with relevant information or update that applies to your life.
  • Ask hard questions, including hypotheticals.
  • Pay attention to what questions they ask during the discovery call.
  • Ask them why and how they chose this career.

Q: Is there anything that comes up frequently in your initial meeting with University of Vermont employees that surprises you?

Nev: All my initial meetings focus on getting to know my clients as people and we rarely even talk about the work. One piece that often comes through from the UVM employees is the commitment to life-long learning and desire to make the world better for the future generations, but that’s not suprising.

Q: For highly compensated University of Vermont employees, are there any special benefits you believe it’s important to take into consideration when preparing their financial plan?

Nev: In short yes, but it all depends on who, where, when… given the multitude of different options it’s really hard to give a quick answer as I believe it’s very much individual impact vs group as a whole.

Q: Is there a particularly memorable experience or a moment you recall with a client who worked at University of Vermont when you realized they have unique opportunities and circumstances when it comes to their financial planning needs?

Nev: I believe that every client has unique opportunities, circumstances and challenges no matter where they work. Partially, it is about the place of employment, but family, age, upbringing, gender, how we process information, etc make a much larger differential in planning needs. What is perhaps unique about public higher education institutions like UVM is the reliance on federal and state funding (in addition to enrollment) and impact on the workforce and the community when those shift.

Get to Know Nev Kraguljevic, Financial Advisor for University of Vermont Employees:

View Nev’s profile page on Wealthtender or visit his website to learn more.

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About the Author
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Brian Thorp

Founder and CEO, Wealthtender

Brian is CEO and founder of Wealthtender and Editor-in-Chief. He and his wife live in Austin, Texas.

With over 25 years in the financial services industry, Brian is applying his experience and passion at Wealthtender to help more people enjoy life with less money stress.

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You’re asking the wrong question; ask this instead!

I see it everywhere, and I’m sure you’ve seen it too.

“Delay claiming Social Security to age 70. It’ll grow your guaranteed benefits by 24%!”

If you’re asking, “When should I claim Social Security to get the most money?” delaying is often good advice, and sometimes even excellent advice. But it can lead you into a trap that even smart retirees fall into.

When to claim is the wrong question to ask first.

The better first question is, “What risk am I trying to protect myself from through my Social Security claiming strategy?”

If you ask the wrong question, you may end up making a decision that looks great on the surface, but quietly works against you, given your personal situation.

Two Potentially Valid Approaches

If you ask when to claim, your best answer could be at age 70 to maximize your monthly benefit, or early, to start (smaller) benefits sooner.

Let’s do a deeper dive into the two paths.

Morningstar’s Approach: Treat Social Security as Longevity Insurance

Morningstar’s research frames Social Security less as an investment decision and more as insurance against the risk that you’ll live for a long time in retirement.

Into your late 80s, 90s, or beyond.

If that’s what you’re solving for, you want to maximize your guaranteed income by delaying until age 70.

The problem is that, unless you plan to keep working until age 70, your income will be much lower between retirement and age 70. Given that those will be your youngest, healthiest retirement years, you’ll want to spend more then, not less.

Morningstar’s solution is to “bridge” the income gap by drawing more from your nest egg during those years. They analyze three bridge strategies.

  1. A ladder of Treasury Inflation-Protected Securities (TIPS): Withdraw several years’ worth of planned draws from your portfolio and buy TIPS maturing in a year, two years, and three years. This protects you from sequence-of-returns risk by covering your expenses for the first few years of retirement, and ensures the money keeps up with inflation, even if it spikes.
  2. Forgoing inflation adjustment if your portfolio drops: This somewhat reduces how much of your portfolio you may need to sell at lower prices, at the cost of potentially trimming your planned spending. If inflation spikes at the same time, that cut could be large.
  3. Forgoing inflation plus cutting draws by 20%: While this can significantly increase your lifetime spending and remaining balance after 30 years in retirement, it does so by aggressively cutting your spending exactly when you want to spend the most.

All three draw more from your portfolio until age 70 to let you delay claiming Social Security benefits until that age.

This is emotionally appealing for several reasons:

  • Maximal guaranteed benefits to address fast-rising health expenses, which is especially helpful once financial flexibility declines and cognitive capability may drop. 
  • Reduced dependence on market returns.
  • Targets one of retirees’ biggest fears – running out of money late in life. 

Even if you end up with lower lifetime benefits (if you die before breaking even), you’re buying current confidence for your oldest possible age. That emotional payoff can be more important than optimizing your financial math.

Vanguard’s Approach: Protect Against Regret and Overspending Risk

Vanguard looks at the same decision and highlights a different risk.

Instead of asking, “How do I insure against living a very long time?” Vanguard asks, “What happens if I delay and that turns out to be the wrong bet?”

They don’t say delaying is necessarily a bad choice, but rather that it isn’t optimal for everyone. For example, if you’re wealthy enough (relative to your desired retirement lifestyle) that running out of money isn’t a real concern, and/or you’re not likely to live long enough to break even.

Their suggested approach works to reduce regret and mismatch.

They point out the costs of delaying to age 70:

  • Drawing down investments faster than comfortable until age 70.
  • Being forced to constrain spending exactly when you’re healthiest and likely want to spend more, especially if the markets don’t do well during those early years.
  • Potentially spending less than you could, because you’re uncomfortable seeing your portfolio shrink.
  • The risk of lower lifetime benefits if you die before breakeven.
  • The mismatch of higher eventual income in years when most retirees naturally spend less (the so-called “slow-go” and “no-go” years).

If you’re unlikely to live past breakeven, the math of delaying gets flipped.

But even if your personal life expectancy makes you likely to live beyond the breakeven age, if your portfolio throws off far more income than your desired retirement budget, and especially if much of your budget is discretionary (think travel, dining out, gifts, etc.), so you can draw less in market down years, Social Security isn’t your safety net. It’s just one element of a larger financial picture.

As such, early claiming offers multiple benefits:

  • Reduces the risk of having to sell assets during down years, preserving your portfolio’s longevity.
  • Supports estate goals.
  • Offers higher income when you’re healthier and can enjoy spending more.

This approach is emotionally appealing because:

  • Most people dislike spending more of their assets if they can avoid it.
  • It reduces the impact of a bad sequence of returns by reducing your dependence on portfolio-based income before age 70.
  • Many people prefer “a bird in the hand” rather than “two in the bush.”
  • People want to take advantage of their best health in retirement by spending more when they’re younger.

The emotional punch of this approach doesn’t come from longevity insurance, optimizing your longest-term future at the expense of your present self. 

It comes from a feeling of greater control and predictability where you live – in the present.

Reconciling the Differences

At first glance, these conclusions seem to contradict each other. They don’t.

The two finance giants are looking at the same problem, so why do they arrive at such different conclusions?

The answer is that they have different objectives.

Morningstar is concerned with mitigating the so-called longevity risk. That’s the risk that a retiree will survive to a very old age and may run out of money before they die. Vanguard, on the other hand, is trying to mitigate the more immediate risks of regret, stress over spending in early retirement, and a potential mismatch between lifestyle and available income.

Trying to compare their approaches is a classic “apples and oranges” problem. Both are fruits, but different ones, so neither is better nor worse than the other. It’s just a matter of which one you prefer to bite into.

The real mistake is if you try to think of Social Security as an investment to maximize, rather than an insurance to optimize.

The Problem with Considering Social Security as an Investment

Thinking of Social Security as an investment leads you to focus on lifetime benefits and breakeven age. This optimizes for:

  • The age with the highest probable lifetime payout.
  • The age you need to exceed to “win” the game.
  • The internal rate of return.

All are interesting questions, just not the most important ones to consider.

It’s more useful to consider Social Security as insurance against specific retirement-related risks.

These are the real risks you’re insuring against:

  1. Living longer than expected.
  2. Dealing with eventual cognitive decline.
  3. Loss of spending flexibility later in life.
  4. Regret if you end up dying before breakeven.
  5. Your widow(er)’s survivor benefits if you die first and your benefits are higher than hers/his.
  6. Emotional stress over higher spending early in your retirement, leading to a mismatch between your desired lifestyle and what you allow yourself to spend.
  7. Sequence of returns risk, if the market crashes just before retirement or in your early retirement years, in which case not having guaranteed Social Security income hurts your portfolio worse.
  8. Poor health limiting your ability to enjoy spending later in your retirement.

By focusing on risk management over maximizing returns, you realize that you aren’t choosing a claiming age for the eventual financial return. Instead, your choice should be against which risks you want more protection.

Infographic with two columns: left in blue lists risks of Delay Bias—living very long, late-life poverty, cognitive decline, rising healthcare costs; right in red lists Early Claim Bias—regret, early market crashes, overspending anxiety, missing healthy years.

If your highest priority is protecting against the first four risks, that tilts the balance toward late claiming. If, on the other hand, you want better protection against the last four risks, early claiming will serve you better.

The decision isn’t a mathematical one that you can solve with a calculator or spreadsheet. It’s a philosophical/emotional one.

It’s about which risks you’re more comfortable with; which potential problems you’re better positioned to deal with financially, and more importantly, from an emotional perspective; and how you want those risks and issues to distribute over the length of your retirement.

The best plan isn’t necessarily the one that offers the better idealized spreadsheet solution; it’s the one you will be comfortable executing. A technically optimal strategy that makes you anxious is not optimal for you.

If you’re more fearful of late-life poverty, you should strongly consider delaying your claim to age 70. If you’re more fearful of missing out on doing things when you’re still healthy enough to enjoy them, an early claim is likely to be a better fit for you.

Both fears are justified.

The problem isn’t that you have them. It’s pretending they don’t apply to you, leading you to ask and answer the wrong question.

What the Pros Say

I asked several financial advisors for their take on Social Security claiming strategies and their experience with clients around this topic. Here’s what they say.

Brett N. Fry, Managing Director at Forteris Wealth Management, relates, “A couple I met with today recently retired and were looking to optimize when to claim Social Security. The numbers came back saying to delay until age 70, but for them, it was a hurdle to know that they would be relying on their portfolio so heavily for the next few years until they got their benefits. 

One of the primary reasons was that they spent their entire lives saving this amount up, and it was hard for them to fathom dipping into the principal to fund their retirement. They were also concerned they would hesitate enjoying life in retirement if they didn’t have some sort of ‘mailbox money’ coming in. Fortunately for them, the numbers for claiming Social Security at their full retirement age, much earlier than 70, also worked, so it was a win-win.

Claire Pywell, CFP®, of Highline Advisors, reports, “As an advisor, I frequently have open conversations with my clients about their mortality (and feelings about it)! Fear of missing out (FOMO) is a big driver behind the decision to take Social Security earlier than age 70.

Chris Chen, CFP®, owner of Insight Financial Strategists, agrees and expands, “I find that many people fear not getting a return on their Social Security contributions if they happen to pass away before 70, a form of FOMO. 

It makes sense for most people to delay Social Security to 70. The return you get is difficult to match. It makes a meaningful difference in most financial plans. The best example of when taking social security early makes sense is when people have terminal conditions, so they expect to pass away soon. More generally, people who don’t have enough income or assets to bridge until 70 may need to take social security early. 

My only rule of thumb here is that if you don’t actually need the benefits, you should postpone claiming.

The biggest regret I see happens when a husband who is a few years older takes the benefit early, and then realizes their wife could have had a higher benefit when he eventually passes away, especially if the wife’s benefit is significantly lower.

Brady Lochte, Fee-only Financial Advisor & Founder of Axon Capital Management, offers a similar take, “Delaying to 70 is a clear win for clients with longevity in their family, sufficient assets to bridge the gap without portfolio stress, and a need for inflation-protected guaranteed income later in retirement. It doesn’t necessarily make sense if you’re in poor health, need the cash flow now to avoid selling depressed assets, or would deplete retirement accounts so aggressively that you’d face higher RMDs and tax bombs later. 

If you delay claiming and have to bridge, the biggest mistake is using taxable brokerage accounts while leaving 401(k)s untouched, then getting hammered by Required Minimum Distributions (RMDs) later on.

Fear of missing out on early retirement years drives far more decisions than the math suggests it should. Clients routinely say, ‘I want to enjoy it while I’m healthy,’ even when they have $3 million in assets. It’s emotional, not financial. 

The most common regret I see is claiming early without understanding the permanent haircut to survivor benefits. Widows who lose the higher earner’s benefit because they both claimed early realize too late they optimized for the short term and sacrificed decades of higher income.

Overall, we find that behavior dominates the math. The math says delay if you can, but clients who are psychologically uncomfortable spending down assets will claim early, no matter what the breakeven analysis shows. They view Social Security as ‘permission’ to retire, not as longevity insurance to optimize.

Ben Simerly, CFP®, Financial Advisor & Founder of Lakehouse Family Wealth, rounds things out, “​If a client is more concerned with maintaining a current account balance than with growth, we encourage them to wait before claiming Social Security. An overly conservative investment portfolio is a common reason why the Social Security amount may grow faster in the government’s hands than in your own accounts. 

​​“Often, clients who are willing to take more risk could do better by taking Social Security earlier and investing the money while they continue to work. Starting Social Security does not mean you need to spend the money. This can also work great for those concerned about future cuts, but still willing to work. 

By and large, the wealthier the client, the more it’s about the math. For clients on the cusp of having enough money to retire, in the $600,000 to $2,000,000 range at retirement in current dollars, we find many clients have already come up with a retirement age in their mind, and likely won’t deviate from it more than a year or two.  

Fear of delaying retirement is the number one driver I’ve seen in making the final decision to begin Social Security or not. For those willing to work part-time or delay retirement, the decision becomes more math-based. But at some point, if you’re burned out from work, the decision becomes about retirement, not math. 

The most common regret we see is when a client or a spouse gets sick, and they regret not retiring sooner. Often, they made the right decision, but the fear of missing out becomes overwhelming. This is why we often encourage clients who are on the fence regarding retirement, due to the math, to work part-time and find a bit of relief from work, but still reduce distributions from their retirement accounts. 

​“My best advice is, whatever you do, work with someone who can help you do the math. I have yet to see one rule of thumb that consistently works, given how many complex strategies exist surrounding the Social Security decision. Social Security decisions tie into workplace contributions, significant tax planning changes, and more. If I have any rule of thumb, it’s that the first idea folks have often turns out to be the most costly, and doing the math reveals significant gains.

The Bottom Line: Ignore Slogans, Implement Useful Decision Rules

I wish there were a simple and easy choice that I could recommend, and that I could implement in my own life, now that I’m beyond the earliest claiming age and (mostly) retired!

Unfortunately, it isn’t. 

As I often say, personal finance is exactly that – personal.

This applies to Social Security claiming strategies. There’s no universally best claiming age. There’s just the question of which retirement-related risks are your higher priority, which fears take precedence for you.

That’s why both “Always delay claiming to age 70” and “Always claim early” are seductive, but misleadingly incomplete. Following either one blindly replaces a considered, deeply personal insurance decision with a slogan that may not serve you well.

Slogans are catchy and easy to remember.

They’re just not necessarily the best guidance for your personal finances.

Once you accept that Social Security is best understood as insurance against your highest-priority risks, your decision becomes clearer. You stop chasing the highest theoretical payout and design your strategy to help you sleep better at night.

For some, it’s protecting against late-life poverty and loss of independence. For others, it’s mitigating sequence-of-returns risk and matching current income to a desired lifestyle while healthy enough to enjoy it.

Your best bet is to stop obsessing over spreadsheet perfection and optimize for what helps you feel the confidence and emotional stability that lets you execute your financial plans. If that means you want to secure the highest income floor in late retirement, that’s perfectly valid. If it’s enjoying early retirement as much as possible, it’s equally valid.

The trap isn’t in choosing one or the other.

It’s asking the wrong question, solving for the wrong thing, and implementing a slogan rather than what personally helps you most. The right Social Security timing decision isn’t the one that maximizes your benefit check. It’s the one that lets you stop worrying about it.

Now, all I need to do is follow my own advice!

Disclaimer: This article is intended for informational purposes only, and should not be considered financial advice. You should consult a financial professional before making any major financial decisions.

Opher Ganel

About the Author

Opher Ganel, Ph.D.

My career has had many unpredictable twists and turns. A MSc in theoretical physics, PhD in experimental high-energy physics, postdoc in particle detector R&D, research position in experimental cosmic-ray physics (including a couple of visits to Antarctica), a brief stint at a small engineering services company supporting NASA, followed by starting my own small consulting practice supporting NASA projects and programs. Along the way, I started other micro businesses and helped my wife start and grow her own Marriage and Family Therapy practice. Now, I use all these experiences to also offer financial strategy services to help independent professionals achieve their personal and business finance goals. Connect with me on my own site: OpherGanel.com and/or follow my Medium publication: medium.com/financial-strategy/.


Learn More About Opher

If you’re within 5-10 years of retirement, or already drawing from your nest egg, and still using the 4-percent rule, it’s past time to upgrade your plan.

Here’s why and how.

What Is the 4-Percent Rule?

Created by financial planner William Bengen in the 1990s based on historical stock and bond returns, it works like this:

  • Invest your nest egg 50/50 between large-cap US stocks and US bonds.
  • For Year 1 of your retirement, withdraw 4 percent of your portfolio to fund your expenses.
  • For Year 2, adjust your Year-1 withdrawal to account for inflation.
  • Rinse and repeat each year thereafter.

Simple, straightforward, and from the 1920s to the 1990s, there was not a single 30-year period where this would have caused you to run out of money in retirement.

What Are the Main Problems with the 4-Percent Rule?

This “rule,” or more accurately, withdrawal strategy, has several significant drawbacks.

  1. Monte Carlo simulations using more recent market assumptions show about a 13 percent chance of failure for a 30-year retirement.
  2. If your retirement is longer than 30 years, e.g., if you retire very early, your risk of failure grows.
  3. Unless you retire at exactly the wrong point in time, your net worth will likely grow far above where you started. This means you will not enjoy as good a retirement as you can afford to.

What’s a Better Strategy?

Introduced by financial planner Jonathan Guyton and computer scientist William Klinger in 2006, the “Guardrails Approach” is a dynamic retirement withdrawal strategy that aimed to address the shortcomings of static approaches such as the 4-Percent Rule.

The classic version of the Guyton-Klinger Guardrails Approach works like this:

  • Invest your nest egg in a prudently diversified fashion.
  • For Year 1 of your retirement, withdraw a reasonable fraction of your portfolio’s value, say 5.2 percent.
  • For Year 2, adjust the prior year’s withdrawal amount to correct for inflation.
  • Check your new withdrawal rate (new dollar amount divided by current portfolio balance). If it’s 20 percent above your starting rate, cut spending by 10 percent. If it’s 20 percent below, raise spending by 10 percent.
  • Rinse and repeat each year thereafter, until you enter the last 15 years of your retirement, at which point you stop bumping your draws down, no matter what your portfolio does, because you’re beyond the “sequence of returns risk” danger zone.

For example, say you start out with a $1 million portfolio and initially draw 5 percent, or $50,000, and for simplicity, we’ll neglect inflation. At the start of the following year, if your portfolio is worth over $1.25 million, that same $50,000 would be less than 4 percent, which is 20 percent lower than the initial 5 percent draw rate, so you’d bump your draw up 10 percent to $55,000. This lets you enjoy in the present the benefits of strong returns.

On the flip side, if your portfolio dropped to under $833,333, making the $50,000 over 6 percent of the portfolio’s new value, you’d chop your withdrawal by 10 percent, to $45,000. This reduces the number of shares you need to sell at lower prices.

What Are the Benefits of the Guardrails Approach?

This dynamic approach provides important benefits relative to the static 4 percent rule.

  1. It lets you start with a higher initial draw with a lower risk of failure than a static approach, allowing you to spend more over a 30-year retirement.
  2. People naturally tend to reduce spending when their portfolio value drops and increase spending when it soars.

Ben Simerly, CFP, Financial Advisor and Founder of Lakehouse Family Wealth, uses guardrails frequently, “As we primarily work with near/pre-retirees and recently retired people, income strategies are a daily topic of discussion with clients. At a high level, we use a guardrail-type strategy with every client. A Guyton-Klinger guardrail-type strategy improves outcomes in almost all cases. The key is that it can improve not only the likelihood of success, ensuring money lasts throughout retirement, but also increase overall income.

We can account for both current income needs and the need to keep up with and possibly surpass inflation. My favorite aspect of guardrails is that they amplify the success of the portfolio’s underlying components. And when you get down to it, our job as advisors is to provide the client with as many opportunities for success as possible.

Jordan Gilberti, Founder and Financial Planner at Sage Wealth Group, also likes dynamic guardrails. “I discuss dynamic withdrawal strategies with all of my clients who are nearing retirement. It’s an incredibly effective approach to retirement distribution planning, and it works well with clients because they know their retirement spending is not static and that markets are highly unpredictable. The value here is flexibility, but it requires discipline and monitoring, which is not a fit for everyone.

The Guyton-Klinger Guardrails approach can feel intuitive since it ties spending to changes to the performance of your investment accounts, while risk-based guardrails focus more on probability and sustainability of one’s portfolio. The tradeoff is simplicity vs. precision, and neither approach eliminates the need for ongoing monitoring and review.

Dr. Steven Crane, Founder of Financial Legacy Builders, agrees, “I’m a fan of dynamic withdrawal strategies, but not because the math is perfect. I like them because they respect human behavior. Most middle-class retirees don’t fail because their spreadsheet was wrong; they fail because fear or guilt causes them to underspend early or panic later. A flexible approach gives people permission to spend when life is good and pull back when it’s not, which is far more realistic than telling someone to blindly take the same dollar amount every year, no matter what’s happening in their life or the market.

Brennan Decima, Owner, Decima Wealth Consulting, is also a big fan, “I absolutely recommend dynamic withdrawal strategies with my clients. Many of my clients are accustomed to receiving bonuses during their working years. With dynamic spending plans, we help our clients understand the bonus that the market has given them and what their safe amount of additional spending can be. If clients want to save their ‘bonus’ for a rainy day, we really want to determine what they actually consider a rainy day.

But there’s a catch that most people, even some pros (present company excluded 😊), don’t see coming.

Criticism of the Guyton-Klinger Guardrails Framework

The Guyton-Klinger approach is a huge improvement over the static 4-percent rule. But it’s far from perfect, as detailed by Derek Tharp, PhD, and Justin Fitzpatrick on Kitces.com, “ this strategy … can result in sharp reductions in retirement income that would be unfeasible for some retirees. Additionally, these income reductions tend to overcorrect for market losses, meaning that far more capital is often preserved than necessary at the cost of severe reductions in the retiree’s standard of living.

The authors back-tested the Guyton-Klinger Guardrails over the past century or so and found that even if retirees start with a relatively tame 4.3 percent (14 percent smaller than a more typical 5 percent initial draw), four specific periods result in dramatic income cuts (in increasing order of severity).

  • Retiring in 2007, through the Global Financial Crisis, would have resulted in a 28 percent drop in income a few years into retirement, staying at that low for several years, and spending most of the first 15 years of retirement with income below the initial draw.
  • Retiring in 1999, through the Dot-Com Bubble, would have resulted in an almost immediate set of cuts, totaling a 36 percent drop in income, staying at that low for several years, and spending most of retirement with income lower than the initial draw.
  • Retiring in 1936, during the Great Depression, would have resulted in an almost immediate set of cuts, totaling a 45 percent drop in income (!), staying at that low for years, and spending most of retirement with income lower than the initial draw.
  • Retiring in 1965, during the Stagflation Era, would have resulted in an almost immediate set of cuts, totaling a 54 percent drop in income (!), staying for years under half the initial draw, and never recovering to the initial draw.

They also note that another author found that a retirement starting in 1966 would have resulted in a maximum 59 percent cut in income, while a retirement starting in 2000 would have suffered a 50 percent cut. 

Admittedly, these periods were outliers, but the authors note that retirement researcher Wade Pfau published results of a Monte Carlo simulation with a Guardrails approach starting at 4.8 percent draw that showed the median scenario (i.e., one that’s better than half and worse than the other half of scenarios) led to cuts ending at 36 percent below the initial draw by the end of a 30-year retirement.

Most retirees would find such cuts unacceptable. Ironically, rather than resulting from aggressive draws, they stem from overly conservative rules.

A Better Guardrails Approach

To address the above shortcomings, the authors suggest a different method of calculating the necessary draw corrections, using risk scores rather than current portfolio values.

Specifically, they suggest starting with a draw rate that would lead to an 80 percent likelihood of “success,” where that’s defined as the probability of ending retirement with a positive balance (even $0.01 qualifies).

Each year, the probability of success is recalculated, and if the likelihood of success reaches 100 percent (because the portfolio has grown so much), one would increase spending to whatever level would return that likelihood to the initial 80 percent.

On the other hand, if the likelihood of success drops to 25 percent (!), one would reduce the draw to a level with a 45 percent likelihood of success. 

At first glance, a 75 percent failure probability sounds terrifying. However, as the authors state, the whole success/failure terminology is misleading, since the strategy will, by definition, modify draw levels to ensure success. 

Thus, it’s acceptable to wait until the probability of success falls that much before cutting spending. In plain English, you don’t cut spending just because the market had a bad year. You cut only when your long-term plan is genuinely at risk.

An analysis of income levels for retirements starting at the same four periods mentioned above, using the same 4.3 percent initial draw, shows:

  • Income drops by at most 3 percent vs. 28 percent for the Global Financial Crisis, with most of the initial 15 years of retirement spent with higher income.
  • The Dot-Com Bubble start would have resulted in no cut at all, with income rising far above the initial level from about 15 years into retirement.
  • The Great Depression, the worst period for US investments in well over a century, would have led to cuts of at most 8 percent, rather than 45 percent.
  • The Stagflation Era would have resulted in cuts of up to 32 percent, but that’s in place of 54 percent, and would have only lasted a few years instead of through the entire retirement period. Comparatively speaking, while not great, this is a far better worst-case scenario.

The goal isn’t to slash your lifestyle every time markets wobble. It’s to make small, intentional budget adjustments, but only when you need them to avoid catastrophic cuts later.

Finally, the authors evaluated the portfolio size for retirees starting retirement in 2000. They found that by 2023, the original Guardrails Approach with a 4.3 percent initial draw would have led to a portfolio value that’s 59 percent higher than at the start of retirement, while their revised approach would have dropped by 29 percent relative to the starting balance.

The remaining balance, throughout the first 23 years analyzed, would have been lower for the new approach compared to the initial Guardrails strategy. This is a feature, not a bug. Avoiding excessive cuts naturally leaves a smaller remaining balance.

This is ok if leaving a large bequest is not a priority. Obviously, if it is a priority, you can set the upper guardrail target at, say, 90 percent instead of 80 percent, and the lower guardrail at a success likelihood level of, say, 50 percent instead of 25 percent. Such changes would almost certainly result in worse income cuts, but would also leave more for your heirs.

But does all this work for most people? 

Crane isn’t sure. “From a psychological standpoint, guardrails work because they create boundaries, not because they optimize returns. The Guyton-Klinger approach feels more intuitive to real people because it ties spending adjustments to portfolio reality, not abstract probabilities. Risk-based guardrails make sense on paper, but many everyday retirees don’t emotionally connect with percentages and Monte Carlo outcomes. If someone doesn’t understand the rule, they won’t follow it when emotions are high, and that’s when plans usually break.

Decima also points out a potential psychological problem with guardrails: “The single biggest challenge with guardrails is that the majority of people we work with love the option to spend more in good times, but really don’t want to consider reducing their spending in down times. Wealth is meant to be a tool to make our quality of life better. If every headline gives retirees anxiety that their spending will have to be cut, it becomes very difficult to stick with a plan.

Would Retirement Income Jump Up and, More importantly, Down a Lot?

With the original Guardrails approach, the answer depends heavily on the market era. When markets behave themselves, you wouldn’t expect many cuts.

However, as pointed out by Tharp and Fitzpatrick, there were multiple periods when this approach would have hit the upper guardrails repeatedly, leading to massive income cuts. That’s why they proposed their risk-based modification.

The table below compares the depth of maximum income cuts for the two guardrail approaches in four problem periods.

A table compares worst income cuts by year for two methods: Guyton-Klinger and Risk-Based. Cuts range from 28% to 54% for Guyton-Klinger, and 0% to 32% for Risk-Based, across years 2007, 1999, 1936, and 1965.

While no cut is pleasant, all but the worst case here are manageable, and even the worst is temporary and bearable.

Discretionary Budget Size: Your Secret Lever to Higher Safe Initial Draws

The thing that determines how aggressive you can be with your initial draw level is the discretionary fraction of your retirement budget (think travel, entertainment, eating out, gifts, charity, etc.). 

Retirement research shows a significantly higher safe withdrawal rate if a large fraction of your retirement budget is discretionary. This is intuitively clear – If your discretionary spending comprises 50 percent of your budget, you can survive a much deeper income cut than if that fraction is just 5 percent.

Two things can make this even better. 

First, assuming you’re drawing from a tax-deferred retirement account (e.g., a traditional IRA), every dollar you reduce from your spending will result in more than a dollar lower draw since you don’t have to pay taxes on that dollar of avoided draw. Assuming your overall marginal tax rate is, say, 20 percent, a dollar lower spend means $1.25 less needed to be drawn. 

Second, having non-portfolio income means that a 10 percent cut in what you draw from your portfolio would result in a smaller cut in your overall retirement income that year.

Adding Buckets to Mitigate Market Loss Risk

But even with smarter guardrails, there’s still one problem left – what do you actually sell in a bad year?

This can be addressed by the so-called “Bucket System.” 

Here’s how I apply that system.

  1. Hold enough cash to cover 2 years’ worth of draw needs. This isn’t necessarily the same as 2-3 years’ worth of spending, because most retirees have at least some non-portfolio income (e.g., Social Security, annuities, rental income, part-time work, etc.). Assuming a 5 percent initial draw, this equals about a 10 percent cash allocation.
  2. Hold enough bonds to cover another 3 years’ worth of draws (possibly including international bonds to reduce the risk of rising domestic interest rates, but accepting the risk of those foreign markets experiencing increasing rates). With the same 5 percent draw level, this is another 15 percent of your portfolio.
  3. Hold the remainder in diversified stock funds (US and international) and any other growth assets I understand and would be comfortable holding through a downturn. This risk or growth bucket would be 75 percent of the portfolio.

Spending comes out of the cash bucket, which partially depletes it, so I need to refill it. This refill comes out of whichever bucket is highest relative to its initial allocation. 

For example, say the growth bucket balance went up 15 percent, the bond bucket balance increased by 5 percent, and the cash bucket balance dropped by 50 percent (neglecting interest income, having spent half of the initial 2 years’ worth of draw). If we started from a $1 million portfolio, the initial amounts were $750k growth, $150k bonds, and $100k cash. At the end of this hypothetical year, the new balances would be $862.5k growth, $157.5k bonds, and $50k cash, for a total portfolio value of $1.07 million, and allocations of 80.6 percent, 14.7 percent, and 4.7 percent, respectively.

Assuming we don’t need to change the $50k overall draw (i.e., the risk-based guardrails didn’t activate), we need to bring the cash bucket back up to 2 years’ draw, or $100k, so we need to add $50k. The bond bucket, to return to 3 years’ worth of draws, has to return to $150k, so it can shed $7.5k. The growth bucket supplies the remaining $42.5k, dropping to $820k, a 76.6 percent allocation.

Let’s look at a less rosy hypothetical year next. Say the growth bucket crashes 25 percent, the bond bucket increases by 3 percent, and the cash bucket drops by the 50 percent we spend. The resulting balances would be $562.5k growth, $154.5k bonds, and $50k cash. The total balance is $767k, for allocations of 73.3 percent (growth), 20.1 percent (bonds), and 6.5 percent (cash).

We need $50k to top off the cash bucket, but selling $50k of the depressed growth bucket would deplete it by nearly 9 percent, rather than the 6.7 percent it would have taken had the growth bucket stayed flat. Thankfully, the bond bucket is up, so we take $50k from there. This drops the bond bucket to just over 2 years’ worth of draws, but that’s better than either allowing the cash bucket to fully deplete in the coming year or selling a much larger fraction of the remaining growth assets. Once the growth bucket recovers, and before the bond bucket fully depletes, we’ll refill the latter from the former.

But what if both the growth bucket and the bond bucket drop? In that scenario, we may need to trim discretionary expenses (the risk-based guardrails may well require this). We can also refill the cash bucket minimally, so it doesn’t fully deplete, and refill it more the following year from the growth or bond bucket, depending on which one performed better by then.

Since we’re spending from the cash bucket, that should not be impacted by market developments. However, if the growth and bond buckets crash massively, it’s plausible to trim spending mid-year.

What do the pros say about buckets?

Decima says, “Most people have four components to their financial picture when they are working. They have a salary that pays the bills, a bonus they can enjoy or save for a rainy day, an emergency fund for unexpected expenses, and a retirement account for the future. When one pot of money is expected to perform all four tasks, it can be nerve-racking. In my experience, buckets are the best opportunity to align portions of the pot for each task. This allows retirees to know exactly what purpose each part of the plan serves.

Crane also sees benefits. “Buckets aren’t about chasing returns; they’re about buying peace of mind. When retirees can clearly see which money is for ‘now,’ ‘soon,’ and ‘later,’ they make better decisions and sleep better at night. For middle-income retirees especially, buckets reduce the urge to overreact during market downturns because they know next month’s groceries aren’t tied to today’s headlines. The best retirement plans don’t just work financially; they work emotionally, and buckets are one of the simplest ways to make that happen.

Gilberti sees a lot of value too. “Buckets work best as a behavioral tool that helps retirees visually separate short-term spending from long-term growth buckets. When designed with intention, buckets can reduce stress during periods of market downturns. If the markets are down 30 percent, but as an example, you have 2 years in cash that isn’t tied to the volatility of the market at any given time, that can be a massive relief when undergoing stress from the markets and news headlines.

Simerly especially likes guardrails when combined with other systems, such as buckets. “The real power of guardrails and many other retirement strategies comes into play when you combine approaches. For example, combining a guardrails approach with buckets for different spending timelines. If we can help smooth out portfolio dips and use guardrails and buckets together, clients see far less volatile income. If guardrails are the brain, then buckets become our backbone. If a client communicates that they are seriously worried about a recession lasting for, say, 3 years, so they don’t want more aggressive investments, we can address that concern using a short-term bucket holding 3 years’ worth of income. 

In good times, we can pull from the more aggressive investments that are doing well, in line with the income numbers calculated by the guardrails. In bad times, we can pull from cash or the short-term bucket, so the more aggressive bucket can recover.

What Does This Look Like in Practice? (Your Annual Checklist)

To turn all the above into concrete action steps to take once a year:

  1. Update your growth, bond, and cash balances.
  2. Use a planning tool (ideally Monte Carlo) to recalculate your plan’s success probability. If you don’t have one, ask your advisor or use a reputable retirement calculator. However, keep in mind that these will be estimated probabilities, not guarantees.
  3. If needed, adjust your draw (and thus your spending) per the above-described risk-based guardrails approach. However, run a sanity check to ensure the new draw still covers at least all your “needs” spending.
  4. Update your non-portfolio income so you can more accurately determine how much you need in your cash and bond buckets.
  5. Refill your cash bucket by rebalancing from your growth and/or bond buckets if those performed well, and defer full replenishment of the cash bucket if both growth and bond crashed. Note that you don’t need to slavishly rebalance to an exact percentage, just close to where you started.

Several additional steps may require some help, including:

  • Calculating Required Minimum Distributions (RMDs), once they apply to you.
  • Strategize (legal) tax minimization steps and estimate your resulting taxes.
  • Decide on the optimal time to claim your Social Security retirement benefits.
  • Identifying large unbudgeted expenses, if any (e.g., healthcare, long-term care, housing changes, etc.), and modifying your overall retirement plan accordingly. Large health or long-term care expenses aren’t handled by withdrawal strategies. They require insurance, reserves, or separate planning.
  • Estate planning.

The Bottom Line

The venerable 4 percent rule is far riskier than most realize. You can reduce this risk and still start with higher withdrawals by using a dynamic approach such as the Guyton-Klinger Guardrails method.

However, redefining guardrails around plan risk instead of portfolio swings avoids potential unacceptably large cuts in retirement spending without materially increasing the risk of failure.

If you’re concerned about the potential impact of periods of high inflation, that’s why many retirement portfolios keep a large growth allocation, which historically returned about 7 percent above inflation over long periods.

What if you retire straight into a bear market (also known as “sequence of returns risk”)? While clearly not an optimal situation, that’s exactly what the risk-based guardrails and Buckets System are designed to address.

For obvious reasons, I can’t give you “the number” for your initial safe withdrawal rate. However, for most households using guardrails, somewhere in the range of 4-6 percent is common.

Keep in mind, though, this framework (as would be the case for any system) only works if you actually follow it. Continuing to spend more than your plan allows will likely sink your finances.

Finally, using the bucket method, in concert with the above dynamic withdrawal strategy, lets you avoid selling too much in depressed assets when your growth and/or bond holdings crash, so your portfolio recovers more easily from bear markets.

Disclaimer: This article is intended for informational purposes only, and should not be considered financial advice. You should consult a financial professional before making any major financial decisions.

Opher Ganel

About the Author

Opher Ganel, Ph.D.

My career has had many unpredictable twists and turns. A MSc in theoretical physics, PhD in experimental high-energy physics, postdoc in particle detector R&D, research position in experimental cosmic-ray physics (including a couple of visits to Antarctica), a brief stint at a small engineering services company supporting NASA, followed by starting my own small consulting practice supporting NASA projects and programs. Along the way, I started other micro businesses and helped my wife start and grow her own Marriage and Family Therapy practice. Now, I use all these experiences to also offer financial strategy services to help independent professionals achieve their personal and business finance goals. Connect with me on my own site: OpherGanel.com and/or follow my Medium publication: medium.com/financial-strategy/.


Learn More About Opher

Ask an Advisor: How to Withdraw From Investment Accounts in Early Retirement (Without Overpaying Taxes)

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For successful professionals, business owners, and newly retired households, early retirement presents a valuable and often overlooked opportunity for advanced tax planning. After decades focused on wealth accumulation, the transition to retirement requires a shift toward tax-efficient portfolio withdrawals, income sustainability, and long-term wealth preservation.

A well-structured retirement income strategy does more than generate cash flow. It integrates investment management, tax planning, and estate considerations to maximize after-tax returns and extend portfolio longevity.

Moving From Wealth Accumulation to Tax-Efficient Distribution

During your working years, retirement planning typically centers on tax-advantaged savings vehicles such as 401(k)s and IRAs. In retirement, however, the focus shifts to determining the most tax-efficient way to draw income from those assets.

Many investors follow a conventional withdrawal order:

  1. Taxable brokerage accounts
  2. Tax-deferred accounts (401(k)s and traditional IRAs)
  3. Tax-free accounts (Roth IRAs)

While this framework provides a baseline, optimal retirement income planning for high-net-worth individuals requires a personalized analysis. Factors such as marginal tax brackets, capital gains exposure, estate objectives, and future income sources all influence the best strategy.

Why Early Retirement Creates a Unique Tax Planning Window

Prior to claiming Social Security retirement benefits and before required minimum distributions begin under IRS rules, many retirees experience a temporary reduction in taxable income. For affluent retirees, these early years often represent an opportunistic period for proactive tax planning, including:

  • Manage capital gains strategically
  • Reduce lifetime tax liability (i.e., Roth conversions)
  • Reposition assets tax-efficiently
  • Improve long-term portfolio sustainability
  • Control future required distributions

Strategic Withdrawals From Taxable Investment Accounts

Taxable brokerage accounts typically provide flexibility because withdrawals often include a return of principal, which is generally not taxable. However, selling appreciated assets triggers capital gains taxes, making asset selection critical.

When multiple taxable accounts or positions exist with varying levels of unrealized gains, choosing which investments to sell first can materially impact long-term wealth outcomes.

A More Tax-Efficient Approach to Capital Gains

Consider two investment accounts:

  • A long-held portfolio with significant appreciation
  • A newer portfolio with lower unrealized gains

Many investors assume selling the long-held assets first is advantageous. However, this may increase tax liability and reduce overall portfolio efficiency.

A more sophisticated strategy often involves selling assets with lower capital gains first, minimizing current taxes and allowing highly appreciated assets to continue compounding. Selling lower-gain assets first may help investors:

  • Reduce immediate tax exposure
  • Preserve tax-deferred growth on appreciated assets
  • Improve after-tax investment returns
  • Extend portfolio longevity
  • Maintain greater flexibility in future tax planning

This approach supports a core objective for high-net-worth households: maximizing net wealth after taxes, not simply generating income.

Estate Planning Advantages: The Step-Up in Basis

For investors with legacy planning goals, retaining highly appreciated assets may provide an additional benefit. Under current tax law, many assets receive a step-up in cost basis at death, resetting their value to the market price at that time. This can significantly reduce capital gains exposure for heirs. For families focused on intergenerational wealth transfer, this feature can make delaying the sale of highly appreciated investments particularly advantageous.

Key Principles for Tax-Efficient Retirement Withdrawals

An effective early retirement withdrawal strategy typically emphasizes:

  • Selling investments with lower capital gains first
  • Preserving highly appreciated assets when appropriate
  • Leveraging lower tax brackets in early retirement
  • Coordinating withdrawals across account types
  • Integrating estate and tax planning objectives

Final Thoughts: Personalized Planning Matters

There is no universal withdrawal strategy suitable for every investor. High-net-worth retirees benefit most from customized planning that aligns tax efficiency, investment performance, and legacy goals.

A thoughtful retirement income strategy can help minimize taxes, increase after-tax income, and preserve wealth across generations — transforming early retirement into a period of financial efficiency rather than uncertainty.

Have a Question to Ask a Financial Advisor?

When you’re uncertain about money matters, submit your question to Wealthtender, and it may be answered by a financial advisor in an upcoming article or in the Wealthtender Expert Answers Forum.

Need personalized help? Visit wealthtender.com to find the right financial advisor for your unique needs.

This article was originally published on Wealthtender and is intended for informational purposes only and should not be considered financial advice. You should consult a financial professional before making any major financial decisions. Wealthtender earns money from financial professionals, which creates a conflict of interest when these professionals are featured in articles over others. Read the Wealthtender editorial policy and terms of service to learn more. Wealthtender is not a client of these financial services providers.

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John Foligno, CMC®
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John Foligno, CMC® | Grand Life Financial

Ask an Advisor: Is the 60/40 Portfolio Still Enough for Long‑Term Investors?

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The traditional 60/40 portfolio split (60% stocks and 40% bonds) has long been the standard asset allocation for long-term investing. For decades, this strategy has helped investors balance growth and stability, smooth out the impact of market volatility on their portfolio, and follow a logical decision-making framework for investing.

A well-constructed portfolio should continue to balance growth-oriented investments with those designed to provide income, liquidity, and downside protection. But markets and the way economic value is created have changed a lot in recent years, so it might be time to rethink that traditional split.

Ask yourself, if a significant share of economic growth occurs outside the public markets, does a public-only equity allocation still work?

While it’s not for everyone at every stage of their investment journey, strategically incorporating privately held businesses into your portfolio may offer broader growth exposure while managing volatility. The key, however, is doing so thoughtfully, without abandoning your disciplined portfolio construction or a long-term investment strategy.

The Privately Held Opportunity for Investors

By the time a company goes public, it has often already experienced years of substantial growth. While public stocks can still offer attractive returns for investors, waiting until businesses go public may mean missing out on some of the most dynamic phases of value creation.

Today, that opportunity set is far larger than many investors realize. Approximately 86% of companies with more than $250 million in revenue are privately held, meaning public stock markets represent only a subset of the real economy. In other words, a portfolio invested exclusively in public equities captures just a small fragment of American business activity. [1] 

Another potential advantage of venturing outside the public markets? Private companies are diverse. They include family-owned enterprises, founder-led growth companies, highly specialized firms operating in niche industries, and more. From an investment standpoint, accessing that diversity can align well with the core principles of portfolio construction, spreading exposure across different business models and sectors. Relying solely on public markets, on the other hand, can limit access to these important segments of the economy.

Companies Are Staying Private for Longer

In 2000, the typical company went public after about six years. Today, that timeline has stretched to roughly 14 years. Over the same period, the number of publicly listed U.S. companies has declined by about 50%. [1]

For investors focused only on public equities, this can mean gaining exposure later in a company’s lifecycle, after early expansion, operational improvements, and strategic repositioning have already taken place. Private investments, by contrast, may provide access to earlier-stage growth and hands-on business development that public markets increasingly no longer reflect.

Hedging Public Market Volatility with Private Investments

What many individual investors don’t realize is that if you’re only invested in the public markets, you may be exposing your portfolio to concentration risk. Today’s major stock indexes are more heavily influenced by a small group of very large companies than in the past. The Magnificent 7, for example, include seven mega-cap stocks that are weighted heavily in major stock indices. If one company’s performance suffers, the entire index can lose value. 

Private investments, however, have historically behaved differently. One reason is correlation, as private assets tend to move less in lockstep with public equity markets. To be clear, the lack of correlation doesn’t eliminate investment risk altogether, as private investments can certainly experience downturns. However, lower correlation can help smooth overall portfolio volatility over full market cycles.

Private Investing Is More Accessible for Everyday Investors

Historically, private investing was largely reserved for institutions and ultra-wealthy investors. The barriers to entry for individual investors included:

  • High minimums
  • Limited institutional-level access
  • Long lockup periods
  • Complex structures 

In recent years, however, new fund structures, regulatory developments, and investment platforms have made private market exposure more accessible for qualified individuals. Minimum investment sizes have come down in some cases, and product design has evolved to better align with individual portfolio needs.

That said, “more accessible” does not mean they’re appropriate for everyone. Private investments still involve unique risks, including reduced liquidity and longer time horizons. Before putting your money towards something new, you’ll still need to conduct careful due diligence, think about the right asset allocation balance in your portfolio, and consider your long-term investing goals. 

Remember to Maintain Your Portfolio’s Fundamentals

Private investments are best viewed as a complement to traditional assets, not a replacement for them. When incorporated thoughtfully, they can support your diversification objectives and expand growth opportunities without undermining the foundational principles that long-term investing depends on.

If you’re curious whether private investments may have a role in your portfolio, we’re here to help. Reach out and schedule a conversation with our team today to ensure your investment approach remains aligned with your long-term goals.

Sources: 

  1. “Rethinking the 60%.” Blackstone. November 2025.
Sean Gerlin, CFP®, CPWA®, ChFC®, CLU®
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Sean Gerlin, CFP®, CPWA®, ChFC®, CLU® | Envision Wealth Planners

Sean Gerlin, CFP®, CPWA®, ChFC®, CLU®, is the Founder and Principal of Envision Wealth Planners, a fee-only financial advisory firm serving clients across Central Florida, including Orlando, Winter Park, Maitland, and nearby communities. In 2025, he was honored with the Wealthtender Voice of the Client Award, recognizing his commitment to exceptional client experience and long-term relationship-focused planning. Sean specializes in helping high-income families, business owners, and commercial real estate executives align their wealth with their values through a comprehensive Financial Life Planning approach. Learn more about EWP at envisionplanners.com. 

This material has been edited with the assistance of artificial intelligence tools. The information presented is based on sources believed to be reliable and accurate at the time of publication. This material is for educational purposes only and does not necessarily reflect the views of the author, presenter, or affiliated organizations. It should not be construed as investment, tax, legal, or other professional advice. Always consult a qualified professional regarding your specific situation before making any decisions.

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This article was originally published on Wealthtender and is intended for informational purposes only and should not be considered financial advice. You should consult a financial professional before making any major financial decisions. Wealthtender earns money from financial professionals, which creates a conflict of interest when these professionals are featured in articles over others. Read the Wealthtender editorial policy and terms of service to learn more. Wealthtender is not a client of these financial services providers.

Do you work at Google? Get the resources you need and expert insights from financial professionals who specialize in helping Google employees make the most of their compensation package and benefits.

Whether you’re a new Google employee (aka Alphabet employee) or you’ve moved up the ranks into a management or executive leadership role over a multi-year career, it’s important to make smart money moves with your income and employee benefits. For example:

✅ Do you know the right moves to make to get the greatest value from the Google benefits available to you?

✅If you’re thinking about leaving Google for another job or planning to retire from the company in a few years, are you taking the right steps today to ensure you will receive all of the compensation and benefits that you’ve earned?

Get the Most Value from Your Google Benefits and Compensation Package

Throughout the year, Google provides its employees and executives with updates about their benefits ranging from health insurance and health savings plans to retirement plans like a 401(k), deferred compensation plans, and stock options. While the company offers many useful resources and access to knowledgeable staff who can assist with questions, you’ll also find financial professionals not affiliated with Google who specialize in helping Google employees make the most of their income and benefits.

Whether you work in the Google headquarters in Mountain View, California, another office location around the country, or remotely from home, you may have questions about your compensation package and benefits better suited for a financial professional who can offer unbiased advice and guidance.

For example, sensitive topics like discussing the steps you should take before quitting your job at Google to work elsewhere, protecting yourself in advance of a corporate layoff, or deciding when you should plan to retire are all conversations that may be more comfortable with a trusted financial advisor.

Should you hire a Google specialist financial advisor or an advisor close to home?

You’ll likely find dozens of nearby financial advisors well-suited to help you reach your money goals with a personalized plan. But it may be more difficult to find a financial advisor who specializes in serving Google employees.

Fortunately, many financial advisors offer virtual services so you can meet online no matter where you (or they) live.

This means you can choose to hire a specialist financial advisor who lives hundreds of miles away if you decide their knowledge and experience working with Google employees is a better fit to help with your unique needs.


💡 In the Q&A below, you’ll gain insights from financial advisors who work with Google employees to help them make smart decisions to get the most value from their compensation and benefits, reduce their money stress, and prepare for a comfortable retirement.

🙋‍♀️ Do you have questions not yet answered? Use the form below to submit questions anonymously and watch this article for updates with answers to your questions. You can also reach out to the financial advisors below to set up an introductory call or contact them with your questions by email.


Q&A: Financial Planning Tips for Google Employees & Executives

In this section, you’ll learn how you can make the most of your Google employee benefits and gain valuable tips from financial advisors who specialize in working with Google employees and executives.

Answers to Employee Questions with Richard Siminou, MBA

Richard Siminou is a financial advisor based in Long Island, New York who specializes in offering financial planning services to Google employees. Richard helps his clients get the most value from their Google benefits and compensation package so they can enjoy life and feel confident about their financial future.

Q: As a financial advisor with experience helping Google employees save for their retirement, how do you help them make the most of their employee benefits?

Richard: Employees at large companies are often in a fortunate position — the benefits packages tend to be genuinely strong — but that also means there are a lot of moving parts to coordinate, and the stakes are high.

The first thing I do is make sure no one is leaving free money on the table. That means capturing the full 401(k) match before anything else. From there, we look at whether pre-tax or Roth contributions make more sense given where they are in their career and what their income looks like today versus in retirement.

For employees who receive equity compensation — RSUs, stock options, or an ESPP — that’s often where the bigger conversation happens. Equity can be a tremendous wealth-building tool, but it also creates real risks: concentration in a single stock and a tax bill that catches people off guard at vesting. I help clients build a thoughtful diversification strategy so they’re not overexposed to any one position, and we plan proactively for the tax implications so nothing comes as a surprise.

For employees on a high-deductible health plan, I also make sure they’re maximizing their HSA — not just as a healthcare fund, but as a long-term investment vehicle. Most people don’t realize it’s one of the most tax-efficient accounts available.

What I enjoy most about working with employees of large companies is that they’re often sharp, motivated, and have real wealth-building potential through their benefits alone. My job is to bring all the pieces together — the 401(k), the equity, the HSA, the taxable accounts — into one coordinated strategy so that every dollar is working as efficiently as possible.

Q: When you first speak with a Google employee, what questions do you like to ask to better understand their unique circumstances and determine how you can best help them achieve their goals?

Richard: The first conversation is really about listening more than talking. My goal is to understand not just where someone stands financially, but where they want to go — and what’s standing in the way.

I usually start with some foundational questions: Where are you in your career, and how are you thinking about the next five to ten years? Are you planning to stay with this employer long-term, or is there a possibility of a transition down the road? Those answers shape almost everything else.

From there I get into the specifics of their benefits. Are they capturing the full employer match on their 401(k)? How are they invested inside the plan, and does that still make sense given their timeline? If they receive equity compensation — RSUs, stock options, an ESPP — I want to understand how much of their net worth is tied to a single company’s stock, because concentration risk is one of the most common and underappreciated issues I see.

I also ask about taxes. Not in a technical way at first, but questions like: Did anything surprise you on your tax return last year? Are you feeling like you’re paying more than you should? That opens up a conversation about whether we can do better through smarter use of pre-tax accounts, HSAs, or deferred compensation if it’s available.

And then I ask the question that often matters most: What does financial security actually look like for you? The answer is different for everyone. For some people it’s retiring early. For others it’s funding their kids’ education without derailing their own retirement. For executives it might be building enough outside their employer that they have real optionality. Understanding that goal — that specific vision — is what drives everything else we do together.

Q: Is there a particular benefit available to Google employees you feel isn’t as well utilized or understood by employees as it should be?

Richard: Without question — the HSA, or Health Savings Account. It’s the most underutilized financial tool I see across the board, and it’s a shame because the tax advantages are extraordinary.

Most people treat the HSA like a flexible spending account — they contribute a little, pay their medical bills out of it, and move on. What they’re missing is that the HSA is actually a triple tax-advantaged account: contributions go in pre-tax, the money grows tax-free, and withdrawals for qualified medical expenses are tax-free. No other account does all three.

What I encourage clients to do, if their cash flow allows, is pay current medical expenses out of pocket and let the HSA grow invested for the long term. After age 65, you can withdraw the money for any reason — not just medical — and it essentially functions like a traditional IRA. But if you do use it for healthcare costs in retirement, which most people will have plenty of, it’s completely tax-free. That’s a powerful combination.

The other benefit I’d mention is deferred compensation, for those who have access to it. Non-qualified deferred compensation plans are available at many large employers for higher-earning employees, and they can be a meaningful way to reduce current taxable income and build wealth outside of the standard retirement account limits. But they come with real complexity and risk that needs to be understood before participating — which is exactly where having an advisor in your corner makes a difference.

Q: Beyond Google employee benefits for retirement savings, are there other types of benefits offered by the company that you find valuable to discuss with your clients (e.g., stock, education savings, health savings)?

Richard: Absolutely — and this is actually one of my favorite conversations to have, because most employees are sitting on benefits they’ve never fully explored.

Equity compensation is usually the first place I look. Whether it’s RSUs, stock options, or an Employee Stock Purchase Plan, these can represent a significant portion of someone’s total compensation — and they come with real decisions attached. When do you sell? How much do you hold? What’s the tax impact? I see a lot of employees either ignore these questions entirely or make emotional decisions about their company stock rather than strategic ones. Getting this right can make a meaningful difference in long-term wealth building.

Education savings is another area worth a dedicated conversation, particularly for employees with young children. A 529 plan isn’t an employer benefit in the traditional sense, but many large employers offer payroll deduction into 529 accounts, which makes the habit easy to build. More importantly, it’s a conversation that often gets delayed until it’s too late to let compounding do its work.

Life insurance and disability coverage are benefits people tend to click through during open enrollment without really thinking about. Group coverage through an employer is a great starting point, but it’s rarely sufficient on its own — especially for higher earners — and it doesn’t travel with you if you leave the company. I like to make sure clients understand what they actually have and where the gaps are.

Finally, I always ask about any financial wellness programs or legal services the employer offers. These are frequently overlooked and can provide real value, particularly around estate planning basics like wills and healthcare directives — documents that everyone needs but most people put off indefinitely.

The common thread across all of these is that benefits only create value if you actually understand and use them. My job is to make sure nothing valuable falls through the cracks.

Q: For Google employees thinking about leaving the company to accept a job elsewhere, what actions do you recommend they take before resigning and shortly thereafter?

Richard: A job transition is one of those moments where the financial decisions you make in a short window can have a lasting impact — for better or worse. I always encourage clients to slow down and think through a few key areas before they hand in their notice.

The first thing I look at is vesting schedules. Whether it’s a 401(k) employer match, RSUs, or stock options, leaving before a vesting date can mean walking away from meaningful compensation. Sometimes it’s worth negotiating a start date with the new employer to capture a vesting event that’s just weeks away. That’s a conversation most people don’t think to have.

Equity is the other big pre-resignation consideration. If you hold vested stock options, there’s typically a limited window — often 90 days — to exercise them after you leave. Missing that deadline means forfeiting them entirely. RSUs that haven’t vested yet are generally gone when you walk out the door, so understanding exactly what you’re leaving on the table is critical before making any final decision.

On the benefits side, I encourage clients to take stock of their health insurance situation before their last day. COBRA is always an option but can be expensive, so knowing how quickly the new employer’s coverage kicks in helps avoid any gaps.

For the 401(k), there’s no need to rush a decision, but shortly after leaving I’d recommend rolling it over to an IRA or the new employer’s plan rather than leaving it scattered across former employers. It’s easier to manage, typically opens up more investment options, and keeps your financial picture clean and consolidated.

And finally — the offer letter itself. Before signing, I always encourage clients to look at the full compensation picture at the new employer, not just the base salary. How does the equity package compare? What’s the 401(k) match? Is there a vesting cliff? Understanding the complete package helps make sure the move actually makes financial sense from day one.

Q: For Google employees approaching retirement age, how do you recommend they prepare to make the transition from living off their salary to relying upon other sources of income?

Richard: The transition from a steady paycheck to drawing down from multiple income sources is one of the most significant financial shifts a person will ever make — and in my experience, the people who navigate it most successfully are the ones who start planning it seriously three to five years out, not three to five months out.

The first thing I work through with clients approaching retirement is what I call the income gap analysis. We add up all the guaranteed income sources they’ll have — Social Security, any pension, annuity income if applicable — and compare that to what they actually need to live comfortably. Whatever’s left is what the portfolio needs to cover, and that shapes everything from asset allocation to withdrawal strategy.

Social Security timing is one of the highest-impact decisions in this phase and one of the most misunderstood. Claiming early can make sense in certain situations, but for many people delaying — even by a few years — results in a meaningfully higher monthly benefit for the rest of their life. We model this out carefully based on health, other income sources, and whether there’s a spouse involved.

Healthcare is another area that deserves serious attention, particularly for anyone looking to retire before Medicare eligibility at 65. Bridging that gap can be expensive, and it needs to be factored into the retirement budget explicitly rather than treated as an afterthought.

On the portfolio side, I work with clients to gradually shift their thinking from accumulation to distribution — which is a fundamentally different challenge. It’s not just about how much you’ve saved, it’s about sequencing withdrawals intelligently across taxable accounts, tax-deferred accounts like IRAs and 401(k)s, and tax-free accounts like Roth IRAs to minimize the tax drag over time. Getting that order of operations right can add real longevity to a portfolio.

And then there’s the psychological side, which doesn’t get talked about enough. After decades of saving and accumulating, actually spending that money can feel deeply uncomfortable for a lot of people. Part of my job in this phase is helping clients feel confident and grounded in their plan — so they can enjoy retirement rather than worry their way through it.

Q: For Google employees who have managed their finances on their own to this point, what would you suggest they consider to help them decide if they should begin working with a financial advisor at this stage in their lives?

Richard: I have a lot of respect for people who have taken ownership of their finances and done the work on their own. That discipline and engagement is actually a great foundation for a productive relationship with an advisor. The question I’d encourage them to ask isn’t “have I done okay so far?” — because the answer is probably yes — but rather “is doing this alone still the right approach given where I am and where I’m headed?”

The complexity argument is the most straightforward one. Early in a career, personal finance is relatively simple — contribute to the 401(k), build an emergency fund, avoid bad debt. But as income grows, equity compensation enters the picture, taxable accounts accumulate, families expand, and retirement starts moving from a distant concept to an actual horizon, the number of interconnected decisions multiplies quickly. At that point, the cost of a suboptimal decision — whether it’s a tax mistake, a poorly timed equity sale, or a Social Security claiming error — can far exceed the cost of professional guidance.

I’d also ask: how much time are you actually spending on this, and is that the best use of your time? Many of the people I work with are high achievers who are extremely capable of managing their own finances. But capability and bandwidth are two different things. If financial decisions are getting made reactively — or worse, getting deferred — because life is busy, that’s worth examining honestly.

Another honest question is around blind spots. We all have them. A good advisor isn’t just a technician — they’re a thinking partner who can challenge assumptions, stress test a plan, and flag things you might not know to look for. Most people don’t know what they don’t know until something goes wrong, and by then the cost of finding out can be significant.

And finally, I’d suggest looking at a few key moments as natural triggers for seeking a second opinion: a job change, an inheritance, a major equity vesting event, a divorce, or the death of a spouse. Any one of those situations involves enough complexity and enough at stake that having an experienced guide in your corner is genuinely valuable — not just reassuring.

The goal of a first conversation with an advisor shouldn’t be to hand everything over. It should be to get an honest assessment of where you stand, what you might be missing, and whether there’s enough value on the table to make the relationship worthwhile. A good advisor will tell you the truth either way.

Q: What are some of the unique financial planning challenges you commonly see among your clients who are Google employees and how do you help them overcome these obstacles?

Richard: Working with employees of large companies over the years, a few patterns come up consistently — and they’re worth naming because recognizing them is half the battle.

The first is what I’d call benefits paralysis. Large employers offer generous and often complex benefits packages, and the sheer number of decisions — 401(k) elections, health plan choices, equity grants, deferred compensation options, life insurance levels — can be genuinely overwhelming. The path of least resistance is to set something up during onboarding and never revisit it. I see people years into their careers still invested in the default target-date fund they selected on day one, with life insurance coverage that made sense when they were single but is now completely inadequate for a family. My job is to bring structure and intentionality to decisions that otherwise get made by default.

Concentration risk is another challenge I encounter constantly. When someone has worked at the same company for a long time and received equity compensation along the way, it’s very common for a disproportionate share of their net worth to be tied up in a single stock — their employer’s. There’s often an emotional attachment to that stock, a sense that loyalty or conviction should translate into holding. But from a pure risk management standpoint, having your income and your investment portfolio both dependent on the same company’s fortunes is a vulnerability. I help clients think through diversification in a way that feels rational rather than disloyal.

Lifestyle creep is a quieter challenge but a very real one, particularly among high earners at large companies. As compensation grows — base salary increases, bonuses, equity — spending tends to grow with it, sometimes faster. I work with clients to make sure that as their income rises, their savings rate and investment contributions are rising proportionally, not just their expenses. Building real wealth is about the gap between what you earn and what you spend, not the absolute level of either.

Tax complexity is something a lot of employees underestimate until it bites them. Between equity vesting events, bonus income, potential deferred compensation, and investment accounts, the tax picture for a high-earning employee at a large company can get complicated quickly. I work closely with clients — and coordinate with their CPAs where appropriate — to make sure we’re being proactive rather than reactive when it comes to tax planning.

And finally, there’s the challenge of integration — or the lack of it. Most people manage different pieces of their financial life in isolation. The 401(k) is one conversation, the equity compensation is another, the mortgage is another, the insurance is another. Nobody is looking at the whole picture at once. That’s precisely what I do. Bringing everything together into a single, coherent strategy is where the real value of financial planning lives.

Q: What questions do you recommend Google employees ask financial advisors they’re considering hiring to help them decide if they’re a good fit?

Richard: This is a question I genuinely love, because I think everyone should approach hiring a financial advisor the way they’d approach any other important professional relationship — with real curiosity and a willingness to ask direct questions. The right advisor will welcome the scrutiny. Here’s what I’d encourage people to ask:

How are you compensated? This is the most important question on the list and the one people are most reluctant to ask. Understanding whether an advisor is fee-only, fee-based, or commission-based tells you a great deal about where their incentives lie. There’s no single right answer, but you deserve a clear and honest explanation — not a vague or defensive one.

Are you a fiduciary, and in what capacity? A fiduciary is legally required to act in your best interest. Some advisors are fiduciaries all the time, some only in certain contexts, and some not at all. Knowing where your advisor stands on this — and when — matters enormously.

What is your experience working with clients in situations like mine? If you receive equity compensation, have significant assets in a company retirement plan, or are navigating a specific life transition, you want an advisor who has real familiarity with those circumstances — not someone who will be learning on your time.

What does your typical client look like? This helps you understand whether you’ll be a priority or an afterthought. An advisor whose practice is built around clients at a very different income or asset level may not be the best fit, regardless of how capable they are.

How often will we meet, and what does ongoing service look like? A financial plan isn’t a document — it’s a living relationship. You want to understand upfront how proactive the advisor will be, how accessible they are between scheduled meetings, and what you can expect when your circumstances change.

Who else is on your team, and who will I actually be working with day to day? At larger firms especially, the person you meet with initially isn’t always the person managing your relationship. It’s worth understanding the structure before you commit.

And finally — can you explain a time you told a client something they didn’t want to hear? A good advisor isn’t just a validator. They push back when it matters, flag risks you might be overlooking, and prioritize your long-term interests over your short-term comfort. How an advisor answers this question tells you a lot about their character and their willingness to have honest conversations.

The goal of these questions isn’t to trip anyone up — it’s to find someone you can trust completely with one of the most important areas of your life. The right advisor will answer every one of them directly and without hesitation.

Q: Is there anything that comes up frequently in your initial meeting with Google employees that surprises you?

Richard: Honestly, yes — and the same few things come up more often than you’d expect, even among people who are financially engaged and working at sophisticated organizations.

The one that surprises me most consistently is how many people don’t know what they actually own inside their 401(k). They know they’re contributing, they have a general sense of the balance, but when I ask what they’re invested in and why, there’s often a long pause. A lot of people are in whatever default option they selected years ago and have never revisited it. For something that may ultimately be one of their largest assets, that level of inattention is striking — though I understand how it happens. Life gets busy, the account is out of sight, and as long as the balance is going up it’s easy to assume everything is fine.

Another thing that comes up frequently is a genuine surprise at how much equity compensation they’ve accumulated — and how concentrated that makes them. People receive grants periodically, the stock does well, and before long a significant portion of their net worth is tied to a single company. When I show someone that number visually, as a percentage of their total picture, it often lands differently than they expected.

I’m also consistently surprised by how many people have never looked carefully at their insurance coverage — life, disability, long-term care. They enrolled in whatever the employer offered during onboarding, accepted the default amounts, and haven’t thought about it since. For someone whose income and family situation have changed substantially over the years, that coverage is often badly misaligned with their actual needs.

And then there’s estate planning. I would say the majority of people I meet for the first time — across all income levels — either have no will at all or have one that’s badly out of date. People know they need it, they intend to get to it, and somehow it never rises to the top of the list. It’s one of the first things I encourage clients to address, because it’s not just a financial document — it’s how you take care of the people you love when you’re no longer able to do it yourself.

What ties all of these together is that they’re not failures of intelligence or effort — they’re failures of attention and integration. People are busy, the financial system is complex, and without someone periodically looking at the whole picture, important things quietly fall through the cracks. That’s exactly the gap a good advisor fills.

Q: For highly compensated Google employees and executives, are there any special benefits you believe it’s important to take into consideration when preparing their financial plan?

Richard: Absolutely — and this is an area where the complexity increases significantly and the cost of not having a coordinated plan can be substantial. Highly compensated employees and executives often have access to a layer of benefits that goes well beyond what’s available to the broader workforce, and each one comes with its own set of decisions, tax implications, and risks.

Nonqualified deferred compensation plans are one of the most powerful tools available to executives, and also one of the most misunderstood. The ability to defer a significant portion of income — sometimes hundreds of thousands of dollars — into a future tax year can be enormously valuable for someone in a high bracket today who expects to be in a lower bracket in retirement. But these plans are fundamentally different from a 401(k). The deferred amounts are technically still a liability of the employer, meaning they’re at risk if the company runs into financial trouble. The distribution elections are also largely irrevocable once made. Getting the strategy right from the beginning matters enormously.

Executive equity compensation tends to be more complex than standard RSU grants. Stock options — particularly incentive stock options, or ISOs — come with specific tax treatment that requires careful planning around exercise timing, alternative minimum tax exposure, and holding periods. The difference between a well-timed and a poorly timed exercise can be measured in tens of thousands of dollars or more.

Supplemental executive retirement plans, sometimes called SERPs, are another benefit worth understanding thoroughly. These are employer-funded retirement arrangements designed to provide additional income beyond what qualified plans like the 401(k) allow, and the terms vary widely from company to company.

Executive life insurance arrangements — things like split-dollar policies or executive bonus plans — also come up frequently at this level and require a careful look to make sure they’re structured in a way that actually serves the executive’s interests and integrates properly with their overall estate plan.

And speaking of estate planning — at the executive level this conversation becomes significantly more involved. We’re often talking about wealth transfer strategies, trust structures, charitable giving vehicles, and in some cases business succession considerations. The financial plan and the estate plan need to be built together, not treated as separate exercises.

What I find most important with highly compensated clients is that all of these pieces — the deferred comp, the equity, the insurance, the estate plan, the investment portfolio — are looked at holistically and updated regularly as circumstances change. The opportunities at this level are genuinely significant, but so are the consequences of getting it wrong.

Q: Is there a particularly memorable experience or a moment you recall with a client who worked at Google when you realized they have unique opportunities and circumstances when it comes to their financial planning needs?

Richard: There’s one that comes to mind that I think illustrates the point really well — and it’s a situation I’ve seen play out in different variations more times than I can count.

I met with a client who had been with a large employer for about twelve years. She was sharp, successful, and by any measure financially responsible. She had been contributing to her 401(k) consistently, had no significant debt, and felt like she had a reasonable handle on her finances. She came to me not because something was wrong, but because her compensation had grown considerably and she wanted a second set of eyes.

When we sat down and actually mapped out her complete financial picture, a few things became immediately clear. First, she had accumulated a substantial amount of vested company stock through RSU grants over the years — far more than she had mentally accounted for — and it represented nearly half of her investable net worth. She had always thought of her portfolio and her equity compensation as two separate things. They weren’t. They were deeply connected, and the concentration risk was significant.

Second, she had been eligible for her company’s nonqualified deferred compensation plan for three years and had never enrolled. Nobody had ever walked her through how it worked or why it might be worth considering. Given her tax bracket, that was a meaningful missed opportunity — not catastrophic, but real.

And third, her estate plan consisted of a will she had drafted before she was married, before she had children, and before her net worth had grown to its current level. It was essentially obsolete.

None of these were failures on her part. She had done a lot of things right. But they were a perfect illustration of what happens when the pieces of a financial life are managed in isolation rather than as a whole. The moment I laid it all out on one page — the portfolio, the equity, the deferred comp eligibility, the estate plan gap — I could see the shift in her expression. It wasn’t alarm, it was clarity. She finally saw her complete financial picture for the first time.

That’s the moment I find most meaningful in this work. Not when something has gone wrong, but when someone who has been doing well realizes they could be doing significantly better — and that the path to get there is clearer than they thought.

Q: For employees who receive a large, unexpected financial windfall — such as a major equity vesting event, a bonus, or an inheritance — what do you recommend they do, and what mistakes do you caution them to avoid?

Richard: If I could instill one habit above all others, it would be this: treat saving as a fixed expense, not an afterthought.

Most people save whatever is left over after they’ve paid their bills and lived their lives. The problem is that for most people, there’s rarely much left over — expenses have a way of expanding to fill available income. The people I’ve seen build real wealth consistently over time are the ones who decided early on to pay themselves first. They automated their contributions, set their savings rate, and built their lifestyle around what remained rather than the other way around.

It sounds simple, and it is — but the discipline of making it non-negotiable, even when the amounts are small, creates a habit and a mindset that compounds just as powerfully as the money itself. The clients I work with who started this early, even modestly, are almost always in a dramatically stronger position than those who waited until they felt they could afford to save more. The right time to start is always sooner than it feels.

Get to Know Richard Siminou, Financial Advisor for Google Employees:

View Richard’s profile page on Wealthtender or visit his website to learn more.

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Quick Facts & Resources for Google Employees

Google Quick Facts & ResourcesDetails / Useful Links
Google Corporate Headquarters Address1600 Amphitheatre Parkway, Mountain View, CA 94043 (📍 Google Maps)
Overview of Google BenefitsCareers.Google.com/Benefits
How much do Google employees Make?View Google Salary Research on Glassdoor
Where can I learn more about careers at Google?Visit Careers.Google.com
How many people work for Google?Google has over 156,000 employees worldwide (Source: Statista)
What is the ticker symbol for Google stock?Google’s ticker symbols are GOOG and GOOGL, and today, represent equity ownership in Google’s parent company, Alphabet. GOOG shares have no voting rights, while GOOGL shares do.

🙋‍♀️ Have Questions About Your Google Benefits or Career?

Reader Questions Answered

Q: Does Google have a deferred comp plan? If so, who is eligible to participate, and do you have any opinions on the value of the plan to Google employees? – Dan B.

Rebecca Jackson, CPA, CFP® (January 20, 2023): Yes, Google does offer the ability to defer part of bonus compensation on a pre-tax basis.  Depending on your level of bonus compensation and your goals, this could be a great value.


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Brian Thorp

Founder and CEO, Wealthtender

Brian and his wife live in Texas, enjoying the diversity of Houston and the vibrancy of Austin.

With over 25 years in the financial services industry, Brian is applying his experience and passion at Wealthtender to help more people enjoy life with less money stress.

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Do you work at NVIDIA? Get the resources you need and expert insights from financial professionals who specialize in helping NVIDIA employees make the most of their compensation package and benefits.

Whether you’re a new NVIDIA employee or you’ve moved up the ranks into a management or executive leadership role over a multi-year career, it’s important to make smart money moves with your income and employee benefits. For example:

✅ Do you know the right moves to make to get the greatest value from the NVIDIA benefits available to you?

✅If you’re thinking about leaving NVIDIA for another job or planning to retire from the company in a few years, are you taking the right steps today to ensure you will receive all of the compensation and benefits that you’ve earned?

Get the Most Value from Your NVIDIA Benefits and Compensation Package

Throughout the year, NVIDIA provides its employees and executives with updates about their benefits ranging from health insurance and health savings plans to retirement plans like a 401(k), deferred compensation plans, and stock options. While the company offers many useful resources and access to knowledgeable staff who can assist with questions, you’ll also find financial professionals not affiliated with NVIDIA who specialize in helping NVIDIA employees make the most of their income and benefits.

Whether you work in the NVIDIA headquarters in Santa Clara, California, another office location around the country, or remotely from home, you may have questions about your compensation package and benefits better suited for a financial professional who can offer unbiased advice and guidance.

For example, sensitive topics like discussing the steps you should take before quitting your job at NVIDIA to work elsewhere, protecting yourself in advance of a corporate layoff, or deciding when you should plan to retire are all conversations that may be more comfortable with a trusted financial advisor.

Should you hire an NVIDIA specialist financial advisor or an advisor close to home?

You’ll likely find dozens of nearby financial advisors well-suited to help you reach your money goals with a personalized plan. But it may be more difficult to find a financial advisor who specializes in serving NVIDIA employees.

Fortunately, many financial advisors offer virtual services so you can meet online no matter where you (or they) live.

This means you can choose to hire a specialist financial advisor who lives hundreds of miles away if you decide their knowledge and experience working with NVIDIA employees is a better fit to help with your unique needs.

💡 In the Q&A below, you’ll gain insights from financial advisors who work with NVIDIA employees to help them make smart decisions to get the most value from their compensation and benefits, reduce their money stress, and prepare for a comfortable retirement.

🙋‍♀️ Do you have questions not yet answered? Use the form below to submit questions anonymously and watch this article for updates with answers to your questions. You can also reach out to the financial advisors below to set up an introductory call or contact them with your questions by email.


💸 Smart Money Insights for NVIDIA Employees & Executives

This page is organized into sections to help you quickly find the information you need and get answers to your questions:

  1. Q&A: Financial Planning Tips for NVIDIA Employees & Executives
  2. Get Answers to Your Questions About Your NVIDIA Benefits and Career
  3. Browse Related Articles

Q&A: Financial Planning Tips for NVIDIA Employees & Executives

In this section, you’ll learn how you can make the most of your NVIDIA employee benefits and gain valuable tips from financial advisors who specialize in working with NVIDIA employees and executives.

Answers to Employee Questions with Richard Siminou, MBA

Richard Siminou is a financial advisor based in Long Island, New York who specializes in offering financial planning services to Nvidia employees. Richard helps his clients get the most value from their Nvidia benefits and compensation package so they can enjoy life and feel confident about their financial future.

Q: As a financial advisor with experience helping Nvidia employees save for their retirement, how do you help them make the most of their employee benefits?

Richard: Employees at large companies are often in a fortunate position — the benefits packages tend to be genuinely strong — but that also means there are a lot of moving parts to coordinate, and the stakes are high.

The first thing I do is make sure no one is leaving free money on the table. That means capturing the full 401(k) match before anything else. From there, we look at whether pre-tax or Roth contributions make more sense given where they are in their career and what their income looks like today versus in retirement.

For employees who receive equity compensation — RSUs, stock options, or an ESPP — that’s often where the bigger conversation happens. Equity can be a tremendous wealth-building tool, but it also creates real risks: concentration in a single stock and a tax bill that catches people off guard at vesting. I help clients build a thoughtful diversification strategy so they’re not overexposed to any one position, and we plan proactively for the tax implications so nothing comes as a surprise.

For employees on a high-deductible health plan, I also make sure they’re maximizing their HSA — not just as a healthcare fund, but as a long-term investment vehicle. Most people don’t realize it’s one of the most tax-efficient accounts available.

What I enjoy most about working with employees of large companies is that they’re often sharp, motivated, and have real wealth-building potential through their benefits alone. My job is to bring all the pieces together — the 401(k), the equity, the HSA, the taxable accounts — into one coordinated strategy so that every dollar is working as efficiently as possible.

Q: When you first speak with a Nvidia employee, what questions do you like to ask to better understand their unique circumstances and determine how you can best help them achieve their goals?

Richard: The first conversation is really about listening more than talking. My goal is to understand not just where someone stands financially, but where they want to go — and what’s standing in the way.

I usually start with some foundational questions: Where are you in your career, and how are you thinking about the next five to ten years? Are you planning to stay with this employer long-term, or is there a possibility of a transition down the road? Those answers shape almost everything else.

From there I get into the specifics of their benefits. Are they capturing the full employer match on their 401(k)? How are they invested inside the plan, and does that still make sense given their timeline? If they receive equity compensation — RSUs, stock options, an ESPP — I want to understand how much of their net worth is tied to a single company’s stock, because concentration risk is one of the most common and underappreciated issues I see.

I also ask about taxes. Not in a technical way at first, but questions like: Did anything surprise you on your tax return last year? Are you feeling like you’re paying more than you should? That opens up a conversation about whether we can do better through smarter use of pre-tax accounts, HSAs, or deferred compensation if it’s available.

And then I ask the question that often matters most: What does financial security actually look like for you? The answer is different for everyone. For some people it’s retiring early. For others it’s funding their kids’ education without derailing their own retirement. For executives it might be building enough outside their employer that they have real optionality. Understanding that goal — that specific vision — is what drives everything else we do together.

Q: Is there a particular benefit available to Nvidia employees you feel isn’t as well utilized or understood by employees as it should be?

Richard: Without question — the HSA, or Health Savings Account. It’s the most underutilized financial tool I see across the board, and it’s a shame because the tax advantages are extraordinary.

Most people treat the HSA like a flexible spending account — they contribute a little, pay their medical bills out of it, and move on. What they’re missing is that the HSA is actually a triple tax-advantaged account: contributions go in pre-tax, the money grows tax-free, and withdrawals for qualified medical expenses are tax-free. No other account does all three.

What I encourage clients to do, if their cash flow allows, is pay current medical expenses out of pocket and let the HSA grow invested for the long term. After age 65, you can withdraw the money for any reason — not just medical — and it essentially functions like a traditional IRA. But if you do use it for healthcare costs in retirement, which most people will have plenty of, it’s completely tax-free. That’s a powerful combination.

The other benefit I’d mention is deferred compensation, for those who have access to it. Non-qualified deferred compensation plans are available at many large employers for higher-earning employees, and they can be a meaningful way to reduce current taxable income and build wealth outside of the standard retirement account limits. But they come with real complexity and risk that needs to be understood before participating — which is exactly where having an advisor in your corner makes a difference.

Q: Beyond Nvidia employee benefits for retirement savings, are there other types of benefits offered by the company that you find valuable to discuss with your clients?

Richard: Absolutely — and this is actually one of my favorite conversations to have, because most employees are sitting on benefits they’ve never fully explored.

Equity compensation is usually the first place I look. Whether it’s RSUs, stock options, or an Employee Stock Purchase Plan, these can represent a significant portion of someone’s total compensation — and they come with real decisions attached. When do you sell? How much do you hold? What’s the tax impact? I see a lot of employees either ignore these questions entirely or make emotional decisions about their company stock rather than strategic ones. Getting this right can make a meaningful difference in long-term wealth building.

Education savings is another area worth a dedicated conversation, particularly for employees with young children. A 529 plan isn’t an employer benefit in the traditional sense, but many large employers offer payroll deduction into 529 accounts, which makes the habit easy to build. More importantly, it’s a conversation that often gets delayed until it’s too late to let compounding do its work.

Life insurance and disability coverage are benefits people tend to click through during open enrollment without really thinking about. Group coverage through an employer is a great starting point, but it’s rarely sufficient on its own — especially for higher earners — and it doesn’t travel with you if you leave the company. I like to make sure clients understand what they actually have and where the gaps are.

Finally, I always ask about any financial wellness programs or legal services the employer offers. These are frequently overlooked and can provide real value, particularly around estate planning basics like wills and healthcare directives — documents that everyone needs but most people put off indefinitely.

The common thread across all of these is that benefits only create value if you actually understand and use them. My job is to make sure nothing valuable falls through the cracks.

Q: For Nvidia employees thinking about leaving the company to accept a job elsewhere, what actions do you recommend they take before resigning and shortly thereafter?

Richard: A job transition is one of those moments where the financial decisions you make in a short window can have a lasting impact — for better or worse. I always encourage clients to slow down and think through a few key areas before they hand in their notice.

The first thing I look at is vesting schedules. Whether it’s a 401(k) employer match, RSUs, or stock options, leaving before a vesting date can mean walking away from meaningful compensation. Sometimes it’s worth negotiating a start date with the new employer to capture a vesting event that’s just weeks away. That’s a conversation most people don’t think to have.

Equity is the other big pre-resignation consideration. If you hold vested stock options, there’s typically a limited window — often 90 days — to exercise them after you leave. Missing that deadline means forfeiting them entirely. RSUs that haven’t vested yet are generally gone when you walk out the door, so understanding exactly what you’re leaving on the table is critical before making any final decision.

On the benefits side, I encourage clients to take stock of their health insurance situation before their last day. COBRA is always an option but can be expensive, so knowing how quickly the new employer’s coverage kicks in helps avoid any gaps.

For the 401(k), there’s no need to rush a decision, but shortly after leaving I’d recommend rolling it over to an IRA or the new employer’s plan rather than leaving it scattered across former employers. It’s easier to manage, typically opens up more investment options, and keeps your financial picture clean and consolidated.

And finally — the offer letter itself. Before signing, I always encourage clients to look at the full compensation picture at the new employer, not just the base salary. How does the equity package compare? What’s the 401(k) match? Is there a vesting cliff? Understanding the complete package helps make sure the move actually makes financial sense from day one.

Q: For Nvidia employees approaching retirement age, how do you recommend they prepare to make the transition from living off their salary to relying upon other sources of income?

Richard: The transition from a steady paycheck to drawing down from multiple income sources is one of the most significant financial shifts a person will ever make — and in my experience, the people who navigate it most successfully are the ones who start planning it seriously three to five years out, not three to five months out.

The first thing I work through with clients approaching retirement is what I call the income gap analysis. We add up all the guaranteed income sources they’ll have — Social Security, any pension, annuity income if applicable — and compare that to what they actually need to live comfortably. Whatever’s left is what the portfolio needs to cover, and that shapes everything from asset allocation to withdrawal strategy.

Social Security timing is one of the highest-impact decisions in this phase and one of the most misunderstood. Claiming early can make sense in certain situations, but for many people delaying — even by a few years — results in a meaningfully higher monthly benefit for the rest of their life. We model this out carefully based on health, other income sources, and whether there’s a spouse involved.

Healthcare is another area that deserves serious attention, particularly for anyone looking to retire before Medicare eligibility at 65. Bridging that gap can be expensive, and it needs to be factored into the retirement budget explicitly rather than treated as an afterthought.

On the portfolio side, I work with clients to gradually shift their thinking from accumulation to distribution — which is a fundamentally different challenge. It’s not just about how much you’ve saved, it’s about sequencing withdrawals intelligently across taxable accounts, tax-deferred accounts like IRAs and 401(k)s, and tax-free accounts like Roth IRAs to minimize the tax drag over time. Getting that order of operations right can add real longevity to a portfolio.

And then there’s the psychological side, which doesn’t get talked about enough. After decades of saving and accumulating, actually spending that money can feel deeply uncomfortable for a lot of people. Part of my job in this phase is helping clients feel confident and grounded in their plan — so they can enjoy retirement rather than worry their way through it.

Q: For Nvidia employees who have managed their finances on their own to this point, what would you suggest they consider to help them decide if they should begin working with a financial advisor at this stage in their lives?

Richard: I have a lot of respect for people who have taken ownership of their finances and done the work on their own. That discipline and engagement is actually a great foundation for a productive relationship with an advisor. The question I’d encourage them to ask isn’t “have I done okay so far?” — because the answer is probably yes — but rather “is doing this alone still the right approach given where I am and where I’m headed?”

The complexity argument is the most straightforward one. Early in a career, personal finance is relatively simple — contribute to the 401(k), build an emergency fund, avoid bad debt. But as income grows, equity compensation enters the picture, taxable accounts accumulate, families expand, and retirement starts moving from a distant concept to an actual horizon, the number of interconnected decisions multiplies quickly. At that point, the cost of a suboptimal decision — whether it’s a tax mistake, a poorly timed equity sale, or a Social Security claiming error — can far exceed the cost of professional guidance.

I’d also ask: how much time are you actually spending on this, and is that the best use of your time? Many of the people I work with are high achievers who are extremely capable of managing their own finances. But capability and bandwidth are two different things. If financial decisions are getting made reactively — or worse, getting deferred — because life is busy, that’s worth examining honestly.

Another honest question is around blind spots. We all have them. A good advisor isn’t just a technician — they’re a thinking partner who can challenge assumptions, stress test a plan, and flag things you might not know to look for. Most people don’t know what they don’t know until something goes wrong, and by then the cost of finding out can be significant.

And finally, I’d suggest looking at a few key moments as natural triggers for seeking a second opinion: a job change, an inheritance, a major equity vesting event, a divorce, or the death of a spouse. Any one of those situations involves enough complexity and enough at stake that having an experienced guide in your corner is genuinely valuable — not just reassuring.

The goal of a first conversation with an advisor shouldn’t be to hand everything over. It should be to get an honest assessment of where you stand, what you might be missing, and whether there’s enough value on the table to make the relationship worthwhile. A good advisor will tell you the truth either way.

Q: What are some of the unique financial planning challenges you commonly see among your clients who are Nvidia employees and how do you help them overcome these obstacles?

Richard: Working with employees of large companies over the years, a few patterns come up consistently — and they’re worth naming because recognizing them is half the battle.

The first is what I’d call benefits paralysis. Large employers offer generous and often complex benefits packages, and the sheer number of decisions — 401(k) elections, health plan choices, equity grants, deferred compensation options, life insurance levels — can be genuinely overwhelming. The path of least resistance is to set something up during onboarding and never revisit it. I see people years into their careers still invested in the default target-date fund they selected on day one, with life insurance coverage that made sense when they were single but is now completely inadequate for a family. My job is to bring structure and intentionality to decisions that otherwise get made by default.

Concentration risk is another challenge I encounter constantly. When someone has worked at the same company for a long time and received equity compensation along the way, it’s very common for a disproportionate share of their net worth to be tied up in a single stock — their employer’s. There’s often an emotional attachment to that stock, a sense that loyalty or conviction should translate into holding. But from a pure risk management standpoint, having your income and your investment portfolio both dependent on the same company’s fortunes is a vulnerability. I help clients think through diversification in a way that feels rational rather than disloyal.

Lifestyle creep is a quieter challenge but a very real one, particularly among high earners at large companies. As compensation grows — base salary increases, bonuses, equity — spending tends to grow with it, sometimes faster. I work with clients to make sure that as their income rises, their savings rate and investment contributions are rising proportionally, not just their expenses. Building real wealth is about the gap between what you earn and what you spend, not the absolute level of either.

Tax complexity is something a lot of employees underestimate until it bites them. Between equity vesting events, bonus income, potential deferred compensation, and investment accounts, the tax picture for a high-earning employee at a large company can get complicated quickly. I work closely with clients — and coordinate with their CPAs where appropriate — to make sure we’re being proactive rather than reactive when it comes to tax planning.

And finally, there’s the challenge of integration — or the lack of it. Most people manage different pieces of their financial life in isolation. The 401(k) is one conversation, the equity compensation is another, the mortgage is another, the insurance is another. Nobody is looking at the whole picture at once. That’s precisely what I do. Bringing everything together into a single, coherent strategy is where the real value of financial planning lives.

Q: What questions do you recommend Nvidia employees ask financial advisors they’re considering hiring to help them decide if they’re a good fit?

Richard: This is a question I genuinely love, because I think everyone should approach hiring a financial advisor the way they’d approach any other important professional relationship — with real curiosity and a willingness to ask direct questions. The right advisor will welcome the scrutiny. Here’s what I’d encourage people to ask:

How are you compensated? This is the most important question on the list and the one people are most reluctant to ask. Understanding whether an advisor is fee-only, fee-based, or commission-based tells you a great deal about where their incentives lie. There’s no single right answer, but you deserve a clear and honest explanation — not a vague or defensive one.

Are you a fiduciary, and in what capacity? A fiduciary is legally required to act in your best interest. Some advisors are fiduciaries all the time, some only in certain contexts, and some not at all. Knowing where your advisor stands on this — and when — matters enormously.

What is your experience working with clients in situations like mine? If you receive equity compensation, have significant assets in a company retirement plan, or are navigating a specific life transition, you want an advisor who has real familiarity with those circumstances — not someone who will be learning on your time.

What does your typical client look like? This helps you understand whether you’ll be a priority or an afterthought. An advisor whose practice is built around clients at a very different income or asset level may not be the best fit, regardless of how capable they are.

How often will we meet, and what does ongoing service look like? A financial plan isn’t a document — it’s a living relationship. You want to understand upfront how proactive the advisor will be, how accessible they are between scheduled meetings, and what you can expect when your circumstances change.

Who else is on your team, and who will I actually be working with day to day? At larger firms especially, the person you meet with initially isn’t always the person managing your relationship. It’s worth understanding the structure before you commit.

And finally — can you explain a time you told a client something they didn’t want to hear? A good advisor isn’t just a validator. They push back when it matters, flag risks you might be overlooking, and prioritize your long-term interests over your short-term comfort. How an advisor answers this question tells you a lot about their character and their willingness to have honest conversations.

The goal of these questions isn’t to trip anyone up — it’s to find someone you can trust completely with one of the most important areas of your life. The right advisor will answer every one of them directly and without hesitation.

Q: Is there anything that comes up frequently in your initial meeting with Nvidia employees that surprises you?

Richard: Honestly, yes — and the same few things come up more often than you’d expect, even among people who are financially engaged and working at sophisticated organizations.

The one that surprises me most consistently is how many people don’t know what they actually own inside their 401(k). They know they’re contributing, they have a general sense of the balance, but when I ask what they’re invested in and why, there’s often a long pause. A lot of people are in whatever default option they selected years ago and have never revisited it. For something that may ultimately be one of their largest assets, that level of inattention is striking — though I understand how it happens. Life gets busy, the account is out of sight, and as long as the balance is going up it’s easy to assume everything is fine.

Another thing that comes up frequently is a genuine surprise at how much equity compensation they’ve accumulated — and how concentrated that makes them. People receive grants periodically, the stock does well, and before long a significant portion of their net worth is tied to a single company. When I show someone that number visually, as a percentage of their total picture, it often lands differently than they expected.

I’m also consistently surprised by how many people have never looked carefully at their insurance coverage — life, disability, long-term care. They enrolled in whatever the employer offered during onboarding, accepted the default amounts, and haven’t thought about it since. For someone whose income and family situation have changed substantially over the years, that coverage is often badly misaligned with their actual needs.

And then there’s estate planning. I would say the majority of people I meet for the first time — across all income levels — either have no will at all or have one that’s badly out of date. People know they need it, they intend to get to it, and somehow it never rises to the top of the list. It’s one of the first things I encourage clients to address, because it’s not just a financial document — it’s how you take care of the people you love when you’re no longer able to do it yourself.

What ties all of these together is that they’re not failures of intelligence or effort — they’re failures of attention and integration. People are busy, the financial system is complex, and without someone periodically looking at the whole picture, important things quietly fall through the cracks. That’s exactly the gap a good advisor fills.

Q: For highly compensated Nvidia employees and executives, are there any special benefits you believe it’s important to take into consideration when preparing their financial plan?

Richard: Absolutely — and this is an area where the complexity increases significantly and the cost of not having a coordinated plan can be substantial. Highly compensated employees and executives often have access to a layer of benefits that goes well beyond what’s available to the broader workforce, and each one comes with its own set of decisions, tax implications, and risks.

Nonqualified deferred compensation plans are one of the most powerful tools available to executives, and also one of the most misunderstood. The ability to defer a significant portion of income — sometimes hundreds of thousands of dollars — into a future tax year can be enormously valuable for someone in a high bracket today who expects to be in a lower bracket in retirement. But these plans are fundamentally different from a 401(k). The deferred amounts are technically still a liability of the employer, meaning they’re at risk if the company runs into financial trouble. The distribution elections are also largely irrevocable once made. Getting the strategy right from the beginning matters enormously.

Executive equity compensation tends to be more complex than standard RSU grants. Stock options — particularly incentive stock options, or ISOs — come with specific tax treatment that requires careful planning around exercise timing, alternative minimum tax exposure, and holding periods. The difference between a well-timed and a poorly timed exercise can be measured in tens of thousands of dollars or more.

Supplemental executive retirement plans, sometimes called SERPs, are another benefit worth understanding thoroughly. These are employer-funded retirement arrangements designed to provide additional income beyond what qualified plans like the 401(k) allow, and the terms vary widely from company to company.

Executive life insurance arrangements — things like split-dollar policies or executive bonus plans — also come up frequently at this level and require a careful look to make sure they’re structured in a way that actually serves the executive’s interests and integrates properly with their overall estate plan.

And speaking of estate planning — at the executive level this conversation becomes significantly more involved. We’re often talking about wealth transfer strategies, trust structures, charitable giving vehicles, and in some cases business succession considerations. The financial plan and the estate plan need to be built together, not treated as separate exercises.

What I find most important with highly compensated clients is that all of these pieces — the deferred comp, the equity, the insurance, the estate plan, the investment portfolio — are looked at holistically and updated regularly as circumstances change. The opportunities at this level are genuinely significant, but so are the consequences of getting it wrong.

Q: Is there a particularly memorable experience or a moment you recall with a client who worked at Nvidia when you realized they have unique opportunities and circumstances when it comes to their financial planning needs?

Richard: There’s one that comes to mind that I think illustrates the point really well — and it’s a situation I’ve seen play out in different variations more times than I can count.

I met with a client who had been with a large employer for about twelve years. She was sharp, successful, and by any measure financially responsible. She had been contributing to her 401(k) consistently, had no significant debt, and felt like she had a reasonable handle on her finances. She came to me not because something was wrong, but because her compensation had grown considerably and she wanted a second set of eyes.

When we sat down and actually mapped out her complete financial picture, a few things became immediately clear. First, she had accumulated a substantial amount of vested company stock through RSU grants over the years — far more than she had mentally accounted for — and it represented nearly half of her investable net worth. She had always thought of her portfolio and her equity compensation as two separate things. They weren’t. They were deeply connected, and the concentration risk was significant.

Second, she had been eligible for her company’s nonqualified deferred compensation plan for three years and had never enrolled. Nobody had ever walked her through how it worked or why it might be worth considering. Given her tax bracket, that was a meaningful missed opportunity — not catastrophic, but real.

And third, her estate plan consisted of a will she had drafted before she was married, before she had children, and before her net worth had grown to its current level. It was essentially obsolete.

None of these were failures on her part. She had done a lot of things right. But they were a perfect illustration of what happens when the pieces of a financial life are managed in isolation rather than as a whole. The moment I laid it all out on one page — the portfolio, the equity, the deferred comp eligibility, the estate plan gap — I could see the shift in her expression. It wasn’t alarm, it was clarity. She finally saw her complete financial picture for the first time.

That’s the moment I find most meaningful in this work. Not when something has gone wrong, but when someone who has been doing well realizes they could be doing significantly better — and that the path to get there is clearer than they thought.

Q: For employees who receive a large, unexpected financial windfall — such as a major equity vesting event, a bonus, or an inheritance — what do you recommend they do, and what mistakes do you caution them to avoid?

Richard: If I could instill one habit above all others, it would be this: treat saving as a fixed expense, not an afterthought.

Most people save whatever is left over after they’ve paid their bills and lived their lives. The problem is that for most people, there’s rarely much left over — expenses have a way of expanding to fill available income. The people I’ve seen build real wealth consistently over time are the ones who decided early on to pay themselves first. They automated their contributions, set their savings rate, and built their lifestyle around what remained rather than the other way around.

It sounds simple, and it is — but the discipline of making it non-negotiable, even when the amounts are small, creates a habit and a mindset that compounds just as powerfully as the money itself. The clients I work with who started this early, even modestly, are almost always in a dramatically stronger position than those who waited until they felt they could afford to save more. The right time to start is always sooner than it feels.

Get to Know Richard Siminou, Financial Advisor for Nvidia Employees:

View Richard’s profile page on Wealthtender or visit his website to learn more.

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Quick Facts & Resources for NVIDIA Employees

NVIDIA Quick Facts & ResourcesDetails / Useful Links
NVIDIA Corporate Headquarters Address2788 San Tomas Expressway, Santa Clara, CA 95051 (📍 Google Maps)
Overview of NVIDIA BenefitsVisit Life at Nvidia
How much do NVIDIA employees Make?View NVIDIA Salary Research on Glassdoor
Where can I learn more about careers at NVIDIA?Visit this Career Page on NVIDIA.com
What is the ticker symbol for NVIDIA stock?The NVIDIA ticker symbol is NVDA. Visit NVIDIA Investor Relations


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Find financial advisors in Newport News, Virginia ready to help with your financial planning needs so you can enjoy life more with less money stress.

Whether you have lived in Newport News for years or recently moved to town, you may need help finding the right financial advisor in the community best suited for your individual needs.

It’s important to first consider your own financial planning priorities before choosing an advisor. Here are a few quick tips to help you get started along with financial advisors in Newport News featured on Wealthtender you may want to add to your shortlist.

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The Benefits of Hiring a Financial Advisor in Newport News

Hiring a financial advisor can be a great move to help you build a long-term investing strategy. Advisors can help you build an investment portfolio to meet your financial goals and help you plan appropriately for retirement.

As a resident living in Newport News, hiring a financial advisor who lives nearby and understands the local economy, cost of living, and regional employers can be quite valuable, especially if your individual circumstances are deeply tied to such factors.

Do you work for one of the largest employers in Newport News? If so, there’s a good chance the local financial advisor you hire will also have other clients who work there. This knowledge could prove valuable if they are already familiar with your employee benefits, such as a 401(k) plan, Health Savings Accounts, and other components of your total compensation package.

When you reach out to financial advisors you’re considering hiring, let them know where you work and ask if they are familiar with your employer’s unique benefits and compensation structure.

Quick Tips For Hiring an Newport News Financial Advisor

Before hiring a financial advisor in Newport News, here are a few quick tips to help you find the best advisor for you.

1. Decide Which Services You Need

Before hiring an advisor, determine what services you need from them. Whether it’s full-service investment management or a plan focused on a specific area of your finances, put together a list of what you’d like help with before contacting an advisor.

Though most people use a financial planner simply to invest for retirement, this is only a small part of what many advisors offer. Here’s a quick rundown of potential services a financial advisor may offer you:

  • Budgeting and money management
  • Debt management
  • Insurance planning
  • Retirement planning
  • Other investment planning
  • Inheritance planning
  • Estate planning
  • Tax planning

As you can see, financial advisors can help you with your entire financial picture, not just investing. As you start to plan for life’s bigger milestones, you should consider finding a financial advisor that specializes in those areas.

Finding the right advisor can help you minimize risk, maximize gains and take advantage of tax breaks while investing for your future. They can also help you protect your assets with the right kinds of insurance and help you pass on your financial legacy with a proper estate plan.

2. Consider Your Budget and Payment Preferences

Once you have a list of services you would like, review the fee structures financial advisors offer. Finding a balance between the services you need and the cost of those services will help narrow down the field of advisors you may want to work with.

If you are looking for a full-service advisor to manage all of your investments, consider searching among fee-based financial advisors. If you want to manage your money yourself, consider the flat fee and monthly subscription advisors for ongoing support.

3. Interview Multiple Financial Advisors

Once you have chosen the services and fee structure you prefer, it’s time to contact a few advisors and interview them. Here are questions to ask financial advisors:

  • What services do you provide?
  • What are all the ways you get paid? (fee transparency)
  • What is your investment strategy?
  • How do you measure investment performance?
  • How do we communicate about my plan?

Interview multiple advisors to get a feel for who you want to work with. A combination of fees, services, and customer service will help you determine the best fit for your financial advice.

4. Review Financial Advisor Credentials

Once you find an advisor (or two) you feel comfortable with, it’s always a good practice to check their credentials and the firm’s details. You can do this at the Investment Adviser Public Disclosure (IAPD) website

You can check both the individual and the firm to view their background and experience details, as well as any disciplinary action taken against them or their firm.

As licensed financial professionals, there is oversight into how financial advisors conduct business, so running a quick (free) check on them is recommended.

For additional information about advisor credentials, read our article to learn the most popular designations held by financial advisors, as well as specialized credentials which may be important to consider if you have unique financial planning needs.


Frequently Asked Questions & Additional Resources

How do I know if I’m ready to hire a financial advisor?

You should strongly consider hiring a financial advisor if you have a significant amount of money available for saving or investing. This could occur after years of making annual contributions to a retirement plan like a 401(k) through your employer or suddenly if you receive a large inheritance or sell your house for a large profit.

But even if you don’t have a lot of money saved, many financial advisors and planners provide reasonable pricing options and valuable services you should consider, especially if you’re facing a significant life event. For example, if you’re starting a new job, getting married, starting a family, getting divorced, lost your job, starting or selling a business, or approaching retirement age, working with a trusted financial advisor or planner may prove worthwhile.

Before I hire a new financial advisor, should I fire my current advisor?

You don’t need to fire your current advisor before beginning your search for a new financial advisor. In fact, your new advisor can help coordinate the transition of your assets from your previous financial advisor.

Where can I read reviews about financial advisors written by their clients to help me decide if I should hire them?

After 60 years of regulatory prohibition of financial advisor reviews in the US, a rule issued by the Securities and Exchange Commission (SEC) became effective on May 4, 2021 that means both financial advisors and directory websites that help consumers search for a financial advisor can collect and display financial advisor reviews, an important factor worth considering when choosing who you’ll hire to manage your investments and life savings. 

Wealthtender is the first independent advisor review platform designed to be fully compliant with the new SEC rule, and we look forward to helping you evaluate financial advisors based on reviews written by their clients.

I’m a local financial advisor interested in being featured in this guide. How do I get started?

Thanks for your interest. We look forward to learning more about your practice and helping you attract your ideal clients where you may be a good fit based on their individual needs and circumstances. Please click here to learn how you can join local financial advisors featured on Wealthtender.

How Much Does a Financial Advisor Cost?

➡️ How Much Does a Financial Advisor Cost? Read the Article

About the Author
A headshot of Brian Thorp, the founder and CEO of Wealthtender

About the Author

Brian Thorp

Brian is CEO and founder of Wealthtender and Editor-in-Chief. He and his wife live in Austin, Texas. With over 25 years in the financial services industry, Brian is applying his experience and passion at Wealthtender to help more people enjoy life with less money stress. Learn More about Brian

Securing extra income is never a bad thing, but it can feel like you’ve made a mistake when the tax bill arrives. As a high-net-worth individual in the thick of your top-earning years, you’re steering important decisions, capitalizing on opportunities, and winning big. But that success can come at a steep price without careful tax planning. 

If you’ve ever been shocked to see what you owe Uncle Sam, you’re not alone. And if you’ve been surprised to find that there’s no quick, easy fix to this, you’re in good company. I regularly meet with successful business owners who are not only taken aback but deeply frustrated by how much they owe, especially after a strong year or unexpected income event. 

The reality is that effective tax planning takes years of strategic, proactive positioning and attentive execution to get it right. Working with a knowledgeable advisor who understands your unique situation can make a considerable difference, helping you keep more of what you’ve worked so hard to earn.

Tax Alpha as the Foundation

Before diving into the importance of strategic tax planning, it helps to zoom out and revisit a concept I’ve written about before: tax alpha

In that article, I explained that tax alpha is the value created by managing investments with taxes in mind—not by chasing performance, but by narrowing the gap between what your portfolio earns before taxes and what you actually keep after them. Strategies like smart retirement contributions, deliberate asset location, tax-loss harvesting, and charitable planning all work together over time to improve after-tax results. 

The takeaway is that two investors can earn the same market returns and walk away with very different outcomes depending on how tax-aware their portfolios are. And the framework is intentionally broad and ongoing, focusing on improving efficiency year after year as your portfolio grows.

Long-term tax planning, however, takes that idea a step further. Instead of asking, “How do I make my portfolio more tax-efficient this year?” it asks, “What do I expect, given multiple possible scenarios, and how do I prepare for it now?”

When a future taxable event is on the horizon, such as a business sale, a partnership exit, or the eventual sale of highly appreciated stock, your planning window opens well before the transaction occurs. This is where multi-year strategies become powerful. By harvesting losses in advance, using tax-aware long/short strategies, and structuring portfolios with future gains in mind, you can stay invested while building a reservoir of tax offsets.

In short, tax alpha improves outcomes over time. Proactive tax planning shapes the outcome of major financial moments, often years before they happen.

When You Know a Taxable Event Is Coming

It’s common for clients to hold back on sharing news about potential additional income with their advisor. Maybe you’re not sure it’ll come through, don’t want to get ahead of yourself, or simply aren’t used to talking about financial windfalls until they’re real. But when you have a trusted relationship with your advisor, it’s worth mentioning these possibilities early, even if they feel uncertain. It gives you more room to plan thoughtfully and avoid surprises later.

A taxable event is any financial action that creates a tax obligation, such as selling an asset at a profit, earning income, receiving dividends or interest, or taking distributions from retirement accounts. For business owners and high earners, the most impactful taxable events are often capital gains tied to a future sale or liquidity event—something you’ve likely been anticipating for some time. [1] 

The key is recognizing these triggers early. Even if timing isn’t certain, planning for possibilities opens the door to smarter strategies, like harvesting losses in advance or positioning investments more thoughtfully. You don’t need perfect clarity to plan well. You just need openness, foresight, and time on your side.

Capital Gains and the Power of Planning Ahead

For many business owners and high earners, capital gains taxes are the single largest cost tied to success. A capital gain occurs when you sell an asset, such as a business, partnership interest, or stock, for more than you paid for it. Long-term capital gains are taxed at preferential federal rates (0%, 15%, or 20%), but they’re often layered with the 3.8% net investment income tax and state taxes. When you add it all up, the bite can be a big one, particularly in a large liquidity event. [2]

Research from the Brookings Institution and the Tax Foundation highlights why this matters so much for entrepreneurs. In essence, capital gains taxes influence how and when owners sell, how deals are structured, and how much they ultimately keep. The challenge is that by the time a sale is imminent, many of the best planning opportunities are already behind you. [3, 4]

That’s where planning ahead changes the equation. If you expect to sell a business or unwind a highly appreciated position in the future, even if timing isn’t certain, you can start preparing years in advance. One of the most effective tools is tax-loss harvesting, which involves intentionally realizing losses to offset future gains. Harvested losses can be carried forward indefinitely, creating a valuable reservoir to apply against future capital gains. [5, 6]

Let’s take a look at how this could work.

Consider my client, Tom (name changed to maintain confidentiality). He knew he would be selling his business a few years down the line; at least that was the plan. So Tom began tax-loss harvesting in his brokerage account, ultimately three years before selling his company. Because he started making strategic moves well in advance, he was able to realize losses in down markets while staying invested, accumulating $400,000 in carried-forward losses. 

When Tom eventually sold the business for a $2 million gain, those losses immediately offset $400,000 of taxable income. Tax-loss harvesting saved him roughly $95,000 in combined federal and state taxes. Without leveraging this multi-year approach, Tom would have faced the full tax bill with limited options. The planning didn’t happen overnight, but the payoff was substantial when it mattered most.

You don’t have to sit on the sidelines. With smart positioning, you can remain invested, participate in market growth, and quietly reduce the tax impact of a future sale. Capital gains may be unavoidable, but the size of the bill is often negotiable with time, planning, and the right strategy.

Using Tax-Aware Long/Short Strategies to Manage Future Capital Gains

Tax-aware long/short strategies are designed primarily to stay invested while being intentional about when gains are realized. Instead of relying solely on selling appreciated assets, which can trigger large capital gains taxes, the move is to separate market exposure from tax consequences.

At a high level, a long/short approach pairs long positions (investments you expect to grow) with short positions (stocks you believe will decrease in value), and sells borrowed shares to offset market risk. When implemented with tax awareness, the strategy seeks to realize losses during normal market volatility while deferring gains for as long as possible. Those realized losses can then be used to offset future capital gains, including gains tied to a business sale or the sale of concentrated company stock.

The benefit isn’t just tax reduction; it’s flexibility. You can remain invested, maintain diversified exposure, and gradually build a bank of losses that may be applied when a large taxable event occurs down the line. Over time, this approach can materially reduce the after-tax cost of success.

These strategies aren’t about avoiding taxes or making aggressive bets. They’re the result of thoughtful execution, disciplined risk management, and alignment of investment decisions with known or likely future tax outcomes. When used properly, tax-aware long/short strategies turn time into an advantage rather than a constraint.

Why Choosing the Right Financial Advisor Matters

Strategies like multi-year loss harvesting and tax-aware long/short investing only work when they’re executed correctly. Choosing the right advisor goes beyond assessing credentials alone. High earners and business owners should work with a financial professional who understands complexity and collaborates with other experts as needed. These strategies require disciplined trading, accurate reporting, and ongoing coordination across investment, tax, and planning teams. 

The goal is to apply the right strategies at the right time, in the right way. If you know a major tax event may be ahead, now is the time to start the conversation. Planning early creates options and better outcomes. Reach out to discuss how proactive, coordinated tax planning could work for you.

Sources: 

  1. https://www.investopedia.com/terms/t/taxableevent.asp
  2. https://www.brookings.edu/articles/what-are-capital-gains-taxes-and-how-could-they-be-reformed/
  3. https://www.investopedia.com/terms/c/capital_gains_tax.asp
  4. https://taxfoundation.org/blog/how-does-capital-gains-taxation-affect-entrepreneurial-activity/
  5. https://www.investopedia.com/terms/t/taxgainlossharvesting.asp
  6. https://www.morganstanley.com/articles/tax-loss-harvesting

This article was originally published here and is republished on Wealthtender with permission.

About the Author

Headshot of Sean Gerlin, CFP®, CPWA®, ChFC®, CLU®
Sean Gerlin, CFP®, CPWA®, ChFC®, CLU® Creating Clarity Out Of Complexity

Sean Gerlin, CFP®, CPWA®, ChFC®, CLU® | Envision Wealth Planners