Capitalist Investor

AI Investment Spending, Portfolio Concentration, and Retirement Risk

The growing financial commitments behind artificial intelligence are raising important questions about corporate profitability, market concentration, and portfolio diversification. For investors approaching or living in retirement, understanding these risks is an important part of preserving accumulated wealth.

In this episode of The Capitalist Investor, Tony Zabiegala, CRPC® and Derek Gabrielsen, CRPC® examine the capital expenditures of major technology companies, the pressure on free cash flow, and the implications of concentrated exposure to large-cap technology stocks.

They also discuss potential changes to Social Security, Me...

Social Security benefits are set to receive a 3.6% cost of living adjustment in 2027, giving millions of Americans a larger monthly check. But rising Medicare premiums and other retirement expenses could reduce how much of that increase retirees actually feel.

In this episode, the team breaks down what the new COLA means for Social Security recipients, how Medicare and prescription drug costs factor into retirement income, and why inflation can affect retirees differently than younger workers.

They also discuss the long term funding challenges facing Social Security, possible changes to how future cost of living adjustments...

Private equity, private credit and private real estate could soon become more common inside 401(k) plans, opening the door to investments that have traditionally been limited to institutions and wealthy investors.

In this episode, the team breaks down the potential benefits and risks of adding private assets to retirement accounts, including diversification, higher fees, limited liquidity and the difficulty of valuing investments that do not trade publicly.

They also discuss how these investments could eventually appear inside target date funds, why education and due diligence will be critical and what retirement savers should understand before...

One of the most influential voices in retirement research has changed her thinking on three major planning topics, and those shifts could have real implications for retirees and do it yourself investors.

In this episode, the team breaks down why retirement planning involves much more than simply choosing investments, including taxes, Social Security, Medicare, income planning and withdrawal strategies. They also discuss the limitations of target date funds as investors move from saving for retirement to actually living on their portfolios.  

The conversation also examines TIPS and other fixed income strategies, why inflation protected securities ma...

With the end of 2026 approaching, there are several important retirement planning deadlines that could impact your taxes, savings and Medicare costs heading into the new year.

In this episode, the team breaks down three key areas to review before year end: maximizing 401(k) contributions and catch up provisions, completing Roth conversions before the December 31 deadline and preparing for Medicare open enrollment.

They also discuss the new Roth catch up rules for higher earners, how Roth conversions can affect future Medicare premiums and why waiting until the last minute could create unnecessary complications.

If...

The baby boomer retirement wave isn’t coming, it’s already here.

In this episode of The Capitalist Investor, the conversation focuses on what record numbers of Americans reaching retirement age could mean for Social Security, Medicare, the labor market, housing, and retirement planning. The discussion covers the growing strain on Social Security, rising healthcare costs, retirement readiness, the concentration of wealth among older Americans, and how a massive generational shift could affect markets and the economy in the years ahead.

They also discuss why near-retirees may want to prepare for the possibility of reduced Soci...

For individuals approaching or already in retirement, retirement account structure can become just as important as investment performance. Decisions involving 401(k) plans, traditional IRAs, Roth IRAs, rollovers, and future required distributions can have meaningful tax and planning implications.

In this episode, the discussion explores why substantial retirement assets often migrate from employer-sponsored plans into IRAs and what investors should consider once that happens. Topics include traditional versus Roth contributions, backdoor Roth strategies, spousal contributions, income and deductibility limits, in-service distributions, investment flexibility, fees, and the importance of evaluating future tax brackets.

The larger point is...

Changes to the tax code can have meaningful consequences for retirement planning, particularly when provisions include income limits, expiration dates, and different rules depending on age or account type. 

In this episode, Tony Zabiegala and Derek Gabrielsen review several tax provisions affecting retirees and families. Topics include the temporary senior deduction, current tax brackets, estate tax exemptions, Roth conversion timing, new Trump Accounts for minors, and enhanced catch-up contribution limits for certain workers approaching retirement. 

The discussion emphasizes understanding how these rules may apply to an individual situation rather than treating broad tax changes as un...

As 2026 enters its final third, investors face an unusual combination of strong market fundamentals and several potential sources of volatility. 

In this episode, Tony Zabiegala and Derek Gabrielsen examine what has supported the market so far, including broader market participation, a rotation from growth toward value, and earnings and revenue growth. They also consider what could challenge that outlook, including Federal Reserve uncertainty, the midterm elections, geopolitical developments, energy prices, and the possibility that current earnings strength represents an unusually favorable environment. 

The conversation emphasizes diversification, appropriate risk tolerance, and maintaining a disciplined investment plan ra...

After spending decades accumulating wealth, shifting into retirement spending can be more difficult than expected. For many retirees, the challenge is not simply determining whether they have enough assets. It is becoming comfortable using those assets without feeling that they are jeopardizing the future. 

Derek Gabrielsen, CRPC®, and Dave Abate, CFP®, discuss the psychology behind this transition and the role a financial plan can play in evaluating spending decisions. The conversation covers retirement anxiety, individualized spending goals, stress testing, withdrawal sequencing, tax efficiency, lifestyle expenses, and the balance between enjoying wealth today and preserving assets for future gen...

Workplace retirement plans are beginning to offer more ways for participants to convert accumulated savings into retirement income. For investors nearing retirement, these options raise an important planning question: should a portion of a 401(k) be used to create a predictable lifetime income stream? 

In this episode, Derek Gabrielsen, CRPC® and Dave Abate, CFP® discuss the evolution of 401(k) plans, the increasing availability of annuity and lifetime-income options, and the potential limitations of relying too heavily on a single solution. The conversation considers flexibility, spending needs, taxes, investment risk, product quality, and the role these options may pla...

Women often face a different retirement planning equation. Longer life expectancies, career interruptions related to caregiving, lower average retirement savings, and the increased likelihood of managing finances alone later in life can all influence retirement income decisions.

This episode examines Social Security timing, survivor benefits, pension elections, long-term care risk, and the role of guaranteed income in creating a more dependable retirement structure. The discussion also explains why married couples should evaluate how the financial plan would function after the death of either spouse.

The episode offers a practical framework for understanding these risks and...

Roth conversions can provide meaningful tax-planning flexibility, but they are not automatically appropriate for every investor. The decision depends on current income, expected future tax rates, required minimum distributions, Medicare considerations, retirement cash flow, and the intended use of inherited assets. 

Derek Gabrielsen, CRPC® — Senior Wealth Advisor, and Tony Zabiegala, CRPC® — Senior Wealth Advisor, examine the growing role of Roth accounts in retirement planning. Their conversation covers the potential conversion window after leaving the workforce, Roth and traditional workplace contributions, required distributions, catch-up contribution provisions, unused 529 assets, and the differences between leaving heirs a traditional retirement account and a R...

Retiring into a bear market can put even a well-funded retirement plan under immediate pressure. The danger is not only the decline itself, but having to fund spending from depressed investments—and making emotional decisions that lock in losses.

Derek Gabrielsen, CRPC® — Senior Wealth Advisor, and Tony Zabiegala, CRPC® — Senior Wealth Advisor, examine three retirement scenarios and the choices that changed the outcome. They discuss maintaining a reserve for portfolio-funded living expenses, using cash and short-term bonds before selling equities, adjusting discretionary spending, considering part-time income, rebalancing, evaluating Roth conversions during a downturn, and using annuity income when app...

Rate cuts were expected at the beginning of 2026. Then inflation concerns and rising energy prices put potential rate hikes back on the table. Now, the latest inflation data has changed the outlook once again.

In this episode of The Capitalist Investor, the team breaks down why inflation may remain between 3% and 4% for the foreseeable future and what that could mean for stocks, bonds, real estate, cash, annuities, and retirement income.

They discuss the potential rotation between growth and value stocks, why higher rates may benefit financial companies, how investors should review bond duration, and where...

The Federal Reserve just released data linking immigration to housing market trends. Learn how rising house prices impact your retirement.

This episode of The Capitalist Investor examines recent research from the Federal Reserve regarding the connection between unauthorized immigration and housing market trends. We bypass the political noise to focus strictly on the economic data provided by the central bank. If you are concerned about how shifting demographics might alter your long-term financial stability, this analysis provides a clear look at the current landscape.

Our goal is to help you understand how rising house prices...

Roth or traditional IRA? 401(k) or IRA? Tax deduction now or tax-free withdrawals later?

These are common questions when saving for retirement, but many people get stuck trying to make the “perfect” decision and end up delaying the most important step: actually saving.

In this episode of The Capitalist Investor, the crew breaks down common IRA and retirement account mistakes, including why Roth vs. traditional is not always a simple answer, how required minimum distributions can affect retirement income, why spousal IRA contributions are often overlooked, and how your 401(k) and IRA should work together inst...

A record number of Americans are tapping their 401(k)s through hardship withdrawals, and the reasons are not small or careless expenses. Many people are using retirement savings to avoid foreclosure, cover medical bills, or pay for major home repairs.

In this episode of The Capitalist Investor, Derek and Dave Huberty discuss what is driving the increase in hardship withdrawals, why inflation and rising household costs are putting pressure on retirement plans, and what people should understand before pulling money out of a 401(k).

They also talk about the real cost of early...

SpaceX just made history with the largest IPO ever, raising $75 billion and quickly becoming one of the most valuable companies in the world. The excitement has investors asking one question: Should you buy SpaceX stock?

In this episode of The Capitalist Investor, Derek and Jack take a balanced look at the opportunities and risks surrounding SpaceX's public debut. Rather than focusing on hype, they discuss whether this high-growth company belongs in a retirement portfolio.

Topics include:

Most retirement planning focuses on building wealth. But what happens when age, illness, or cognitive decline make it difficult, or impossible, to manage your money?

In this episode of The Capitalist Investor, Diamond Hands D is joined by Sam and Jack to talk through one of the most important retirement planning conversations families tend to avoid: how to protect your finances before something goes wrong.

They discuss why cognitive decline is a real concern in retirement, why legal documents need to be handled before they are needed, and how tools like durable power of attorney...

For decades, the 4% rule has been one of the most common retirement planning guidelines. The idea was simple: withdraw 4% of your portfolio in the first year of retirement, adjust for inflation each year, and your money should last for 30 years.

But does that rule still work today?

In this episode of The Capitalist Investor, Diamond Hands D is joined by Sam and Jack to break down where the 4% rule came from, why it was never meant to be a one-size-fits-all strategy, and what has changed since it became popular in the 1990s.

They...

Most people assume the key to retirement is aggressively saving every extra dollar possible. But what if working just two more years could have an even bigger impact?

In this episode of The Capitalist Investor, Tony and Derek break down the surprising math behind delaying retirement. They explain how two additional working years can potentially increase 401(k) contributions, allow more time for compound growth, reduce early withdrawals from retirement accounts, and boost Social Security income for the rest of your life.

The conversation also explores the real-life side of retirement planning including burnout, health concerns...

Many Americans dream about retiring early, but few fully understand the healthcare costs that come before Medicare eligibility at age 65. In this episode of the Capitalist Investor, Mark Tepper and Tony Zabiegala break down the real financial impact of retiring early and why healthcare planning needs to be part of every retirement strategy.

They discuss COBRA, Affordable Care Act options, HSA strategies, Roth conversions, tax efficient income planning, and how healthcare costs can dramatically affect long term retirement success. The conversation also highlights why retirement planning is not just about investments and asset levels, but about building...

What happens when one spouse is ready to retire… and the other hasn’t even thought about what retirement actually looks like yet?

In this episode of The Capitalist Investor, the team breaks down the retirement conversations couples often avoid until it’s too late. From retirement timelines and spending habits to travel plans, Social Security decisions, healthcare costs, and lifestyle expectations, this discussion highlights why planning together matters just as much as saving money.

The conversation also covers common financial personality clashes between savers and spenders, why retirement can create unexpected stress inside relationships, and ho...

What happens when the market drops right as you need your money most? 

In this episode, we break down one of the biggest retirement planning mistakes people make: being overexposed to the stock market without a true cash safety net. Using real-world market scenarios like the 2020 crash, we discuss sequence of returns risk, retirement income planning, and why liquidity matters more than most investors realize. 

We also explore how having accessible cash reserves can help retirees avoid selling investments during market downturns, reduce stress during volatile periods, and create more flexibility in a long-term financial st...

Are Social Security increases actually helping retirees or quietly falling behind?

In this episode of The Capitalist Investor, we break down why a recent 2.8% cost of living adjustment may feel more like a loss than a gain. When rising costs for healthcare, groceries, and energy outpace government adjustments, retirees are left asking a simple question: is this really enough?

We also explain how COLA is calculated and why it may not reflect the real expenses people face every day. From inflation to Medicare increases, this conversation highlights the growing gap between perception and reality in...

Most people think they understand retirement planning… but the reality is, small decisions today can completely change your future. Whether you’re contributing to a 401k, exploring a Roth IRA, or just starting to think about saving for retirement, this conversation breaks down what actually matters.

We cover how everyday spending habits impact your ability to save, build retirement income, and reach true financial freedom. From understanding what is a 401k to comparing 401k vs Roth IRA, this is abou...

Building your nest egg is great, but remember that "Uncle Sam" is a silent partner in your retirement planning. The government collects taxes on individual retirement account funds through required minimum distributions (RMDs).

This ensures that funds are taxed before your death, making proper tax planning and understanding taxes in retirement crucial for your financial future. 💰 

For those nearing retirement, the absence of a clearly defined financial plan can create significant risk, regardless of accumulated assets. This episode examines the consequences of delayed planning and the challenges that arise when key factors such as longevity, healthcare costs, inflation, and spending are not properly accounted for.

The discussion explores why individuals often avoid planning, the importance of understanding personal financial behavior, and how structured planning can reveal gaps and provide direction. Through practical examples, including a late-stage retirement scenario, the episode illustrates how early decisions and consistent planning can materially affect long-term outcomes.

In this episode of The Capitalist Investor, Tony Zabiegala speaks with Sam Petitjean about earning the Certified Financial Planner designation and what that process reveals about the depth of financial advice.

They discuss the discipline required to complete the CFP, the difference between basic investment management and true financial planning, and why coordination across tax, legal, and investment strategy matters for long-term outcomes.

For investors with significant assets, understanding how advisors are trained and how they think can play a major role in the quality of guidance they receive.

As retirement approaches, the margin for error narrows. What helped build wealth may no longer be appropriate once income replaces accumulation, and poorly managed risk at this stage can have lasting consequences. 

In this episode, the discussion centers on how portfolio structure should evolve before and after retirement. The conversation explores the impact of market downturns at the wrong time, the importance of rebalancing, the risks of concentrated positions, and why relying on past performance can create blind spots. It also highlights practical frameworks like gradual allocation shifts and the use of structured investment buckets to support i...

For investors with significant assets, geopolitical events can introduce uncertainty that extends beyond short-term market movement. Energy prices, inflation pressures, and supply chain disruptions all play a role in shaping the economic landscape.

This episode examines how current conflict in the Middle East is affecting markets, with a focus on energy dependency, market volatility, and sector-level impacts. The conversation highlights how rising fuel costs can influence inflation, how different industries respond to these shifts, and why a measured, long-term perspective remains essential.

The discussion is intended to provide context and clarity for those evaluating how...

Many experienced investors question whether recent market volatility reflects a deeper structural issue or simply a shift in expectations.

In this episode of The Capitalist Investor, Tony and Dave discuss the difference between headline driven volatility and fundamental market deterioration. They explore how geopolitical developments can influence energy markets, why employment and earnings growth remain important indicators of stability, and how the rapid investment cycle surrounding artificial intelligence may eventually require companies to demonstrate tangible returns.

The conversation offers perspective for investors assessing whether current market movements represent genuine concern or the natural fluctuations that...

Debt can be a powerful financial tool, but it can also become a major obstacle as retirement approaches.

In this episode of The Capitalist Investor, Derek Gabrielsen and Jack Root explore how debt affects retirement planning and why managing liabilities becomes increasingly important as earning years begin to shrink.

The conversation covers how business owners should approach debt tied to their companies, why exit planning matters for entrepreneurs, and why not all debt needs to disappear before retirement. They also explain the difference between mortgage debt and lifestyle debt such as credit cards or home...

For investors nearing retirement, decisions surrounding pension elections and portfolio discipline require careful analysis. In this episode, we examine two foundational areas of retirement planning.

First, we discuss the mechanics of portfolio rebalancing and its role in maintaining intended risk levels over time. Second, we analyze a real world pension scenario involving a $60,000 lifetime annuity versus a $1.2 million lump sum. The conversation explores income durability, estate impact, Monte Carlo outcomes, liquidity considerations, and how a personal pension strategy can alter long term results.

This episode is intended to provide structured perspective for those evaluating significant...

If you are approaching retirement, investment risk is no longer just about chasing higher returns. It becomes about whether you have enough time to recover from market declines and how volatility can affect your ability to retire when planned. 

In this episode of The Capitalist Investor, Diamond Hands - Derek and Jack Root discuss how risk tolerance evolves as retirement nears and why preserving capital, managing allocation, and maintaining discipline become more important than outperforming the market. 

They explain how drawdowns require significantly larger gains to recover, why the “lost decade” illustrates sequencing risk, and how re...

In this episode of The Capitalist Investor, Derek and Tony break down how California’s tax system can impact professional athletes, even after winning a championship.

They also examine whether consumer spending is truly slowing, reviewing retail growth data, job creation numbers, wage trends, and what higher tax refunds in 2026 could mean for the economy.

Finally, they discuss the streaming wars and whether cutting cable has actually saved consumers money, or simply replaced one high bill with many smaller ones.

If you want a grounded discussion on taxes, economic momentum, and consumer behavior, th...

In this episode, Tony and Derrick open with a practical warning about identity theft and financial fraud, sharing real client stories and simple steps you can take today, including changing passwords, freezing credit, and using identity monitoring services.

They then shift into recent market volatility, breaking down gold and silver swings, Bitcoin’s technical patterns, and the surprising connection to the McRib. The conversation explores why timing matters, why emotional reactions hurt returns, and how long-term ownership differs from short-term speculation.

The episode closes with an honest discussion about today’s new investors, instant gratification vers...

In this episode of The Capitalist Investor, Derek and Tony deliver rapid fire hot takes on what’s really driving today’s markets and what investors should be watching as 2026 approaches.

They break down why Costco selling physical gold is grabbing headlines, what soaring gold and silver prices may signal, and why Bitcoin isn’t reacting the way many expected. The conversation also covers the “Big Beautiful Bill,” including who actually benefits from the proposed tax relief and how an estimated $150+ billion back into consumers’ pockets could impact the economy.

Derek and Tony then shift to their 202...

You worked hard to build your wealth. Now comes the real challenge: making sure it lasts.

In this episode, Derek and Tony break down legacy planning strategies to help families preserve wealth across generations. You’ll learn how Roth conversions, estate taxes, trust structures, and family meetings play a role in long term wealth transfer and how to prepare heirs to responsibly manage inherited assets.

This conversation covers practical estate planning concepts, retirement income considerations, and ways high net worth families can reduce taxes while protecting their legacy. If you are thinking about generational wealth, su...