Can Apple Update the 16-Year-Old Siri? The Housing Market Finally Looking Normal Again, Inflation at Three Year High But the Details Differ, How Long Will the AI Buildout Last? Dealing with Basis in an IRA & More

Can Apple Update the 16-Year-Old Siri?

This week marked Apple's annual Worldwide Developers Conference (WWDC) in Cupertino, California. One of the biggest storylines is Apple's effort to reinvent Siri, which many users now view as one of the least capable AI assistants on the market.

The anticipation surrounding a revamped Siri may be one reason Apple stock has recently moved higher, along with growing investor enthusiasm around artificial intelligence. However, it was only two years ago that Apple promised a smarter Siri capable of interacting with messages and apps while understanding what was displayed on a user's screen. Those features never materialized as advertised, leading to criticism and a class-action lawsuit settlement.

Meanwhile, OpenAI has hired Apple's former design chief, Jony Ive to help develop a new AI-focused hardware device. OpenAI also explored an App Store strategy last fall, though results so far have been underwhelming.

Apple's advantage remains its enormous installed base. Roughly 1.5 billion people around the world use an iPhone. After struggling to deliver its own next-generation Siri, Apple has reportedly turned to Google's Gemini technology to help power some of its AI capabilities. That decision could be viewed as an admission that Apple's internal teams were unable to develop a competitive solution on their own.

Financial terms of the arrangement have not been disclosed, but Apple will likely be paying Google a significant amount for access to its technology. The new Siri is expected to offer a more modern search experience, remember past interactions, and access data on a user's device to provide more personalized responses. There are also reports that Apple may eventually offer a premium Siri subscription to compete with other AI services. Whether consumers will be willing to pay for such a service remains an open question, especially given the disappointing reception of Microsoft's Copilot subscription offerings.

The weeks and months ahead should provide a clearer picture of how consumers respond to the new Siri. If Apple finally delivers an AI assistant that users find genuinely useful, it could create a meaningful boost to revenue, profits, and investor sentiment. If the rollout disappoints, Apple stock may simply tread water. In a worst-case scenario, shares could decline significantly, as many investors view AI as Apple's next major growth opportunity.

The Housing Market Is Finally Starting to Look Normal Again

For the last several years, the housing market has felt anything but normal. Ultra-low mortgage rates, limited inventory, bidding wars, and rapidly rising home prices created an environment that left many buyers frustrated and many sellers expecting unrealistic prices.

However, recent data suggests that the market may finally be moving back toward a healthier balance. Existing home sales surged 3.2% in May both on a monthly and an annual basis. This was the best pace since December. While one month does not make a trend, it is another sign that both buyers and sellers are beginning to adjust to the realities of today's market. Transactions are increasing, inventory is improving, and the extreme conditions that defined the post-pandemic housing boom continue to fade.

One of the most encouraging developments is the increase in housing inventory. It rose 3.3% month to month and at the current sales pace there is a 4.5-month supply. For years, the biggest challenge facing buyers was simply finding a home to purchase. The shortage of available homes created fierce competition, often leading to multiple offers, waived contingencies, and homes selling far above asking price. Today, more homes are coming onto the market, giving buyers more choices and reducing some of the pressure that has dominated the market since 2020.

At the same time, sellers are beginning to face a market that is far different from the one they enjoyed a few years ago. During the height of the housing boom, many homeowners could list a property and expect immediate offers. Today's buyers are more price-sensitive, mortgage rates remain significantly higher than pandemic-era lows, and overpriced homes are often sitting on the market longer. Homes stayed on the market an average of 29 days. This was down from 32 in April, but up from 27 last May. As a result, sellers are becoming more realistic with pricing and negotiations.

Importantly, this shift does not necessarily indicate a housing crash. In fact, home prices have remained relatively stable in many parts of the country. Instead, what appears to be happening is a transition from an overheated market to a more sustainable one. Price appreciation has slowed with the median price rising just 1.3% from the year prior, but demand remains supported by a strong labor market.

Another positive sign is the increasing participation of first-time homebuyers. The group made up 35% of sales, which was an increase from 33% in April and 30% the year before. During the frenzy of recent years, many first-time buyers were effectively priced out of the market. Rising inventory and a more balanced negotiating environment are creating opportunities for these buyers to re-enter the market and compete more effectively.

For prospective homeowners, this may be the most favorable environment seen in several years. Buyers have more time to make decisions, more inventory to choose from, and greater leverage in negotiations. Sellers can still achieve strong prices for well-maintained and appropriately priced homes, but they must adapt to a market where buyers have alternatives.

The housing market works best when neither buyers nor sellers hold all the leverage. The latest data suggests we may finally be moving back toward that equilibrium. While challenges remain, including affordability concerns, a more balanced market is ultimately healthier for homeowners, buyers, lenders, and the broader economy. Though it remains challenged, affordability has improved as income gains have been outpacing home price growth. Mortgage rates have also improved from last year but be careful hoping for much more of a decline as they are essentially at the historical average according to the chief economist at the National Association of Realtors, Lawrence Yun.

After years of extremes, the return of a more normal housing market may be one of the most encouraging economic developments of 2026.

Inflation Hits a Three-Year High, But the Details Tell a Different Story

The latest Consumer Price Index (CPI) report showed inflation rising 4.2% year-over-year, the highest reading since April 2023. At first glance, that sounds concerning. But a deeper look shows that the inflation story is being driven largely by a handful of categories, especially energy and travel.

The biggest culprit is energy. Energy prices rose 23.5% from a year ago, while gasoline prices surged 40.5% year-over-year. In fact, energy accounted for more than 60% of the monthly increase in CPI, meaning most of the headline inflation acceleration can be traced directly to higher fuel costs.

Airline fares were another major contributor, climbing more than 26% from a year ago as higher jet fuel costs worked their way through the travel industry.

However, many of the categories that tend to reflect underlying inflation pressures remain far more subdued.

Core inflation, which excludes food and energy, rose 2.9% year-over-year, significantly below the 4.2% headline figure. On a monthly basis, core inflation increased just 0.2%, suggesting that broad inflation pressures remain relatively contained.

Housing costs continue to moderate as well. Shelter inflation is running around 3.4% year-over-year, well below the pace seen during the post-pandemic inflation surge. Food prices increased 3.1% year-over-year, a level that is much more manageable than the double-digit increases consumers experienced a few years ago. Food at home was even more manageable with an annual gain of 2.7%. This compares to food away from home which climbed 3.5%.

Vehicle-related costs tell an especially interesting story. While many consumers still feel that cars are expensive, new vehicle prices saw an increase of just 0.2% compared to last year and used cars and trucks actually fell 2%. Used vehicle prices have remained relatively stable compared to the dramatic swings seen in recent years. The largest area of vehicle inflation is not the vehicle itself but maintaining it, as motor vehicle repair and maintenance costs were up 6.1% year-over-year. Auto insurance still climbed 6.1% versus last year, but costs fell 1.7% during the month, and I believe there will be less pressure ahead.

If oil prices stabilize and gasoline prices retreat from recent highs, the inflation picture could improve considerably as we move through the second half of the year. With core inflation still below 3%, housing inflation moderating, vehicle prices largely stable, and several consumer categories showing only modest increases, there is a reasonable case that inflation could cool meaningfully by year-end.

As investors, it's important to look beyond the headline number. While 4.2% inflation grabs attention, the underlying data suggests the economy is experiencing an energy shock more than a broad-based inflation resurgence.

How long will the AI buildout cycle really last?

The market has rewarded virtually every company connected to AI infrastructure. Chip manufacturers, networking companies, power providers, cooling suppliers, data center REITs, and cloud providers have all benefited from an unprecedented surge in spending. But history tells us that every capital spending boom eventually slows.

Oracle reported strong growth and rising demand for AI infrastructure, but investors focused on the cost of expansion. Capital expenditures rose to about $55.7 billion in fiscal 2026 and could reach $70 billion next year as the company builds more AI capacity. Free cash flow turned negative at $23.7 billion over the past year, pushing Oracle to raise additional capital. The company is planning to secure another $40 billion through debt and equity, following prior raises of $43 billion in debt and $5 billion in equity.

The markets reaction was telling. Investors weren't questioning AI demand today. They were questioning what happens if demand growth slows tomorrow. When a company is spending tens of billions of dollars before the revenue arrives, the margin for error becomes much smaller. If utilization rates disappoint, projects get delayed, or customers slow their purchases, the economics can change quickly.

The technology is real and will likely transform countless industries. The question is whether current spending levels are sustainable indefinitely. Many investors appear to be assuming that AI infrastructure spending will continue growing at today's pace for years. Yet capital spending cycles have always been cyclical.

As AI spending eventually normalizes, investors may discover that some companies built durable cash-generating businesses while others simply benefited from a temporary surge in capital expenditures.

Financial Planning: Dealing with Basis in an IRA

Generally, contributions to a traditional IRA are most beneficial when they are tax-deductible or when they are part of a backdoor Roth strategy. Tax-deductible contributions can only be made when income is below certain limits, resulting in non-deductible contributions when made by higher earners.  This provides no current tax deduction, and any future earnings will be taxed upon withdrawal. As a result, these contributions create tax inefficiencies and long-term administrative burdens.

The after-tax basis must be tracked every year for the life of the account, even if it is inherited decades in the future. IRA distributions are subject to the pro-rata rule, meaning each withdrawal consists of a taxable and non-taxable portion based on the ratio of basis to total IRA assets. The remaining basis must then be recalculated after each withdrawal. If possible, basis in an IRA should be avoided. For individuals who already have basis in an IRA, there is a workaround if they have a 401(k). 401(k)s may accept only the pre-tax portion of an IRA as a rollover, leaving the after-tax basis behind in the IRA. This remaining basis can then converted to a Roth IRA tax-free. This strategy eliminates future basis tracking and allows future growth to occur tax free in a Roth IRA.

Why Are Insurance Companies Not Paying on Your Claims?

If you look only at the data, it may appear that insurance companies are cheating customers by paying fewer claims. The numbers do show that fewer claims are being paid, but there are several reasons behind that trend.

One major factor is the increasing cost of insurance. To keep premiums affordable, many people, including myself, have chosen higher deductibles in exchange for lower monthly premiums. For example, if you have a $10,000 deductible and suffer $7,000 in damage, your claim will not result in a payout because the loss falls below your deductible.

It is also important to read and understand your insurance policy. Most people do not study their policies in detail and simply assume they will be covered for any loss. However, coverage varies significantly from policy to policy, and understanding what is and is not covered can prevent unpleasant surprises when a claim is filed.

Insurance companies are also looking for ways to control costs and keep premiums from rising even further. In some cases, they may determine that a repair is sufficient rather than approving a full replacement, such as for a damaged roof. While this can be frustrating for policyholders, insurers argue that these decisions help manage overall claim costs.

Consumers should also be cautious when purchasing policies with unusually low premiums. There is often a reason a policy is less expensive than others, and it may involve reduced coverage, higher deductibles, or additional exclusions. Shopping around for competitive rates is a good idea, but it is equally important to understand exactly what you are buying.

Personally, I believe higher deductibles can be a smart financial decision for many people, provided they are prepared to cover smaller losses out of pocket. Over time, this approach can help keep insurance costs lower because fewer small claims are submitted, reducing the pressure on insurers to raise premiums.

Insurance is ultimately about protecting yourself from significant financial losses. The key is finding the right balance between affordable premiums, reasonable deductibles, and adequate coverage for your specific needs.

The Hidden Retirement Risk: Spending Too Little

When most people think about retirement, their biggest fear is running out of money. As a result, many retirees become extremely cautious with their spending, often withdrawing far less than they could safely afford.

A recent CNBC article highlighted a surprising reality: many retirees are actually underspending their retirement savings. Studies show that a significant percentage of retirees reach their 80s with as much or even more than they had when they first retired. The fear of running out of money can prevent people from enjoying the retirement they worked decades to build.

The goal of retirement planning is not simply to die with the largest account balance possible. It is to create a lifestyle that allows you to enjoy your retirement years while maintaining financial security and, if desired, leaving a legacy for your family.

At our firm, we have found that when a portfolio is properly managed with a long-term perspective, a distribution rate of 6% can often provide a reasonable balance between enjoying retirement today and preserving assets for future generations. Every situation is unique, but many retirees can comfortably spend more than they think without jeopardizing their long-term financial goals. The key to this assumption though is the assets must be invested properly!

Retirement should be about more than just protecting your nest egg. It should also be about using the resources you've accumulated to travel, spend time with family, support causes you care about, and create meaningful experiences. The challenge is finding the right balance between enjoying your wealth and preserving it. Outside of running out of money, the greatest retirement mistake may be never allowing yourself to enjoy what you've spent a lifetime building.

This Year’s World Cup Will Be the Biggest Ever. Will You Be Watching?

It has taken some time, but soccer has finally earned its place among the major sports in the United States.

Back in the 1990s, you rarely heard much about soccer unless your children were playing on a local team. It was primarily a youth sport, and I always felt that when those kids grew up, soccer would become much more popular in America. That prediction appears to be coming true.

People my age who grew up in the 1960s and 1970s generally didn’t play organized soccer, or much soccer at all, so there wasn’t much interest in the sport beyond watching our kids participate. Today's younger generations are different. Many grew up playing soccer and following international leagues, creating a much larger fan base than ever before.

The 2026 FIFA World Cup will be the largest in history, featuring 48 teams and 104 matches played over 39 days across the United States, Canada, and Mexico. Personally, that feels like a long tournament compared with the NFL playoffs or even the baseball postseason, which conclude much sooner. But times are changing, and soccer's popularity continues to grow.

Attendance is expected to reach roughly 6.5 million fans, making it one of the largest sporting events ever held. Since it is a global audience viewership is tremendous. The last World Cup Finals had 1.5 billion viewers, and more than five billion people watched at least some of the competition. This compares with the Super Bowl where around 200 million people will watch it. The economic impact is equally impressive, with estimates suggesting the tournament could generate more than $40 billion in global economic activity.

And given America's growing appetite for sports betting, it's no surprise that wagering on the World Cup is expected to be enormous. Analysts estimate that wagers could top $50 billion on the tournament worldwide, with many Americans participating for the first time. This compares to the $35 billion that was bet during the 2022 tournament.

I believe soccer's popularity will continue to rise in the years ahead. However, it is entering an already crowded sports landscape where football, baseball, and basketball still dominate the American market.

One final interesting fact: when the winning team lifts the World Cup trophy, they're holding a trophy made of solid 18-karat gold. The gold alone is worth hundreds of thousands of dollars, making it one of the most valuable trophies in all of sports.

Will you be watching?

PPI Jumps, But This Looks More Like an Energy Story Than a Broad Inflation Problem

The latest Producer Price Index (PPI) report showed wholesale inflation rising 1.1% in May and 6.5% over the last year, the highest annual reading since late 2022. At first glance, those numbers appear alarming. However, a closer look shows that energy prices were responsible for the vast majority of the increase.

Gasoline prices alone surged 23.4% during the month, and energy costs as a whole rose 10.7% and accounted for nearly 80% of the overall increase in final demand goods prices. Because of this surge, nearly 80% of the acceleration in the PPI was from the 2.8% increase in final demand goods prices. This was the biggest increase ever for the data series that dates back to December 2009.

While headline inflation grabbed the headlines, the underlying picture was much less dramatic. Core PPI, which excludes food and energy, rose far more modestly than the headline figure as it climbed 0.4% month over month and 4.9% year over year. This was lower than the consensus of 5.4% and suggests that inflation pressures remain concentrated in energy-related sectors rather than spreading broadly throughout the economy.

One interesting detail in the report was that portfolio management fees increased 4.8% during the month, reflecting the strong performance and rising values in financial markets. As markets advance, assets under management rise, which naturally increases fee revenues throughout the investment industry and causes the PPI to climb.

Another factor investors should watch is artificial intelligence. While many view AI as a future productivity miracle that will eventually lower costs, we are currently in the investment phase. Companies are spending hundreds of billions of dollars on data centers, semiconductor capacity, electrical infrastructure, networking equipment, and specialized talent. Those expenditures are inflationary today because they increase demand for labor, energy, construction materials, and computing hardware.

Over the long run, AI may prove highly deflationary by boosting productivity and reducing labor costs. In the near term, however, the race to build AI infrastructure is adding demand to an economy that is already operating near full capacity.

The bottom line is that this PPI report was hot, but it was largely an energy story. Unless higher energy prices persist long enough to spread throughout the broader economy, investors should avoid confusing a commodity shock with a sustained inflation cycle. Maintaining a disciplined, diversified portfolio remains the most effective way to navigate periods like this.

Marriage Between Two People Makes Financial Sense — Divorce Destroys That

Marriage can provide significant financial benefits, while divorce often creates substantial financial challenges. Unfortunately, divorce remains common in the United States. Current estimates suggest that roughly 40% to 50% of first marriages end in divorce. If you’re in your second marriage, the odds increase to 60 or 70%.

The divorce rate for first marriages is up substantially from the 60s when it was only 25 to 30%.

One of the biggest financial advantages of marriage is the ability to combine resources. Two incomes can make it easier to purchase a home, save for retirement, fund children's education, and enjoy vacations and other lifestyle expenses. Married couples may also benefit from certain tax advantages and economies of scale that can lower overall living costs.

Divorce, however, often reverses many of those benefits. Legal fees, court costs, and the division of assets can be expensive. Couples may be forced to sell homes, investments, or other assets at less-than-ideal times, often paying commissions and transaction costs along the way. Retirement accounts, such as 401(k)s, may be divided, reducing the savings each person has accumulated over the years. For many people, rebuilding financially after a divorce can take years. The transition from supporting one household to maintaining two often results in higher living expenses and reduced financial flexibility.

While there may be personal reasons why divorce is the right decision, there is rarely a financial advantage to ending a marriage. If you find yourself going through a divorce, it is important to take a careful look at your finances, create a realistic budget, and develop a plan to regain financial stability. Avoid accumulating unnecessary debt, keep credit card spending under control, and focus on rebuilding your financial foundation one step at a time. With patience, discipline, and a sound financial plan, it is possible to recover and move forward successfully after divorce.