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As I write this, we're wrapping up one of the busiest stretches of the year in the tax world. September 15 marks the deadline for extended corporate and partnership tax returns, while October 15 is the due date for extended individual tax returns. For many people, these deadlines pass without much notice. For our higher-net-worth and family office clients, however, this season involves months of gathering information, reviewing strategies, coordinating with multiple professionals, and ensuring every opportunity is properly captured. In truth, much of my time since July has been devoted to helping clients navigate this process. The work can be complex, but it's also when some of the most valuable planning opportunities are uncovered. As we move toward year-end, here are a few items worth reviewing for yourself and your family. Don't Miss the New Above-the-Line Charitable Deduction One of the more attractive provisions in the One Big Beautiful Bill (OBBB) is the ability to claim up to $2,000 of charitable contributions as an above-the-line deduction. There is an important catch: the gift must be made in cash directly to a qualified charity. Contributions made through a Donor Advised Fund (DAF) do not qualify for this particular deduction. My personal approach is simple. I plan to make this gift early in the year, check the box, and then handle the remainder of my charitable giving through my Donor Advised Fund. If charitable giving is already part of your financial plan, make sure you're structuring gifts in a way that captures every deduction available. Consider Using a Donor Advised Fund for Appreciated Investments While a Donor Advised Fund may not qualify for the new above-the-line deduction, it remains one of the most powerful charitable planning tools available. If you own appreciated stocks, ETFs, mutual funds, or certain private investments, you may be able to contribute those assets directly to a DAF. Doing so can allow you to:
I personally used this strategy in 2026 after two private investments became publicly traded. Rather than sell and incur capital gains taxes, I contributed a portion of the appreciated shares to my Donor Advised Fund and used those funds for future charitable giving. For charitable individuals and families, this can be one of the most tax-efficient giving strategies available. Has Your Income Declined? It May Be a Great Time to Look at a Roth Conversion Many people assume Roth conversions are only for retirees, but some of the best opportunities arise when income temporarily declines. Examples include:
A Roth conversion allows you to voluntarily pay tax today at your current tax rate and move assets into a Roth IRA where future qualified withdrawals can be tax-free. In addition, Roth IRAs are not subject to Required Minimum Distributions (RMDs) during your lifetime. This can help provide greater control over future taxable income and potentially reduce the likelihood of being pushed into higher tax brackets later in retirement. Every situation is different, but for the right individual, a Roth conversion can be one of the most valuable long-term planning opportunities available. If you've experienced a change in income this year, it may be worth running the numbers. Don't Forget the Age 65+ Deduction One of the simplest planning opportunities is often the easiest to overlook. If you are age 65 or older, be sure you're taking advantage of the additional deduction available to seniors. We've already identified several situations where clients were unaware of how the deduction applied to their circumstances. A quick review with your tax professional can ensure you're receiving the full benefit. A Better Home for Cash? One final idea that is not tax related. For years, we've watched many investors leave substantial cash balances sitting in bank accounts earning little to no interest. While rates have improved from the lows of recent years, the average bank continues to pay far less than many available alternatives. That is one reason we've begun offering cash management solutions to clients. These programs are designed to provide flexibility, liquidity, and potentially higher yields than traditional checking and savings accounts. Current minimums begin at $25,000, and we're rolling out several options to accommodate different client objectives. This is a newer offering for our firm, and you'll be hearing more about it in the months ahead. Final Thoughts Tax planning isn't something that happens only during tax season. In many cases, the most valuable opportunities are identified long before a return is filed. Whether it's maximizing charitable deductions, utilizing a Donor Advised Fund, exploring a Roth conversion, capturing new deductions available under current law, or simply earning a more competitive return on cash, a little planning today can often produce meaningful results tomorrow. If you'd like to discuss any of these strategies and whether they fit your situation, we'd be happy to help. The best tax return is often the one that started with good planning months before it was filed. Important Disclosure: The information contained in this article is for educational purposes only and is not intended as personalized tax, legal, or investment advice. The effectiveness of any tax or financial planning strategy depends on an individual's specific circumstances. Before taking action, consult with your tax advisor, CPA, attorney, or other qualified professional regarding your personal situation. InTrust Advisors does not provide legal or accounting services.
Tax laws and regulations are subject to change and interpretation.
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Have you noticed this lately (well really since Covid)? It seems like everywhere you go someone is asking for a tip.
I understand tipping servers at a sit-down restaurant. They provide service, check on your meal, refill your drink, and help create a positive dining experience. But recently, it feels like the tip screen has become the main event. Buy a coffee? Tip. Pick up a sandwich? Tip. Purchase something at a counter? Tip. Grab carryout? Tip. This week, I stopped for lunch and when it came time to pay, the terminal was spun around toward me. The suggested tip options were 25%, 30%, and "Other." Thirty percent! I found myself wondering when 15% became 20%, when 20% became 25%, and when 25% became the new normal. Then another thought hit me. What if I simply ordered carryout instead (being the cheap skate that I am)? What would all those tips add up to if invested rather than spent? The Six-Figure Tip Jar According to recent consumer spending data, Americans spend a significant portion of their food budget dining away from home, including restaurants, takeout, coffee shops, and delivery services. Americans now spend more on food away from home than groceries in many cases. [escoffier.edu], [ers.usda.gov] Let's keep the math simple. Assume you spend $100 per week eating out. Now assume you leave a 20% tip. That means you're spending:
At first glance, $20 doesn't seem like much. But what if, instead of spending that money, you invested it? Assume you invested $1,040 annually into a low-cost index fund and earned an average return of 8% per year. After 30 years, that account could grow to approximately: $117,815 Let that sink in for a moment. Not from finding the next hot stock. Not from timing the market. Not from taking excessive risk. Just by redirecting one small weekly spending habit and allowing compounding to do what compounding does best. The Real Lesson Isn't About Tipping Before anyone sends me an angry email, this article is not really about tipping. Tip generously when appropriate. Support hardworking people. Be kind. The lesson is bigger than that. The lesson is that small decisions made repeatedly over long periods of time can produce remarkable results. Most people dramatically overestimate what they can accomplish in a year and underestimate what they can accomplish in thirty. We tend to focus on the big wins:
What Else Could Become a Six-Figure Decision? The interesting thing is that dining habits are only one example. Lawn Service Suppose you pay someone $150 per month to cut your lawn. That's $1,800 annually. Invested at 8% for 30 years, that annual amount could grow to nearly $204,000. Valet Parking Choosing valet parking over self-parking might cost an additional $15 each week. That's approximately $780 annually. Invested for 30 years at 8%, that could become roughly $88,000. The Daily Coffee Run Let's say your Starbucks habit costs $6 per day, five days per week. That's about $1,560 annually. Invested for 30 years at 8%, it could grow to approximately $177,000. Suddenly that latte looks a little different. Now, am I suggesting everyone mow their own lawn, park three blocks away, and swear off coffee forever? Absolutely not. Life is meant to be enjoyed. The point is not deprivation. The point is awareness. The Power Isn't in the Savings. It's in the Discipline (and in some cases accountability). Here's the uncomfortable truth. Most people already know how to save money. The challenge isn't knowledge. It's discipline. We know we should:
Yet we often allow convenience and impulse to win. The irony is that lasting wealth is usually built through dozens of small, boring, repeatable decisions rather than one brilliant financial move. Wealth creation often looks a lot like brushing your teeth. Not exciting. Not glamorous. Just consistent. Day after day. Year after year. Decade after decade. What Are Your "Little Things"?
The important question isn't, "Where can I cut spending?" The important question is: "If I redirected just a few small habits toward my future self, what could that become over time?" The answer might surprise you. Ready to Discover Your Biggest Opportunities? Most people cannot see the opportunities hiding in their own financial lives. That's exactly why we created our Strategy Session. In a 45-minute session, we'll help you identify planning opportunities, uncover blind spots, and show you where small adjustments today could create meaningful results in the years ahead. As we often tell clients, financial success is rarely about finding a magic bullet. It's about making smarter decisions consistently and letting time do the heavy lifting. If you'd like a fresh perspective on your finances, schedule your session today: 👉 Schedule Your Financial Strategy Session Because sometimes the difference between where you are and where you want to be is nothing more than a few small habits repeated over a very long time. My wife and I were recently planning our day around the weather. Living in Florida, that usually means paying attention to when—not if—the rain will arrive. The funny thing is that we're currently experiencing one of the driest stretches we've seen in what is supposed to be our rainy season. That particular morning, the weather app showed a 45% chance of rain. As the day progressed, however, the forecast kept changing. Forty-five percent became thirty. Thirty became twenty-five. Eventually, the chance of rain dropped all the way to zero. Needless to say, it was disappointing as we had planned our day around a strong chance of rain and doing indoor activities. But it also got me thinking. If meteorologists with satellites, radar systems, supercomputers, and an enormous amount of historical data struggle to predict the weather accurately from one day to the next, how much harder must it be to predict what the stock market will do next? The answer is: much harder. At least weather follows the laws of physics. Markets, on the other hand, are driven by human beings. The Good Old Days Weren't Necessarily Easier—Just Simpler I have to admit that there was a time when forecasting market direction seemed more straightforward. Investors could focus on fundamentals like earnings, economic growth, interest rates, and valuations. Those factors still matter, but their influence has become increasingly obscured by forces that barely existed a generation ago. The result is a market environment that often appears disconnected from traditional valuation measures and economic reality. Here are four reasons why. 1. Politics Has Become a Market Force Markets have always reacted to politics, but today politics often seems designed to influence markets. Both political parties understand that voters pay attention to their retirement accounts, investment portfolios, and economic confidence. Strong stock market performance can create a sense of prosperity, even when many underlying economic indicators are mixed. Governments can influence investor sentiment through fiscal spending, tax policy, regulatory changes, trade policy, and public messaging. The result is that market participants must not only forecast corporate earnings and economic conditions but also predict how political leaders will respond to those conditions. That adds an entirely new layer of uncertainty. Political incentives don't always align with economic fundamentals. Sometimes policy decisions can temporarily boost markets while creating longer-term consequences that are harder to see in real time. 2. Passive Investing Has Changed Price Discovery In last month's article, I discussed the explosive growth of passive investing through index funds and retirement plans. See the Robots are Coming! This trend has fundamentally altered how capital flows into markets. According to data from Morningstar and the Investment Company Institute (ICI), passive strategies now hold a larger share of U.S. fund assets than actively managed strategies. Every payday, millions of workers automatically direct money into 401(k) plans that then flow into index funds regardless of valuation. The process is largely automatic. A company's stock may receive substantial buying pressure not because investors have concluded it is undervalued, but simply because it is included in a major index and receives a proportionate share of incoming funds. This can reduce the market's ability to accurately reflect fair value. Traditional valuation metrics such as price-to-earnings ratios, dividend yields, or book values still provide useful information, but they often appear less influential than they were decades ago. When massive quantities of money are invested automatically, market prices can remain disconnected from fundamental value for much longer periods than investors expect. 3. Central Bank Liquidity Matters More Than Many Realize If there is one lesson investors have learned over the past two decades, it is that liquidity matters. A great deal. Following the financial crisis of 2008 and again during the pandemic, central banks around the world injected extraordinary amounts of liquidity into financial systems. Researchers at the Bank for International Settlements (BIS), the Federal Reserve, and other institutions have documented how liquidity conditions can significantly affect asset prices. When money is abundant, investors tend to take more risk. Stocks, bonds, real estate, and alternative assets often rise together. When liquidity contracts, the opposite can happen. This has led many market professionals to focus less on traditional economic indicators and more on questions such as:
Markets today often react as much—or more—to liquidity conditions than they do to earnings growth or valuation levels. That makes forecasting significantly more complicated because liquidity itself is influenced by monetary policy, government borrowing, banking activity, and international capital flows. 4. Speculation Has Become Mainstream Perhaps the biggest change of all is the sheer number of participants now involved in financial markets. Technology has dramatically lowered the barriers to entry. Trading apps, social media, financial podcasts, online influencers, and twenty-four-hour financial news networks have brought investing into everyday life. This democratization of investing has many benefits. More people have access to wealth-building opportunities than ever before. However, it has also increased speculative behavior. Entire market narratives can emerge and spread globally within hours. Trending stocks can attract massive inflows of capital regardless of business fundamentals. Meme stocks, cryptocurrency booms, options speculation, and social-media-driven trading all demonstrate how investor psychology can exert an outsized influence on prices. Human behavior has always mattered in markets. Today, it travels at the speed of the internet. What This Means for Investors None of this means investing is impossible. Far from it. History suggests that disciplined investors who stay focused on long-term objectives generally have better outcomes than those who constantly react to headlines. However, it does mean that forecasting markets may be more difficult today than at any point in modern history. Investors are trying to predict the interaction of political incentives, passive investment flows, central bank liquidity, economic data, corporate earnings, technological disruption, and human psychology, all at the same time. That is an incredibly complex puzzle. Which brings me back to the weather. The meteorologists weren't wrong because they lacked intelligence, experience, or sophisticated tools. They were trying to predict a complex system influenced by countless variables. The stock market is no different. Except instead of clouds and wind patterns, we're dealing with governments, central banks, corporate executives, institutional investors, algorithms, and millions of individual market participants all making decisions simultaneously. If forecasting the weather is difficult, forecasting the stock market may be nearly impossible. Why Professional Oversight Matters This is precisely why investors need someone actively supervising their investments.
Not because anyone can consistently predict the future, but because someone should be monitoring changing conditions, evaluating risks, and making adjustments when circumstances warrant. Sometimes that means tactically rotating among sectors or asset classes. Sometimes it means reducing risk exposure. And sometimes it may even mean raising significant cash positions when conditions become especially challenging. Our view is that forecasting markets is not going to get easier from here. In fact, it may become even more difficult as investors potentially face a future characterized by lower long-term returns and higher volatility than what many experienced during the extraordinary bull market of the past decade. In an environment like that, disciplined portfolio management becomes more important—not less. If you'd like a second set of eyes on your portfolio, we'd be happy to help. Why not get a complimentary second opinion on your investments? After all, while no one can control the weather or perfectly predict the markets, you can control how prepared you are for whatever comes next. A few weeks ago, I spoke with a client whose son had just graduated from a solid university with a business degree. Good student. Hard worker. The kind of person who, ten years ago, would have had multiple offers before graduation.
Today? Crickets. Not because he isn’t capable but because companies are hesitating. They’re hiring more slowly. They’re experimenting with AI tools. They’re asking, quietly: “Can we do more with fewer people?” You’ve probably heard the same narrative: robots and AI are coming for our jobs. At InTrust, we see it differently. We don’t believe they’re here to take our jobs. We believe they’re here to make us dramatically more productive. The unanswered question is what happens next. Do we simply produce more with the same number of workers? Or does it ultimately require fewer workers? Or perhaps it gives us more time, more flexibility, more space for life outside of work? That part hasn’t been sorted out yet. But one thing is already becoming clear: the transition is creating friction, especially in white-collar job markets. And that friction may have ripple effects well beyond employment, including in the financial markets themselves. For decades, markets have quietly relied on a very simple, very powerful engine: People worked. They got paid. They saved. And those savings flowed—automatically—into the market. It didn’t require forecasts or conviction. It just happened every two weeks through 401(k) contributions. That steady, invisible current helped lift markets in ways most investors barely noticed. Now, consider what changes when that system begins to shift. Robots don’t contribute to retirement plans. They don’t defer income. They don’t dollar-cost-average into equity funds. As automation grows, even gradually, the long-term effect may simply be less organic buying pressure. At the same time, the largest generation in history is moving into a different phase of life. Baby Boomers are no longer primarily saving; they’re beginning to spend. Required distributions are increasing. Income needs are real. And over time, what was once a tailwind, steady inflows, begins to tilt the other direction. Layer on top of that a slowing hiring environment. If employment growth softens, or declines, the effect isn’t just economic. It’s behavioral. Fewer workers mean fewer contributors. Financial pressure leads to 401(k) loans or withdrawals. The same pipeline that fed the market can quietly begin to drain it. None of this happens overnight. But markets often turn not on dramatic events, but on gradual shifts in direction. There’s another structural change worth paying attention to. Today, a large portion of market activity is driven by passive investing where money flows into index funds without regard to valuation. It’s been a tremendous innovation. Lower costs. Simplicity. Broad access. But it also changes the way money moves. Flows increasingly go where weight already exists. The biggest companies receive the most capital not necessarily because they’re the most attractive, but because they’re the largest. It becomes a self-reinforcing system. And as some, like Mike Green of Simplify Investments, have pointed out, there is a reasonable question of whether that system becomes less stable as it grows. If too much money moves without regard to price, markets can begin to lose some of their natural balance. Again, not a prediction of failure, but a recognition that structure matters. And structure cuts both ways. Because if inflows slow or reverse, the same mechanism that lifted large-cap stocks can work in the opposite direction. Cap-weighted indexes, by design, concentrate exposure in the biggest names. That means when money leaves, it tends to hit those same names hardest. The unwind, if it happens, is rarely as smooth as the build. So, what do we do with all of this? This isn’t a call to panic. Markets are resilient. Innovation is real. And long-term investing still works. But it is a reminder that the backdrop may be changing. The last few decades benefited from a powerful combination: strong demographics, consistent inflows, and expanding participation. If those tailwinds soften, markets may feel a bit less forgiving and a bit more dependent on how you invest—not just where you invest. That’s where a more active, tactical approach can begin to make sense—not as a constant reaction to noise, but as a disciplined process for navigating a more complex environment.
The robots are coming. That part is true. But the real story, the one investors should care about, is what happens to the flow of money around them. That’s where the next challenges—and opportunities—are likely to be found. If you’d like a clear, objective look at your current portfolio through this lens, we’d be happy to provide a Free Second Opinion - InTrust Advisors. Get started today! Love him or hate him (and his obsession with naming things after himself), there is a new type of investment account that is coming soon called a “Trump Account” or “TA” (based on Section 530A). You may start hearing about it, especially for kids and young families. But just because something is new does not mean it is right for everyone. Here is a simple way to think about when it may — and may not — make sense. The Basics - What Is a Trump Account? At its core, a Trump Account is:
In simple terms: It is a long-term investment account designed to give children a financial head start. When It Makes Sense A TA works best in a few simple situations. First, if you’re getting free money, it’s usually worth it. Some accounts may receive a $1,000 government contribution or other outside funding. That’s hard to pass up. Second, it can make sense if you want to start saving early for a child and let the money grow for a long time. Third, it’s a good fit if your own financial plan is already in good shape—you’re saving for retirement, have reserves, and have covered major goals, such as college savings for your children. When It Does Not Make Sense A Trump Account has some clear limits. You can’t access the money before age 18, and even after that, there may be taxes or penalties depending on how it’s used. It may also not make sense if you are still working on your own finances. In most cases, your retirement and stability should come first. Finally, there are often better options for specific goals, like 529 plans for college or Roth IRAs for working teens. Bottom Line A Trump Account is best viewed as a nice extra, not a core strategy. If you’re getting free money and already have your plan in place, it’s worth considering. If not, you’re probably better off sticking with more flexible and proven options unless you have exhausted all other ways to save and defer taxes. Have questions? Why not schedule a Strategy Session. Click here to find out more. |