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It is a simple question. And for most investors holding concentrated stock positions, the honest answer is no.
On this week's Financial Commute, Chris Galeski and Chief Investment Officer Meghan Pinchuk walk through why the answer is almost always taxes, why letting the tax decision drive the investment decision is a risk in itself, and what the after-tax value of a highly appreciated position actually looks like when you do the math.
They also cover the middle path most investors do not consider: trimming gradually, staying in favorable long term capital gains treatment, and using the rebalancing process to reduce concentration without triggering a single large tax event.
If you are holding something you would not buy at today's price, this one is worth eight minutes.
Questions This Episode Answers
If I wouldn't buy my stock at today's price, should I sell it?Why do people hold stocks they know they should sell?Does tax loss harvesting actually eliminate taxes on gains?What is the “tax tail wagging the dog?”What is the real after-tax value of my investment portfolio?How much of a gain should I realize from my taxable account each year? -
Most of the conversations clients have had about long-term care insurance are based on products that no longer exist.
On this week's Financial Commute, Chris Galeski sits down with Russell Boring, Founder of Elevated Strategies Insurance Services, to walk through what has actually changed. The carriers that mispriced their policies are mostly gone. What replaced them are hybrid and annuity-based structures that solve the biggest objection people have always had: what happens to the money if you never need care?
The short answer: it comes back.
They also cover why people in their 70s who assumed they had aged out of the conversation now have options they did not before, and why the clients who can afford to self-fund are sometimes the ones who need this conversation most. -
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Everyone has been waiting for rates to come down.
It has not happened. And on this week's Financial Commute, Chris Galeski and Chief Investment Officer Meghan Pinchuk explain why the Fed's new chair is holding firm, what energy prices and the war in Iran have to do with your portfolio, and why the national debt makes this moment more complicated than the headlines suggest.
They also get into the practical side: how to think about inflation as a slow tax on cash, why gold has held its value for over a century, and the one mistake a lot of people are quietly making right now.
If you have been making any financial decisions based on the assumption that rates are coming down soon, this one is worth a listen. -
If you have been watching housing prices and wondering whether the new executive order restricting institutional investors is the fix everyone is hoping for, you are not alone. The frustration is real, and the concern for affordability is legitimate.
In this episode of Financial Commute, Chris Galeski sits down with Mikey Taylor, Mayor of Thousand Oaks and CEO of Commune Capital, to examine what the data actually says about who owns single-family homes, why the ban on institutions is unlikely to move the needle on prices, and what the real barrier to housing affordability in California looks like.
Questions This Episode Answers
- Should institutions be banned from buying single-family homes?
- Why is housing so unaffordable in California right now?
- What percentage of single-family homes do institutional investors actually own?
- What is the Builder's Remedy in California housing law?
- Is it better to rent or buy in Southern California right now?
- Will California home prices go down? -
Most people come to a wealth manager for one reason: their finances. But what if focusing exclusively on financial wealth is actually making it harder to achieve? Nurturing the various types of wealth (social, physical, mental, time, and financial) is the central idea behind Sahil Bloom's book, The 5 Types of Wealth.
In this episode, host Chris Galeski sits down with Wealth Advisor Bruce Tyson to reflect on Bloom's framework. The conversation weaves together philosophy, personal experience, and practical wisdom, including Bruce's own story of losing his home in the Palisades Fire and how decades of intentional relationship building showed up exactly when it mattered most.
Key Takeaways
Financial wealth is the starting point, not the destination. Focusing exclusively on money at the expense of your health, relationships, and time can make the very life you are building toward feel empty when you arrive. The five types of wealth work together as a system. Social wealth is the one most likely to get sacrificed — and the hardest to rebuild. People who spend years prioritizing work over relationships often retire to find their social circle has quietly disappeared. The time to invest in relationships is before you need them. Curiosity is one of the few things that can permanently raise your baseline happiness. Most achievements — awards, promotions, financial milestones — produce a temporary lift before happiness returns to its baseline. Intellectual curiosity is different. It compounds. Time wealth is what most people are actually trying to buy. The goal of financial planning is not a number. It is control over your time. Understanding that early changes how you save, spend, and make decisions throughout your life. Living within your means is not a limitation — it is a foundation. The pursuit of wealth that exceeds your actual assets is a reliable source of stress. Knowing what is enough, and being honest about it, is one of the most underrated financial decisions a person can make. -
SpaceX is going public and everyone is talking about it. Neighbors, friends, group chats... the excitement is real. But most of the conversation is missing the most important question: what are you actually paying for?
In this episode of Financial Commute, host Chris Galeski sits down with CEO and Partner Jeff Sarti to break down the SpaceX IPO from a valuation standpoint. Recorded on June 8th, this is the conversation the headlines are not having. Chris and Jeff walk through what price to sales ratio means, why a $10 stock is not cheap and a $1,000 stock is not expensive, and what history tells us about companies trading at extreme valuations. The story is incredible. The price is another matter entirely.
Key Takeaways
Stock price tells you nothing about value. A $10 stock is not cheap and a $1,000 stock is not expensive. What matters is the underlying valuation — and SpaceX at roughly 100 times price to sales is extreme by any historical measure. A great company is not automatically a great stock. Rivian grew its revenue 100 times over and is still down 90% from its IPO price. Cisco was the largest company in the world during the dot-com boom and collapsed 90% — taking 27 years to recover. Growth does not guarantee returns at any price. 100 times price to sales is not a growth premium — it is speculation. The S&P 500 is currently at an all-time high of roughly 3.5 times price to sales. SpaceX is trading at nearly 30 times that. Even if SpaceX fell 80% from its IPO price, it would still be more expensive than Nvidia on a price to sales basis. Volatility is near-certain even in good outcomes. Facebook fell 50% within six months of its IPO before going on to become one of the most valuable companies in the world. Buyers of the SpaceX IPO should expect a similarly turbulent ride regardless of the long-term outcome. -
Most clients trust their wealth manager to make sound investment decisions on their behalf. Far fewer ever get to see exactly how those decisions are made. This episode is for the ones who want to know.
In this special edition of Financial Commute, Executive Vice President Eric Selter sits down with Chief Investment Officer Meghan Pinchuk to pull back the curtain on Morton Wealth's full investment research process. From what triggers a new idea to how funds get vetted, how structures get scrutinized, and what it actually takes to earn conviction, this is the conversation most firms never have in public.
Key Takeaways
The investment process starts long before any money moves. From initial sourcing to final funding, a new investment can take 18 months or more. That is not a flaw in the process. It is the process. The structure around an investment matters as much as the investment itself. A great underlying asset in a poorly structured fund can leave you locked out, illiquid, or exposed to risks that have nothing to do with market performance. Good market conditions hide a lot. It is easy to look like a strong fund in a good market. The real test is how someone handles adversity. Morton Wealth actively looks for funds that have been tested and can clearly articulate what they learned. People are still the most important variable. AI can streamline data processing. It cannot assess character. Whether a fund will do the right thing when things are hard is a judgment call that requires real relationships and real time. -
It's one of the most common questions people type into Google once they hit 50: should I be taking less investment risk? It feels like a reasonable question. But according to Chief Investment Officer Meghan Pinchuk, it may be the wrong one entirely.
In this episode of Financial Commute, Meghan and host Chris Galeski unpack what drives the right level of investment risk at any age, from longevity and sequence of returns risk to the emotional factors that quietly derail even well-built plans. Spoiler: age is further down the list than most people think.
Questions This Episode AnswersShould I take less investment risk now that I'm 50?
Not necessarily, and maybe not at all. Age by itself is not the right variable. The more useful question is: how close are you to the spending phase of your life, and how long does your portfolio need to last? Someone retiring at 65 with a life expectancy well into their 80s or 90s has a 25 to 30 year window their money needs to cover. A portfolio that's too conservative early in that window may not grow fast enough to last the distance. The old model of shifting heavily into bonds at retirement was designed for a world where retirement lasted 10 or 15 years. That world is largely gone.
What is the biggest investment risk people over 50 actually face?
Two things come up repeatedly in this conversation. The first is behavioral risk: abandoning a sound investment strategy during a market downturn. Meghan and Chris point to 2008, 2020, and 2022 as examples of periods when investors who panicked and sold missed the recovery entirely, permanently reducing their long-term returns. Research consistently shows that retail investors earn significantly less than the indices they invest in, largely because of this pattern. The second is sequence of returns risk: being forced to sell assets early in retirement, when prices are depressed, in order to cover living expenses. That combination, selling low and losing compounding time, is what genuinely harms long-term plans.
What is sequence of returns risk, and why does it matter so much at retirement?
Sequence of returns risk is the danger of experiencing a major market decline right at the moment you transition from accumulating assets to spending them. If your portfolio drops 30 or 50 percent in the first years of retirement and you're selling shares to cover expenses, you lock in those losses and shrink the base that would otherwise recover and compound. The timing matters as much as the magnitude. A 50 percent decline early in retirement is far more damaging than the same decline ten years in, when you've already drawn down a portion of your portfolio and have fewer assets exposed.
How does longevity change the risk equation for people over 50?
Significantly. Earlier generations could plan for a retirement of 10 to 15 years. Today, a 65-year-old retiring without a pension may need their savings to last 25 to 35 years. That length of time changes almost everything about portfolio design. It means you likely need more growth assets, not fewer, to outpace inflation and sustain your lifestyle. It also means the risk of running out of money may be a greater threat than the risk of a temporary market decline. At the same time, most of this generation is the first to fund retirement entirely on their own, without a pension providing a guaranteed income floor.
How do advisors think about how much risk to take in a portfolio?
Meghan and Chris break it into two questions. First, how much growth do you mathematically need? Given your expenses, savings, and expected retirement length, what return does your portfolio need to deliver for your plan to work? That's a numbers question. Second, what is your actual emotional tolerance for volatility? Someone who needs strong returns but cannot psychologically handle large drawdowns is in a difficult position that pure math can't resolve. A good financial plan has to account for both, because a strategy you abandon in a panic is worse than a more conservative strategy you can stick with.
What is the bucket approach, and how does it help manage risk in retirement?
The bucket approach divides your portfolio by time horizon and purpose rather than treating it as a single pool. Bucket one covers your emergency fund and near-term expenses, held in stable, liquid assets that won't lose significant value in a downturn. Bucket two generates the income you need to cover living expenses over the medium term. Bucket three is your long-term growth engine, invested in equities and other higher-volatility assets. The practical benefit: when markets fall, you draw from bucket one rather than selling growth assets at depressed prices. You don't need to react emotionally because you already have a structured plan.
What if I take less risk and miss out on a strong market run?
This is a real risk that doesn't get discussed enough. If you reduce your equity allocation because you feel you don't need the growth, and then markets rise 20 or 30 percent over several years, the emotional pressure to chase that return can cause investors to buy back in at much higher prices than they would have paid originally. Meghan calls this FOMO risk, and it's worth running through before you make changes. If the market keeps running and your portfolio doesn't keep pace, what would you actually do? Being honest about that in advance leads to a more realistic allocation decision.
When is the right time to buy more stocks?
In theory, the best time to buy growth assets is when they've gotten significantly cheaper, during recessions and sharp corrections. In practice, almost no one does it. Chris notes that across market downturns in 2009, 2011, 2018, 2020, and 2022, very few clients called eager to buy more stocks. The ones who did are, in hindsight, easy to identify as the ones who made the best long-term decisions. Understanding this tendency ahead of time, and building a plan that doesn't rely on making courageous decisions in the middle of a crisis, is one of the most practical things a financial advisor can help with.
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For most of your working life, the financial question is straightforward: earn more, save more, invest wisely. Then retirement arrives, and the question flips entirely. How do you turn decades of saving into a reliable paycheck that lasts as long as you do?
In this episode of Financial Commute, Morton Wealth advisors Chris Galeski and Mike sit down to tackle the retirement income questions clients ask most: the 4% rule, Social Security timing, sequence of returns risk, and the three-bucket strategy that can protect your lifestyle through any market cycle.
Questions This Episode AnswersThese are the questions people approaching and entering retirement are genuinely asking. We’ve addressed them directly below, and the full conversation is available as a transcript further down the page.
What questions should I be asking my advisor that I’m not?
The most important question isn’t about a number — it’s about the framework: what decisions today will have the biggest impact 10–20 years from now, and what am I not asking that I should be? The right advisor helps you find those blind spots before they become costly gaps.
Does the 4% rule still work today?
A useful starting point, but not a strategy. The 4% rule was designed for simplicity, not sophistication. A real plan accounts for your full picture — Social Security, pensions, annuities, taxable and tax-deferred accounts, real estate — each with different tax treatment. Think of 4% as a floor, not a ceiling, and not a substitute for personalized planning.
When should I take Social Security?
There’s no universal right answer — and regret runs both ways. Timing depends on your health, savings, and other income. Delaying to 70 maximizes your benefit, but if you’ve saved enough to invest early payments and grow them, taking it sooner can make mathematical sense. Run projections across multiple scenarios with your advisor and make the best decision with today’s information.
What is the three-bucket strategy, and why does it matter in retirement?
The bucket approach organizes assets by time horizon rather than treating everything as one pool. Bucket one is your safety net (2+ years of living expenses in low-volatility assets). Bucket two holds income-generating bonds for the medium term. Bucket three is long-term growth — equities you can leave alone through market cycles. When a recession hits, you draw from bucket one, never forced to sell growth assets at the worst possible time.
What is sequence of returns risk, and how does it affect retirement income?
The danger of major market losses early in retirement — right when you start drawing down. If your portfolio drops 30% in year one and you’re selling shares to cover expenses, you lock in losses and permanently reduce future growth potential. The bucket strategy protects against this: draw from your stable bucket in downturns and leave growth assets untouched until they recover.
Which account should I draw from first in retirement?
Order matters enormously for tax efficiency. Assess your account types (taxable brokerage, traditional IRA/401(k), Roth), your current bracket, and expected Social Security income — then “fill” each bracket optimally. Some years that means pulling extra from an IRA; others it means realizing long-term capital gains from a taxable account. There’s no single right answer — revisit it every year.
How often should I update my retirement financial plan?
At minimum, once a year — and after any major life change. Tax laws shift, markets move, and family situations evolve. An annual check-in lets you ask: does last year’s plan still fit this year’s life? Most years you won’t need dramatic changes, but small course corrections prevent big drift over time.
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Most business owners spend years, sometimes decades, building something remarkable. But when it comes time to exit, the majority aren't prepared for what happens next. According to research from the Exit Planning Institute, 75% of business owners regret selling their business within the first year.
In this episode of Financial Commute, Wealth Advisor Joe Seetoo sits down with host Chris to walk through the exit planning framework Morton Wealth uses with business-owner clients, from protecting against the Five D's to building transferable enterprise value and knowing who you'll be on the Monday after closing day.
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Giving money to your children is one of the most generous things a parent can do. It’s also one of the most consequential. And the consequences aren’t always the ones you planned for.
In this episode of Couchside Conversations, Stacey McKinnon and Chris Galeski walk through what actually happens when families transfer wealth without a plan, the five mistakes they see most often, and what it looks like when families get it right.
Tune in if you're thinking about...
Whether you can afford to give and how much is actually safe to gift right nowWhat happens when you treat children equally instead of equitablyHow to give without quietly creating dependency or resentmentWhether to tell your kids what they'll eventually receive, and whenWhether the real risk is the money itself, or the silence around itTo watch this episode or read the transcript, visit our website here.
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Markets don’t move in straight lines, and the first quarter of 2026 was a perfect reminder of that. Between geopolitical conflict, rising oil prices, and renewed inflation concerns, investors faced a volatile environment that left markets unsettled.
In this episode, Chief Executive Officer Jeff Sarti and Chief Investment Officer Meghan Pinchuk break down Q1, exploring consumer sentiment, why traditional diversification didn’t behave as expected, and how different asset classes responded during this period of uncertainty. The conversation highlights a key theme: resilience doesn’t come from predicting markets. It comes from preparing for multiple outcomes.
Tune in if you’re interested in…
What drove market volatility in Q1 2026Why we remain confident in gold despite short-term volatilityHow stocks, bonds, and alternative assets behaved differentlyWhy traditional bonds didn’t provide a safe havenWhat stagflation is and how it impacts portfoliosHow Morton’s approach to diversification made clients resilient during this period of volatility -
About 54% of teenagers are worried about financing their futures. How can parents help their adolescents gain financial confidence and responsibility, especially in a world where money is invisible and gratification is immediate?
Join host Chris and Wealth Advisor Patrice Bening, a mom of two young adults, as they discuss various conversations and principles to implement with your kids as they grow an understanding of money and how to use it.If you’re interested in learning about…
The importance of starting early when instilling money habits.Giving money a purpose through simple frameworks (like 50/30/20) to plan before it’s spent.Making currency "feel real" in a digital world by allowing your kids to see the exchange of cash Encouraging adolescents to make the most of their biggest asset: time. Even small amounts grow meaningfully when you start early and stay consistent.Modeling behavior for your teens. Kids learn more from what you do than what you say -
What if you could give more to charity and pay less in taxes? In this episode, host Chris invites Wealth Advisor Austin Overholt to explore how strategies like donor-advised funds and qualified charitable distributions can help you give more intentionally while potentially reducing taxes. From donating appreciated stock to planning around high-income years, they highlight how thoughtful giving can align with retirement, estate planning, and long-term legacy goals.
Tune in if you're interested in…
Tax-efficient ways to give, including donor-advised funds and QCDsWhen to use different strategies based on age, income, and account typesHow to maximize deductions in high-income yearsThe benefits of “bunching” donations for greater tax impactUsing charitable giving to create a lasting family legacy -
In today’s increasingly digital world, cybersecurity is more important than ever and often comes down to simple habits. In this conversation, Adam Moseley and Patrick Hennessey of Charles Schwab share practical, real-world strategies to help individuals protect themselves from evolving cyber threats.
Key takeaways:
Best practices when it comes to email, passwords, Wi-Fi, VPNs, and moreThe rise of AI-powered scams and social engineering tacticsThe importance of regularly updating devices and softwareThe growing sophistication of global cybercrime operations -
Retirement isn’t just a financial transition. It’s a psychological one. In this episode, host Chris and Wealth Advisor Priscilla Brehm explore what it means to shift from earning a paycheck to living off your wealth, and why this transition can feel more challenging than expected. They break down the four phases of financial life (survival, accumulation, preservation, and distribution) and focus on the often-overlooked shift into retirement.
Tune in if you’re interested in…
The four seasons of financial life and why the transition to retirement can be so difficultHow to replace your paycheck and create confidence in retirement incomeWhy mindset matters just as much as math when leaving the workforceThe concept of ikigai and how to find purpose in retirementHow to avoid common pitfalls like over-monitoring your portfolio or underspendingHow thoughtful planning can help you enjoy your wealth -
Is paying off your mortgage always the smartest financial move? Not necessarily. In this conversation, host Chris invites Wealth Advisor Ian Rennick to challenge one of the most common assumptions in financial planning: that being debt-free is always the goal. They explore the trade-offs between aggressively paying down a mortgage and maintaining liquidity, highlighting how excessive home equity can leave retirees “house rich but cash poor.” The key takeaway: financial freedom is about having options.
Tune in if you’re interested in…
Whether paying off your mortgage should be a priority before retirementWhat it means to be “house rich but cash poor”The tradeoffs between home equity and accessible liquidityHow debt can sometimes be a strategic tool, not just a liabilityWhy having multiple “buckets” of money creates more flexibilityReal examples of how financial decisions can impact long-term goals -
Paying taxes now to save later may sound counterintuitive, but for many investors, it can be a powerful strategy. In this conversation, Kevin and Chris break down Roth conversions: what they are, when they make sense, and how they can create more control over your financial future. By converting pre-tax retirement dollars into a Roth IRA, investors can pay taxes today in exchange for tax-free growth and withdrawals later.
Tune in if you’re interested in…
What a Roth conversion is and why it can create long-term tax flexibilityHow required minimum distributions (RMDs) can increase future tax burdensWhy timing, tax brackets, and life events (like retirement or losing a spouse) matterHow recent tax law changes impact Roth conversion strategiesThe importance of having “buckets of money” for flexibility in retirementWhen Roth conversions may benefit your heirs under new inheritance rules -
From geopolitical tensions to surging energy prices, investors are navigating a wave of uncertainty and volatility. Join Chief Investment Officer Meghan Pinchuk and Managing Director of Investments Sasan Faiz as they break down how recent global events are influencing markets and what they could mean for the economy and portfolios.
Tune in if you’re interested in…
How geopolitical tensions are influencing global energy marketsWhy rising oil prices could trigger stagflation risksThe potential ripple effects on inflation, interest rates, and consumer spendingWhy stocks and bonds can struggle during inflationary periodsHow true diversification, including alternatives and gold, can help navigate uncertainty -
Does a financial advisor’s experience matter more than their perspective? Or is the real strength found in combining both?
In this thoughtful conversation, host Chris Galeski and Executive Vice President Eric Selter explore the value different generations of advisors bring to client relationships and why age alone doesn’t define wisdom. While life experience offers perspective that can only be earned over time, younger advisors contribute deep technical knowledge, fresh thinking, and tech fluency. Together, they share that Morton’s true strength lies in its team-based approach.
Tune in if you’re interested in…
Why a multi-generational advisory team can strengthen client outcomesThe importance of mentorship and collaboration behind the scenesWhether AI can truly replace human financial advice - Mehr anzeigen
